General properties of tetracycline Classification, Indications and

Side-effects

INTRODUCTION
Tetracyclines are a class of antibiotics that may be used to treat infections caused by susceptible
microorganisms such as gram positive and gram negative bacteria, chlamydiae, mycoplasma,
protozoans, or rickettsia.
These are broad-spectrum antibiotics used in the management and treatment of a variety of
infectious diseases. Naturally occurring drugs in this class are tetracycline, chlortetracycline and
oxytetracycline.

PROPERTIES
 Molecular weight: 444.44.
 Molecular formula: C22H24N2O8.
 Melting Point: 170-173°C (with decomposition)
 Tetracyclines inhibit a lot of enzymatic reactions essential for the vital processes of
bacterial cells.
 Tetracycline works by binding specifically to the 30S ribosome of the bacteria,
preventing attachment of the amino acyl tRNA to the RNA-ribosome complex.
 The reactions that tetracyclines undergo are generally of a sophisticated nature, dictated
by the complex functionality and the sensitivity of the molecules to mild reaction
conditions (acid, base, heat).

Acidic conditions:
When exposed to dilute acidic conditions, tetracycline undergoes dehydration to yield
anhydrotetracycline. Anhydroterramycin suffers further cleavage and lactonization to
apoterramycin.
Basic condition:
Mild alkali attacks 11a carbon of tetracycline, which is transformed to isotetracycline.
Formation of complexes:
Tetracycline possesses a great tendency to form complexes with a number of chemical species,
due to its B- and C-ring oxygen atoms.

CLASSIFICATION
Tetracyclines can be classified According to:
1. The duration of action.
2. To source.
1. According to duration of action:
Short acting:
Short acting tetracyclines are the tetracyclines having a short half-life i.e. 6-8 hrs.
For example:
Tetracycline
Oxytetracycline
Intermediate acting:
Intermediate acting tetracyclines are the tetracyclines having an intermediate half line i.e. 12 hrs.
For example:
Demeclocycline
Methacylcline
Long acting:
Long acting tetracyclines are the tetracyclines having long half-life i.e. 16 hrs.
For example:
Doxycycline
Minocycline
2. According to source:
Naturally occurring:
These are called first generation tetracyclines.
For example:
Tetracycline
Chlortetracycline
Demeclocycline
Semi synthetic:
These are called second generation tetracyclines.
For example:
Doxycycline
Lymecycline
Meclocycline
Total synthetic:
These are called third generation tetracyclines.
For example:
Tigecycline

INDICATIONS
Chronic Bronchitis, Acute Exacerbation:
 Usual daily dose: 500 mg PO q12hr or 250 mg PO q6hr (i.e. 1000 mg/day).
 Higher doses (e.g. 500 mg PO q6hr) may be required for severe infections or for those
infections which do not respond to the smaller doses.
Moderate-to- Severe Acne:
 Recommended initial dosage: 1g/day PO in divided doses (based on the judgment of the
clinician).
 When improvement is noted, gradually reduce dose to maintenance levels ranging from
125-500 mg/day.
 Some patients may be able to maintain adequate remission of lesions with alternate day
or intermittent therapy.
 Duration of long-term treatment which can safely be recommended has not been
established.
Brucellosis:
 500 mg PO q6hr for 3 weeks accompanied by streptomycin, 1g IM BID for the first
week.
Syphilis:
Patients allergic to penicillin;
 Early syphilis (duration <1 year): 500 mg PO q6hr for 15 days.
 Syphilis (duration >1 year [except neurosyphilis]): 500 mg PO q6hr for 30 days.
Gonorrhea:
  Recommended dose: 500 mg PO q6hr for 7 days.
 Uncomplicated urethral, endocervical or rectal infections.
 Infections in adults caused by Chlamydia trachomatis 500 mg PO q6hr for at least seven
days.
Other Infections:
 Upper respiratory tract infections caused by Streptococcus pyogenes, Streptococcus
pneumoniae and Haemophilus influenza.
 Lower respiratory tract infections caused by Streptococcus pyogenes, Streptococcus
pneumoniae, Mycoplasma pneumoniae (Eaton agent, and Klebsiella spp).
 Skin and soft tissue infections caused by Streptococcus pyogenes, Staphylococcus
aureus; tetracyclines are not the drugs of choice in the treatment of any type of
staphylococcal infections.
 Infections caused by rickettsia including Rocky Mountain spotted fever, typhus group
infections, Q fever, rickettsia pox.
 Psittacosis caused by Chlamydophila psittaci.
 Infections caused by Chlamydia trachomatis (e.g., uncomplicated urethral, endocervical
or rectal infections, inclusion conjunctivitis, trachoma, and lymphogranuloma venereum).
 Granuloma inguinale caused by Klebsiella granulomatis Relapsing fever caused by
Borrelia spp Bartonellosis caused by Bartonella bacilliformis.
 Chancroid caused by haemophilus ducreyi.
 Tularemia caused by Francisella tularensis.
 Plaque caused by Yersinia pestis.
 Cholera caused by Vibrio cholerae
 Brucellosis caused by Brucella species (tetracycline may be used in conjunction with an
aminoglycoside).
 Infections due to Campylobacter fetus.
 As adjunctive therapy in intestinal amebiasis caused by Entamoeba histolytica.
 Urinary tract infections caused by susceptible strains (e.g., Escherichia coli, Klebsiella).
 Other infections caused by susceptible gram-negative organisms such as E coli,
Enterobacter aerogenes, Shigella spp, Acinetobacter spp, Klebsiella spp, and Bacteroides
spp.
 In severe acne, adjunctive therapy with tetracycline may be useful.
Other Infections (Penicillin-Resistant):
 Syphilis and yaws caused by Treponema palladium and pertenue, respectively.
 Vincent’s infection caused by Fusobacterium fusiform.
 Infections caused by Neisseria gonorrhea.
 Anthrax caused by Bacillus anthracis Infections due to Listeria monocytogenes.
 Actinomycosis caused by Actinomyces spp.
 Infections due to Clostridium spp.
SIDE-EFFECTS
The following are some of the side effects that have been reported with tetracyclines.
 Gastrointestinal effects such as acid reflux, diarrhea, nausea, vomiting, stomach cramps,
or loss of appetite.
 A headache.
 An increase in some laboratory values (such as blood urea nitrogen [BUN]) particularly
in people with impaired renal function. This does not appear to happen with doxycycline.
 Photosensitivity reactions (such as an exaggerated sunburn reaction). Rarely occurs with
minocycline.
 Pigmentation or discoloration of the skin and mucous membranes (minocycline only).
 Skin rash or itching.
 Sore mouth or tongue.
 Vaginal itching or discharge.