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Compound Detail

CHEMBL1486

TENOFOVIR DISOPROXIL FUMARATE
💊 Approved Drug
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💊 Approved Drug
CC(C)OC(=O)OCOP(=O)(CO[C@H](C)Cn1cnc2c(N)ncnc21)OCOC(=O)OC(C)C.O=C(O)/C=C/C(=O)O

Basic Information

ChEMBL ID CHEMBL1486
Name TENOFOVIR DISOPROXIL FUMARATE
Phase Approved
Structure Type MOL
InChI Key VCMJCVGFSROFHV-WZGZYPNHSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL1538
Active Moiety CHEMBL258501

Known Names

GS-4331-05 GS-4331-05- GSK-548470 GSK548470 PMPA PRODRUG PMPA-PRODRUG Tenofovir df Tenofovir disoproxil fumarate Tenofovir disoproxil fumarate component of atripla Tenofovir disoproxil fumarate component of cimduo Tenofovir disoproxil fumarate component of complera Tenofovir disoproxil fumarate component of delstrigo +9 more
4
Targets
28
Activities
2
Assay Types
10
PK Parameters
20
Publications
21
Known Names
19
Indications
1
Mechanisms

Molecular Properties

519.5
MW (Da)
3.04
ALogP
15
HBA
1
HBD
185.4
PSA (Ų)
0.23
QED
2
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2001
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Prodrug
USAN Stem -vir
USAN Year 1999

Extended Properties

Molecular Formula C23H34N5O14P
MW 635.52
Aromatic Rings 2
Heavy Atoms 35
NP-Likeness -0.16

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Human immunodeficiency virus type 1 reverse transcriptase inhibitor INHIBITOR Human immunodeficiency virus type 1 reverse transcriptase

Indications

Hepatitis B, Chronic Hepatitis B, Chronic HIV Infections HIV Infections Infections Liver Diseases Acquired Immunodeficiency Syndrome Severe Acute Respiratory Syndrome Communicable Diseases Hepatitis D Lipodystrophy Liver Cirrhosis, Biliary Multiple Sclerosis Hepatitis C Hepatitis, Chronic Insulin Resistance Lymphoma Parkinson Disease Tuberculosis

Drug Warnings

Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
immune system toxicity
Country: United States

