Entecavir monohydrateProduct ingredient for Entecavir

Name
Entecavir monohydrate
Drug Entry
Entecavir

Entecavir is an oral antiviral drug used in the treatment of hepatitis B infection. It is marketed under the trade name Baraclude (BMS).

Entecavir is a guanine analogue that inhibits all three steps in the viral replication process, and the manufacturer claims that it is more efficacious than previous agents used to treat hepatitis B (lamivudine and adefovir). It was approved by the U.S. Food and Drug Administration (FDA) in March 2005.

Accession Number
DBSALT001748
Structure
Thumb
Synonyms
Entecavir / Entecavir hydrate
UNII
5968Y6H45M
CAS Number
209216-23-9
Weight
Average: 295.299
Monoisotopic: 295.128054047
Chemical Formula
C12H17N5O4
InChI Key
YXPVEXCTPGULBZ-WQYNNSOESA-N
InChI
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
IUPAC Name
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one hydrate
SMILES
O.NC1=NC2=C(N=CN2[[email protected]]2C[[email protected]](O)[[email protected]@H](CO)C2=C)C(=O)N1
KEGG Drug
D04008
ChemSpider
10482312
ChEBI
59902
Wikipedia
Entecavir
Predicted Properties
PropertyValueSource
Water Solubility6.43 mg/mLALOGPS
logP-1.5ALOGPS
logP-2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)10.17ChemAxon
pKa (Strongest Basic)0.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity71.43 m3·mol-1ChemAxon
Polarizability27.29 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon