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Compound Detail

CHEMBL483

TENOFOVIR ANHYDROUS
🧪 Phase III
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🧪 Phase III
C[C@H](Cn1cnc2c(N)ncnc21)OCP(=O)(O)O

Basic Information

ChEMBL ID CHEMBL483
Name TENOFOVIR ANHYDROUS
Phase Phase III
Structure Type MOL
InChI Key SGOIRFVFHAKUTI-ZCFIWIBFSA-N
Active Moiety CHEMBL258501

Known Names

GS-1275 Tenofovir anhydrous
16
Targets
192
Activities
3
Assay Types
30
PK Parameters
20
Publications
2
Known Names
10
Indications
2
Mechanisms

Molecular Properties

287.2
MW (Da)
-0.05
ALogP
7
HBA
3
HBD
136.4
PSA (Ų)
0.65
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product Prodrug
USAN Stem -vir
USAN Year 1999

Extended Properties

Molecular Formula C9H14N5O4P
MW 287.22
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.23

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
DNA polymerase/reverse transcriptase inhibitor INHIBITOR DNA polymerase/reverse transcriptase

Indications

Acquired Immunodeficiency Syndrome Carcinoma, Hepatocellular Hepatitis B, Chronic Hepatitis B, Chronic Hepatitis D HIV Infections HIV Infections Infections Severe Acute Respiratory Syndrome Hepatitis C, Chronic

Activity Summary

EC50 139 meas. best 10.19
IC50 52 meas. best 6.42
Kd 1 meas. best 5.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis B virus
CHEMBL613497
EC50 10.19 5.2713 0.1 24
Human immunodeficiency virus 1
CHEMBL378
EC50 8.48 5.9955 3.3 89
Moloney murine leukemia virus
CHEMBL613500
EC50 6.64 6.64 230.0 1
Core antigen
CHEMBL1075091
EC50 6.62 6.62 241.5 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
IC50 6.42 6.265 380.0 4
Human immunodeficiency virus 1
CHEMBL378
IC50 6.42 5.7021 380.0 14
Unchecked
CHEMBL612545
IC50 6.42 6.42 380.0 1
Hepatitis B virus
CHEMBL613497
IC50 6.31 5.861 490.0 10
Human immunodeficiency virus 2
CHEMBL380
EC50 6.06 5.526 880.0 10
MT4
CHEMBL388
EC50 5.85 5.745 1400.0 2
Human immunodeficiency virus
CHEMBL613758
IC50 5.8 5.7533 1600.0 3
Porcine endogenous retrovirus
CHEMBL613016
EC50 5.55 5.55 2800.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
Kd 5.5 5.5 3200.0 1
Human immunodeficiency virus
CHEMBL613758
EC50 5.44 5.44 3600.0 1
CCRF-CEM
CHEMBL382
EC50 5.43 5.43 3670.0 2
Moloney murine sarcoma virus
CHEMBL613501
EC50 5.34 5.34 4600.0 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 5.3 5.3 5000.0 1
CCRF-CEM
CHEMBL382
IC50 5.16 5.16 6900.0 1
L1210
CHEMBL386
IC50 4.96 4.96 11000.0 1
HeLa
CHEMBL399
IC50 4.77 4.77 17000.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 4.34 4.34 45800.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 510.8 ng.hr.mL-1 Rattus norvegicus
AUC 964.7 ng.hr.mL-1 Rattus norvegicus
AUC 1456.1 ng.hr.mL-1 Rattus norvegicus
AUC 2363.4 ng.hr.mL-1 Rattus norvegicus
AUC 3039.3 ng.hr.mL-1 Rattus norvegicus
AUC 5715.4 ng.hr.mL-1 Rattus norvegicus
AUC 775.2 ng.hr.mL-1 Rattus norvegicus
AUC 1226.9 ng.hr.mL-1 Rattus norvegicus
AUC 1808.1 ng.hr.mL-1 Rattus norvegicus
AUC 2790.5 ng.hr.mL-1 Rattus norvegicus
AUC 3639.5 ng.hr.mL-1 Rattus norvegicus
AUC 7373.4 ng.hr.mL-1 Rattus norvegicus
AUC 15779.0 ng.hr.mL-1 Rattus norvegicus
AUC 888.0 ng.hr.mL-1 Rattus norvegicus
CL 3.1 mL.min-1.kg-1 Homo sapiens
CL 3.1 mL.min-1.kg-1 Homo sapiens
CL 5.35 mL.min-1.kg-1 Rattus norvegicus
Cmax 172.52 nM Rattus norvegicus
Cmax 192.71 nM Rattus norvegicus
Cmax 379.85 nM Rattus norvegicus
Cmax 519.46 nM Rattus norvegicus
Cmax 631.57 nM Rattus norvegicus
Cmax 1121.09 nM Rattus norvegicus
Cmax 1000.0 nM Homo sapiens
Cmax 720.7 nM Rattus norvegicus
F 1.41 % Rattus norvegicus
F 2.0 % Mus musculus
Fu 0.93 - Homo sapiens
MRT 3.8 hr Homo sapiens
T1/2 72.0 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis B virus EC50 = 0.064 nM 10.19 Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as re... 32421339
Human immunodeficiency virus 1 EC50 = 3.3 nM 8.48 Selectivity ratio of EC50 for HIV1 8415-2 harboring reverse transcriptase 65R/18... 20439609
Hepatitis B virus EC50 = 10.0 nM 8.0 Antiviral activity against HBV infected in human HepAD38 cells assessed as reduc... 32421339
Human immunodeficiency virus 1 EC50 = 13.0 nM 7.89 Antiviral activity against HIV1 3B infected in human MT2 cells assessed as inhib... 20409721
Human immunodeficiency virus 1 EC50 = 18.0 nM 7.75 Selectivity ratio of EC50 for HIV1 4755-5 harboring reverse transcriptase 41L/44... 20439609
Human immunodeficiency virus 1 EC50 = 22.0 nM 7.66 Selectivity ratio of EC50 for HIV1 7324-1 harboring reverse transcriptase 41L/67... 20439609
Human immunodeficiency virus 1 EC50 = 32.0 nM 7.5 Antiviral activity against R5-HIV1Ba-L assessed as inhibition of p24 Gag protein... 17548498
Human immunodeficiency virus 1 EC50 = 40.0 nM 7.4 Antiviral activity against HIV1 clade F isolate 2338 infected in human H9 cells ... 21803462
Human immunodeficiency virus 1 EC50 = 47.0 nM 7.33 Antiviral activity against R5-HIV1MDR/C assessed as inhibition of p24 Gag protei... 17548498
Human immunodeficiency virus 1 EC50 = 82.0 nM 7.09 Antiviral activity against R5-HIV1MDR/MM assessed as inhibition of p24 Gag prote... 17548498
Human immunodeficiency virus 1 EC50 = 87.0 nM 7.06 Antiviral activity against R5-HIV1MDR/G assessed as inhibition of p24 Gag protei... 17548498
Human immunodeficiency virus 1 EC50 = 100.0 nM 7.0 Antiviral activity against HIV1 clade D isolate 1649 infected in human H9 cells ... 21803462
Human immunodeficiency virus 1 EC50 = 100.0 nM 7.0 Antiviral activity against tenofovir-resistant CXCR4-tropic HIV-1 NL4-3 harborin... 28682067
Human immunodeficiency virus 1 EC50 = 150.0 nM 6.82 Antiviral activity against HIV1 clade G isolate 3187 infected in human H9 cells ... 21803462
Human immunodeficiency virus 1 EC50 = 230.0 nM 6.64 Antiviral activity against 125 TCID50 wild type HIV1 LAI infected in human H9 ce... 21803462
Moloney murine leukemia virus EC50 = 230.0 nM 6.64 Inhibition of murine sarcoma virus-induced transformation of mouse embryo fibrob... 18556209
Human immunodeficiency virus 1 EC50 = 230.0 nM 6.64 Antiviral activity against HIV1 isolate 157 harboring reverse transcriptase L74V... 20439609
Core antigen EC50 = 241.5 nM 6.62 Inhibition of hepatitis B virus capsid assembly infected in human HepG2.215 cell... 28082068
Human immunodeficiency virus 1 EC50 = 240.0 nM 6.62 Antiviral activity against HIV1 clade B isolate 2101 infected in human H9 cells ... 21803462
Human immunodeficiency virus 1 EC50 = 300.0 nM 6.52 Antiviral activity against HIV1 NL 4-3 expressing wild type reverse transcriptas... 20439609

