Chloramphenicol - C11H12Cl2N2O5 - PubChem

26/12/2019 Chloramphenicol | C11H12Cl2N2O5 - PubChem
COMPOUND SUMMARY
Chloramphenicol
PubChem CID: 5959
Structure:
2D 3D
Find Similar Structures
Chemical Safety:
Health Hazard
Laboratory Chemical Safety Summary (LCSS) Datasheet
Molecular Formula: C11H12Cl2N2O5
chloramphenicol
56-75-7
Chloromycetin
Synonyms: Chlornitromycin
Levomycetin
More...
Molecular Weight: 323.13 g/mol
Modify: Create:
Dates:
2019-12-21 2004-09-16
Chloramphenicol is a semisynthetic, broad-spectrum antibiotic derived from Streptomyces venequelae with primarily bacteriostatic activity.
Chloramphenicol diffuses through the bacterial cell wall and reversibly binds to the bacterial 50S ribosomal subunit. The binding interferes
with peptidyl transferase activity, thereby prevents transfer of amino acids to the growing peptide chains and blocks peptide bond
formation. As a result bacterial protein synthesis is blocked and impede bacterial cell proliferation.
NCI Thesaurus (NCIt)
Chloramphenicol is a broad spectrum antibiotic introduced into clinical practice in 1948, but which was subsequently shown to cause
serious and fatal aplastic anemia and is now used rarely and reserved for severe, life-threatening infections for which other antibiotics are
not available. Chloramphenicol has also been linked to cases of acute, clinically apparent liver injury with jaundice, largely in association
with aplastic anemia.
LiverTox
Chloramphenicol is an organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond
and two alcohol functions. It has a role as an antimicrobial agent, an antibacterial drug, a protein synthesis inhibitor, an Escherichia coli
metabolite and a Mycoplasma genitalium metabolite. It is an organochlorine compound, a diol, a C-nitro compound and a carboxamide.
ChEBI
https://pubchem.ncbi.nlm.nih.gov/compound/Chloramphenicol 1/79
1 Structures
1.1 2D Structure
Chemical Structure
Depiction
PubChem
Source: PubChem
URL: https://pubchem.ncbi.nlm.nih.gov
Description: Data deposited in or computed by PubChem
1.2 3D Conformer
Interactive Chemical
Structure Model
Ball and Stick
Sticks
Wire-Frame
Space-Filling
Show Hydrogens
Animate
PubChem
1.3 Crystal Structures
PDBe Ligand Code CLM
PDBe Structure Code 3CLA
PDBe Conformer Interactive Chemical Structure Model
Ball and Stick Sticks Wire-Frame Space-Filling
Show Hydrogens Animate
Protein Data Bank in Europe (PDBe)
2 Names and Identifiers
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)
PubChem
2.1.2 InChI
InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)
PubChem
2.1.3 InChI Key
WIIZWVCIJKGZOK-RKDXNWHRSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)
PubChem
2.1.4 Canonical SMILES
C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
Computed by OEChem 2.1.5 (PubChem release 2019.06.18)
PubChem
2.1.5 Isomeric SMILES
C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
Computed by OEChem 2.1.5 (PubChem release 2019.06.18)
PubChem
2.2 Molecular Formula

C11H12Cl2N2O5
Computed by PubChem 2.1 (PubChem release 2019.06.18)
PubChem
2.3 Other Identifiers
2.3.1 CAS
56-75-7
ChemIDplus; DrugBank; DTP/NCI; EPA Chemicals under the TSCA; EPA DSSTox; European Chemicals Agency (ECHA); HSDB; Human Metabolome Database (HMDB)
2787-09-9
ChemIDplus
2.3.1 Other CAS
137731-90-9, 15313-32-3, 55172-72-0, 59112-59-3, 85666-84-8

ChemIDplus
2.3.2 European Community (EC) Number
200-287-4
European Chemicals Agency (ECHA)
2.3.3 NSC Number
3069
DTP/NCI
2.3.4 UNII
66974FR9Q1
FDA/SPL Indexing Data
2.3.5 DSSTox Substance ID
DTXSID7020265
EPA DSSTox
2.3.6 Wikipedia
Chloramphenicol
Wikipedia
2.4 Synonyms
2.4.1 MeSH Entry Terms
Amphenicol
Amphenicols
Chloramphenicol
Chlornitromycin
Chlorocid
Chloromycetin
Cloranfenicol
Detreomycin
Kloramfenikol
Levomycetin
Ophthochlor
Syntomycin
MeSH
2.4.2 Depositor-Supplied Synonyms
chloramphenicol Detreomycin Sificetina Anacetin Chloroptic Erbaplast Micoclorina Kamaver Cloramfe

56-75-7 Oleomycetin Chloronitrin Austracil Chlorovules Farmicetina Microcetina Klorita Novochlo
Chloromycetin Fenicol Ciplamycetin Austracol Cidocetine Hortfenicol Novomycetin Mychel Sintomice
Chlornitromycin Amphenicol Detreomycine Biocetin Cloramficin Isicetin Ophthochlor Isopto fenicol Synthomy
Levomycetin Aquamycetin Dextromycetin Biophenicol Cloramidina Ismicetina Rivomycin Chlora-tabs Chloroma
Levomicetina Chloramficin Intramycetin Chemicetin Clorocyn Isophenicol Ambofen Chlorocidin C Oftalent
Halomycetin Chloramfilin Levomitsetin Chemicetina Cloromisan Kemicetina Catilan Chloramphenicolum Otachron
Chlorocid Cloramicol Mediamycetine Chlomycol Clorosintex Kemicetine Chlomin Chloroject L Pantovern
Globenicol D-Chloramphenicol Micochlorine Chloramsaar Comycetin Leukomyan Desphen Normimycin V Pentamyc
Chloroamphenicol Enteromycetin Novophenicol Chlorasol Cylphenicol Loromisin Emetren Chlorocid S Quemicet
Alficetyn Juvamycetin Stanomycetin Chloricol Doctamicina Mastiphen Enicol Klorocid S Romphen
Chloramex Laevomycetinum Amphicol Chlorocaps Econochlor Medichol Ertilen Mychel-Vet Ronphen
Chlorocol Leukomycin Amseclor Chlorocide Embacetin Micloretin Glorous Chloramfenikol Septicol
PubChem
3 Chemical and Physical Properties
3.1 Computed Properties
Property Name Property Value Reference
Molecular Weight 323.13 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)
XLogP3 1.1 Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Hydrogen Bond Donor Count 3 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count 5 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count 5 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass 322.012327 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Mass 322.012327 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Area 115 Å² Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count 20 Computed by PubChem
Formal Charge 0 Computed by PubChem
Complexity 342 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Count 0 Computed by PubChem
Defined Atom Stereocenter Count 2 Computed by PubChem
Undefined Atom Stereocenter Count 0 Computed by PubChem
Defined Bond Stereocenter Count 0 Computed by PubChem
Undefined Bond Stereocenter Count 0 Computed by PubChem
Covalently-Bonded Unit Count 1 Computed by PubChem
Compound Is Canonicalized Yes Computed by PubChem (release 2019.01.04)
PubChem
3.2 Experimental Properties
3.2.1 Physical Description
Solid
Human Metabolome Database (HMDB)
3.2.2 Color/Form
Needles or elongated plates from water or ethylene dichloride

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 367
HSDB
White to greyish-white or yellowish-white fine crystalline powder or fine crystals, needles or elongated plates. Of the four possible
stereoisomers, only the alphaR,betaR (or D-threo) form is active ... .
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on
Cancer, 1972-PRESENT. (Multivolume work). Available at: http://monographs.iarc.fr/ENG/Classification/index.php, p. V50: 170 (1990)
HSDB
Pale yellow plates or needles from water

Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-96
HSDB
3.2.3 Taste
Bitter to taste
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 303
HSDB
3.2.4 Boiling Point
Sublimes in high vacuum

HSDB
3.2.5 Melting Point
171
Bartz, Q.R.; U.S. Patent 2,483,871; October 4, 1949; assigned to Parke, Davis & Company Crooks, H.M., Jr., Rebstock, M.C., Controulis, J. and Bartz, Q.R.; U.S. Patent
2,483,884; October 4, 1949; assigned to Parke, Davis & Company. Ehrlich, J., Smith, R.M. and Penner, M.A.; U.S. Patent 2,483,892; October 4, 1949; assigned to Parke,
Davis & Company. Carrara, G.; U.S. Patent 2,776,312; January 1, 1957 Slack, R.; U.S. Patent 2,786,870; March 26, 1957; assigned to Parke, Davis & Company.
DrugBank
150.5 °C
EPA DSSTox
150.5-151.5 °C
HSDB
150.5°C
3.2.6 Solubility
2500 mg/L (at 25 °C)

MERCK INDEX (2001)
DrugBank
Water Solubility
0.01 M
MERCK INDEX (2001)
EPA DSSTox
In water, 2.5 mg/mL at 25 °C

HSDB
Solubility in propylene glycol: 150.8 mg/mol. Very sol in methanol, ethanol, butanol, ethyl acetate, acetone. Fairly soluble in ether. Insoluble in
benzene, petroleum ether, vegetable oils. Solubility in 50% acetamide solution about 5%.
HSDB
Very soluble in acetone, chloroform, ethanol

Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-96
HSDB
4.61e-01 g/L
3.2.7 Vapor Pressure
1.7X10-12 mm Hg at 25 °C (est)
US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of April 18, 2017: http://www2.epa.gov/tsca-screening-tools
HSDB
3.2.8 Octanol/Water Partition Coefficient
1.14
HANSCH,C ET AL. (1995)
DrugBank
1.14 (LogP)
HANSCH,C ET AL. (1995)
EPA DSSTox
log Kow = 1.14

Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 84
HSDB
LogP
0.7
3.2.9 LogS
-2.11
ADME Research, USCD
DrugBank
3.2.10 Stability/Shelf Life
Stable under recommended storage conditions.

Sigma-Aldrich; Safety Data Sheet for Chloramphenicol. Product Number: C0378, Version 4.11 (Revision Date 02/01/2015). Available from, as of April 7, 2017:
http://www.sigmaaldrich.com/safety-center.html
HSDB
Following reconstitution with sterile water for injection, chloramphenicol sodium succinate injection containing 100 mg of chloramphenicol per
mL has a pH of 6.4-7.0 and is stable for 30 days at room temperature. Cloudy solutions of chloramphenicol succinate should not be used.
/Chloramphenicol sodium succinate/
American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017
HSDB
Neutral and acid solutions are stable on heating

HSDB
Chloramphenicol is stable for several years at room temperature ... . Chloramphenicol is exceptionally stable in the presence of high pH,
although it is destroyed at pH's in excess of 10. Dissolved in distilled water, it can withstand boiling for five hours.
NIH; DailyMed. Current Medication Information for Viceton- chloramphenicol tablet, coated (veterinary drug) (Updated: November 2015). Available from, as of April
13, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=698aaa0a-9fd3-40c2-ec93-0dc2170a75ba&audience=consumer3
HSDB
Stable in the solid state as a bulk drug and when present in solid dosage forms. Reasonable precautions taken to prevent excessive exposure to
light or moisture are adequate to prevent significant decomposition over an extended period.
Cancer, 1972-PRESENT. (Multivolume work). Available at: http://monographs.iarc.fr/ENG/Classification/index.php, p. V50 170 (1990)
HSDB
In soln, chloramphenicol undergoes a number of degradative changes related to pH, temperature, photolysis and microbiological effects.
HSDB
3.2.11 Optical Rotation
Specific optical rotation: +18.6 deg at 20 °C/D (c= 4.86 in ethanol); -25.5 deg at 25 °C/D (ethyl acetate).
HSDB
3.2.12 Decomposition
When heated to decomposition it emits very toxic fumes of /nitrogen oxides and chloride/.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 753
HSDB
3.2.13 pH
Neutral to litmus
HSDB
3.2.14 Caco2 Permeability
-4.69
ADME Research, USCD
DrugBank
3.2.15 Kovats Retention Index
Standard non-polar 2310, 2310
NIST Mass Spectrometry Data Center
3.2.16 Other Experimental Properties
MP: 149-153 °C
HSDB
Aqueous solutions are neutral. Neutral and acid solutions are stable on heating.
HSDB
Crystals from benzene. MP 90 °C. Practically tasteless. Specific optical rotation: +24.6 deg at 26 °C/D (c= 5 in ethanol), UV max (ethanol): 271
nm (E(1%)(1cm) 179). Very slightly soluble in water (1.05 mg/mL at 28 °C); petroleum ether (0.225 mg/mL). Freely soluble in methanol, ethanol,
chloroform, ether, benzene. /Chloramphenicol palmitate/
HSDB
MW: 597.41, mp 135-145 °C (decomposes) /Chloramphenicaol monosuccinate arginine salt/

HSDB
MW: 445.19. Freely soluble in water (about 50% wt/wt) /Chloramphenical monosuccinate sodium salt/
HSDB
Henry's Law constant = 2.3X10-18 atm-cu m/mol at 25 °C (est)

US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of April 18, 2017: http://www2.epa.gov/tsca-screening-tools
HSDB
4 Spectral Information
4.1 1D NMR Spectra
4.1.1 1H NMR Spectra
Instrument Name Varian CFT-20
Copyright Copyright © 2009-2018 Bio-Rad Laboratories, Inc. All Rights Reserved.
Thumbnail
SpectraBase
4.1.2 13C NMR Spectra
Source of Sample Fluka AG, Buchs, Switzerland
Copyright Copyright © 1980, 1981-2018 Bio-Rad Laboratories, Inc. All Rights Reserved.
Thumbnail
SpectraBase
4.2 Mass Spectrometry

Showing 2 of 6 View More
MoNA ID SM831806
MS Category Experimental
MS Type Chromatography identified as LC-MS
MS Level MS2
Precursor Type [M+H]+
precursor m/z 323.0196
Instrument Q Exactive Plus Orbitrap Thermo Scientific
Instrument Type LC-ESI-QFT
Ionization ESI
Ionization Mode positive
Collision Energy 35 (nominal)
Retention Time 6.853 min
Splash splash10-0600-0592000000-129db104bb506af06de0
Thumbnail
Submitter CASMI Team, UFZ, Eawag
MassBank of North America (MoNA)
MoNA ID SM831851
MS Category Experimental
MS Type Chromatography identified as LC-MS
MS Level MS2
Precursor Type [M-H]-
precursor m/z 321.0051
Instrument Q Exactive Plus Orbitrap Thermo Scientific
Instrument Type LC-ESI-QFT
Ionization ESI
Ionization Mode negative
Collision Energy 35 (nominal)
Retention Time 6.873 min
Splash splash10-0uk9-0923000000-86308db0ec59b40b1533
Thumbnail
Submitter CASMI Team, UFZ, Eawag
MassBank of North America (MoNA)
4.2.1 GC-MS
GC-MS Spectrum 15666 - HMDB HMDB0014589

GC-MS
GC-MS Spectrum 40367 - HMDB HMDB0014589
4.2.2 MS-MS
MS-MS Spectrum 81429 - HMDB HMDB0014589 MS-MS Spectrum 439466 - HMDB HMDB0014589
MS-MS MS-MS Spectrum 374583 - HMDB HMDB0014589 MS-MS Spectrum 443615 - HMDB HMDB0014589
MS-MS Spectrum 436331 - HMDB HMDB0014589
4.2.3 Other MS
MASS: 236 (The Aldrich Handbook of Organic Chemicals and Biochemicals, Aldrich Chemical Co., Inc., Aldrich Chemical Co.,
Other MS
Milwaukee, WI)
HSDB
4.3 UV Spectra
UV max: 278 (E(1%)(1cm): 298)
HSDB
UV: 385 (Adsorption Spectra in the UV and Visible Region, Academic Press, New York)
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 41
HSDB
4.4 IR Spectra
IR Spectra IR: u 5174 (Coblentz Society spectral collection)
HSDB
4.4.1 FTIR Spectra
Technique KBr WAFER
Source of Sample Fluka Chemie AG, Buchs, Switzerland
Catalog Number 23275
Thumbnail
SpectraBase
Technique KBr WAFER
Source of Sample Allergan Pharmaceuticals Inc.
Thumbnail
SpectraBase
4.4.2 ATR-IR Spectra
Instrument Name Bio-Rad FTS
Technique ATR-Neat (DuraSamplIR II)
Source of Spectrum Forensic Spectral Research
Source of Sample Fluka Vetranal, Sigma-Aldrich Inc.
Lot Number 8294X
Thumbnail
SpectraBase
4.5 Raman Spectra
Technique FT-Raman
Source of Spectrum Forensic Spectral Research
Source of Sample Fluka Vetranal, Sigma-Aldrich Inc.
Lot Number 8294X
Thumbnail
SpectraBase
5 Related Records
5.1 Related Compounds with Annotation
PubChem
5.2 Related Compounds
Same Connectivity 22 Records
Same Stereo 10 Records
Same Isotope 9 Records
Same Parent, Connectivity 39 Records
Same Parent, Stereo 27 Records
Same Parent, Isotope 26 Records
Same Parent, Exact 18 Records
Mixtures, Components, and

113 Records
Neutralized Forms
Similar Compounds 181 Records
Similar Conformers 339 Records
PubChem
5.3 Substances
5.3.1 Related Substances
All 395 Records
Same 221 Records
Mixture 174 Records
PubChem
5.3.2 Substances by Category
PubChem
5.4 Entrez Crosslinks
PubMed 6,867 Records
Protein Structures 18 Records
Taxonomy 315 Records
OMIM 10 Records
Gene 29 Records
PubChem
5.5 Associated Chemicals

Chloramphenicol sodium succinate; 982-57-0
HSDB
Chloramphenicol palmitate; 530-43-8

HSDB
5.6 NCBI LinkOut
NCBI
6 Chemical Vendors
PubChem
7 Drug and Medication Information
7.1 Drug Indication