Activity Summary

EC50 19 meas. best 8.54
IC50 9 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
EC50 8.54 7.3721 2.9 14
Human immunodeficiency virus 2
CHEMBL380
EC50 8.52 8.52 3.0 2
Hepatitis B virus
CHEMBL613497
EC50 7.86 6.9333 13.8 3
Human immunodeficiency virus 1
CHEMBL378
IC50 7.85 6.3583 14.0 6
Hepatitis B virus
CHEMBL613497
IC50 6.07 5.68 850.0 2
HepG2
CHEMBL395
IC50 5.64 5.64 2310.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2148.0 ng.hr.mL-1 Rattus norvegicus
Cmax 1345.65 nM Rattus norvegicus
F 3.4 % Rattus norvegicus
T1/2 6.14 hr Rattus norvegicus
t1/2 - - Homo sapiens
T1/2 27.8 hr -
t1/2 - - Sus scrofa
T1/2 0.1667 hr Homo sapiens
T1/2 0.1667 hr Homo sapiens
Tmax 0.25 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 2.9 nM 8.54 Antiviral activity against single-round HIV1 NLX.Lux-R harboring inactivating mu... 21060108
Human immunodeficiency virus 2 EC50 = 3.0 nM 8.52 Antiviral activity against HIV-2 ROD infected in wild type human CEM/0 cells ass... 38086193
Human immunodeficiency virus 2 EC50 = 3.0 nM 8.52 Antiviral activity against HIV-2 ROD infected in thymidine kinase deficient huma... 38086193
Human immunodeficiency virus 1 EC50 = 4.5 nM 8.35 Antiviral activity against HIV1 infected in human PBMC assessed as reduction in ... 27933889
Human immunodeficiency virus 1 EC50 = 4.6 nM 8.34 Antiviral activity against HIV1 infected in human PBMC assessed as inhibition of... 27405794
Human immunodeficiency virus 1 EC50 = 6.8 nM 8.17 Antiviral activity against HIV1 3B infected in human MT-2 cells by two fold dilu... 19104010
Human immunodeficiency virus 1 EC50 = 13.0 nM 7.89 Antiviral activity against HIV-1 HE infected in wild type human CEM/0 cells asse... 38086193
Hepatitis B virus EC50 = 13.79 nM 7.86 Antiviral activity against Hepatitis B virus infected in human HepG2.2.15 cells ... 33080351
Human immunodeficiency virus 1 IC50 = 14.0 nM 7.85 Antiviral activity against HIV1 infected in human PBMC assessed as inhibition of... 19596885
Human immunodeficiency virus 1 EC50 = 15.0 nM 7.82 Inhibition of virus-induced cytopathic effect in wild type HIV 3a infected MT2 c... 17562366
Human immunodeficiency virus 1 EC50 = 28.0 nM 7.55 Antiviral activity against HIV1 NL4-3.Luc in human MDM assessed as infectivity t... 21060108
Human immunodeficiency virus 1 EC50 = 34.0 nM 7.47 Antiviral activity against HIV1 NL4-3.Luc assessed as infectivity using human MD... 21060108
Human immunodeficiency virus 1 EC50 = 46.0 nM 7.34 Antiviral activity against HIV1 NL4-3.Luc in human PBMC assessed as infectivity ... 21060108
Human immunodeficiency virus 1 EC50 = 50.0 nM 7.3 Antiviral activity against HIV-1 34713696
Human immunodeficiency virus 1 EC50 = 55.0 nM 7.26 Antiviral activity against HIV1 NL4-3.Luc assessed as infectivity using human PB... 21060108
Human immunodeficiency virus 1 IC50 = 80.0 nM 7.1 Antiviral activity against CXCR4-tropic HIV-1 NL4-3 infected in human PHA-stimul... 28682067
Human immunodeficiency virus 1 EC50 = 120.0 nM 6.92 Antiviral activity against single-round HIV1 NLX.Lux-R harboring inactivating mu... 21060108
Human immunodeficiency virus 1 IC50 = 220.0 nM 6.66 Antiviral activity against CCR5 tropic HIV1 BaL infected in human PHA-stimulated... 28682067
Hepatitis B virus EC50 = 340.0 nM 6.47 Antiviral activity against HBV infected in human HepG2 assessed as reduction in ... 27933889
Hepatitis B virus EC50 = 340.0 nM 6.47 Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as in... 27405794

Literature References

PubMed DOI Target Context # Activities
18676881 10.1128/aac.00654-08 Woodchuck hepatitis virus 26
19104010 10.1128/aac.00984-08 Human immunodeficiency virus 1 23
21060108 10.1128/aac.01064-10 Human immunodeficiency virus 1 14
19596885 10.1128/aac.00392-09 Human immunodeficiency virus 1 11
17438052 10.1128/aac.00831-06 PBMC 11
17438052 10.1128/aac.00831-06 ADMET 10
18676881 10.1128/aac.00654-08 Marmota monax 9
31223460 10.1021/acsmedchemlett.9b00184 ADMET 7
17664327 10.1128/aac.00671-07 Unchecked 5
28682067 10.1021/acs.jmedchem.7b00416 Human immunodeficiency virus 1 5
20439609 10.1128/aac.00068-10 ADMET 5
38086193 10.1016/j.ejmech.2023.116020 ADMET 4
17562366 10.1016/j.bmc.2007.05.047 Human immunodeficiency virus 1 3
17664327 10.1128/aac.00671-07 Caco-2 3
36089112 10.1016/j.bmcl.2022.128977 Hepatitis B virus 3
31223460 10.1021/acsmedchemlett.9b00184 Hepatitis B virus 3
27405794 10.1021/acs.jmedchem.6b00428 ADMET 3
38086193 10.1016/j.ejmech.2023.116020 Human immunodeficiency virus 2 2
28682067 10.1021/acs.jmedchem.7b00416 Unchecked 2
31223460 10.1021/acsmedchemlett.9b00184 HBV genotype D 2

Data from ChEMBL 36 via Core Engine