Tenofovir disoproxil

Tenofovir disoproxil, sold under the trade name Viread among others, is
Tenofovir disoproxil
a medication used to treat chronic hepatitis B and to prevent and treat
HIV/AIDS.[1] It is generally recommended for use with other
antiretrovirals.[1] It may be used for prevention of HIV/AIDS among those
at high risk before exposure, and after a needlestick injury or other
potential exposure.[1] It is sold both by itself and together as
emtricitabine/tenofovir and efavirenz/emtricitabine/tenofovir.[1] It does
not cure HIV/AIDS or hepatitis B.[1][2] It is available by mouth as a tablet
or powder.[1]
Clinical data
Common side effects include nausea, rash, diarrhea, headache, pain, Trade names Viread, others
depression, and weakness.[1] Severe side effects include high blood lactate Synonyms Tenofovir disoproxil
and an enlarged liver.[1] There are no absolute contraindications.[1] It is
fumarate,
often recommended during pregnancy and appears to be safe.[1] It is a
Bis(POC)PMPA
nucleotide reverse transcriptase inhibitor and works by decreasing the
AHFS/Drugs.com Monograph (https://ww
ability of the viruses to replicate.[1]
w.drugs.com/monogra
Tenofovir was patented in 1996 and approved for use in the United States ph/tenofovir-disoproxil-
in 2001.[3] It is on the World Health Organization's List of Essential fumarate.html)
Medicines, the most effective and safe medicines needed in a health License data EU EMA: by INN (htt
system.[4] It is available as a generic medication as of 2017.[5] The p://www.ema.europa.e
wholesale cost in the developing world is between US$3.30 and $29.13 u/ema/index.jsp?curl
per month.[6] As of 2015 the cost for a typical month of medication in the =%2Fpages%2Fmedic
United States is more than $200.[7] ines%2Flanding%2Fep
ar_search.jsp&mid=&s
earchTab=searchByKe
Contents y&alreadyLoaded=true
&isNewQuery=true&st
Medical uses
atus=Authorised&statu
HIV risk reduction
s=Withdrawn&status=
Adverse effects
Suspended&status=Re
Interactions fused&keywordSearch
Pharmacology =Submit&searchType=
Mechanism of action
inn&taxonomyPath=&tr
Pharmacokinetics
eeNumber=&searchGe
History nericType=generics&k
Drug forms eyword=Tenofovir+diso
Chemistry proxil)
Detection in body fluids
Pregnancy AU: B3
References category
US: B (No risk in non-
External links
human studies)

Routes of By mouth (tablets)

 administration
Medical uses ATC code J05AF07 (WHO (http
Tenofovir disoproxil is used for HIV-1 infection and chronic hepatitis B s://www.whocc.no/atc_
treatment. For HIV-1 infection, tenofovir is indicated in combination with ddd_index/?code=J05
other antiretroviral agents for people 2 years of age and older. For chronic AF07))
hepatitis B patients, tenofovir is indicated for patients 12 years of age and
Legal status
older.[8]
Legal status AU: S4 (Prescription
only)
HIV risk reduction
CA: ℞-only
Tenofovir can be used for HIV prevention in people who are at high risk
UK: POM (Prescription
for infection through sexual transmission or injecting drug use. A
only)
Cochrane review examined the use of tenofovir for prevention of HIV
US: ℞-only
before exposure and found that both tenofovir alone and the
tenofovir/emtricitabine combination decreased the risk of contracting HIV Pharmacokinetic data
for high risk patients.[9] The U.S. Centers for Disease Control and Bioavailability 25%
Prevention (CDC) also conducted a study in partnership with the Thailand
Identifiers
Ministry of Public Health to ascertain the effectiveness of providing
people who inject drugs illicitly with daily doses of tenofovir as a IUPAC name
prevention measure. The results revealed a 48.9% reduced incidence of the Bis{[(isopropoxycarbonyl)oxy]methyl} ({[(2R)-1-(6-ami

virus among the group of subjects who received the drug in comparison to no-9H-purin-9-yl)-2-propanyl]oxy}methyl)phosph
the control group who received a placebo.[10] onate