Used in treatment of cholera, as it destroys the vibrios and decreases the diarrhea. It is effective against tetracycline-resistant vibrios. It is also
used in eye drops or ointment to treat bacterial conjunctivitis.
DrugBank
FDA Label
DrugBank
7.2 LiverTox Summary

Chloramphenicol is a broad spectrum antibiotic introduced into clinical practice in 1948, but which was subsequently shown to cause serious
and fatal aplastic anemia and is now used rarely and reserved for severe, life-threatening infections for which other antibiotics are not available.
Chloramphenicol has also been linked to cases of acute, clinically apparent liver injury with jaundice, largely in association with aplastic anemia.
LiverTox
7.3 Drug Classes

Antiinfective Agents
LiverTox
7.4 FDA Orange Book
FDA Orange Book
7.5 Drug Labels for Ingredients
Label Information Total 21 labels
Drug Ingredient CHLORAMPHENICOL
0071-3070-07, 57955-0723-2, 57955-2206-2, 57955-6501-2, 58597-7007-4, 61133-2210-1, 61133-2212-1, 61133-2213-1,

62157-047-01, 62157-263-01, 62157-364-01, 62157-481-01, 62157-597-01, 62157-830-01, 63323-011-15, 64578-0060-1,
NDC Code(s)
64578-0064-1, 64578-0067-1, 64578-0145-1, 66579-0038-1, 68703-121-59, 68703-125-59, 75839-189-01, 75839-189-05,
75839-189-25, 75839-189-50
AMERICAN PHARMACEUTICAL INGREDIENTS LLC; AX Pharmaceutical Corp; Attix Pharmaceuticals; Bimeda, Inc.; Energetix Corp;
Packagers
Energetix Corporation; Fresenius Kabi USA, LLC; King Bio Inc.; Native Remedies, LLC; New Sun Inc.; PARKE-DAVIS
DailyMed
7.6 Clinical Trials
7.6.1 ClinicalTrials.gov
ClinicalTrials.gov
7.7 NCI Cancer Drugs

caf
Drugs in the CAF combination: C= Cyclophosphamide; A= Doxorubicin Hydrochloride(Adriamycin); F= Fluorouracil

CAF is used to treat: Breast cancer.
This combination may also be used with other drugs or treatments or to treat other types of cancer.
NCI Cancer Drugs
7.8 Therapeutic Uses

Anti-Bacterial Agents; Protein Synthesis Inhibitors
National Library of Medicine's Medical Subject Headings. Chloramphenicol. Online file (MeSH, 2017). Available from, as of April 10, 2017:
https://www.nlm.nih.gov/mesh/2017/mesh_browser/MBrowser.html
HSDB
/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants
conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH).
Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition;
Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements
for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to
relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and
abstracts for scholarly articles in the field of medicine. Chloramphenicol is included in the database.
NIH/NLM; ClinicalTrials.Gov. Available from, as of April 10, 2017: https://clinicaltrials.gov/
HSDB
Chloramphenicol is an antibiotic produced by Streptomyces venezuelae ... recommended for serious infections in which the location of the
infection, susceptibility of the pathogen or poor response to other therapy indicate restricted antimicrobial option. It has been used since the
1950s for a wide range of microbial infections, including typhoid fever and other forms of salmonellosis, and central nervous system, anaerobic
and ocular infections ... .
HSDB
(VET): Chloramphenicol Tablets are recommended for oral treatment of the following conditions in dogs: Bacterial pulmonary infections caused
by susceptible microorganisms such as: Staphylococcus aureus, Streptococcus pyogenes and Brucella bronchiseptica; infections of the urinary
tract caused by susceptible microorganisms such as: Escherichia coli, Proteus vulgaris, Corynebacterium renale, Streptococcus spp., and
hemolytic Staphylococcus; enteritis caused by susceptible microorganisms such as: E. coli, Proteus spp., Salmonella spp., and Pseudomonas spp.;
infections associated with canine distemper caused by susceptible microorganims such as: B. bronchiseptica, E. coli, P. aeruginosa, Proteus spp.,
Shigella spp. and Neisseria catarrhalis. Additional adjunctive therapy should be used when indicated. Most susceptible infectious disease
organisms will respond to chloramphenicol therapy in three to five days when the recommended dosage regimen is followed. If no response to
chloramphenicol therapy is obtained in three to five days, discontinue its use and review the diagnosis. Also, a change of therapy should be
considered. Laboratory tests should be conducted including in vitro culturing and susceptibility tests on samples collected prior to treatment.
HSDB
Chloramphenicol is an antibiotic that is clinically useful for, and should be reserved for, serious infections caused by organisms susceptible to its
antimicrobial effects when less potentially hazardous therapeutic agents are ineffective or contraindicated. Sensitivity testing is essential to
determine its indicated use, but may be performed concurrently with therapy initiated on clinical impression that one of the indicated conditions
exists.
NIH; DailyMed. Current Medication Information for Chloramphenicol sodium succinate injection (Updated: January 2017). Available from, as of April 12, 2017:
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aed29594-211d-49ef-813f-131975a8d0e3
HSDB
Chloramphenicol has been shown to be active against most strains of the following microorganisms, both in vitro and in clinical infections ... :
Haemophilus influenzae; Salmonella species, including Salmonella typhi; Lymphogranuloma-psittacosis group, Rickettsia.
HSDB
... Chloramphenicol must be used only in those serious infections for which less potentially dangerous drugs are ineffective or contraindicated.
However, chloramphenicol may be chosen to initiate antibiotic therapy on the clinical impression that one of the conditions below is believed to
be present: /accute infections caused by Salmonella typhi; serious infections caused by susceptible strains (Salmonella species, H. influenzae,
specially meningeal infections, Rickettsia, Lymphogranuloma-psittacosis group, various gram-negative bacteria causing bacteremia, meningitis
or other serious gram-negative infections, and other susceptible organisms which have been demonstrated to be resistant to all other
appropriate antimicrobial agents); cystic fibrosis regimens/; in vitro sensitivity tests should be performed concurrently so that the drug may be
discontinued as soon as possible if less potentially dangerous agents are indicated by such tests. The decision to continue use of
chloramphenicol rather than another antibiotic when both are suggested by in vitro studies to be effective against a specific pathogen should
be based upon severity of the infection, susceptibility of the pathogen to the various antimicrobial drugs, /and/ efficacy of the various drugs in
the infection ... .
HSDB
Chloromycetin Ophthalmic Ointment, 1% (Chloramphenicol Ophthalmic Ointment, USP) is indicated for the treatment of surface ocular
infections involving the conjunctiva and/or cornea caused by chloramphenicol-susceptible organisms. The particular antiinfective drug in this
product is active against the following common bacterial eye pathogens: Staphylococcus aureus, Streptococcus, including Streptococcus
pneumoniae, Escherichia coli, Haemophilus influenzae, Klebsiella/Enterobacter species, Moraxella lucunata (Morax-Axenfeld bacillus), Neisseria
species. This product does not provide adequate coverage against: Pseudomonas aeruginosa, Serratia marcescens.
NIH; DailyMed. Current Medication Information for Chloromycetin Ophthalmic Ointment (Updated: October 2006). Available from, as of April 13, 2017:
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=698aaa0a-9fd3-40c2-ec93-0dc2170a75ba&audience=consumer3
HSDB
Chloramphenicol should be used only for the treatment of serious infections caused by susceptible bacteria or Rickettsia when potentially less
toxic drugs are ineffective or contraindicated. The drug must not be used for the treatment of trivial infections, as a prophylactic agent to
prevent bacterial infections, or when it is not indicated as in the treatment of colds, influenza, or throat infections. Prior to initiation of
chloramphenicol therapy, appropriate specimens should be collected for identification of the causative organism and in vitro susceptibility tests.
Chloramphenicol therapy may be started pending results of susceptibility tests, but the drug should be discontinued if tests show the causative
organism to be resistant to chloramphenicol or if the organism is found to be susceptible to potentially less toxic drugs.
American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 192
HSDB
Chloramphenicol is used for the treatment of meningitis caused by susceptible bacteria, including susceptible strains of Neisseria meningitidis,
Haemophilus influenzae, or Streptococcus pneumoniae. However, chloramphenicol is not considered a drug of first choice for the treatment of
meningitis and generally is used only when penicillins and cephalosporins are contraindicated or ineffective. Chloramphenicol should not be
used for the treatment of meningitis caused by gram-negative bacilli and, despite evidence of in vitro activity against Listeria monocytogenes,
the drug usually is ineffective for the treatment of meningitis caused by this organism.
HSDB
Chloramphenicol is used as an alternative to penicillins and cephalosporins for the treatment of meningitis caused by penicillin-susceptible S.
pneumoniae.
HSDB
Chloramphenicol can be used as an alternative to penicillins and cephalosporins for the treatment of meningitis caused by beta-lactamase-
producing or non-beta-lactamase-producing H. influenzae.
HSDB
... Chloramphenicol is considered an alternative to penicillins and cephalosporins for the treatment of N. meningitidis meningitis.
HSDB
Chloramphenicol is used as an alternative agent in the treatment of anthrax. Parenteral penicillins generally have been considered the drugs of
choice for the treatment of naturally occurring or endemic anthrax caused by susceptible Bacillus anthracis, including clinically apparent GI,
inhalational, or meningeal anthrax and anthrax septicemia, although IV ciprofloxacin or IV doxycycline also are recommended. Chloramphenicol
is suggested as an alternative to penicillin G for use in patients hypersensitive to penicillins, especially for the treatment of anthrax
meningoencephalitis. /NOT included in US product label/
HSDB
Although tetracyclines generally are the drugs of choice for the treatment of Rocky Mountain spotted fever and other rickettsial infections,
chloramphenicol is the drug of choice for rickettsial infections when tetracyclines cannot be used. Chloramphenicol generally is considered the
drug of choice for the treatment of rickettsial infections in children younger than 8 years of age and in pregnant women ... since tetracyclines
should be avoided in these patients ... .
American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 192-3
HSDB
Chloramphenicol has been used in the treatment of orofacial, intra-abdominal, or soft-tissue anaerobic bacterial infections, but generally is used
in these infections only when other appropriate anti-infectives (e.g., metronidazole, clindamycin) are contraindicated or ineffective. Some
clinicians suggest that chloramphenicol can be used as an alternative in the treatment of infections caused by Clostridium perfringens,
Fusobacterium, or Bacteroides when the drugs of first choice and other less toxic alternatives cannot be used.
HSDB
Chloramphenicol has been used as an adjunct to fluid and electrolyte replacement in the treatment of cholera. /NOT included in US product
label/
HSDB
Chloramphenicol is used in conjunction with doxycycline and co-trimoxazole for the treatment of melioidosis, a life-threatening disease caused
by Burkholderia pseudomallei (formerly Ps. pseudomallei). /NOT included in US product label/
HSDB
Some clinicians suggest that chloramphenicol and streptomycin can be used as an alternative to tetracycline and streptomycin for the
treatment of glanders caused by B. mallei (formerly Ps. mallei). /NOT included in US product label.
HSDB
Some clinicians suggest that chloramphenicol can be used for the treatment of infections caused by Burkholderia cepaci (formerly Ps. cepacia).
/NOT included in US product label/
HSDB
Chloramphenicol is used as an alternative agent for the treatment of plague caused by Yersinia pestis. /NOT indicated in US product label/
HSDB
Chloramphenicol is used as an alternative to streptomycin (or gentamicin) for the treatment of tularemia caused by Francisella tularensis.
HSDB
For the treatment of brucellosis, some clinicians suggest that a regimen of chloramphenicol (with or without streptomycin) can be used as an
alternative to a tetracycline regimen when the tetracycline regimen cannot be used ... .
HSDB
Chloramphenicol has been used in some patients for the treatment of ehrlichiosis caused by Ehrlichia chaffeensis or E. canis. While some
clinicians suggest that chloramphenicol can be used as an alternative agent for the treatment of E. chaffeensis infections when tetracyclines are
contraindicated ... . /NOT included in US product label/
HSDB
Chloramphenicol is indicated in the topical treatment of superficial infections of the external ear canal caused by susceptible organisms,
including Staphylococcus aureus. Escherichia coli, Hemophilus influenza, Pseudomonas aruginosa, Enterobacter aerogenes (Aerobacter
aerogenes), Klebsiella pneumonia, and Proteus species. /Included in US product labeling/
Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial
Convention, Inc. Greenwood Village, CO. 2004., p. 799
HSDB
Chloramphenicol is used in the topical treatment of bacterial blepharitis, blepharoconjunctivitis, bacterial conjunctivitis, and bacterial keratitis.
/NOT included in US product labeling/
Convention, Inc. Greenwood Village, CO. 2004.
HSDB
Chloramphenicol is used in the topical treatment of exposure keratitis and neuroparalytic keratitis when a secondary bacterial infection is
present. /NOT included in US product labeling/
HSDB
Chloramphenicol is used in the topical treatment of bacterial keratoconjunctivitis. /NOT included in US product labeling/
HSDB
Chloramphenicol is indicated in the treatment of brain abscess caused by B. fragilis or other susceptible organisms. /Included in US product
labeling/
HSDB
Chloramphenicol is indicated in the treatment of paratyphoid fever caused by S. paratyphi A. /Included in US product labeling/
HSDB
Chloramphenicol is indicated in the treatment of Q fever caused by Coxiella burnetii. /Included in US product labeling/
HSDB
Suberin fatty acids (SFAs) isolated from outer birch bark were investigated as an antimicrobial agent and biomaterial in nanofibrous mats
intended for wound treatment. Electrospinning (ES) was used in preparing the composite nonwoven nanomats containing chloramphenicol
(CAM; as a primary antimicrobial drug), SFAs, and polyvinylpyrrolidone (as a carrier polymer for ES). The X-ray powder diffraction, differential
scanning calorimetry, scanning electron microscopy, atomic force microscopy, and texture analysis were used for the physicochemical and
mechanical characterization of the nanomats. ES produced nanofibrous mats with uniform structure and with an average fiber diameter ranging
from 370 to 425 nm. Microcrystalline SFAs and crystalline CAM were found to undergo a solid-state transformation during ES processing. The ES
process caused also the loss of CAM in the final nanofibers. In the texture analysis, the SFAs containing nanofibers exhibited significantly higher
maximum detachment force to an isolated pig skin (p < 0.05) than that obtained with the reference nanofibers. CAM exists in an amorphous
form in the nanofibers which needs to be taken into account in controlling the physical storage stability. In conclusion, homogeneous composite
nanofibrous mats for wound healing can be electrospun from the ternary mixture(s) of CAM, SFAs, and polyvinylpyrrolidone.
PMID:26886306
Tamm I et al; J Pharm Sci 105 (3): 1239-47 (2016)
HSDB
The aim of this study was to compare the effect of chloramphenicol eye drops or ointment, high-concentration hyaluronic acid, or no treatment
on reepithelialization of corneal erosions in an experimental model. Uniform 6-mm corneal erosions were created in 23 rabbit eyes. The rabbits
were randomized to 4 treatment groups: (1) chloramphenicol eye drops group, (2) chloramphenicol ointment, (3) hyaluronic acid 2.3%, and (4)
untreated. Treatment was administered every 8 hours until reepithelialization occurred. Eyes were photographed every 8 hours with a cobalt
blue-filtered light with fluorescein drops until reepithelialization occurred. The area of the erosion at each time point was analyzed. There were
no significant differences in the reepithelialization of the corneal erosion among the 3 treatment groups (72-75 hours, P > 0.05). The time was
significantly shorter (51 hours) for the control untreated group (P = 0.005). The use of chloramphenicol in the form of eye drops or ointment for
prophylaxis in corneal erosions has a similar effect on the healing rate of the erosion. Both forms of the antibiotic and high-concentration
hyaluronic acid had an effect of slowing down the healing of the erosion when compared with when no treatment was given. Therefore, the
decision to treat erosions with eye drops or ointment can be based on the patient's comfort.
PMID:25119960
Barequet IS et al; Cornea 33 (10): 1080-2 (2014)
HSDB
/The study objective was/ to compare penetration in the aqueous humor of topically applied antibiotics. /This was a/ randomized prospective
study /at the/ Department of Ophthalmology, University of Perugia, Italy. /The participants were/ patients undergoing cataract surgery. One
hundred twenty-two patients were included: 14 received one drop of chloramphenicol suspension; 12 one application of chloramphenicol gel;
11 one drop of netilmicin suspension; 13 one drop of tobramycin suspension; 37 repeated instillations of chloramphenicol suspension every
10?min for a total of four drops; and 35 repeated instillations of chloramphenicol gel every 10 min for a total of four drops. Samples were taken
immediately before surgery from the anterior chamber in order to determine the antibiotic by means of high-performance liquid
chromatography. Samples were taken 45-190 min after the eye drops were instilled. /Measurements were taken of/ intraocular penetration of
chloramphenicol, netilmicin and tobramicyn. After a single administration, netilmicin and tobramycin were undetectable, whereas the
chloramphenicol suspension reached a mean concentration of 0.23 +/- 0.21 ug/mL, and the chloramphenicol gel a mean concentration of 0.13
+/- 0.14 ug/mL. After repeated administrations, the mean concentrations of the chloramphenicol suspension and gel were 0.60 +/- 0.26 ug/mL
and 0.58 +/- 0.18 ug/mL, respectively. Tobramycin and netilmicin do not reach detectable concentrations, whereas chloramphenicol, after
multiple administrations, reaches concentrations that are effective against Haemophilus influenzae and Haemophilus parainfluenzae, Legionella
pneumophila, Moraxella catarrhalis, Neisseria meningitidis, Pasteurella multocida and Streptococcus pneumoniae. This means that
chloramphenicol can be rationally used in the prophylaxis and treatment of infections supported by sensitive germs.
PMID:23433257
Cagini C et al; Clin Exp Ophthalmol 41 (7): 644-7 (2013)
HSDB
/EXPL THER/ The ribosomal exit tunnel had recently become the center of many functional and structural studies. Accumulated evidence
indicates that the tunnel is not simply a passive conduit for the nascent chain, but a rather functionally important compartment where nascent
peptide sequences can interact with the ribosome to signal translation to slow down or even stop. To explore further this interaction, we have
synthesized short peptides attached to the amino group of a chloramphenicol (CAM) base, such that when bound to the ribosome these
compounds mimic a nascent peptidyl-tRNA chain bound to the A-site of the peptidyltransferase center (PTC). Here we show that these CAM-
peptides interact with the PTC of the ribosome while their effectiveness can be modulated by the sequence of the peptide, suggesting a direct
interaction of the peptide with the ribosomal tunnel. Indeed, chemical footprinting in the presence of CAM-P2, one of the tested CAM-peptides,
reveals protection of 23S rRNA nucleotides located deep within the tunnel, indicating a potential interaction with specific components of the
ribosomal tunnel. Collectively, our findings suggest that the CAM-based peptide derivatives will be useful tools for targeting polypeptide chain
mimics to the ribosomal tunnel, allowing their conformation and interaction with the ribosomal tunnel to be explored using further biochemical
and structural methods.
PMID:23770443
Mamos P et al; Biochimie 95 (9): 1765-72 (2013)
HSDB
/EXPL THER/ Salmonella Paratyphi A is a food-borne Gram-negative pathogen and a major public health challenge in the developing world.
Upon reaching the intestine, S. Paratyphi A penetrates the intestinal epithelial barrier; and infects phagocytes such as macrophages and
dendritic cells. S. Paratyphi A surviving within macrophages is protected from the lethal action of antibiotics due to their poor penetration into
the intracellular compartments. Hence we have developed chloramphenicol loaded chondroitin sulfate (CS-Cm Nps) and dextran sulfate (DS-
Cm Nps) nanoparticles through ionotropic-gelation method for the intracellular delivery of chloramphenicol. The size of these nanoparticles
ranged between 100 and 200 nm in diameter. The encapsulation efficiency of both the nanoparticles was found to be around 65%. Both the
nanoparticles are found to be non-hemolytic and non-toxic to fibroblast and epithelial cells. The prepared nanoparticles exhibited sustained
release of the drug of up to 40% at pH 5 and 20-25% at pH 7.0 after 168 hr. The anti-microbial activities of both nanoparticles were tested
under in vitro and ex vivo conditions. The delivery of DS-Cm Nps into the intracellular compartments of the macrophages was 4 fold more
compared to the CS-Cm Nps which lead to the enhanced intracellular antimicrobial activity of Ds-Cm Nps. Enhanced anti-microbial activity of
Ds-Cm Nps was further confirmed in an ex vivo chicken intestine infection model. Our results showed that Cm loaded DS Nps can be used to
treat intracellular Salmonella infections.
PMID:25645750
Kiruthika V et al; Colloids Surf B Biointerfaces 127: 33-40 (2015)
HSDB
/EXPL THER/ Nine mature koalas with chlamydiosis, typically keratoconjunctivitis and/or urogenital tract infection, were treated with daily
subcutaneous injections of chloramphenicol at 60 mg/kg for 45 days (five koalas), or for a shorter duration (four koalas). All koalas were initially
positive for Chlamydia pecorum as determined by real-time polymerase chain reaction (qPCR). Plasma chloramphenicol concentrations were
determined at t = 0, 1, 2, 4, 8, and 24 hr after the day 1 injection (nine koalas) and after the day 15 injection (seven koalas). Chloramphenicol
reached a median (and range) maximum plasma concentration of 3.03 (1.32-5.03 ug/mL) at 4 (1-8 hr) after the day 1 injection and 4.82 (1.97-
27.55 ug/mL) at 1 (1-2 hr) after day 15. The median (and range) of AUC(0-24) on day 1 and day 15 were 48.14 (22.37-81.14 ug-hr/mL) and 50.83
(28.43-123.99 ug-hr/mL), respectively. The area under the moment curve (AUMC)(0-24) median (and range) for day 1 and day 15 were 530.03
(233.05-798.97 hr) and 458.15 (291.72-1093.58 hr), respectively. Swabs were positive for chlamydial DNA pretreatment, and all koalas except
one, produced swabs negative for chlamydial DNA during treatment and which remained so, for 2-63 days after treatment, however whether
chloramphenicol treatment prevented long-term recrudescence of infection was not established. At this dose and dosing frequency,
chloramphenicol appeared to control mild chlamydial infection and prevent shedding, but severe urogenital disease did not appear to respond
to chloramphenicol at this dosage regime. For koalas affected by severe chlamydiosis, antibiotics alone are not sufficient to effect a cure,
possibly because of structural or metabolic changes associated with chronic disease and inflammation.
PMID:21569052
Govendir M et al; J Vet Pharmacol Ther 35 (2): 147-54 (2012)
HSDB
/EXPL THER/ The emergence of methicillin-resistant Staphylococcus aureus (MRSA) infection has increased precipitously over the past several
decades, with far-reaching health care and societal costs. MRSA infections in the context of burn wounds lead to invasive disease that could
potentially cause mortality. ... Here, we report a novel chloramphenicol loaded with poly(epsilon-caprolactone) (PCL)-pluronic composite
nanoparticles (CAM-PCL-P NPs), physicochemical characterizations, and its bioactivity evaluation in a MRSA-infected burn-wound animal model.
CAM-PCL-P NPs could encapsulate 98.3% of the drug in the nanoparticles and release 81% of the encapsulated drug over 36 days with a time to
50% drug release of 72 hours (51%). Nanoparticle suspensions maintained the initial properties with respect to size and encapsulation efficiency,
even after 6 months of storage at 4 °C and 25 °C, respectively (P>0.05). Significant reduction in the level of toxicity was observed for CAM-PCL-P
NPs compared with that of free drug as confirmed from hemolytic activity against human blood erythrocytes and cytotoxicity assay against an
MCF-7 breast cancer cell line. In vitro antibacterial activities were performed by zone of inhibition, minimum inhibitory concentrations, minimum
bacterial concentration, and time-kill assays, which showed that CAM-PCL-P NPs exhibited significantly enhanced anti-MRSA activity against ten
clinical isolates of MRSA strains. The augmented activity of CAM-PCL-P NPs was further tested on a MRSA-infected burn-wound animal model
and achieved quicker efficacy in MRSA clearance and improved the survival rate compared with free-chloramphenicol treatment. Thus, we
propose CAM-PCL-P NPs as a promising novel antimicrobial candidate that may have a good potential for preclinical applications.
PMID:25931822
Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4404939
Kalita S et al; Int J Nanomedicine 10: 2971-84 (2015)
HSDB
7.9 Drug Warnings

