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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H15N5O3.H2O
Molecular Weight 295.2945
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENTECAVIR

SMILES

O.NC1=NC2=C(N=CN2[C@H]3C[C@H](O)[C@@H](CO)C3=C)C(=O)N1

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

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.004 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Entecavir

Cmax

ValueDoseCo-administeredAnalytePopulation
4.23 ng/mL
0.5 mg 1 times / day steady-state, oral
ENTECAVIR plasma
Homo sapiens
8.24 ng/mL
1 mg 1 times / day steady-state, oral
ENTECAVIR plasma
Homo sapiens
8.1 ng/mL
1 mg single, oral
ENTECAVIR plasma
Homo sapiens
4.2 ng/mL
0.5 mg 1 times / day steady-state, oral
ENTECAVIR plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
14.78 ng × h/mL
0.5 mg 1 times / day steady-state, oral
ENTECAVIR plasma
Homo sapiens
26.38 ng × h/mL
1 mg 1 times / day steady-state, oral
ENTECAVIR plasma
Homo sapiens
27.9 ng × h/mL
1 mg single, oral
ENTECAVIR plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
129.9 h
0.5 mg 1 times / day steady-state, oral
ENTECAVIR plasma
Homo sapiens
148.89 h
1 mg 1 times / day steady-state, oral
ENTECAVIR plasma
Homo sapiens
138.5 h
0.5 mg 1 times / day steady-state, oral
ENTECAVIR plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
87%
0.5 mg 1 times / day steady-state, oral
ENTECAVIR plasma
Homo sapiens

Doses

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Nucleoside-naive Individuals Oral 0.5 mg once daily. Lamivudine-refractory HBV or known lamivudine- or telbivudine-associated resistance mutations Oral 1 mg once daily
Route of Administration: Oral
In Vitro Use Guide
Dendritic cells (DCs) derived from chronic hepatitis B (CHB) patients were treated with 0.05 ug/mL of Entecavir.