General
Preferred name
TENOFOVIR
Synonyms
PMPA ()
GS-1278 ()
Tenofovir (maleate) ()
GS 1278 maleate ()
PMPA maleate ()
TDF maleate ()
TDF hydrate ()
GS1278 hydrate ()
GS 1278 hydrate ()
PMPA hydrate ()
TDF ()
GS 1278 ()
Tenofovir (Viread) ()
TENOFOVIR ANHYDROUS ()
Tenofovir (TFV) ()
Tenofovir (hydrate) ()
GS 1278 (hydrate) ()
PMPA (hydrate) ()
GS-1278 hydrate ()
Tenofovir hydrate ()
Tenofovir maleate ()
GS-1275 ()
Tenofovir monohydrate ()
PMP-A ()
Tenofovir ()
P&D ID
PD001133
CAS
206184-49-8
147127-20-6
1236287-04-9
Tags
available
prodrug
drug
drug candidate
Approved by
PMDA
FDA
First approval
2004
Drug indication
Human immunodeficiency virus infection
HIV-1 infection
Drug Status
approved
experimental
investigational
Max Phase
3.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS
Tenofovir has been shown to be highly effective in patients that have never had an antiretroviral therapy and it seemed to have lower toxicity than other antivirals such as [stavudine]. In phase 3 clinical trials, tenofovir presented a similar efficacy than [efavirenz] in treatment-naive HIV patients.[A178330] In hepatitis B infected patients, after one year of tenofovir treatment, the viral DNA levels were undetectable.[A178360]
HALF-LIFE
The reported half-life of tenofovir is of 32 hours.[A178231]
ROE
Tenofovir is eliminated in the urine by tubular secretion and glomerular filtration. The elimination of this compound is driven by the activity of the human organic anion transporters 1 and 3 and its secretion is mainly ruled by the activity of the multidrug resistance-associated protein 4.[A178060]
MOA
Once tenofovir is activated by a bi-phosphorylation it acts as an antiviral acyclic nucleoside phosphonate. It is a potent inhibitor of the viral reverse transcriptase with an inhibitory constant of approximately 0.022 micromolar.[A18473] ; ; Once activated, tenofovir acts with different mechanisms including the inhibition of viral polymerase causing chain termination and the inhibition of viral synthesis.[L6241] All these activities are attained by its competition with deoxyadenosine 5'-triphosphate in the generation of new viral DNA. Once tenofovir is incorporated in the chain, it induces a chain termination which in order inhibits viral replication.[A178330] The safety of tenofovir relies on its low affinity towards the cellular DNA polymerase including the mitochondrial DNA polymerase gamma.[T324]
INDICATION
Tenofovir has been shown to be effective against HIV, herpes simplex virus-2, and hepatitis B virus.[A178330]; ; To know more about the specific product indications, please visit the information in the orally available forms of tenofovir, [tenofovir alafenamide] and [tenofovir disoproxil].
TOXICITY
There haven't been reports regarding the LD50 of the parent compound nor the effects of an overdose. However, based on the reports with the derivative that most rapidly transforms into tenofovir, tenofovir disoproxil, it is recommended to monitor overdose patients. As well, it is widely known that tenofovir is efficiently removed by hemodialysis.[A178528]; ; Administration of high doses of tenofovir has been reported to produce bone toxicity reported as osteomalacia and reduced bone mineral density and to produce some degree of renal toxicity.[L6346]; ; To know more about the carcinogenicity and mutagenic potential of tenofovir, as well as the effect on fertility, please visit the drug entries for the derivatives [tenofovir disoproxil] and [tenofovir alafenamide].
METABOLISM
Tenofovir activation is performed by a bi-phosphorylation which in order forms the biologically active compound, tenofovir biphosphate.[A178060] This metabolic activation has been shown to be performed in hepG2 cells and human hepatocytes.[A174640] After activation, it does present minimal metabolic processing by the cytochrome enzyme isoenzyme CYP3A.[L6277]
ABSORPTION
Tenofovir as the active moiety presents a very low bioavailability when orally administered. Hence, the administration of this active agent is required to be under its two prodrug forms, [tenofovir disoproxil] and [tenofovir alafenamide]. This reduced absorption is suggested to be related to the presence of two negative charges among its structure. This negative charge limits its cellular penetration, and its passive diffusion across cellular membranes and intestinal mucosa hindering its availability for oral administration.[A178060]; ; Intravenous tenofovir has been shown to produce a maximum plasma concentration of 2500 ng/ml with an AUC of 4800 ng.h/ml.[A18473]
DESCRIPTION
Tenofovir is a nucleotide reverse transcriptase inhibitor (NtRTI) antiretroviral compound. The R-enantiomer, as shown here, is more effective at inhibiting retroviruses than the S-enantiomer . Tenofovir has poor oral bioavailability and is delivered as either the prodrug tenofovir disoproxil fumarate (Viread®) or tenofovir alafenamide fumerate (Vemlidy®).
(GtoPdb)
DESCRIPTION
Tenofovir (GS 1278) is a nucleotide reverse transcriptase inhibitor to treat HIV and chronic Hepatitis B (HBV)[1].