/BOXED WARNING/ WARNING Serious and fatal blood dyscrasias (aplastic anemia, hypoplastic anemia, thrombocytopenia and
granulocytopenia) are known to occur after the administration of chloramphenicol. In addition, there have been reports of aplastic anemia
attributed to chloramphenicol which later terminated in leukemia. Blood dyscrasias have occurred after both short-term and prolonged therapy
with this drug. Chloramphenicol must not be used when less potentially dangerous agents will be effective, as described in the INDICATIONS
AND USAGE section. It must not be used in the treatment of trivial infections or where it is not indicated, as in colds, influenza, infections of the
throat; or as a prophylactic agent to prevent bacterial infections. Precautions: It is essential that adequate blood studies be made during
treatment with the drug. While blood studies may detect early peripheral blood changes, such as leukopenia, reticulocytopenia, or
granulocytopenia, before they become irreversible, such studies cannot be relied on to detect bone marrow depression prior to development of
aplastic anemia. To facilitate appropriate studies and observation during therapy, it is desirable that patients be hospitalized.
HSDB
/BOXED WARNING/ WARNING Bone marrow hypoplasia including aplastic anemia and death has been reported following topical application of
chloramphenicol. Chloramphenicol should not be used when less potentially dangerous agents would be expected to provide effective
treatment.
HSDB
/Chloramphenicol/ is not recommended for the routine treatment of the typhoid carrier state.
HSDB
Chloramphenicol is contraindicated in individuals with a history of previous hypersensitivity and/or toxic reaction to it. It must not be used in the
treatment of trivial infections or where it is not indicated, as in colds, influenza, infections of the throat; or as a prophylactic agent to prevent
bacterial infections.
HSDB
For more Drug Warnings (Complete) data for Chloramphenicol (44 total), please visit the HSDB record page.
HSDB
7.10 Maximum Drug Dose

(VET): A single intravenous dose of 150 mg/kg (approximately 68 mg/lb) in propylene glycol is the maximum dose tolerated by the dog.
HSDB
8 Food Additives and Ingredients
8.1 Food Additive Classes

JECFA Functional Classes
Veterinary Drug: ANTIMICROBIAL_AGENT

FAO/WHO Food Additive Evaluations (JECFA)
8.2 Food Additive Status

FDA Food Additive Status
Chloramphenicol - VET, REG, ZERO - Drug in any form may not be used in food (meat, milk, and egg) producing animals
FDA Center for Food Safety and Applied Nutrition (CFSAN)
8.3 Evaluations of the Joint FAO/WHO Expert Committee on Food Additives - JECFA
Chemical Name CHLORAMPHENICOL
ADI NO ADI ALLOCATED
Evaluation Year 2004
Chloramphenicol was previously evaluated at the Committee's 12th, 32nd, and 42nd meetings. Concerns have been expressed
about the genotoxicity of chloramphenicol and its metabolites, its embryo- and fetotoxicity, its carcinogenic potential in
humans and the lack of a dose response for the induction of aplastic anaemia, which may be fatal. The Committee noted that
aplastic anaemia induced by chloramphenicol is a rare idiosyncratic response in humans, which may have an immunological
component.As such, no animal model could be developed. Due to these factors and the lack of data concerning the mechanism
Comments o chloramphenicol-induced aplastic anaemia, the Committee could not identify any studies in animals or epidemiological
studies that would assist the further toxicological evaluation and concluded that it was not appropriate to establish an ADI for
chloramphenicol. The Committee was also unable to propose options for regulating traces of chloramphenicol in foods. The
human exposure which may have resulted from consumption of contaminated seafood in the years 2001–2003 was probably
lower than the systemic exposure resulting from the use of ophthalmic formulations. However, the resulting risk could not be
estimated.
Report TRS 925-JECFA 62/49
9 Pharmacology and Biochemistry
9.1 Pharmacology
Chloramphenicol is a broad-spectrum antibiotic that was derived from the bacterium Streptomyces venezuelae and is now produced
synthetically. Chloramphenicol is effective against a wide variety of microorganisms, but due to serious side-effects (e.g., damage to the bone
marrow, including aplastic anemia) in humans, it is usually reserved for the treatment of serious and life-threatening infections (e.g., typhoid
fever). Chloramphenicol is bacteriostatic but may be bactericidal in high concentrations or when used against highly susceptible organisms.
Chloramphenicol stops bacterial growth by binding to the bacterial ribosome (blocking peptidyl transferase) and inhibiting protein synthesis.
DrugBank
Chloramphenicol is a semisynthetic, broad-spectrum antibiotic derived from Streptomyces venequelae with primarily bacteriostatic activity.
Chloramphenicol diffuses through the bacterial cell wall and reversibly binds to the bacterial 50S ribosomal subunit. The binding interferes with
peptidyl transferase activity, thereby prevents transfer of amino acids to the growing peptide chains and blocks peptide bond formation. As a
result bacterial protein synthesis is blocked and impede bacterial cell proliferation.
NCI Thesaurus (NCIt)
9.2 MeSH Pharmacological Classification

Protein Synthesis Inhibitors
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition
includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the
prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)
MeSH
Anti-Bacterial Agents
Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)
MeSH
9.3 FDA Pharmacological Classification
FDA UNII 66974FR9Q1
Active Moiety CHLORAMPHENICOL
Pharmacological Classes Established Pharmacologic Class [EPC] - Amphenicol-class Antibacterial
Pharmacological Classes Chemical/Ingredient structural concept [Chemical/Ingredient] - Amphenicols
FDA Pharmacology Summary Chloramphenicol is an Amphenicol-class Antibacterial. The chemical classification of chloramphenicol is Amphenicols.
FDA Pharm Classes
9.4 ATC Code

D - Dermatologicals
D06 - Antibiotics and chemotherapeutics for dermatological use

D06A - Antibiotics for topical use
D06AX - Other antibiotics for topical use
D06AX02 - Chloramphenicol
WHO ATC
D - Dermatologicals
D10 - Anti-acne preparations

D10A - Anti-acne preparations for topical use
D10AF - Antiinfectives for treatment of acne
D10AF03 - Chloramphenicol
WHO ATC
G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics
G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids
G01AA - Antibiotics
G01AA05 - Chloramphenicol
WHO ATC
J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use
J01B - Amphenicols
J01BA - Amphenicols
J01BA01 - Chloramphenicol
WHO ATC
S - Sensory organs
S01 - Ophthalmologicals
S01A - Antiinfectives
S01AA - Antibiotics
S01AA01 - Chloramphenicol
WHO ATC
S - Sensory organs
S02 - Otologicals
S02AA - Antiinfectives
WHO ATC
S - Sensory organs
S03 - Ophthalmological and otological preparations

S03AA - Antiinfectives
WHO ATC
9.5 Absorption, Distribution and Excretion

Absorption
Rapidly and completely absorbed from gastrointestinal tract following oral administration (bioavailability 80%). Well absorbed following
intramuscular administration (bioavailability 70%). Intraocular and some systemic absorption also occurs after topical application to the eye.
DrugBank
Hepatic metabolism to the inactive glucuronide is the major route of elimination. This metabolite and chloramphenicol itself are excreted in the
urine following filtration and secretion.
Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p.
1527
HSDB
Chloramphenicol administered orally is absorbed rapidly from the intestinal tract. In controlled studies in adult volunteers using the
recommended dosage of 50 mg/kg/day, a dosage of 1 g every 6 hours for 8 doses was given. Using the microbiological assay method, the
average peak serum level was 11.2 ug/mL one hour after the first dose. A cumulative effect gave a peak rise to 18.4 ug/mL after the fifth dose of
1 g. Mean serum levels ranged from 8 to 14 ug/mL over the 48-hour period. Total urinary excretion of chloramphenicol in these studies ranged
from a low of 68% to a high of 99% over a three-day period. From 8% to 12% of the antibiotic excreted is in the form of free chloramphenicol;
the remainder consists of microbiologically inactive metabolites, principally the conjugate with glucuronic acid. Since the glucuronide is
excreted rapidly, most chloramphenicol detected in the blood is in the microbiologically active free form. Despite the small proportion of
unchanged drug excreted in the urine, the concentration of free chloramphenicol is relatively high, amounting to several hundred mcg/mL in
patients receiving divided doses of 50 mg/kg/day. Small amounts of active drug are found in bile and feces. Chloramphenicol diffuses rapidly,
but its distribution is not uniform. Highest concentrations are found in liver and kidney, and lowest concentrations are found in brain and
cerebrospinal fluid. Chloramphenicol enters cerebrospinal fluid even in the absence of meningeal inflammation, appearing in concentrations
about half of those found in the blood. Measurable levels are also detected in pleural and in ascitic fluids, saliva, milk, and in the aqueous and
vitreous humors. Transport across the placental barrier occurs with somewhat lower concentration in cord blood of neonates than in maternal
blood.
HSDB
Chloramphenicol achieves maximum serum levels very rapidly following oral, intravenous and intraperitoneal administration. Intramuscular
injection with chloramphenicol, except certain soluble forms, results in a somewhat delayed absorption and lower serum levels than when given
by the oral, intravenous, or intraperitoneal route. Chloramphenicol diffuses readily into all body tissues, but at different concentrations. Highest
concentrations are found in the liver and kidney of dogs indicating that these organs are the main route of inactivation and excretion of the
metabolites. The lungs, spleen, heart and skeletal muscles contain concentrations similar to that of the blood. Chloramphenicol reaches
significant concentration in the aqueous and vitreous humors of the eye from the blood. A significant difference from other antibiotics is its
marked ability to diffuse into the cerebrospinal fluid. Within three to four hours after administration, the concentration in the cerebrospinal fluid
has reached, on the average, 50% of the concentration in the serum. If the meninges are inflamed, the percentage may be even higher.
Chloramphenicol diffuses readily into milk, pleural and ascitic fluids and crosses the placenta attaining concentrations of about 75% of that of
the maternal blood.
HSDB
Approximately 55% of a single daily dose can be recovered from the urine of a treated dog. A small fraction of this is in the form of unchanged
chloramphenicol.
HSDB
For more Absorption, Distribution and Excretion (Complete) data for Chloramphenicol (21 total), please visit the HSDB record page.
HSDB
9.6 Metabolism/Metabolites
Hepatic, with 90% conjugated to inactive glucuronide.
DrugBank
Chloramphenicol is rather rapidly metabolized, mainly in the liver, by conjugation with glucuronic acid.
HSDB
Yields d-threo-2-amino-1-(p-nitrophenyl)-1,3-propanediol and chloramphenicol-beta-d-glucuronide in man. In rat. /from table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-14
HSDB
... /undergoes/ direct conjugation. Formation of glucuronide was shown to occur at primary rather than at secondary alcoholic group ... its major
reaction of inactivation and detoxication of drug in man, and any factor which decreases its importance ... results in greatly increased toxicity. ...
In newborns ... bilirubin ... acts as competitive endogenous acceptor.
Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 191
HSDB
Chloramphenicol 3-glucuronide was the major metabolite of chloramphenicol produced by isolated rat hepatocytes although a minor
metabolite was also formed.
Siliciano RF et al; Biochem Pharmacol 27 (23): 2759 (1978)
HSDB
In addition to free chloramphenicol and the glucuronide, the oxamic acid, alcohol, base, acetylarylamine and arylamine metabolites have been
found in the urine of rats given intramuscular doses of (3H)-chloramphenicol (the 1R,2R-isomer). On the basis of recovered radioactivity, the
major metabolites were assumed to be chloramphenicol base (approx 26%) and the acetylarylamine derivative (approx 20%) ... .
HSDB
In dogs, chloramphenicol base and chloramphenicol glucuronide conjugate were reported to be the major metabolites ... . Chloramphenicol,
the glucuronide conjugate and the oxamic acid, acetylarylamine, arylamine and base derivatives were found in the urine of goats given
intramuscular injections of chloramphenicol ... .
HSDB
The glucuronide is the main metabolic product in isolated rat heptocytes exposed to chloramphenicol ... . A study using perfused rat liver and
rat liver microsomes indicated that the arylamine derivative may undergo N-oxidation to form nitrosochloramphenicol ... .
HSDB
Approximately 48% of the chloramphenicol excreted in /human/ urine within 8 hr of an oral dosing was the glucuronide conjugate; only 6% was
excreted as the parent cmpd and 4% as the base derivative ... . The alcohol derivative has been detected in the urine of neonates ... .
HSDB
Chloramphenicol arylamide is formed by intestinal bacterial reduction of the NO2 groups to NH2, which is acetylated and excreted in urine ...
Oxamic acid (formed by oxidative dechlorination of the side chain) was identified as a major metabolite in one human volunteer ... .
HSDB
Metabolites of chloramphenicol, such as dehydrochloramphenicol, produced by intestinal bacteria, are more than 20-fold more cytotoxic than
the parent drug ... .
HSDB
9.7 Biological Half-Life

