U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H15N5O3.H2O
Molecular Weight 295.295
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENTECAVIR

SMILES

C=C1[C@]([H])(CO)[C@]([H])(C[C@]1([H])n2cnc3c2[nH]c(=N)nc3O)O.O

InChI

InChIKey=YXPVEXCTPGULBZ-WQYNNSOESA-N
InChI=1S/C12H15N5O3.H2O/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20;/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20);1H2/t6-,7-,8-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C12H15N5O3
Molecular Weight 277.2797
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several resourses, including http://www.drugs.com/monograph/entecavir.html and http://www.drugbank.ca/drugs/DB00442

BARACLUDE® is the tradename for entecavir, a guanosine nucleoside analogue with selective activity against hepatitis B virus (HBV). It inhibits all three steps in the viral replication process. By competing with the natural substrate deoxyguanosine triphosphate, entecavir functionally inhibits all three activities of the HBV polymerase (reverse transcriptase, rt): (1) base priming, (2) reverse transcription of the negative strand from the pregenomic messenger RNA, and (3) synthesis of the positive strand of HBV DNA. Upon activation by kinases, the drug can be incorporated into the DNA which has the ultimate effect of inhibiting the HBV polymerase activity. Entecavir is used for the treatment of chronic hepatitis B virus infection in adults with evidence of active viral replication and either evidence of persistent elevations in serum aminotransferases (ALT or AST) or histologically active disease.

CNS Activity

Curator's Comment:: Low concentrations of entecavir were found in the cerebrospinal fluid of mice, rats, dogs and monkeys indicating that entecavir can cross the blood brain barrier.

Originator

Curator's Comment:: # Bristol-Myers Squibb Pharmaceutical Co.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
0.0040000000000000001 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Entecavir

Approved Use

BARACLUDE (entecavir) is indicated for the treatment of chronic hepatitis B virus infection in adults with evidence of active viral replication and either evidence of persistent elevations in serum aminotransferases (ALT or AST) or histologically active disease.

Launch Date

1112054400000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.23 ng/mL
0.5 mg 1 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENTECAVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
8.24 ng/mL
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENTECAVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
8.1 ng/mL
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENTECAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.2 ng/mL
0.5 mg 1 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENTECAVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
14.78 ng × h/mL
0.5 mg 1 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENTECAVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
26.38 ng × h/mL
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENTECAVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
27.9 ng × h/mL
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENTECAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
129.9 h
0.5 mg 1 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENTECAVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
148.89 h
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENTECAVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
138.5 h
0.5 mg 1 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENTECAVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
87%
0.5 mg 1 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENTECAVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 mg 1 times / day steady, oral
Highest studied dose
Dose: 1 mg, 1 times / day
Route: oral
Route: steady
Dose: 1 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive
no [IC50 >300 uM]
no (co-administration study)
Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with phenacetin
Page: 42, 154, 155
no [IC50 >300 uM]
no (co-administration study)
Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with S-mephentytoin
Page: 42, 154, 155
no [IC50 >300 uM]
no (co-administration study)
Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with S-mephentytoin
Page: 42, 154, 155
no [IC50 >300 uM]
no (co-administration study)
Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with diclofenac
Page: 42, 154, 155
no [IC50 >300 uM]
no (co-administration study)
Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with bufuralol
Page: 42, 154, 155
no [IC50 >300 uM]
no (co-administration study)
Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with p-nitrophenol
Page: 42, 154, 155
no [IC50 >300 uM]
no (co-administration study)
Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with testosterone
Page: 42, 154, 155
no
no
no
no
no
no
no
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Hepatitis B in children: natural history and therapy].
2001
Antiviral drugs: current state of the art.
2001 Aug
Detection of hepatitis B virus resistance to antivirals.
2001 Jun
Safety and efficacy of oral entecavir given for 28 days in patients with chronic hepatitis B virus infection.
2001 Sep
Management of patients with chronic hepatitis B.
2002 Apr
Antiviral therapy for hepatitis B virus infections: new targets and technical challenges.
2002 Dec
Potent efficacy of entecavir (BMS-200475) in a duck model of hepatitis B virus replication.
2002 Jan
Viral dynamics during and after entecavir therapy in patients with chronic hepatitis B.
2002 Jul
Gateways to clinical trials.
2002 Oct
Prevention of recurrent hepatitis B post-liver transplantation.
2002 Oct
Treatment of HBeAg negative chronic hepatitis B with new drugs (adefovir and others).
2003
[Nucleoside analogues resistance in the treatment of chronic hepatitis B virus infection].
2003 Dec
Selection of a hepatitis B virus strain resistant to adefovir in a liver transplantation patient.
2003 Dec
Current and future antiviral agents for chronic hepatitis B.
2003 Mar
Doctor to patient transmission of hepatitis B virus: implications of HBV DNA levels and potential new solutions.
2003 Oct
Molecular virology of hepatitis B virus.
2004
[Advances in the treatment of acute hepatitis B].
2004 Aug
Entecavir for the treatment of chronic hepatitis B.
2004 Dec
Editorial comment: HIV and HBV coinfection--a coming-of-age in treatment strategies.
2004 Mar
Gateways to clinical trials.
2004 Nov
Gateways to clinical trials.
2004 Sep
Clinical emergence of entecavir-resistant hepatitis B virus requires additional substitutions in virus already resistant to Lamivudine.
2004 Sep
Management of HBV/HIV-coinfected Patients.
2005
The current status of antiviral therapy of chronic hepatitis B.
2005 Dec
Hepatitis B virus infection: current status.
2005 Dec
Complications in treating chronic hepatitis B in patients with HIV.
2005 Dec
Gateways to clinical trials.
2005 Jan-Feb
Entecavir.
2005 Jul
New treatment for chronic hepatitis B.
2005 Jul-Aug
Clinical course of patients with chronic hepatitis B with viral breakthrough during long-term lamivudine treatment.
2005 Jun
Management of patients co-infected with hepatitis B virus and HIV.
2005 Jun
Susceptibility to antivirals of a human HBV strain with mutations conferring resistance to both lamivudine and adefovir.
2005 Jun
Entecavir (Baraclude) for chronic hepatitis B.
2005 Jun 6
Current and future treatment of chronic hepatitis B.
2005 Mar
[Treatment of chronic hepatitis B].
2005 Mar 31
New drugs: entecavir, ibandronate sodium, and pegaptanib sodium.
2005 May-Jun
Gateways to clinical trials.
2005 Nov
A review of entecavir in the treatment of chronic hepatitis B infection.
2005 Nov
[New aspect in the treatment of chronic hepatis B].
2005 Sep 7
Optimizing management strategies in special patient populations.
2006
Looking to the future: new agents for chronic hepatitis B.
2006
Therapeutic options for chronic hepatitis B: considerations and controversies.
2006
Introduction to chronic hepatitis B infection.
2006
Emerging therapeutics for chronic hepatitis B.
2006
Treatment algorithm for chronic hepatitis B in HIV-infected patients.
2006
Cellular and virological mechanisms of HBV drug resistance.
2006 Feb
Patents