CAS Number 201341-05-1 (http://ww

Adverse effects w.commonchemistry.or
g/ChemicalDetail.asp
Tenofovir disoproxil is generally well tolerated with low discontinuation
x?ref=201341-05-1)
rates among the HIV and chronic hepatitis B population.[11] There are no
contraindications for use of this drug.[8] The most commonly reported side PubChem CID 5481350 (https://pubch
effects due to use of tenofovir disoproxil were dizziness, nausea, and em.ncbi.nlm.nih.gov/co
diarrhea.[11] Other adverse effects include depression, sleep disturbances, mpound/5481350)
headache, itching, rash, and fever. The US box warning cautions potential ChemSpider 4587262 (http://www.c
onset of lactic acidosis or liver damage due to use of tenofovir
hemspider.com/Chemi
disoproxil.[12]
cal-Structure.4587262.
Long term use of tenofovir disoproxil is associated with nephrotoxicity html)
and bone loss. Presentation of nephrotoxicity can appear as Fanconi UNII F4YU4LON7I (https://f
syndrome, acute kidney injury, or decline of glomerular filtration rate dasis.nlm.nih.gov/srs/s
(GFR).[13] Discontinuation of tenofovir disoproxil can potentially lead to rsdirect.jsp?regno=F4
reversal of renal impairment. Nephrotoxicity may be due to proximal YU4LON7I)
tubules accumulation of Tenofovir disoproxil leading to elevated serum
ChEBI CHEBI:63717 (https://
concentrations.[11]
www.ebi.ac.uk/chebi/s
earchId.do?chebiId=C
Interactions HEBI:63717)
Tenofovir interacts with didanosine and HIV-1 protease inhibitors. NIAID ChemDB 080741 (https://chemd
Tenofovir increases didanosine concentrations and can result in adverse b.niaid.nih.gov/Compo
effects such as pancreatitis and neuropathy. Tenofovir also interacts with undDetails.aspx?AIDS
HIV-1 protease inhibitors such as atazanavir, by decreasing atazanavir NO=080741)
concentrations while increasing tenofovir concentrations.[8] In addition, CompTox DTXSID9040132 (http
since tenofovir is excreted by the kidney, medications that impair renal Dashboard (EPA)
s://comptox.epa.gov/d
function can also cause problems.[14] ashboard/DTXSID904
0132)
Pharmacology ECHA InfoCard 100.129.993 (https://ec
ha.europa.eu/substanc
e-information/-/substan
Mechanism of action ceinfo/100.129.993)
Tenofovir disoproxil is a nucleotide analog reverse-transcriptase inhibitor Chemical and physical data
(NtRTI).[15] It selectively inhibits viral reverse transcriptase, a crucial
Formula C19H30N5O10P
enzyme in retroviruses such as human immunodeficiency virus (HIV),
while showing limited inhibition of human enzymes, such as DNA
Molar mass 519.443 g/mol g·mol−1
polymerases α, β, and mitochondrial DNA polymerase γ.[8][15] In vivo 3D model Interactive image (http
(JSmol)
tenofovir disoproxil fumarate is converted to tenofovir, an acyclic analog s://chemapps.stolaf.ed
of deoxyadenosine 5'-monophosphate (d-AMP). Tenofovir lacks a u/jmol/jmol.php?model
hydroxyl group in the position corresponding to the 3' carbon of the d- =C%5BC%40H%5D%
AMP, preventing the formation of the 5′ to 3′ phosphodiester linkage 28Cn1cnc2c1ncnc2
essential for DNA chain elongation.[15] Once incorporated into a growing N%29OCP%28%3D
DNA strand, tenofovir causes premature termination of DNA O%29%28OCOC%2
transcription, preventing viral replication.[15] 8%3DO%29OC%28
C%29C%29OCOC%2
8%3DO%29OC%28
Pharmacokinetics
C%29C)
Tenofovir disoproxil is a prodrug that is quickly absorbed from the gut and
SMILES
cleaved to release tenofovir.[8] Inside cells, tenofovir is phosphorylated to
C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(OCOC(=O)O
tenofovir diphosphate (which is actually a triphosphate, as tenofovir itself C(C)C)OCOC(=O)OC(C)C
already has one phosphate residue), the active compound that inhibits InChI
reverse transcriptase via chain termination.[14][15] InChI=1S/C19H30N5O10P/c1-12(2)33-18(25)28-9-3
1-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-
24-8-23-15-16(20)21-7-22-17(15)24/h7-8,12-14H,
In fasting persons, bioavailability is 25%, and highest blood plasma
6,9-11H2,1-5H3,(H2,20,21,22)/t14-/m1/s1
concentrations are reached after one hour.[15] When taken with fatty food, Key:JFVZFKDSXNQEJW-CQSZACIVSA-N
highest plasma concentrations are reached after two hours, and the area
under the curve is increased by 40%.[15] It is an inhibitor of cytochrome Tenofovir
P450 1A2.[16]

Tenofovir is mainly excreted via the kidneys, both by glomerular filtration

and by tubular secretion using the transport proteins OAT1, OAT3 and
ABCC4.[14]

History
Tenofovir was initially synthesized by Antonín Holý at the Institute of Clinical data
Organic Chemistry and Biochemistry of the Academy of Sciences of the Synonyms 9-(2-Phosphonyl-
Czech Republic in Prague. The patent[17] filed by Holý in 1984 makes no
methoxypropyly)adenine
mention of the potential use of the compound for the treatment of HIV
(PMPA)
infection, which had only been discovered one year earlier.
MedlinePlus a602018 (https://medlin
eplus.gov/druginfo/med
In 1985, De Clercq and Holý described the activity of PMPA against HIV in s/a602018.html)
cell culture.[18] Shortly thereafter, a collaboration with the biotechnology Routes of Oral
company Gilead Sciences led to the investigation of PMPA's potential as a administration
treatment for HIV infected patients. In 1997 researchers from Gilead and the ATC code None
University of California, San Francisco demonstrated that tenofovir exhibits
Pharmacokinetic data
anti-HIV effects in humans when dosed by subcutaneous injection.[19]
Protein < 1%
The initial form of tenofovir used in these studies had limited potential for binding
widespread use because it was not absorbed when administered orally. A Elimination 17 hours
half-life
medicinal chemistry team at Gilead developed a modified version of
Excretion Kidney
tenofovir, tenofovir disoproxil.[20] This version of tenofovir is often referred
to simply as "tenofovir". In this version of the drug, the two negative charges Identifiers
of the tenofovir phosphonic acid group are masked, thus enhancing oral IUPAC name
absorption. ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}m

ethyl)phosphonic acid
Tenofovir disoproxil was approved by the U.S. FDA on October 26, 2001,
for the treatment of HIV, and on August 11, 2008, for the treatment of CAS Number 147127-20-6 (http://ww
chronic hepatitis B.[21][22] w.commonchemistry.or
g/ChemicalDetail.aspx?r
Drug forms ef=147127-20-6)
PubChem CID 464205 (https://pubche
Tenofovir disoproxil can be taken orally and is sold under the brand name
m.ncbi.nlm.nih.gov/com
Viread, among others.[23] Tenofovir disoproxil is a pro-drug form of
pound/464205)
tenofovir disphophate.[24] It is marketed by Gilead Sciences (as the
fumarate, abbreviated TDF).[25] DrugBank DB00300 (https://www.d
rugbank.ca/drugs/DB00
Tenofovir disoproxil is also available in pills which combine a number of
300)
antiviral drugs into a single dose. Well-known combinations include Atripla
(tenofovir disoproxil/emtricitabine/efavirenz), Complera (tenofovir
ChemSpider 408154 (http://www.che
disoproxil/emtricitabine/rilpivirine), Stribild (tenofovir mspider.com/Chemical-
disoproxil/emtricitabine/elvitegravir/cobicistat), and Truvada (tenofovir Structure.408154.html)
disoproxil/emtricitabine).[23] UNII 99YXE507IL (https://fda
Gilead has created a second pro-drug form of the active drug, tenofovir
sis.nlm.nih.gov/srs/srsdi
diphosphate, called tenofovir alafenamide. It differs from tenofovir
rect.jsp?regno=99YXE5
disoproxil due to its activation in the lymphoid cells. This allows the active
07IL)
metabolites to accumulate in those cells, leading to lower systemic exposure KEGG D06074 (http://www.keg
and potential toxicities.[11] g.jp/entry/D06074)
ChEBI CHEBI:63625 (https://w
Chemistry ww.ebi.ac.uk/chebi/sear
Tenofovir has a melting point of 279 °C (534 °F).[26] Tenofovir disoproxil
chId.do?chebiId=CHEB
fumarate is a white to off-white crystalline powder that is soluble in
I:63625)
methanol, slightly soluble in water (13.4 mg/ml[27]), and very slightly ChEMBL ChEMBL483 (https://ww
soluble in dichloromethane.[28] w.ebi.ac.uk/chembldb/in
dex.php/compound/insp
ect/ChEMBL483)
Detection in body fluids
CompTox DTXSID9040132 (http
Dashboard
Tenofovir may be measured in plasma by liquid chromatography. Such (EPA) s://comptox.epa.gov/das
testing is useful for monitoring therapy and to prevent drug accumulation hboard/DTXSID904013
and toxicity in people with kidney or liver problems.[29][30][31] 2)
ECHA 100.129.993 (https://ech
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External links
 Official Viread website (http://www.viread.com/)

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