Half-life in adults with normal hepatic and renal function is 1.5 - 3.5 hours. In patients with impaired renal function half-life is 3 - 4 hours. In
patients with severely impaired hepatic function half-life is 4.6 - 11.6 hours. Half-life in children 1 month to 16 years old is 3 - 6.5 hours, while
half-life in infants 1 to 2 days old is 24 hours or longer and is highly variable, especially in low birth-weight infants.
DrugBank
Chloramphenicol has a half-time /in humans/ ranging from 1.6 to 4.6 hr; using different techniques and in different adult patients, apparent
volumes of distribution ranging from 0.2 to 3.1 l/kg have been measured ... . The half-time is considerably longer in neonates ... in 1- to 8-day-
old infants the half-life ranged from 10 to over 48 hr, and in 11-day to 8-wk-old infants the range was 5-16 hr ... .
HSDB
The plasma half-life of chloramphenicol in adults with normal renal and hepatic function is 1.5-4.1 hours. ... The plasma half-life is 24 hours or
longer in infants 1-2 days of age and approximately 10 hours in infants 10-16 days of age. The plasma half-life of chloramphenicol is prolonged
in patients with markedly reduced hepatic function. In patients with impaired renal function, the plasma half-life of chloramphenicol is not
significantly prolonged, although half-lives of the inactive conjugated derivatives may be prolonged.
HSDB
9.8 Mechanism of Action

Chloramphenicol is lipid-soluble, allowing it to diffuse through the bacterial cell membrane. It then reversibly binds to the L16 protein of the 50S
subunit of bacterial ribosomes, where transfer of amino acids to growing peptide chains is prevented (perhaps by suppression of peptidyl
transferase activity), thus inhibiting peptide bond formation and subsequent protein synthesis.
DrugBank
Chloramphenicol inhibits protein synthesis in bacteria, and to a lesser extent, in eukaryotic cells. The drug readily penetrates bacterial cells,
probably by facilitated diffusion. Chloramphenicol acts primarily by binding reversibly to the 50S ribosomal subunit (near the binding site for the
macrolide antibiotics and clindamycin, which chloramphenicol inhibits competitively). Although binding of tRNA at the codon recognition site
on the 30S ribosomal subunit is undisturbed, the drug apparently prevents the binding of the amino acid-containing end of the aminoacyl tRNA
to the acceptor site on the 50S ribosomal subunit. The interaction between peptidyltransferase and its amino acid substrate cannot occur, and
peptide bond formation is inhibited.
1527
HSDB
Chloramphenicol ... can inhibit mitochondrial protein synthesis in mammalian cells, perhaps because mitochondrial ribosomes resemble
bacterial ribosomes (both are 70S) more than they do the 80S cytoplasmic ribosomes of mammalian cells. The peptidyltransferase of
mitochondrial ribosomes, but not of cytoplasmic ribosomes, is inhibited by chloramphenicol. Mammalian erythropoietic cells are particularly
sensitive to the drug.
1527
HSDB
/Chloramphenicol/ inhibits bacterial protein synthesis by interfering with the transfer of activated amino acids from soluble RNA to ribosomes.
In vitro, chloramphenicol exerts mainly a bacteriostatic effect on a wide range of gram-negative and gram-positive bacteria.
HSDB
/Chloramphenicol/ acts by inhibition of protein synthesis by interfering with the transfer of activated amino acids from soluble RNA to
ribosomes.
HSDB
Chloramphenicol exerts its bacteriostatic action by inhibiting protein synthesis in susceptible organisms. Complete suppression of the
assimilation of ammonia and of the incorporation of amino acids, particularly glutamic acid, together with an increased formation of ribonucleic
acid (RNA), lead to an inhibition of bacterial growth.
HSDB
Chloramphenicol usually is bacteriostatic in action, but may be bactericidal in high concentrations or against highly susceptible organisms.
Chloramphenicol sodium succinate is inactive until hydrolyzed to free chloramphenicol. This hydrolysis occurs rapidly in vivo. Chloramphenicol
appears to inhibit protein synthesis in susceptible organisms by binding to 50S ribosomal subunits; the primary effect is inhibition of peptide
bond formation. The site of action appears to be the same as that of erythromycin, clindamycin, lincomycin, oleandomycin, and
troleandomycin. Chloramphenicol also appears to inhibit protein synthesis in rapidly proliferating mammalian cells; reversible bone marrow
depression due to chloramphenicol may be the result of inhibition of protein synthesis in mitochondria of bone marrow cells. Chloramphenicol
has been shown to possess immunosuppressive activity when the drug is administered systemically prior to an antigenic stimulus; however,
antibody response may not be significantly affected when the drug is administered following the antigen.
HSDB
Mucopolysaccharidosis I (MPS I) is a genetic disorder caused by mutations on alpha-L-iduronidase (IDUA) gene, leading to low or null enzyme
activity. As nonsense mutations are present in about two thirds of the patients, stop codon read through (SCRT) is a potential alternative to
achieve enhanced enzyme activity. This mechanism suppresses premature stop codon mutations allowing the protein to be fully translated.
Chloramphenicol is a peptidyl transferase inhibitor able to induce readthrough and is efficient in cross the blood brain barrier. In this work,
fibroblasts from MPS I patients (p.W402X/p.W402X; p.R89W/p.W402X and p.Q70X/c.1739-1g > t) were treated with chloramphenicol, which
resulted in 100-fold increase on IDUA activity on compound heterozygous fibroblasts. cDNA sequencing showed that only the alleles without
the nonsense mutation were being amplified, even after treatment, leading us to suggest that the nonsense alleles were targeted to nonsense-
mediated mRNA decay and that chloramphenicol acts through a mechanism other than SCRT.
PMID:23167761
Mayer FQ et al; Curr Pharm Biotechnol 14 (2): 194-8 (2013)
HSDB
Overuse and abuse of antibiotics can increase the risk of cancer. Chloramphenicol can inhibit both bacterial and mitochondrial protein synthesis,
causing mitochondrial stress and decreased ATP biosynthesis. Chloramphenicol can accelerate cancer progression; however, the underlying
mechanisms of chloramphenicol in carcinogenesis and cancer progression are still unclear. We found that chloramphenicol can induce matrix
metalloproteinase (MMP)-13 expression and increase MMP-13 protein in conditioned medium, resulting in an increase in cancer cell invasion.
Chloramphenicol also activated c-Jun N-terminal kinases (JNK) and phosphatidylinositol 3-kinase (PI-3K)/Akt signaling, leading to c-Jun protein
phosphorylation. The activated c-Jun protein has been proven to activate binding to the MMP-13 promoter and also upregulate the amount of
MMP-13. Both the SP 600125 (JNK inhibitor) and LY 294002 (PI-3K/Akt inhibitor) can inhibit chloramphenicol-induced c-Jun phosphorylation,
MMP-13 expression, and cell invasion. Overexpression of the dominant-negative JNK and PI-3K p85 subunit also negate chloramphenicol-
induced responses. Other antibiotics that cause mitochondrial stress and a decrease in ATP biosynthesis also induce MMP-13 expression. These
findings suggest that chloramphenicol-induced PI-3K/Akt, JNK phosphorylation, and activator protein 1 activation might function as a novel
mitochondrial stress signal that result in an increase of MMP-13 expression and MMP-13-associated cancer cell invasion. The findings of this
study confirms that chloramphenicol, and other 70S ribosomal inhibitors, should be administered with caution, especially during cancer therapy.
PMID:20338993
Li CH et al; Toxicol Sci 116 (1): 140-50 (2010)
HSDB
... By investigating the effects of chloramphenicol on the activation of mouse T cells stimulated with anti-CD3 antibody or staphylococcal
enterotoxin B, we found that chloramphenicol induces the differentiation of activated T cells into lymphoblastic leukemia-like cells, characterized
by large cell size, multiploid nuclei, and expression of CD7, a maker for immature T cells and T-cell lymphocytic leukemia, thus phenotypically
indicating differentiation toward leukemogenesis. High expression of cyclin B1, but not p53, c-myc, and CDC25A, was detected in
chloramphenicol-treated activated T cells, which may relate to abnormal cell differentiation. Chloramphenicol inhibited the activation-induced
cell death of mouse and human T-cell receptor-activated T cells by down-regulating the expression of Fas ligand. Our findings show that
abnormal cell differentiation and inhibition of apoptosis may contribute to the development of leukemia associated with clinical applications of
chloramphenicol.
PMID:18559535
Yuan ZR, Shi Y; Cancer Res 68 (12): 4875-81 (2008)
HSDB
9.9 Human Metabolite Information
9.9.1 Metabolite Description
Description
An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure
and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic.
(From Martindale, The Extra Pharmacopoeia, 29th ed, p106).
9.9.2 Cellular Locations
Membrane
9.9.3 Metabolite Pathways
Chloramphenicol Action Pathway

9.10 Biochemical Reactions
Rhea - annotated reactions database
10 Use and Manufacturing
10.1 Overview
Chloramphenicol is used as a medication. An overview is available from MedlinePlus, a consumer health web site produced by the National
Library of Medicine.
FOR MORE INFORMATION: (1) National Library of Medicine. MedlinePlus. Available from, as of Aug 30, 2018:
https://medlineplus.gov/druginfo/meds/a608008.html
HSDB
10.2 Use Classification
JECFA Functional Classes Veterinary Drug: ANTIMICROBIAL_AGENT
10.3 Uses
EPA CPDat Chemical and Product Categories
EPA Chemical and Products Database (CPDat)
Anti-Bacterial Agents; Protein Synthesis Inhibitors

National Library of Medicine's Medical Subject Headings. Chloramphenicol. Online file (MeSH, 2017). Available from, as of April 10, 2017:
https://www.nlm.nih.gov/mesh/2017/mesh_browser/MBrowser.html
HSDB
MEDICATION
HSDB
MEDICATION (VET)
HSDB
10.4 Methods of Manufacturing

Broad spectrum antibiotic obtained from cultures of the soil bacterium Streptomyces venezuelae.
HSDB
An antibiotic derived from Streptomyces venezuelae or by organic synthesis ... .

HSDB
Chloramphenicol can be obtained from the filtrate of a Streptomyces venezuelae culture by extraction with ethyl acetate. If the charcoal extract
is rich in chloramphenicol, the latter can be crystallized from the ethyl acetate by diluting with many volumes of kerosene.
Troy, D.B. (Ed); Remmington The Science and Practice of Pharmacy. 21 st Edition. Lippincott Williams & Williams, Philadelphia, PA 2005, p. 1659
HSDB
Chloramphenicol can be synthesized by condensation of para-nitrobenzoyl chloride with ethyl malonate to give para-nitroacetophenone,
followed by bromination in acetic acid to form para-nitro-alpha-bromoacetophenone, and reaction of this with hexamethylene tetramine,
followed by hydrolysis to give para-nitro-alpha-aminoacetophenone; subsequent acetylation of the amine group and condensation with
formaldehyde gives a hydroxymethyl group alpha to the amine group. Treatment with aluminium isopropylate reduces the keto group to a
secondary alcohol, and, after deacetylation, condensation of the amine group with methyl dichloroacetate give chloramphenicol. Chemical
syntheses of chloramphenicol usually include a resolution step to separate stereoisomers.
HSDB
Chloramphenicol is a broad-spectrum antibiotic originally isolated from Streptomyces venezuelae. /Chloramphenicol sodium succinate/
HSDB
During the 1960s and 1970s: addition of benzaldehyde to beta-nitroethanol to yield 2-nitro-1-phenyl-1,3-propanediol, reduction to the
aminodiol, swing resolution, subsequent nitration, and dichloroacetylation to create chloramphenicol.
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V2 922
HSDB
In Western Europe: cinnamyl alcohol converted to its bromohydrin, then to the bromodioxane, reaction with ammonia to the aminodioxane
which is resolved, acylated to the dichloroacetamido, nitrated, and gently hydrolyzed to chloramphenicol.
HSDB
In Eastern Europe: p-nitrobenzaldehyde is condensed with glycine to obtain the Schiff's base, cleavage followed by esterification gives the D,L-
p-nitrophenyl serine methyl ester which is resolved with D-tartaric acid and the ester of the correct configuration reduced by sodium or calcium
borohydride to the desired p-nitrophenyl serinol to form chloramphenicol.
HSDB
10.5 Formulations/Preparations
Table: Chloramphenicol Sodium Succinate Preparations
Route of Dosage
Strength Brand or Generic Form (Manufacturer)
Administration Form
For 1 g (of Chloramphenicol Sodium Succinate Sterile (Available from one or more manufacturer, distributor, and/or
Parenteral
injection chloramphenicol) repackager by generic (nonproprietary) name)
For 1 g (of
Parenteral Chloromycetin Sodium Succinate (Monarch)
injection chloramphenicol)
HSDB
Chloromycetin Ophthalmic Ointment, 1% (Chloramphenicol Ophthalmic Ointment, USP) is supplied, sterile, in ophthalmic ointment tubes of 3.5
grams.
HSDB
Three common forms are used for systemic therapy, depending on the route of administration; a free base form of chloramphenicol,
chloramphenicol palmitate and chloramphenicol succinate. Other formulations are also available for topical use.
FAO/WHO Joint Expert Committee on Food Additives; WHO Food Additives Series 53: Toxicological evaluation of certain veterinary drug residues in food (2004).
Available from, as of April 14, 2017: http://www.inchem.org/pages/jecfa.html
HSDB
Ak chlor liq 0.5%; Ak chlor oph ont 1%; Chloromycetin succinate injection 1 gm; Diochloram ointment 1%; Diochloram solution 0.5%;
Pentamycetin liq 2.5 mg/mL; Pentamycetin ont 10 mg/gm; Pentamycetin ophthalmic solution 0.5% - liq; Pentamycetin/hc (combination product);
PMS-chloramphenicol ophthalmic soln 0.5%. /Chloramphenicol sodium succinate/
American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017
HSDB
For more Formulations/Preparations (Complete) data for Chloramphenicol (6 total), please visit the HSDB record page.
HSDB
10.6 U.S. Production

(1977) PROBABLY GREATER THAN 9.08X10+5 G
SRI
HSDB
(1979) PROBABLY GREATER THAN 9.08X10+5 G

SRI
HSDB
10.7 U.S. Imports

(1977) 8.15X10+6 G (PRINCPL CUSTMS DISTS)
SRI
HSDB
(1979) 8.20X10+6 G (PRINCPL CUSTMS DISTS)

SRI
HSDB
10.8 General Manufacturing Information

EPA TSCA Commercial Activity Status
Acetamide, 2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-: ACTIVE

https://www.epa.gov/tsca-inventory
EPA Chemicals under the TSCA
The antibiotic is unique among natural compounds in that it contains nitrobenzene moiety and is a derivative of dichloroacetic acid.
1526
HSDB
11 Identification
11.1 Analytic Laboratory Methods

Microbiological turbidimetric assay for chloramphenicol in preparations for human and veterinary use.
United States Food and Drug Administration; Fed Regist 48 (20): 3959 (1983)
HSDB
Use of thin layer chromatography and densitometry in the analysis of prescription drugs.
Kessler A, Krzek J; Farm Pol 38 (9): 357 (1982)
HSDB
Spectrophotometric determination of chloramphenicol by reaction with thiourea.

Das A et al; Indian J Pharmacol Sci 44 (6): 149 (1982)
HSDB
Thin-layer and HPLC determination of chloramphenicol residues in edible tissues.

Johannes B et al; Arch Lebensmittelhyg 34 (1): 1 (1983)
HSDB
For more Analytic Laboratory Methods (Complete) data for Chloramphenicol (27 total), please visit the HSDB record page.
HSDB
11.2 Clinical Laboratory Methods

This paper presents a sensitive and confirmatory multi-residue method for the analysis of 23 veterinary drugs and metabolites belonging to
three classes (nitroimidazoles, benzimidazoles, and chloramphenicols) in porcine muscle, liver, and kidney. After extracted with ethyl acetate and
basic ethyl acetate sequentially, the crude extracts were defatted with hexane and further purified using Oasis MCX solid-phase extraction
cartridges. Rapid determination was carried out by ultra-high performance liquid chromatography-electrospray ionization tandem mass
spectrometry. Data acquisition was performed under positive and negative mode simultaneously. Recoveries based on matrix-matched
calibrations for meat, liver, and kidney ranged from 50.6 to 108.1%. The method quantification limits were in the range of 3-100 ng/kg.
PMID:23017446
Xia X et al; J Chromatogr A 1292: 96-103 (2013)
HSDB
A method for the detection and confirmation of organic solvent extractable residues of the neutral, acidic, and basic analytes of the amphenicol
class veterinary drugs and selected metabolites was developed and validated. Using a modified QuEChERS extraction with SPE cleanup and LC-
MS/MS analysis, limits of detection and confirmation for the different analytes in bovine, equine, and porcine liver ranged from 0.1 ng/g for
chloramphenicol to 1 ng/g for florfenicol amine. Tissue homogenization with an ammonium formate/EDTA solution and subsequent analyte
partitioning against 7:3 acetonitrile:isopropanol solution and mixed-mode strong-cation exchange solid-phase extraction cartridge cleanup
allowed for the extraction of all compounds from tissues with mean recoveries ranging from 50% (chloramphenicol 3-O-beta-d-glucuronide) to
90% (thiamphenicol). Matrix effects ranged from greater than 85% suppression for florfenicol amine to 70% matrix enhancement for
chloramphenicol 3-O-beta-d-glucuronide. Quantitation and confirmation were accomplished using commercially available penta-deuterated
chloramphenicol as internal standard and multiple reaction monitoring (MRM) of two or three transitions per target analyte. Method accuracy
was greater than 15% for all compounds except the glucuronide metabolite. Intra-lab method repeatability estimates ranged from 73% RSD for
chloramphenicol 3-O-beta-d-glucuronide to 14% RSD for chloramphenicol. Only chloramphenicol 3-O-beta-d-glucuronide and florfenicol
amine at the low end of their calibration ranges (0.25 and 1 ng/g, respectively) did not meet AOAC recommended HorRatr guidelines for intra-
lab repeatabilities. Preliminary tests show that the method's extraction protocol can be used to recover analytes of the ?-agonists,
corticosteroids, fluoroquinolones, sulfonamides, and tetracycline drug classes from the same matrices. Requirements for use in national
chemical monitoring programs as a detection/confirmatory (florfenicol amine and chloramphenicol 3-O-beta-d-glucuronide) and
determinative/confirmatory (chloramphenicol, florfenicol, thiamphenicol) analytical methodology are met.
PMID:25913426
Fedeniuk RW et al; J Chromatogr B Analyt Technol Biomed Life Sci 991: 68-78 (2015)
HSDB
A highly sensitive and low-cost electrochemical aptasensor was developed for the determination of chloramphenicol (CAP). The system was
based on a CAP-binding aptamer, a molecular recognition element, and 1,4-diazabicyclo[2.2.2]octane (DABCO)-supported mesoporous silica
SBA-15 on the surface of a screen-printed graphite electrode for formation of dendritic gold nanostructures and improving the performance
and conductivity of the biosensor. Hemin has been applied as an electrochemical indicator which interacted with the guanine bases of the
aptamer. In the absence of CAP, hemin binds to the aptamer and produces a weak differential pulse voltammetric (DPV) signal. The presence of
CAP led to stabilization of the folded aptamer, which generated an amplified DPV signal. The peak current of hemin increased linearly with the
concentration of CAP. Under optimal conditions, two linear ranges were obtained from 0.03 to 0.15 uM and 0.15 to 7.0 uM, respectively, and the
detection limit was 4.0 nM. The prepared biosensor has good selectivity against other non-target drugs. Thus, the sensor could provide a
promising platform for the fabrication of aptasensors. The feasibility of using this aptasensor was demonstrated by determination of CAP in a
human blood serum sample.
PMID:26879648
Bagheri Hashkavayi A et al; Anal Bioanal Chem 408 (10): 2557-65 (2016)
HSDB
High-performance liquid chromatography method for determination of chloramphenicol in blood is described.

Crechiolo J, Hill RE; J Chromatogr 162 (3): 480 (1979)
HSDB
Chloramphenicol was detected in blood serum, plasma, or CFS by high-pressure liquid chromatography.
PMID:464579
Sample RH et al; Antimicrob Agents Chemother 15 (3): 491 (1979)
HSDB
12 Safety and Hazards
12.1 Hazards Identification
12.1.1 GHS Classification
Pictogram(s)
Health Hazard
Signal Danger
Aggregated GHS information provided by 122 companies from 25 notifications to the ECHA C&L Inventory. Each notification
may be associated with multiple companies.
Reported as not meeting GHS hazard criteria by 6 of 122 companies. For more detailed information, please visit ECHA C&L
website
Of the 24 notification(s) provided by 116 of 122 companies with hazard statement code(s):
GHS Hazard Statements
H350 (93.1%): May cause cancer [Danger Carcinogenicity]
H361 (30.17%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in
parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with
percentage values above 10% are shown.
Precautionary Statement P201, P202, P281, P308+P313, P405, and P501

Codes (The corresponding statement to each P-code can be found at the GHS Classification page.)
European Chemicals Agency (ECHA)
12.2 Fire Fighting
12.2.1 Fire Fighting Procedures
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
HSDB
Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.
HSDB
Use dry chemical, carbon dioxide, water spray, or foam extinguishers. ... If material or contaminated runoff enters waterways, notify downstream
users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof
location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank
discolors, or shows any signs of deforming), withdraw immediately to a secure position. ... The only respirators recommended for firefighting are
self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode.
Pohanish, R.P. (ed). Sittig's Handbook of Toxic and Hazardous Chemical Carcinogens 6th Edition Volume 1: A-K,Volume 2: L-Z. William Andrew, Waltham, MA 2012, p.
599
HSDB
12.3 Accidental Release Measures
12.3.1 Cleanup Methods
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment.
Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for
containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for
disposal.
HSDB
Evacuate persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Collect
powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after cleanup is complete. It may be
necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream
users of potentially contaminated waters.
599
HSDB
PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen
in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be
transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately
after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed
or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in
plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be
decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
Montesano, R., H. Bartsch, E.Boyland, G. Della Porta, L. Fishbein, R. A. Griesemer, A.B. Swan, L. Tomatis, and W. Davis (eds.). Handling Chemical Carcinogens in the
Laboratory: Problems of Safety. IARC Scientific Publications No. 33. Lyon, France: International Agency for Research on Cancer, 1979., p. 15
HSDB
12.3.2 Disposal Methods
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to
dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for
proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled,
securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste
landfill or incinerator.
HSDB
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and
evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental
discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after
review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation
worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the
chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the
appropriate local, state and federal requirements for disposal.
HSDB
Product: Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible
solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed
disposal company; Contaminated packaging: Dispose of as unused product.
HSDB
PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic
compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary
of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological
expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage
combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous
& organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem
destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal
filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an
incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE:
Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of
chem carcinogens or their metabolites. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules
can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for
destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are
easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears
to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous
sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with
appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ...
& is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in
ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be
inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-
nitrobenzyl)-pyridine. /Chemical Carcinogens/
HSDB
12.3.3 Preventive Measures
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment.
Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
HSDB
Precautions for safe handling: Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of
combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs.
Provide appropriate exhaust ventilation at places where dust is formed.
HSDB
Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the
end of workday.
HSDB
Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with
this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
HSDB
Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash.
599
HSDB
PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application
of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which
carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration
should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be
recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably
disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded
immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should
always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary
when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a
reminder that they should not be worn outside of lab. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood.
Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be
obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for
decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove
boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not
occur. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ...
provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that
are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area
towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with
fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural
changes. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": Principles that apply to chem or biochem lab also apply to microbiological & cell-culture labs ... Special
consideration should be given to route of admin. ... Safest method of administering volatile carcinogen is by injection of a soln. Admin by topical
application, gavage, or intratracheal instillation should be performed under hood. If chem will be exhaled, animals should be kept under hood
during this period. Inhalation exposure requires special equipment. ... Unless specifically required, routes of admin other than in the diet should
be used. Mixing of carcinogen in diet should be carried out in sealed mixers under fume hood, from which the exhaust is fitted with an efficient
particulate filter. Techniques for cleaning mixer & hood should be devised before expt begun. When mixing diets, special protective clothing &,
possibly, respirators may be required. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": When ... admin in diet or applied to skin, animals should be kept in cages with solid bottoms & sides &
fitted with a filter top. When volatile carcinogens are given, filter tops should not be used. Cages which have been used to house animals that
received carcinogens should be decontaminated. Cage-cleaning facilities should be installed in area in which carcinogens are being used, to
avoid moving of ... contaminated /cages/. It is difficult to ensure that cages are decontaminated, & monitoring methods are necessary.
Situations may exist in which the use of disposable cages should be recommended, depending on type & amt of carcinogen & efficiency with
which it can be removed. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": To eliminate risk that ... contamination in lab could build up during conduct of expt, periodic checks
should be carried out on lab atmospheres, surfaces, such as walls, floors & benches, & ... interior of fume hoods & airducts. As well as regular
monitoring, check must be carried out after cleaning-up of spillage. Sensitive methods are required when testing lab atmospheres. ... Methods ...
should ... where possible, be simple & sensitive. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": Rooms in which obvious contamination has occurred, such as spillage, should be decontaminated by lab
personnel engaged in expt. Design of expt should ... avoid contamination of permanent equipment. ... Procedures should ensure that
maintenance workers are not exposed to carcinogens. ... Particular care should be taken to avoid contamination of drains or ventilation ducts. In
cleaning labs, procedures should be used which do not produce aerosols or dispersal of dust, ie, wet mop or vacuum cleaner equipped with
high-efficiency particulate filter on exhaust, which are avail commercially, should be used. Sweeping, brushing & use of dry dusters or mops
should be prohibited. Grossly contaminated cleaning materials should not be re-used ... If gowns or towels are contaminated, they should not
be sent to laundry, but ... decontaminated or burnt, to avoid any hazard to laundry personnel. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": Doors leading into areas where carcinogens are used ... should be marked distinctively with appropriate
labels. Access ... limited to persons involved in expt. ... A prominently displayed notice should give the name of the Scientific Investigator or
other person who can advise in an emergency & who can inform others (such as firemen) on the handling of carcinogenic substances. /Chemical
Carcinogens/
HSDB
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated
contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest
method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the
worker.
HSDB
SRP: Contaminated protective clothing should be segregated in a manner such that there is no direct personal contact by personnel who
handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated
protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain
at employee's place of work for cleaning.
HSDB
12.4 Handling and Storage
12.4.1 Storage Conditions
Keep container tightly closed in a dry and well-ventilated place.

HSDB
Store at 20 deg to 25 °C (68 deg to 77 °F). /Chloramphenicol sodium succinate/

HSDB
Store at or below 25 °C (77 °F) in a dry place.

HSDB
Chloramphenicol sodium succinate sterile powder for injection should be stored at 15-25 °C. /Chloramphenicol sodium succinate/
HSDB
Store in a secure poison location. ... A regulated, marked area should be established where this chemical is handled, used, or stored in
compliance with OSHA Standard 1910.1045. Store in tightly closed containers in a cool, well-ventilated area.
599
HSDB
PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small
quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator
or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of
carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/
HSDB
12.5 Exposure Control and Personal Protection
12.5.1 Other Standards Regulations and Guidelines
Workplace Environmental Exposure Level (WEEL): 8-hr Time-weighted Average (TWA) 0.5 mg/cu m. Last Revised: 2008.
Toxicology Excellence for Risk Assessment; Occupational Alliance for Risk Science - Workplace Environmental Exposure Levels. Chloramphenicol (56-75-7). Available
from, as of April 21, 2017: http://www.tera.org/OARS/WEEL.html
HSDB
12.5.2 Acceptable Daily Intakes
An allowed daily intake (ADI) could not be set for chloramphenicol because of the dose-independence of chloramphenicol-induced aplastic
anaemia ... .
HSDB
12.5.3 Personal Protective Equipment (PPE)
Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
HSDB
Skin protection: Handle with gloves.

HSDB
Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the
dangerous substance at the specific workplace.
HSDB
Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US)
or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face
supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or
CEN (EU).
HSDB
Wear protective gloves and clothing to prevent any reasonable probability of skin contact. ... All protective clothing (suits, gloves, footwear,
headgear) should be clean, available each day, and put on before work. ... Wear dust-proof chemical goggles and face shield unless full face-
piece respiratory protection is worn.
599
HSDB
PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In
animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair
covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide
full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons
might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the
laboratory. /Chemical Carcinogens/
HSDB
12.6 Stability and Reactivity
12.6.1 Hazardous Reactivities and Incompatibilities
Incompatible materials: Acids, acid chlorides, acid anhydrides, oxidizing agents.