PRICE
38
DESCRIPTION
Tenofovir hydrate is a nucleotide reverse transcriptase inhibitor to treat HIV and chronic Hepatitis B.
PRICE
42
DESCRIPTION
Potent, selective Rho-kinase (ROCK) inhibitor
(Tocris Bioactive Compound Library)
DESCRIPTION
Tenofovir acts as an antiviral acyclic nucleoside phosphonate. It acts with different mechanisms including the inhibition of viral polymerase causing chain termination and the inhibition of viral synthesis. Tenofovir has been shown to be effective against HIV, herpes simplex virus-2, and hepatitis B virus.
(Enamine Bioactive Compounds)
DESCRIPTION
Tenofovir (GS 1278) is an adenine analog REVERSE TRANSC-RIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B. It is used to treat HIV INFECTIONS and CHRONIC HEPATITIS B, in combination with other ANTIVIRAL AGENTS, due to the emergence of ANTIVIRAL DRUG RESISTANCE when it is used alone.
(TargetMol Bioactive Compound Library)
DESCRIPTION
Tenofovir(GS 1278, PMPA) is an antiretroviral drug known as nucleotide analogue reverse transcriptase inhibitors (NRTIs), which block reverse transcriptase, a crucial virus enzyme in HIV-1 and HBV.
(BOC Sciences Bioactive Compounds)
DESCRIPTION
Tenofovir hydrate (GS 1278 hydrate) is a nucleotide reverse transcriptase inhibitor with antiviral activity, inhibits EBV replication, and is used in the study of HIV and HBV.
(TargetMol Bioactive Compound Library)
DESCRIPTION
Tenofovir hydrate reduces the viral cytopathic effect of HIV-1(IIIB), HIV-2(ROD) and HIV(EHO) with EC50 of 1.15 μg/mL, 1.12 μg/mL and 1.05 μg/mL in MT-4 cells. Tenofovir hydrate also reduces the viral cytopathic effect of SIV(mac251) , SIV(B670) ,SHIV(89.6) and SHIV(RTSHIV). Tenofovir hydrate inhibits hepatitis B virus (HBV) activity in HepG2 2.2.15, HepAD38 and HepAD79 cells. Tenofovir hydrate (4 μM) completely inhibits the growth of HIVIIIB in MT-2 cells. Tenofovir hydrate inhibits synthesis of negative strand strong-stop DNA with IC50 of 9 ?M for wild-type RT, 6 ?M for M184V RT and 50 ?M for K65R RT.
Tenofovir hydrate (30 mg/kg) completely prevents SIV infection in all macaques without toxicity. Tenofovir hydrate treatment reduces plasma viral RNA levels to undetectable, with parallel decreases in the infectivity of plasma and infectious cells in peripheral blood mononuclear cells and cerebrospinal fluid (CSF) and stabilization of CD4+ T-cell numbers. Tenofovir hydrate (30 mg/kg, s.c.) completely abrogates HIV infection via intravaginal exposure in pig-tailed macaques. (BOC Sciences Bioactive Compounds)
Tenofovir hydrate (30 mg/kg) completely prevents SIV infection in all macaques without toxicity. Tenofovir hydrate treatment reduces plasma viral RNA levels to undetectable, with parallel decreases in the infectivity of plasma and infectious cells in peripheral blood mononuclear cells and cerebrospinal fluid (CSF) and stabilization of CD4+ T-cell numbers. Tenofovir hydrate (30 mg/kg, s.c.) completely abrogates HIV infection via intravaginal exposure in pig-tailed macaques. (BOC Sciences Bioactive Compounds)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
4
Organisms
7
Compound Sets
23
AdooQ Bioactive Compound Library
Axon Medchem Screening Library
BOC Sciences Bioactive Compounds
Cayman Chemical Bioactives
ChEMBL Drugs
Concise Guide to Pharmacology 2021/22
Drug Repurposing Hub
DrugBank
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Enamine Bioactive Compounds
Enamine BioReference Compounds
Guide to Pharmacology
NCATS Inxight Approved Drugs
Pandemic Response Box
ReFrame library
Selleckchem Bioactive Compound Library
The Spectrum Collection
Tocris Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
54
Molecular Weight
287.08
Hydrogen Bond Acceptors
7
Hydrogen Bond Donors
3
Rotatable Bonds
5
Ring Count
2
Aromatic Ring Count
2
cLogP
-0.05
TPSA
136.38
Fraction CSP3
0.44
Chiral centers
1.0
Largest ring
6.0
QED
0.65
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
Reverse Transcriptase
HIV
HBV
HIV-1 RT inhibitor
Antiviral,COVID-19,Reverse Transcriptase
Antiviral,Reverse Transcriptase
Pathway
Anti-infection
Microbiology/virology
Proteases/Proteasome
Primary Target
RNA/DNA Polymerase
MOA
Inhibitor
HIV integrase inhibitor, nucleoside reverse transcriptase inhibitor
Indication
human immunodeficiency virus (HIV-1), hepatitis B
Therapeutic Class
Anti-HIV Agents
Solubility
DMSO : ≥ 6 mg/mL (19.66 mM)
In vitro:<br/>10 mM in DMSO
Source data