Patents

Sample Use Guides

Nucleoside-naive Individuals
Route of Administration: Oral
Dendritic cells (DCs) derived from chronic hepatitis B (CHB) patients were treated with 0.05 ug/mL of Entecavir.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:06:16 UTC 2021
Edited
by admin
on Fri Jun 25 21:06:16 UTC 2021
Record UNII
5968Y6H45M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENTECAVIR
EMA EPAR   MART.   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
SQ-34676
Code English
ENTECAVIR MONOHYDRATE [USP-RS]
Common Name English
ENTECAVIR MONOHYDRATE
MI   USP-RS   WHO-DD  
Common Name English
ENTECAVIR [USP MONOGRAPH]
Common Name English
9-((1S,3R,4S)-4-HYDROXY-3-(HYDROXYMETHYL)-2-METHYLENECYCLOPENTYL)GUANINE MONOHYDRATE
Systematic Name English
ENTECAVIR [USAN]
Common Name English
ENTECAVIR [ORANGE BOOK]
Common Name English
ENTECAVIR MONOHYDRATE [MI]
Common Name English
ENTECAVIR HYDRATE
JAN  
Common Name English
6H-PURIN-6-ONE, 2-AMINO-1,9-DIHYDRO-9-((1S,3R,4S)-4-HYDROXY-3-(HYDROXYMETHYL)-2-METHYLENECYCLOPENTYL)- MONOHYDRATE
Systematic Name English
ENTECAVIR MONOHYDRATE [EP MONOGRAPH]
Common Name English
BARACLUDE
Brand Name English
SQ34676
Code English
ENTECAVIR [EMA EPAR]
Common Name English
BMS-200475-01
Code English
ENTECAVIR [VANDF]
Common Name English
ENTECAVIR HYDRATE [JAN]
Common Name English
ENTECAVIR [MART.]
Common Name English
ENTECAVIR MONOHYDRATE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C97452
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
WHO-VATC QJ05AF10
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
WHO-ATC J05AF10
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
LIVERTOX 353
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
EMA ASSESSMENT REPORTS BARACLUDE (AUTHORIZED: HEPATITIS B, CHRONIC)
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
NDF-RT N0000175656
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
Code System Code Type Description
CAS
209216-23-9
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY
ChEMBL
CHEMBL713
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY
RXCUI
306266
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00442
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY
USP_CATALOG
1235966
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY USP-RS
FDA UNII
5968Y6H45M
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY
WIKIPEDIA
ENTECAVIR
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY
PUBCHEM
135526609
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY
LACTMED
Entecavir
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY
DRUG CENTRAL
1019
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY
MESH
C413685
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY
EVMPD
SUB25434
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY
NCI_THESAURUS
C65513
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY
MERCK INDEX
M4919
Created by admin on Fri Jun 25 21:06:16 UTC 2021 , Edited by admin on Fri Jun 25 21:06:16 UTC 2021
PRIMARY Merck Index
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