HSDB
Chloramphenicol has been reported to be physically incompatible with many drugs, but the compatibility depends on several factors (e.g., the
concentration of the drugs, specific diluents used, resulting pH, temperature). Specialized references should be consulted for specific
compatibility information.
HSDB
12.7 Transport Information
12.7.1 Shipment Methods and Regulations
PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be
transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that
will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ...
National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These
authorities should be consulted before ... material is shipped. /Chemical Carcinogens/
HSDB
PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed
in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will
withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with
absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary
container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the
secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest &
most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that
immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical
Carcinogens/
HSDB
12.8 Regulatory Information
12.8.1 FDA Requirements
The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including
chloramphenicol sodium succinate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug,
and Cosmetic Act. /Chloramphenicol sodium succinate/
DHHS/FDA; Electronic Orange Book-Approved Drug Products with Therapeutic Equivalence Evaluations. Available from, as of April 21, 2017:
http://www.fda.gov/cder/ob/
HSDB
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain
information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal
drug products approved for safety and effectiveness, be made available to the public. Chloramphenicol is included on this list.
US FDA/Center for Veterinary Medicine; The Green Book - On Line, Active Ingredients. Chloramphenicol (56-75-7). Available from, as of April 21, 2017:
http://www.fda.gov/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/default.htm
HSDB
Drug products withdrawn or removed from the market for reasons of safety or effectiveness. The following drug products were withdrawn or
removed from the market because such drug products or components of such drug products have been found to be unsafe or not effective. The
following drug products may not be compounded under the exemptions provided by section 503A(a) or section 503B(a) of the Federal Food,
Drug, and Cosmetic Act. Included on list: Chloramphenicol: All oral drug products containing chloramphenicol.
21 CFR 216.24 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of April 18, 2017:
http://www.ecfr.gov
HSDB
Implantation or injectable dosage form new animal drugs. Chloramphenicol. ... Indications for use /in dogs/: Treatment of infections of the
respiratory tract, the urinary tract, and enteritis and tonsillitis caused by organisms susceptible to chloramphenicol. ... Limitations. Federal law
restricts this drug to use by or on the order of a licensed veterinarian. Federal law prohibits the extralabel use of this drug in food-producing
animals.
http://www.ecfr.gov
HSDB
Extralabel drug use in animals. Drugs prohibited for extralabel use in animals. The following drugs, families of drugs, and substances are
prohibited for extralabel animal and human drug uses in food-producing animals. Chloramphenicol is included on this list.
http://www.ecfr.gov
HSDB
12.9 Other Safety Information
12.9.1 Toxic Combustion Products
Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx), hydrogen chloride gas.
HSDB
Poisonous gases are produced in fire, including chlorine and nitrogen oxides.
599
HSDB
12.9.2 Special Reports
Lietman PS; Chloramphenicol and the Neonate- 1979 View; Clin Perinatol 6 (1): 151 (1979). Review of chloramphenicol use in newborn infant.
HSDB
DHHS/National Toxicology Program; Report on Carcinogens, Fourteenth Edition: Chloramphenico (November 2016). The Report on Carcinogens
is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure
circumstances) that may pose a carcinogenic hazard to human health. Chloramphenico (56-75-7) is listed as reasonably anticipated to be a
human carcinogen.[Available from, as of April 10, 2017: http://ntp.niehs.nih.gov/pubhealth/roc/index-1.html]
HSDB
13 Toxicity
13.1 Toxicological Information
13.1.1 Hepatotoxicity
A proportion of patients with blood dyscrasias due to chloramphenicol also developed clinically apparent liver injury with jaundice, usually
occurring before the appearance of aplastic anemia or severe thrombocytopenia. Jaundice arises in 10% to 25% of cases of aplastic anemia,
usually within 1 to 2 months of starting chloramphenicol and often shortly after it is stopped. Aplastic anemia and the accompanying liver injury
occur most frequently in patients who receive multiple courses of chloramphenicol or prolonged therapy. The serum enzyme pattern is usually
hepatocellular and the clinical presentation is an acute hepatitis-like syndrome with onset of fatigue, nausea, anorexia and abdominal
discomfort followed by dark urine and jaundice. Rare instances have a cholestatic pattern of presentation with jaundice and itching and
prominent elevations in alkaline phosphatase. Some cases occur in the absence of bone marrow involvement. Immunoallergic and autoimmune
features are rarely present. The course is self-limited in most instances, but examples of acute liver failure have been reported, particularly in
patients without aplastic anemia. In most cases, however, the liver injury associated with chloramphenicol use is eclipsed by the severe bone
marrow aplasia.
Likelihood score: B (highly likely cause of clinically apparent liver injury, now rarely seen).
LiverTox
13.1.2 Evidence for Carcinogenicity
Evaluation: There is limited evidence for the carcinogenicity of chloramphenicol in humans. There is inadequate evidence for the carcinogenicity
of chloramphenicol in experimental animals. The Working Group also took note of the following information. Chloramphenicol induces aplastic
anemia, and this condition is related to the occurrence of leukemia. Overall Evaluation: Chloramphenicol is probably carcinogenic to humans
(Group 2A).
HSDB
Chloramphenicol is reasonably anticipated to be a human carcinogen, based on limited evidence of carcinogenicity from studies in humans.
DHHS/National Toxicology Program; Report on Carcinogens, Fourteenth Edition: Chloramphenicol (November 2016). Available from, as of April 10, 2017:
http://ntp.niehs.nih.gov/pubhealth/roc/index-1.html
HSDB
13.1.3 Acute Effects
ChemIDplus
13.1.4 Interactions
Chloramphenicol-treated patient may respond poorly to cyanocobalamin therapy since chloramphenicol interferes with erythrocyte maturation.
Evaluations of Drug Interactions. 2nd ed. and supplements. Washington, DC: American Pharmaceutical Assn., 1976, 1978., p. 450
HSDB
Concurrent therapy with other drugs that may cause bone marrow depression should be avoided.
HSDB
Chloramphenicol antagonizes the action of such antibiotics as penicillin and streptomycin, which act only on growing cells, but is synergistic to
tetracycline, which also acts by inhibiting protein synthesis. It is possible the chloramphenicol would produce similar synergism with other
antibiotics which act by inhibiting protein synthesis.
HSDB
Clinical observations in man and corresponding investigations in laboratory animals experimentally infected with various pathogenic bacteria
have shown that a combination of chloramphenicol with gamma-globulin or specific antisera has a greater therapeutic effect than would be
expected from a mere addition of the individual effects.
HSDB
For more Interactions (Complete) data for Chloramphenicol (26 total), please visit the HSDB record page.
HSDB
13.1.5 Toxicity Summary
Oral, mouse: LD50 = 1500 mg/kg; Oral, rat: LD50 = 2500 mg/kg. Toxic reactions including fatalities have occurred in the premature and newborn;
the signs and symptoms associated with these reactions have been referred to as the gray syndrome. Symptoms include (in order of
appearance) abdominal distension with or without emesis, progressive pallid cyanosis, vasomotor collapse frequently accompanied by irregular
respiration, and death within a few hours of onset of these symptoms.
DrugBank
IDENTIFICATION AND USE: Chloramphenicol is an antibiotic for human and veterinary use, originally isolated from the soil bacterium
Streptomyces venzeuelae. HUMAN STUDIES: Chloramphenicol is known to produce major adverse effects in humans. One of these is generally
irreversible aplastic anemia and reversible bone marrow suppression. A link between chloramphenicol and liver disease has been noted. Acute
myeloid leukemia is also associated with chloramphenicol exposure. Neonates, especially if premature, may develop a serious illness termed
"gray baby syndrome" if exposed to excessive doses of chloramphenicol. This syndrome usually begins 2-9 days (average of 4 days) after
treatment is started. Within the first 24 hours, vomiting, refusal to suck, irregular and rapid respiration, abdominal distention, periods of
cyanosis, and passage of loose green stools occur. The children are severely ill by the end of the first day, and in the next 24 hours turn an
ashen-gray color and become flaccid and hypothermic. A similar "gray syndrome" has been reported in adults who were accidentally overdosed
with the drug. Allergic contact dermatitis has been noted from a patient using a topical cream containing chloramphenicol. Optic neuritis and
scotoma with failing vision has also been reported. Chloramphenicol has been implicated in cleft lip. Chromosomal anomalies were noted in
human lymphocytes treated with chloramphenicol in vitro. ANIMAL STUDIES: After three groups of ten 3-month old mice were given daily
intraperitoneal injections of chloramphenicol at 20, 40 or 100 mg/kg bw for 3 months, splenomegaly, hepatomegaly, lymph adenopathy and
hypertrophy of the thymus occurred in a dose-dependent fashion. An increased incidence in lymphomas in two strains of mice were noted after
exposure to chloramphenicol in drinking water. Chloramphenicol has been shown to cause DNA strand breaks in bacterial cells and to inhibit
DNA synthesis in lymphocytes and in the phage of Escherichia coli. Chromosomal anomalies were noted in mouse bone marrow cells given
chloramphenicol ip or im in F1 generation mouse liver. When groups of 3-9 female Sprague-Dawley rats were given chloramphenicol in drinking
water with or without exposure to short duration high intensity noise, ototoxicity was noted. Oral doses of this antibiotic suppressed paradoxical
sleep in cats. Chloramphenicol administered to pregnant monkeys had no effect on fetal development. High oral doses of chloramphenicol of
500-2000 mg/kg to rats and mice and of 500 and 1000 mg/kg to rabbits produced high incidences of embryonic and fetal deaths and fetal
growth retardation in all three species. Teratogenic effects, predominantly umbilical hernia, were observed only in rats. The pregnant animals
showed no toxic sign, except that those given the highest dose gained significantly less weight than controls. Progeny of chloramphenicol-
treated mice had reduced learning ability, higher brain seizure threshold and poorer performance in the open-field test. ECOTOXICITY STUDIES:
Chloramphenicol was added to cultures of one freshwater green alga, Chlorella pyrenoidosa, and two marine algae, Isochrysis galbana and
Tetraselmis chui. It was more toxic to the freshwater algae. Chloramphenicol exposure could significantly inhibit the growth of Scenedesmus
obliquus, while Chlorella pyrenoidosa exhibited less sensitivity. Abnormal behavioral changes were observed in fish Clarias gariepinus exposed
to chloramphenicol. Hematological parameters were also affected. In Egyptian toads (Bufo regularis) given a dose of chloramphenicol of 5
mg/40 g body weight for 12 weeks, it induced numerous, severe ultrastructural changes in almost all types of leukocytes.
HSDB
13.1.6 Antidote and Emergency Treatment
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration,
preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush
contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-
down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature.
Obtain medical attention. /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 160
HSDB
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of
respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary
edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination,
flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion,
rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ...
. Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 160
HSDB
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe
pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial.
Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor
cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9%
saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously.
Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... .
/Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 160-1
HSDB
Emergency and supportive measures: 1. Maintain an open airway and assist ventilation if necessary. 2. Treat coma, seizures, hypotension,
anaphylaxis, and hemolysis if they occur. 3. Replace fluid losses resulting form gastroenteritis with IV crystalloids. ... /Antibacterial Agents/.
OLSON, K.R. (Ed). Poisoning and Drug Overdose, Sixth Edition. McGraw-Hill, New York, NY 2012, p. 90
HSDB
Decontamination: Administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate
ingestions if activated charcoal can be given promptly. /Antibacterial Agents/.
HSDB
Enhanced elimination: Most antibiotics are excreted unchanged in the urine, so maintenance of adequate urine flow is important. The role of
forced diuresis is unclear. Hemodialysis is not usually indicated, except perhaps in patients with renal dysfunction and a high level of a toxic
agent. 1. Charcoal hemoperfusion effectively removes chloramphenicol and is indicated after a severe overdose with a high serum level and
metabolic acidosis. ... /Antibacterial Agents/.
HSDB
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and
lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with
soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using
universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a
medical facility. When this chemical has been swallowed, get medical attention.
698
HSDB
13.1.7 Medical Surveillance
Baseline blood studies should be followed by periodic blood studies approximately every two days during therapy. The drug should be
discontinued upon appearance of reticulocytopenia, leukopenia, thrombocytopenia, anemia or any other blood study findings attributable to
chloramphenicol. However, it should be noted that such studies do not exclude the possible later appearance of the irreversible type of bone
marrow depression. /Chloramphenicol sodium succinate/
HSDB
PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad
hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/
HSDB
13.1.8 Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Serious and fatal blood dyscrasias (aplastic anemia, hypoplastic anemia, thrombocytopenia and granulocytopenia) are
known to occur after the administration of chloramphenicol. In addition, there have been reports of aplastic anemia attributed to
chloramphenicol which later terminated in leukemia. Blood dyscrasias have occurred after both short-term and prolonged therapy with this
drug.
HSDB
/SIGNS AND SYMPTOMS/ Bone marrow hypoplasia including aplastic anemia and death has been reported following topical application of
chloramphenicol.
HSDB
/SIGNS AND SYMPTOMS/ Neonates, especially if premature, may develop a serious illness termed "gray baby syndrome" if exposed to excessive
doses of chloramphenicol. This syndrome usually begins 2-9 days (average of 4 days) after treatment is started. Within the first 24 hours,
vomiting, refusal to suck, irregular and rapid respiration, abdominal distention, periods of cyanosis, and passage of loose green stools occur. The
children all are severely ill by the end of the first day, and in the next 24 hours turn an ashen-gray color and become flaccid and hypothermic. A
similar "gray syndrome" has been reported in adults who were accidentally overdosed with the drug. Death occurs in approximately 40% of
patients within 2 days of initial symptoms. Those who recover usually exhibit no sequelae.
1528
HSDB
/CASE REPORTS/ For an adolescent with bacterial meningitis and subsequent cerebral aspergillosis, intravenous voriconazole dose requirements
substantially decreased during coadministration with intravenous chloramphenicol and considerably rose after discontinuation of the antibiotic.
In agreement with in vitro evidence, these data suggest that chloramphenicol is a rather significant inhibitor of hepatic CYP3A4 and/or CYP2C19.
PMID:18794387
Hafner V et al; Antimicrob Agents Chemother 52 (11): 4172-4 (2008)
HSDB
For more Human Toxicity Excerpts (Complete) data for Chloramphenicol (17 total), please visit the HSDB record page.
HSDB
13.1.9 Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ After three groups of ten 3-month old Swiss mice were given daily intraperitoneal
injections of chloramphenicol at 20, 40 or 100 mg/kg bw for 3 months, splenomegaly, hepatomegaly, lymph adenopathy and hypertrophy of the
thymus occurred in a dose-dependent fashion ... .
HSDB
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Groups of 50 male and 50 female BALB/c mice, 6 wk of age, were administered
chloramphenicol (purity unspecified) at 0, 500 or 2000 mg/L in drinking water for 104 wk, at which time all survivors were killed. The incidences
of lymphomas in mice of each sex (combined) were 3% in controls, 6% in low-dose animals and 12% in high-dose animals (p<0.05). The
incidences of other types of tumor were similar in treated and control animals ... .
HSDB
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ ... Groups of 50 male and 50 female C57B1/6N mice, 6 wk of age, were
administered chloramphenicol (purity unspecified) at 0, 500 or 2000 mg/L in drinking water for 104 wk ... The incidences of lymphomas in mice
of each sex (combined) were 8% in controls, 22% in low-dose animals (p<0.05) and 23% in high-dose animals (p<0.01). The incidences of
malignant liver-cell tumors in mice of each sex (combined) were: control, 0; low-dose, 2/90; and high-dose, 11/91 (p<0.01) ... .
HSDB
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Two groups of 45 male BALB/c x AF1 mice, 6-8 wk of age, received four
intraperitoneal injections of 0.25 mL acetone in distilled water. After a 20 wk rest period, one group received daily intraperitoneal injections of
chloramphenicol (purity unspecified) at 0.25 mL (2.5 mg) in 0.9% saline soln on 5 days/wk for 5 wk. The mice were killed on day 350. Controls
received injections of saline soln only. No increase in the incidence of tumors was observed ... .
HSDB
For more Non-Human Toxicity Excerpts (Complete) data for Chloramphenicol (28 total), please visit the HSDB record page.
HSDB
13.1.10 Non-Human Toxicity Values
LD50 Rat ip 1811 mg/kg

HSDB
LD50 Rat sc 5 g/kg

HSDB
LD50 Rat iv 171 mg/kg

HSDB
LD50 Mouse oral 1500 mg/kg

HSDB
LD50 Mouse ip 1100 mg/kg

HSDB
LD50 Mouse sc 400 mg/kg

HSDB
LD50 Mouse iv 110 mg/kg

HSDB
LD50 Rabbit iv 117 mg/kg

HSDB
LD50 Guinea pig oral 500 mg/kg

HSDB
LD50 Guinea pig iv 560 mg/kg

HSDB
LD50 Mouse iv 150-250 mg/kg bw

HSDB
LD50 Albino mouse iv 200 mg/kg bw

HSDB
LD50 Albino mouse ip 1320 mg/kg bw

HSDB
LD50 Rat iv 170 mg/kg bw

HSDB
13.1.11 Ecotoxicity Values
EC50; Species: Desmodesmus subspicatus (Green Algae) 86.71 SAG, 10+4 algae/mL; Conditions: freshwater, static, 23 °C; Concentration: 780
ug/L for 72 hr (95% confidence interval: 210-2930 ug/L); Effect: decreased population growth rate /formulation/
Eisentraeger A et al; Ecotoxicol Environ Saf 54 (3): 346-54 (2003) as cited in the ECOTOX database. Available from, as of May 3, 2017:
https://cfpub.epa.gov/ecotox/quick_query.htm
HSDB
ug/L for 72 hr (95% confidence interval: 150-240 ug/L); Effect: decreased population biomass /formulation/
HSDB
ug/L for 72 hr (95% confidence interval: 6-240 ug/L); Effect: decreased population, general /formulation/
HSDB
LC50; Species: Artemia franciscana (San Francisco Brine Shrimp) age ~48 hr nauplii; Conditions: saltwater, static, 25 °C; Concentration: 0.00197 M
for 48 hr /formulation/
Chrysayi-Tokousbalides M et al; Bull Environ Contam Toxicol 79 (5): 499-503 (2007) as cited in the ECOTOX database. Available from, as of May 3, 2017:
HSDB
EC50; Species: Crassostrea gigas (Pacific Oyster) newly fertilized larva; Conditions: saltwater, static, 20 °C, pH 8.06-8.08, dissolved oxygen 7.47
mg/L; Concentration: 325000 ug/L for 48 hr (95% confidence interval: 0-1976000 ug/L); Effect: decreased development /formulation/
Cardwell RD et al; Wash Dept of Fisheries, Technical Report No.45: 71 (1979) as cited in the ECOTOX database. Available from, as of June 19, 2017:
HSDB
LC50; Species: Crassostrea gigas (Pacific Oyster) newly fertilized larva; Conditions: saltwater, static, 20 °C, pH 8.06-8.08, dissolved oxygen 7.47
mg/L; Concentration: 323000 ug/L for 48 hr (95% confidence interval: 0-2157000 ug/L) /formulation/
Cardwell RD et al; Wash Dept of Fisheries, Technical Report No.45: 71 (1979) as cited in the ECOTOX database. Available from, as of June 19, 2017:
HSDB
13.1.12 Ecotoxicity Excerpts
/AQUATIC SPECIES/ This study investigated the growth inhibition effects of three phenicol antibiotics on microalgae used in aquaculture.
Different dose levels of chloramphenicol (CAP), florfenicol (FF), and thiamphenicol (TAP) were added to cultures of one freshwater green alga,
Chlorella pyrenoidosa, and two marine algae, Isochrysis galbana and Tetraselmis chui. For the two marine algae, FF showed higher toxicity levels
(EC50, 1.3-8 mg/L) than CAP (4-41 mg/L) and TAP (38-158 mg/L). CAP was more toxic to the freshwater algae (EC50, 14 mg/L) than FF (215
mg/L) and TAP (1283 mg/L). TAP was the least toxic to the three algae, but maintained the highest stability during the test period. Among the
tested algae, T. chui was the species most sensitive to the three antibiotics. This study demonstrates that all three phenicol antibiotics can inhibit
growth of the three microalgae and should be carefully used in aquaculture.
PMID:18439675
Lai HT et al; Ecotoxicol Environ Saf 72 (2): 329-34 (2009)
HSDB
/AQUATIC SPECIES/ ... The present work aimed to assess the persistence of chloramphenicol (a banned but illegally used antibiotic) in seawater,
together with its effects on the growth of the green macroalgae Ulva lactuca. Moreover, the potential use of this species as a bioindicator was
assessed. Results showed CAP presented an exponential degradation pattern in seawater with concentrations decreasing faster than expected.
As for the effects on U. lactuca it acted as a growth promoter also contradicting the initial assumptions. Regarding the role of this species in
biomonitoring it successfully took up CAP in solution while reflecting the concentrations present conferring it good characteristics as a
bioindicator. On the other hand, this ability points to a possibility of CAP being accumulated and transferred along the trophic web through the
consumption of U. lactuca by organisms in higher levels.
PMID:23395526
Leston S et al; Chemosphere 91 (4): 552-7 (2013)
HSDB
/AQUATIC SPECIES/ ... The indoor experiments were ... to observe and analyze the chloramphenicol (CAP) induced changes /on Scenedesmus
obliquus and Chlorella pyrenoidosa/. Results of the observations ... showed that CAP exposure could significantly inhibit the growth of
Scenedesmus obliquus in almost all the treated groups, while Chlorella pyrenoidosa exhibited less sensitivity. Chlorophyll-a syntheses of
Scenedesmus obliquus were all inhibited by CAP exposure, while Chlorella pyrenoidosa displayed obvious stimulation effect. Catalase (CAT) and
Superoxide dismutase (SOD) activities of both algae were promoted in all the treatments. The experimental results indicated that the growth
and Chlorophyll-a syntheses of Scenedesmus obliquus were more sensitive in response to CAP exposure than that of Chlorella pyrenoidosa.
While for CAT and SOD activities, Chlorella pyrenoidosa showed more susceptible. ...
PMID:24003598
Zhang W et al; Water Environ Res 85 (8): 725-32 (2013)
HSDB
/AQUATIC SPECIES/ The present study was aimed at evaluating the effects of different concentrations of the most commonly used fish
antimicrobial drug, chloramphenicol (CAP), on the behavior and hematological parameters of Clarias gariepinus. Fish specimens were exposed
to three (2.5, 5.0 and 10.0 mg/L) sublethal concentrations of CAP and a control. Abnormal behavioral changes were observed in fish exposed to
higher concentration of CAP. Blood erythrocytes were sampled on days 1, 5, 10 and 15 postexposure to evaluate hematological parameters.
Results showed concentration- and time-dependent significant increase in packed cell volume after day 5 of exposure (p<0.05). Hemoglobin
values also significantly decreased from day 5, whereas values of mean cellular volume significantly decreased throughout the experimental
period (p<0.05). A mixed trend was observed in the mean values of red blood cells, white blood cells, mean cellular hemoglobin and mean
cellular hemoglobin concentration as well as neutrophils. Activities of lymphocytes were significantly increased in all CAP-treated fish during the
exposure period, whereas no significant differences were observed in values of monocytes, eosinophils and basophils among the treatment
groups and control. Consequently, precautions must be taken, especially when high concentrations of CAP are used in long-term treatments of
C. gariepinus in aquaculture.
PMID:24099453
Nwani CD et al; Drug Chem Toxicol 37 (1): 107-13 (2014)
HSDB
For more Ecotoxicity Excerpts (Complete) data for Chloramphenicol (6 total), please visit the HSDB record page.
HSDB
13.1.13 Ongoing Test Status
EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore
rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal
Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS
Dashboard Application; Available from, as of May 1, 2017: http://actor.epa.gov/dashboard/]
HSDB
The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and
current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology
Studies", etc., performed with this chemical. Testing status for Chloramphenicol sodium succinate is available. /Chloramphenicol sodium
succinate/[Available from, as of April 10, 2017: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status]
HSDB
13.1.14 Populations at Special Risk
The most important adverse effects of chloramphenicol involve the hematopoietic system ... . Potentially fatal toxicity may develop in neonates
exposed to excessive doses of chloramphenicol ... . This so-called 'grey baby syndrome' may also occur in older children and in adults receiving
doses resulting in serum concentrations of 40-200 ug/mL ... .
HSDB
Chloramphenicol is widely distributed into most body tissues and fluids including saliva, ascitic fluid, pleural fluid, synovial fluid, and aqueous
and vitreous humor. Highest concentrations of the drug are found in the liver and kidneys. The concentration of chloramphenicol in CSF is
reported to be 21-50% of concurrent plasma concentrations in patients with uninflamed meninges and 45-89% of concurrent plasma
concentrations in patients with inflamed meninges. Chloramphenicol readily crosses the placenta, and fetal plasma concentrations of the drug
may be 30-80% of concurrent maternal plasma concentrations. Chloramphenicol is distributed into milk. Chloramphenicol is approximately 60%
bound to plasma proteins.
HSDB
Chloramphenicol should be used with caution in patients with impaired renal and/or hepatic function and in neonates and infants with
immature metabolic processes. Plasma chloramphenicol concentrations should be monitored closely in these patients and dosage should be
proportionately reduced.
HSDB
Neonates, especially if premature, may develop a serious illness termed "gray baby syndrome" if exposed to excessive doses of
chloramphenicol. This syndrome usually begins 2-9 days (average of 4 days) after treatment is started. Within the first 24 hours, vomiting, refusal
to suck, irregular and rapid respiration, abdominal distention, periods of cyanosis, and passage of loose green stools occur. The children all are
severely ill by the end of the first day, and in the next 24 hours turn an ashen-gray color and become flaccid and hypothermic. A similar "gray
syndrome" has been reported in adults who were accidentally overdosed with the drug. Death occurs in approximately 40% of patients within 2
days of initial symptoms. Those who recover usually exhibit no sequelae.
1528
HSDB
Precaution should be used in therapy of premature and full-term neonates and infants to avoid "gray syndrome" toxicity. Due to immature
metabolic processes in the neonate and infant, excessive blood levels may result from administration of the recommended dose. The dosage
should be adjusted accordingly or, preferable, the blood concentration should be determined at appropriate intervals ... .
HSDB
Clinical studies of chloramphenicol sodium succinate did not include sufficient numbers of subjects aged 65 and over to determine whether
they respond differently from younger subjects. Other reported clinical experience has not identified differences in responses between the
elderly and younger patients. In general, dose selection for an elderly patient should be cautious, usually starting at the low end of the dosing
range, reflecting the greater frequency of decreased hepatic, renal, or cardiac function, and of concomitant disease or other drug therapy. This
drug is known to be substantially excreted by the kidney, and the risk of toxic reactions to this drug may be greater in patients with impaired
renal function. Because elderly patients are more likely to have decreased renal function, care should be taken in dose selection, and it may be
useful to monitor renal function. /Chloramphenicol sodium succinate/
HSDB
Toxic reactions including fatalities have occurred in the premature and neonate; the signs and symptoms associated with these reactions have
been referred to as the "gray syndrome." One case of gray syndrome has been reported in a neonate born to a mother having received
chloramphenicol during labor. One case has been reported in a 3-month-old infant. The following summarizes the clinical and laboratory
studies that have been made on these patients: a) In most cases therapy with chloramphenicol had been instituted within the first 48 hours of
life. b) Symptoms first appeared after 3 to 4 days of continued treatment with high doses of chloramphenicol. c) The symptoms appeared in the
following order: (1) abdominal distension with or without emesis; (2) progressive pallid cyanosis; (3) vasomotor collapse, frequently
accompanied by irregular respiration; (4) death within a few hours of onset of these symptoms. d) The progression of symptoms from onset to
exitus was accelerated with higher dose schedules. e) Preliminary blood serum level studies revealed unusually high concentrations of
chloramphenicol (over 90 ug/mL after repeated doses). f) Termination of therapy upon early evidence of the associated symptomatology
frequently reversed the process with complete recovery.
HSDB
13.1.15 Protein Binding
Plasma protein binding is 50-60% in adults and 32% is premature neonates.

