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Compound Detail

CHEMBL5314362

ENTECAVIR
💊 Approved Drug
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💊 Approved Drug
C=C1[C@H](CO)[C@@H](O)C[C@@H]1n1cnc2c(=O)[nH]c(N)nc21.O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5314362
Name ENTECAVIR
Phase Approved
Structure Type MOL
InChI Key YXPVEXCTPGULBZ-WQYNNSOESA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL713
Active Moiety CHEMBL473882

Known Names

Baraclude BMS-200475-01 Entecavir Entecavir accord Entecavir hydrate Entecavir monohydrate Entecavir mylan Entecavir viatris (previously entecavir mylan) SQ-34676 SQ34676
9
Targets
84
Activities
2
Assay Types
3
PK Parameters
20
Publications
10
Known Names
13
Indications
1
Mechanisms

Molecular Properties

277.3
MW (Da)
-0.83
ALogP
7
HBA
4
HBD
130.1
PSA (Ų)
0.53
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2005
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Prodrug
USAN Stem -vir
USAN Year 1999

Extended Properties

Molecular Formula C12H17N5O4
MW 295.30
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 1.03

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA polymerase/reverse transcriptase inhibitor INHIBITOR DNA polymerase/reverse transcriptase ✓ ✓

Indications

Hepatitis B Hepatitis B, Chronic Hepatitis B, Chronic Liver Diseases Virus Diseases Carcinoma, Hepatocellular Colorectal Neoplasms Hepatitis C, Chronic Hepatitis D Infections Liver Failure Liver Neoplasms Stomach Neoplasms

ATC Classification

J05AF10
entecavir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

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

Activity Summary

EC50 82 meas. best 10.0
IC50 2 meas. best 10.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis B virus
CHEMBL613497
 IC50 10.22 9.98 0.1 2
Human immunodeficiency virus
CHEMBL613758
 EC50 10.0 10.0 0.1 1
Core antigen
CHEMBL1075091
 EC50 9.62 9.62 0.2 1
Hepatitis B virus
CHEMBL613497
 EC50 9.46 7.1611 0.3 38
HepG2
CHEMBL395
 EC50 8.52 8.52 3.0 1
HBV genotype D
CHEMBL612769
 EC50 8.42 8.42 3.8 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 7.58 5.8531 26.0 35
HFF
CHEMBL614071
 EC50 4.82 4.82 15000.0 1
CEM-SS
CHEMBL614548
 EC50 4.68 4.68 21000.0 1
WI-38
CHEMBL614391
 EC50 4.52 4.52 30000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 30.0 nM Homo sapiens
Cmax 30.0 nM Homo sapiens
F 100.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis B virus IC50 = 0.06 nM 10.22 Antiviral activity against Hepatitis B virus infected in human dHepaRG cells ass... 30286292
Human immunodeficiency virus EC50 = 0.1 nM 10.0 Antiviral activity against HIV infected in CD4+ lymphocyte by fluorescence-activ... 18316521
Hepatitis B virus IC50 = 0.18 nM 9.74 Antiviral activity against Hepatitis B virus infected in human HepG2.2.15.7 asse... 33479662
Core antigen EC50 = 0.24 nM 9.62 Inhibition of hepatitis B virus capsid assembly infected in human HepG2.215 cell... 28082068
Hepatitis B virus EC50 = 0.35 nM 9.46 Antiviral activity against HBV ayw1 infected in human HepG2(2.2.15) cells assess... 28682067
Hepatitis B virus EC50 = 0.6 nM 9.22 Antiviral activity against Hepatitis B virus infected in human HePAD38 cells ass... 33421915
Hepatitis B virus EC50 = 0.7 nM 9.15 Antiviral activity against HBV infected in human HepAD38 cells assessed as reduc... 28688280
Hepatitis B virus EC50 = 2.4 nM 8.62 Inhibition of HBV replication with RT S78T substitution from Lamivudine refracto... 17178796
HepG2 EC50 = 3.0 nM 8.52 Tested for the effective concentration required to inhibit HBV in HepG2.2.15 hum... -
Hepatitis B virus EC50 = 3.75 nM 8.43 Antiviral activity against Hepatitis B virus ayw1 infected in human HepG2 2.2.15... 37922830
HBV genotype D EC50 = 3.8 nM 8.42 Antiviral activity against HBV genotype D infected in human HepG2.2.15 cells ass... 30613328
Hepatitis B virus EC50 = 4.0 nM 8.4 Inhibition of HBV replication with RT M309L substitution from Lamivudine refract... 17178796
Hepatitis B virus EC50 = 4.0 nM 8.4 Antiviral activity against Hepatitis B virus 18316521
Hepatitis B virus EC50 = 5.8 nM 8.24 Inhibition of HBV replication with RT D263G substitution from Lamivudine refract... 17178796
Hepatitis B virus EC50 = 7.6 nM 8.12 Inhibition of HBV replication with RT A200V substitution from Lamivudine refract... 17178796
Hepatitis B virus EC50 = 8.0 nM 8.1 Antiviral activity against wild type Hepatitis B virus infected in human HepG2(2... 21930377
Hepatitis B virus EC50 = 8.0 nM 8.1 Antiviral activity against wild type Hepatitis B virus infected in human HuH7 ce... 23237841
Hepatitis B virus EC50 = 10.2 nM 7.99 Inhibition of HBV replication with RT A200V substitution and L180M, M204I backgr... 17178796
Hepatitis B virus EC50 = 11.0 nM 7.96 Antiviral activity against HBV infected in human HepAD38 cells assessed as reduc... 32421339
Hepatitis B virus EC50 = 11.0 nM 7.96 Inhibition of HBV replication with RT L80V substitution and L180M, M204V backgro... 17178796

Literature References

PubMed DOI Target Context # Activities
18316521 10.1128/aac.01313-07 Human immunodeficiency virus 1 48
20028815 10.1128/aac.01163-09 Homo sapiens 27
17371827 10.1128/aac.01440-06 Hepatitis B virus 26
33191744 10.1021/acs.jmedchem.0c01381 Hepatitis B virus 19
17178796 10.1128/aac.00833-06 Hepatitis B virus 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
21930377 10.1016/j.bmcl.2011.08.113 Hepatitis B virus 14
20308377 10.1128/aac.01703-09 Human immunodeficiency virus 1 11
25905540 10.1021/jm5012963 Hepatitis B virus 7
28082068 10.1016/j.bmc.2016.12.017 Hepatitis B virus 6
30286292 10.1021/acs.jmedchem.8b01245 Hepatitis B virus 6
28688280 10.1016/j.ejmech.2017.06.062 Hepatitis B virus 5
34979256 10.1016/j.bmcl.2021.128518 Unchecked 5
36089112 10.1016/j.bmcl.2022.128977 Hepatitis B virus 4
20028815 10.1128/aac.01163-09 Hepatitis B virus 4
23237841 10.1016/j.bmcl.2012.11.027 Hepatitis B virus 4
32421339 10.1021/acs.jmedchem.0c00292 Hepatitis B virus 4
28682067 10.1021/acs.jmedchem.7b00416 Hepatitis B virus 4
- 10.1016/S0960-894X(96)00594-X WI-38 4
32692159 10.1021/acs.jmedchem.0c00346 Hepatitis B virus 3

Data from ChEMBL 36 via Core Engine