Literature References

PubMed DOI Target Context # Activities
20439609 10.1128/aac.00068-10 Human immunodeficiency virus 1 77
17646420 10.1128/aac.00460-07 Rattus norvegicus 30
17371827 10.1128/aac.01440-06 Hepatitis B virus 26
17517852 10.1128/aac.00314-07 Human immunodeficiency virus type 1 reverse transcriptase 19
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
21803462 10.1016/j.ejmech.2011.06.034 Human immunodeficiency virus 1 14
20439609 10.1128/aac.00068-10 PBMC 14
19289522 10.1128/aac.01559-08 Human immunodeficiency virus 1 13
19258271 10.1128/aac.01096-08 Human immunodeficiency virus 1 12
17548498 10.1128/aac.00277-07 Human immunodeficiency virus 1 10
31223460 10.1021/acsmedchemlett.9b00184 ADMET 8
17181162 10.1021/jm060030y No relevant target 8
28682067 10.1021/acs.jmedchem.7b00416 Human immunodeficiency virus 1 7
32293182 10.1021/acs.jmedchem.0c00117 Human immunodeficiency virus 1 7
37801325 10.1021/acs.jmedchem.3c01145 Unchecked 6
19307360 10.1128/aac.01523-08 ADMET 5
20439609 10.1128/aac.00068-10 ADMET 5
17876005 10.1128/aac.00687-07 Human immunodeficiency virus 1 5
22472044 10.1016/j.bmc.2012.03.023 ADMET 4
17646420 10.1128/aac.00460-07 Unchecked 4

Data from ChEMBL 36 via Core Engine