DrugBank
13.2 Ecological Information
13.2.1 Environmental Fate/Exposure Summary
Chloramphenicol's production and administration as a human and veterinary antibiotic may result in its release to the environment through
various waste streams. If released to air, an estimated vapor pressure of 1.7X10-12 mm Hg at 25 °C indicates chloramphenicol will exist solely in
the particulate phase in the atmosphere. Particulate-phase chloramphenicol will be removed from the atmosphere by wet and dry deposition.
Chloramphenicol contains chromophores that absorb at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by
sunlight. If released to soil, chloramphenicol is expected to have low mobility based upon a Koc of 1150. Volatilization from moist soil surfaces is
not expected to be an important fate process based upon an estimated Henry's Law constant of 2.3X10-18 atm-cu m/mole. Chloramphenicol is
not expected to volatilize from dry soil surfaces based upon its estimated vapor pressure. If released into water, chloramphenicol is expected to
adsorb to suspended solids and sediment based upon the Koc. Aerobic and anaerobic half-lives in marine sediment are reported as 2.4-18.4 and
0.4-2.4 days, respectively, and in freshwater sediment half-lives of <12 and < 4 days, respectively, were reported; these half-lives indicate that
biodegradation of chloramphenicol may occur in aquatic environments. Volatilization from water surfaces is not expected based upon this
compound's estimated Henry's Law constant. An estimated BCF of 1 suggests the potential for bioconcentration in aquatic organisms is low.
Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under
environmental conditions (pH 5 to 9). Occupational exposure to chloramphenicol may occur through inhalation and dermal contact with this
compound at workplaces where chloramphenicol is produced or used. The general population may be exposed to chloramphenicol via use of
pharmaceutical products containing this compound. (SRC)
HSDB
13.2.2 Natural Pollution Sources
An antibiotic derived from Streptomyces venezuelae or by organic synthesis, it was the first substance of natural origin to contain an aromatic
nitro group.
HSDB
13.2.3 Artificial Pollution Sources
Chloramphenicol's production and administration as a human and veterinary antibiotic(1) may result in its release to the environment through
various waste streams(SRC). It's use in aquiculture, including farms, hatcheries, feed mills, processing plants and repacking plants, is banned
worldwide(2). Chloramphenicol is banned for food producing animals including poultry in the US and Canada(3). Vertinarians are able to
purchase chloramphenicol legally for treatment of dogs, cats, and zoo animals(4).
(1) O'Neil MJ, ed; The Merck Index. 15th ed. Cambridge, UK: Royal Soc Chem., p. 367 (2013) (2) BAP (Best Aquiculture Practices) Certification. Global Aquaculture
Alliance. Available from, as of April 13, 2017: https://www.bapcertification.org/ (3) Barry C; pp 170-5 in Residues of Veterinary Drugs in Food: Proceed Euro Residue
II Conf., Veldhoven, Netherlands, May 3-5, 1993., Haagsma N et al, eds (1993) (4) VSB; Be Careful with Chloramphenicol. 2012. Queensland Gov., Veterinary Surgeons
Board of Queensland, Australia. Available from, as of Sept 29, 2017: http://www.vsb.qld.gov.au/chloramphenicol.html
HSDB
13.2.4 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 1150(2), indicates that chloramphenicol is expected to have low mobility
in soil(SRC). Volatilization of chloramphenicol from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 2.3X10-
18 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Chloramphenicol is not expected to volatilize from dry soil
surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-12 mm Hg at 25 °C(SRC), determined from a fragment constant method(3).
Half-lives in marine and freshwater sediment of 2.4 to 18.4 days and <12 days, respectively, indicate that biodegradation may occur in terrestrial
environments(4).
(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) Barron L et al; Analyst 134: 663-70 (2009) (3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Nov, 2012.
Available from, as of April 13, 2017: http://www2.epa.gov/tsca-screening-tools (4) Boxall ABA et al; Rev Environ Contam Toxicol 1-91 (2004)
HSDB
AQUATIC FATE: Based on a classification scheme(1), a Koc value of 1150(2), indicates that chloramphenicol is expected to adsorb to suspended
solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.3X10-18
atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Chloramphenicol is not expected to undergo hydrolysis in
the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(5),
an estimated BCF of 1(SRC), from its log Kow of 1.14(6) and a regression-derived equation(4), suggests the potential for bioconcentration in
aquatic organisms is low. Aerobic and anaerobic half-lives in marine sediment are reported as 2.4-18.4 and 0.4-2.4 days, in freshwater sediment
respective half-lives of <12 and < 4 days were reported, these half-lives indicate that biodegradation may occur in aquatic environments(7).
(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) Barron L et al; Analyst 134: 663-70 (2009) (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods.
Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 15-1 to 15-29 (1990) (4) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Nov, 2012. Available from, as of
April 13, 2017: http://www2.epa.gov/tsca-screening-tools (5) Franke C et al; Chemosphere 29: 1501-14 (1994) (6) Hansch C et al; Exploring QSAR. Hydrophobic,
Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 84 (1995) (7) Boxall ABA et al; Rev Environ Contam
Toxicol 180: 1-91 (2004)
HSDB
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1),
chloramphenicol, which has an estimated vapor pressure of 1.7X10-12 mm Hg at 25 °C(SRC), determined from a fragment constant method(2),
is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase chloramphenicol may be removed from the air
by wet and dry deposition(SRC). Chloramphenicol contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be
susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988) (2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Nov, 2012. Available from, as of April 13, 2017:
http://www2.epa.gov/tsca-screening-tools (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12, 8-13
(1990)
HSDB
13.2.5 Environmental Biodegradation
AEROBIC: Using adapted activated sludge as the inoculum, chloramphenicol degraded 86.2% with a biodegradation rate of 3.3 mg
COD/g/hour(1). Half-lives in marine and freshwater sediment have been reported as 2.4-18.4 days and <12 days, respectively, although specific
fate pathways were not identified(2).[
(1) Pitter P; Water Res 10: 231-5 (1976) (2) Boxall ABA et al; Rev Environ Contam Toxicol 180: 1-91 (2004)
HSDB
ANAEROBIC: Half-lives in marine and freshwater sediment have been reported as 0.4-2.4 days and <4 days, respectively, although specific fate
pathways were not identified(1).
PMID:14561076
(1) Boxall ABA et al; Rev Environ Contam Toxicol 180: 1-91 (2004)
HSDB
13.2.6 Environmental Abiotic Degradation
Chloramphenicol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under
environmental conditions(1). Chloramphenicol contains chromophores that absorb at wavelengths >290 nm(1) and, therefore, may be
susceptible to direct photolysis by sunlight(SRC).
(1) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12, 8-13 (1990)
HSDB
13.2.7 Environmental Bioconcentration
An estimated BCF of 1 was calculated in fish for chloramphenicol(SRC), using a log Kow of 1.14(1) and a regression-derived equation(2).
According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.
(1) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 84
(1995) (2) Franke C et al; Chemosphere 29: 1501-14 (1994) (3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Nov, 2012. Available from, as of April 13,
2017: http://www2.epa.gov/tsca-screening-tools/
HSDB
13.2.8 Soil Adsorption/Mobility
The Koc for chloramphenicol in agricultural soil found in Dublin, Ireland was reported as 1150(1). According to a classification scheme(2), this
Koc value suggests that chloramphenicol is expected to have low mobility in soil.
(1) Barron L et al; Analyst 134: 663-70 (2009) (2) Swann RL et al; Res Rev 85: 17-28 (1983)
HSDB
13.2.9 Volatilization from Water/Soil
The Henry's Law constant for chloramphenicol is estimated as 2.3X10-18 atm-cu m/mole(SRC) using a fragment constant estimation method(1).
This Henry's Law constant indicates that chloramphenicol is expected to be essentially nonvolatile from water and moist soil surfaces(2).
Chloramphenicol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-12 mm Hg(SRC),
determined from a fragment constant method(1).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Nov, 2012. Available from, as of April 13, 2017: http://www2.epa.gov/tsca-screening-tools (2) Lyman
WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
HSDB
13.2.10 Environmental Water Concentrations
DRINKING WATER: Chloramphenicol was not detected (detection limit 0.01 ng/L) in water samples collected July and Oct 2011 and Jan 2012
from various stages of a drinking water treatment plant in Spain(1). In one of eleven purchased mineral waters and one of eight tap water
samples from cities along the Turia River Basin, Spain, chloramphenicol was detected at 1 and 2 ng/L, respectively(2).
(1) Azzouz A, Ballesteros E; Chemosphere 93: 2046-54 (2013) (2) Carmona E et al; Sci Total Environ 484: 53-63 (2014)
HSDB
SURFACE WATER: Surface water samples collected Apr-Nov 2003 and Mar-Apr 2004 from the Grand River, Ontario, Canada did not contain
chloramphenicol (reporting limit 5 ng/L)(1). In surface water samples collected Mar 2005, Oct 2005, Jul 2006, and May 2007 from five sites on
the Wascana Creek/Qu'Appelle River system, Canada, chloramphenicol was not detected (detection limit 0.01 ug/L)(2). Concentrations of up to
0.56 ug/L been reported in surface water samples in Germany(3). Chloramphenicol was detected at
(1) Lissemore L et al; Chemosphere 64: 7177-29 (2006) (2) Waiser MJ et al; Environ Toxicol Chem 30: 508-19 (2011) (3) Boxall ABA et al; Rev Environ Contam Toxicol
180: 1-91 (2004) (4) Silva BF et al; Chemosphere 85: 1331-9 (2011) (5) Carmona E et al; Sci Total Environ 484: 53-63 (2014) (6) Zheng S et al; Chemosphere 84: 1677-
85 (2011)
HSDB
13.2.11 Effluent Concentrations
Chloramphenicol was detected in 12 and 46% of waste water influent and effluent at respective LOQ's of 2.0 and 0.6 ng/L, it was not detected
(<0.2 ng/g) in sludge samples, samples were collected from three Spanish treatment plants in eight campaigns over a two year period (July
2007-March 2009)(1). Chloramphenicol was not detected (respective detection limits 0.03 and 0.02 ug/L) in 14 influent and 14 effluent samples
collected June 2008 and Jan 2009 from three waste water treatment plants in Castellon province, Spain(2). Chloramphenicol was not detected
(detection limit 0.01 ng/L) in raw water samples collected July and Oct 2011 and Jan 2012 from a drinking water treatment plant in Spain(3).
Chloramphenicol was detected at 11 ng/L in 21 influent samples and not detected (detection limit 6.5 ng/L) in 21 effluent samples collected Mar
2013 from waste water treatment plants in Valencia, Spain(4). Chloramphenicol was detected in 22 of 24 influent and 20 of 35 effluent samples
collected Feb 2009 to Jan 2010 from two waste water treatment plants in Beijing at less than detection limit to 71.9 ng/L and less than detection
limit to 46.9 ng/L, respectively(5). In influent and effluent samples collected March, June, Oct 2009 and Jan 2010 from two waste water treatment
plants in Hong Kong, chloramphenicol was not detected(6). Chloramphenicol was detected in 8 of 45 sewage sludge samples collected from 20
cities in 13 provinces of China at approximately 11 ug/kg(7). Chloramphenicol was detected in the Marina Catchment system (urban run-off) in
Singapore at <1-15 ng/L, samples were collected in dry months from Apr 2008 to Mar 2009(8).
(1) Jelic A et al; Water Research 45: 1165-76 (2011) (2) Garcia-Lor E et al; Chemosphere 87: 453-62 (2012) (3) Azzouz A, Ballesteros E; Chemosphere 93: 2046-54
(2013) (4) Carmona E et al; Sci Total Environ 484: 53-63 (2014) (5) Sui Q et al; Environ Sci Technol 45: 3341-8 (2011) (6) Li B, Zhang T; Chemosphere 83: 1284-9
(2011) (7) Chen Y et al; Chemosphere 93: 1765-72 (2013) (8) Xu Y et al; Chemosphere 83: 963-9 (2011)
HSDB
13.2.12 Sediment/Soil Concentrations
SEDIMENT: Chloramphenicol was detected at

(1) Silva BF et al; Chemosphere 85: 1331-9 (2011) (2) Maranho LA et al; Ecotoxicology 24: 368-80 (2015) (3) Carmona E et al; Sci Total Environ 484: 53-63 (2014)
HSDB
13.2.13 Food Survey Values
Chloramphenicol was not detected in 203 Canadian egg samples screened for veterinary antibiotics; 99% of the samples in this study were free
of all drug residues(1). Chloramphenicol was not detected in 10 unifloral (orange, eucalyptus, lavender, rosemary, thyme) and 2 multifloral honey
samples collected in Spain(2). Chloramphenicol was not detected (detection limit 0.3 ug/L) in raw, full-fat, half-skimmed or skimmed milk
samples collected from a local farm and local supermarkets of China(3). Chloramphenicol was not detected in eight types of milk (whole, semi-
skim, skim and raw cow's milk; whole and semi-skim goat's milk; human milk; powdered milk) from Spain and Morocco(4).
(1) Quon DJ; J Agric Food Chem 48: 6421-27 (2000) (2) Sanchez-Brunete C et al; Bull Environ Contam Toxicol 75: 459-65 (2005) (3) Tian H Chemosphere 83: 349-55
(2011) (4) Azzouz A et al; J Agric Food Chem 59: 5125-32 (2011)
HSDB
The percentage of violations of veterinary drug content in seafood inspections for chloramphenicol was reported as follows(1):
Seafood % US (2001-2006) % EU (2001-2008) % Canada (2000-2009) % Japan (2000-2009)
finfish not available 20 5 3
shrimp/prawn 63 30 15 39
molluscan shellfish 100 not available not available 75
crabs 100 56 2 0
squid not available not available not available 100
(1) Love DC et al; Environ Sci Technol 45: 7232-40 (2011)
HSDB
13.2.14 Milk Concentrations
Chloramphenicol was not detected (detection limit 0.3 ug/L) in raw, full-fat, half-skimmed or skimmed milk samples collected from a local farm
and local supermarkets of China(1). Chloramphenicol was not detected in eight types of milk (whole, semi-skim, skim and raw cow's milk; whole
and semi-skim goat's milk; human milk; powdered milk) from Spain and Morocco(2).
(1) Tian H Chemosphere 83: 349-55 (2011) (2) Azzouz A et al; J Agric Food Chem 59: 5125-32 (2011)
HSDB
Chloramphenicol is excreted in breast milk in concentrations up to 25 ug per mL.

HSDB
13.2.15 Other Environmental Concentrations
Sedimentation dust collected 1981-2000 in the middle of a 350-420 head pig house in Germany, contained chloramphenicol concentrations of
1.96, 9.07 and 5.49 mg/kg for the respective years of 1989, 1991 and 1992, all other years were not detected(1).
(1) Hamscher G et al; Environ Health Perspect 111: 1590-4 (2003)
HSDB
13.2.16 Probable Routes of Human Exposure
NIOSH (NOES Survey 1981-1983) has statistically estimated that 35,571 workers (23,544 of these are female) were potentially exposed to
chloramphenicol in the US(1). Occupational exposure to chloramphenicol may occur through inhalation and dermal contact with this compound
at workplaces where chloramphenicol is produced or used(SRC). The general population may be exposed to chloramphenicol via use of
pharmaceutical products containing this compound(SRC).
(1) NIOSH; National Occupational Exposure Survey (NOES) (1983)
HSDB
14 Literature
14.1 NLM Curated PubMed Citations
PubChem
14.2 Springer Nature References
Springer Nature
14.3 Thieme References
Thieme Chemistry
14.4 Wiley References
Wiley
14.5 Depositor Provided PubMed Citations
PubChem
14.6 Synthesis References

Guang-Zhong Wu, Wanda I. Tormos, "Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline
intermediates." U.S. Patent US5352832, issued May, 1992.
DrugBank
14.7 Metabolite References
14.8 General References

1. Bhutta ZA, Niazi SK, Suria A: Chloramphenicol clearance in typhoid fever: implications for therapy. Indian J Pediatr. 1992 Mar-
Apr;59(2):213-9. [PMID:1398851]
2. Wali SS, Macfarlane JT, Weir WR, Cleland PG, Ball PA, Hassan-King M, Whittle HC, Greenwood BM: Single injection treatment of
meningococcal meningitis. 2. Long-acting chloramphenicol. Trans R Soc Trop Med Hyg. 1979;73(6):698-702. [PMID:538813]
3. Puddicombe JB, Wali SS, Greenwood BM: A field trial of a single intramuscular injection of long-acting chloramphenicol in the treatment of
meningococcal meningitis. Trans R Soc Trop Med Hyg. 1984;78(3):399-403. [PMID:6464136]
4. Pecoul B, Varaine F, Keita M, Soga G, Djibo A, Soula G, Abdou A, Etienne J, Rey M: Long-acting chloramphenicol versus intravenous
ampicillin for treatment of bacterial meningitis. Lancet. 1991 Oct 5;338(8771):862-6. [PMID:1681224]
5. Nathan N, Borel T, Djibo A, Evans D, Djibo S, Corty JF, Guillerm M, Alberti KP, Pinoges L, Guerin PJ, Legros D: Ceftriaxone as effective as
long-acting chloramphenicol in short-course treatment of meningococcal meningitis during epidemics: a randomised non-inferiority
study. Lancet. 2005 Jul 23-29;366(9482):308-13. [PMID:16039333]
DrugBank
14.9 Chemical Co-Occurrences in Literature
PubChem
14.10 Chemical-Gene Co-Occurrences in Literature
PubChem
14.11 Chemical-Disease Co-Occurrences in Literature
PubChem
15 Patents
15.1 Depositor-Supplied Patent Identifiers
PubChem
Link to all deposited patent identifiers

PubChem
16 Biomolecular Interactions and Pathways
16.1 Protein Bound 3-D Structures
RCSB Protein Data Bank (RCSB PDB)
View 18 proteins in NCBI Structure

PubChem
16.2 Drug-Gene Interactions
Drug Gene Interaction database (DGIdb)
16.3 DrugBank Interactions

Target 50S ribosomal protein L16
Action inhibitor
General Function Trna binding
This protein binds directly to 23S ribosomal RNA and is located at the A site of the peptidyltransferase center. It contacts the A
Specific Function
and P site tRNAs. It has an essential role in subunit assembly, which is not well understood.
1. Murray IA, Cann PA, Day PJ, Derrick JP, Sutcliffe MJ, Shaw WV, Leslie AG: Steroid recognition by chloramphenicol
acetyltransferase: engineering and structural analysis of a high affinity fusidic acid binding site. J Mol Biol. 1995 Dec
15;254(5):993-1005. [PMID:7500366]
Interaction References 2. Nierhaus D, Nierhaus KH: Identification of the chloramphenicol-binding protein in Escherichia coli ribosomes by partial
reconstitution. Proc Natl Acad Sci U S A. 1973 Aug;70(8):2224-8. [PMID:4365366]
3. Baxter RM, Ganoza MC, Zahid N, Chung DG: Reconstruction of peptidyltransferase activity on 50S and 70S ribosomal
particles by peptide fragments of protein L16. Eur J Biochem. 1987 Mar 16;163(3):473-9. [PMID:3549294]
DrugBank
17 Biological Test Results
17.1 BioAssay Results
PubChem
18 Classification
18.1 Ontologies
18.1.1 MeSH Tree
MeSH
18.1.2 ChEBI Ontology
ChEBI
18.1.3 KEGG: Metabolite
KEGG
18.1.4 KEGG: Carcinogen
KEGG
18.1.5 KEGG: Drug
KEGG
18.1.6 KEGG: USP
KEGG
18.1.7 KEGG: ATC
KEGG
18.1.8 KEGG: JP15
KEGG
18.1.9 KEGG: Risk Category of Japanese OTC Drugs
KEGG
18.1.10 KEGG: OTC drugs
KEGG
18.1.11 KEGG: Drug Classes
KEGG
18.1.12 WHO ATC Classification System
WHO ATC
18.1.13 FDA Pharm Classes
FDA Pharm Classes
18.1.14 WIPO IPC
WIPO
18.1.15 ChemIDplus
ChemIDplus
18.1.16 ChEMBL Target Tree

ChEMBL
18.1.17 UN GHS Classification
UN Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
18.1.18 EPA CPDat Classification
EPA Chemical and Products Database (CPDat)
19 Information Sources
FILTER BY SOURCE ALL SOURCES
1. ChEBI
Chloramphenicol
http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17698
ChEBI Ontology
http://www.ebi.ac.uk/chebi/userManualForward.do#ChEBI%20Ontology
2. DrugBank
LICENSE
Creative Commonâ??s Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
https://www.drugbank.ca/legal/terms_of_use
Chloramphenicol
http://www.drugbank.ca/drugs/DB00446
http://www.drugbank.ca/drugs/DB00446#targets
http://www.drugbank.ca/drugs/DB00446#enzymes
http://www.drugbank.ca/drugs/DB00446#transporters
3. FDA Pharm Classes

LICENSE
Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished,
reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated
but not required.
https://www.fda.gov/about-fda/about-website/website-policies#linking
CHLORAMPHENICOL
https://dailymed.nlm.nih.gov/dailymed/browse-drug-classes.cfm
FDA Pharmacological Classification
https://www.fda.gov/ForIndustry/DataStandards/StructuredProductLabeling/ucm162549.htm
4. Human Metabolome Database (HMDB)

LICENSE
HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the
authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant
portions of the database cite the HMDB paper in any resulting publications.
http://www.hmdb.ca/citing
Chloramphenicol
http://www.hmdb.ca/metabolites/HMDB0014589
5. LiverTox
Chloramphenicol
https://www.ncbi.nlm.nih.gov/books/n/livertox/Chloramphenicol/
6. NCI Thesaurus (NCIt)

LICENSE
Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
https://www.cancer.gov/policies/copyright-reuse
Chloramphenicol
https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C363
7. ChemIDplus
Chloramphenicol [USP:INN:BAN:JAN]
https://chem.nlm.nih.gov/chemidplus/sid/0000056757
Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (R*,R*)-(+-)-

https://chem.nlm.nih.gov/chemidplus/sid/0002787099
ChemIDplus Chemical Information Classification
https://chem.sis.nlm.nih.gov/chemidplus/
8. DTP/NCI
chloramphenicol
https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=3069
9. EPA Chemicals under the TSCA

LICENSE
https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources
Acetamide, 2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-
https://www.epa.gov/chemicals-under-tsca
10. EPA DSSTox
LICENSE
Chloramphenicol
https://comptox.epa.gov/dashboard/DTXSID7020265
11. European Chemicals Agency (ECHA)

LICENSE
Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations
provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for
non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be
included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative
conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
https://echa.europa.eu/web/guest/legal-notice
Chloramphenicol
https://echa.europa.eu/substance-information/-/substanceinfo/100.000.262
Chloramphenicol
https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/3764
12. HSDB
Chloramphenicol
https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3027
13. ClinicalTrials.gov
LICENSE
The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the
copyright of third parties; you should consult these entities for any additional terms of use.
https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
https://clinicaltrials.gov/
14. DailyMed
CHLORAMPHENICOL
https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=CHLORAMPHENICOL
15. Drug Gene Interaction database (DGIdb)

http://www.dgidb.org/drugs/CHLORAMPHENICOL
16. EPA Chemical and Products Database (CPDat)

LICENSE
chloramphenicol
https://comptox.epa.gov/dashboard/DTXSID7020265#exposure
EPA CPDat Classification
https://www.epa.gov/chemical-research/chemical-and-products-database-cpdat
17. NITE-CMC
2,2-Dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide; Chloramphenicol
http://www.safe.nite.go.jp/english/ghs/06-imcg-0520e.html
18. FAO/WHO Food Additive Evaluations (JECFA)

CHLORAMPHENICOL
http://apps.who.int/food-additives-contaminants-jecfa-database/chemical.aspx?chemID=551
19. FDA Center for Food Safety and Applied Nutrition (CFSAN)
LICENSE
but not required.
Chloramphenicol
https://www.fda.gov/Food/IngredientsPackagingLabeling/FoodAdditivesIngredients/ucm091048.htm
20. FDA Orange Book

LICENSE
but not required.
https://www.fda.gov/Drugs/InformationOnDrugs/ucm129662.htm
21. FDA/SPL Indexing Data

LICENSE
but not required.
66974FR9Q1
https://www.fda.gov/ForIndustry/DataStandards/SubstanceRegistrationSystem-UniqueIngredientIdentifierUNII/
22. MassBank of North America (MoNA)

LICENSE
The content of the MoNA database is licensed under CC BY 4.0.
https://mona.fiehnlab.ucdavis.edu/documentation/license
Chloramphenicol
http://mona.fiehnlab.ucdavis.edu/spectra/browse?inchikey=WIIZWVCIJKGZOK-RKDXNWHRSA-N
23. SpectraBase
https://spectrabase.com/spectrum/A5WiNnpaUFx
https://spectrabase.com/spectrum/3haMPWzljwA
https://spectrabase.com/spectrum/94Pbrfj4GPP
https://spectrabase.com/spectrum/EedJhgh3L56
https://spectrabase.com/spectrum/5x2T0fLuhaz
https://spectrabase.com/spectrum/em1RLbSZhG
https://spectrabase.com/spectrum/4zdoZ35QDnK
24. NCI Cancer Drugs

caf
https://www.cancer.gov/about-cancer/treatment/drugs/caf
25. NIST Mass Spectrometry Data Center

Chloramphenicol
http://www.nist.gov/srd/nist1a.cfm
26. Protein Data Bank in Europe (PDBe)

http://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/CLM
27. RCSB Protein Data Bank (RCSB PDB)

LICENSE
Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial
use. Users of the data should attribute the original authors of that structural data.
https://www.rcsb.org/pages/policies
http://www.rcsb.org/ligand/CLM
28. Rhea - annotated reactions database

https://www.rhea-db.org/searchresults?q=CHEBI:17698
29. Springer Nature
30. Thieme Chemistry

LICENSE
The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
https://creativecommons.org/licenses/by-nc-nd/4.0/
31. WHO ATC

LICENSE
Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is
not allowed. Changing or manipulating the material is not allowed.
https://www.whocc.no/copyright_disclaimer/
https://www.whocc.no/atc/
ATC Code
https://www.whocc.no/atc_ddd_index/
32. Wikipedia
chloramphenicol
https://en.wikipedia.org/wiki/Chloramphenicol
33. Wiley
https://pubchem.ncbi.nlm.nih.gov/substance/?source=wiley&sourceid=119494
34. MeSH
Chloramphenicol
https://www.ncbi.nlm.nih.gov/mesh/68002701
MeSH Tree
http://www.nlm.nih.gov/mesh/meshhome.html
Protein Synthesis Inhibitors
Anti-Bacterial Agents
35. PubChem
https://pubchem.ncbi.nlm.nih.gov
36. KEGG
Compounds with biological roles
http://www.genome.jp/kegg-bin/get_htext?br08001.keg
Carcinogens
Therapeutic category of drugs in Japan

USP drug classification

Anatomical Therapeutic Chemical (ATC) classification
Drugs listed in the Japanese Pharmacopoeia

Risk category of Japanese OTC drugs

Classification of Japanese OTC drugs

Drug Classes
37. WIPO
International Patent Classification
http://www.wipo.int/classifications/ipc/
38. UN Globally Harmonized System of Classification and Labelling of Chemicals (GHS)

GHS Classification Tree
http://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html
39. ChEMBL
Target Tree
https://www.ebi.ac.uk/chembl/target/browser
40. NCBI
https://www.ncbi.nlm.nih.gov/projects/linkout

Chloramphenicol - C11H12Cl2N2O5 - PubChem

Uploaded by

Copyright:

Available Formats

You might also like

Chloramphenicol - C11H12Cl2N2O5 - PubChem

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Chloramphenicol - C11H12Cl2N2O5 - PubChem

Uploaded by

Copyright:

Available Formats

26/12/2019 Chloramphenicol | C11H12Cl2N2O5 - PubChem

Find Similar Structures

Laboratory Chemical Safety Summary (LCSS) Datasheet

Molecular Formula: C11H12Cl2N2O5

Molecular Weight: 323.13 g/mol

Ball and Stick

1.3 Crystal Structures

PDBe Ligand Code CLM

PDBe Structure Code 3CLA

PDBe Conformer Interactive Chemical Structure Model

Ball and Stick Sticks Wire-Frame Space-Filling

Show Hydrogens Animate

Protein Data Bank in Europe (PDBe)

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2.1.3 InChI Key

2.1.4 Canonical SMILES

2.1.5 Isomeric SMILES

2.2 Molecular Formula

2.3 Other Identifiers

2.3.1 Other CAS

137731-90-9, 15313-32-3, 55172-72-0, 59112-59-3, 85666-84-8

2.3.2 European Community (EC) Number

2.3.3 NSC Number

2.3.5 DSSTox Substance ID

2.4.1 MeSH Entry Terms

2.4.2 Depositor-Supplied Synonyms

chloramphenicol Detreomycin Sificetina Anacetin Chloroptic Erbaplast Micoclorina Kamaver Cloramfe

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name Property Value Reference

XLogP3 1.1 Computed by XLogP3 3.0 (PubChem release 2019.06.18)

Rotatable Bond Count 5 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Heavy Atom Count 20 Computed by PubChem

Formal Charge 0 Computed by PubChem

Complexity 342 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Isotope Atom Count 0 Computed by PubChem

Defined Atom Stereocenter Count 2 Computed by PubChem

Undefined Atom Stereocenter Count 0 Computed by PubChem

Defined Bond Stereocenter Count 0 Computed by PubChem

Undefined Bond Stereocenter Count 0 Computed by PubChem

Covalently-Bonded Unit Count 1 Computed by PubChem

Compound Is Canonicalized Yes Computed by PubChem (release 2019.01.04)

3.2 Experimental Properties

3.2.1 Physical Description

Needles or elongated plates from water or ethylene dichloride

Pale yellow plates or needles from water

3.2.4 Boiling Point

Sublimes in high vacuum

3.2.5 Melting Point

2500 mg/L (at 25 °C)

In water, 2.5 mg/mL at 25 °C

Very soluble in acetone, chloroform, ethanol

3.2.7 Vapor Pressure

3.2.8 Octanol/Water Partition Coefficient

log Kow = 1.14

3.2.10 Stability/Shelf Life