Entecavir
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1H-purin-6-one
Molecular Identity
Entecavir
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1H-purin-6-one
PubChem CID: 135398508
Entecavir (anhydrous) is guanine substituted at the 9 position by a 4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl group. A synthetic analogue of 2'-deoxyguanosine, it is a nucleoside reverse transcriptase inhibitor with selective antiviral activity against hepatitis B virus. Entecavir is phosphorylated intracellularly to the active triphosphate form, which competes with deoxyguanosine triphosphate, the natural substrate of hepatitis B virus reverse transcriptase, inhibiting every stage of the enzyme's activity, although it has no activity against HIV. It is used for the treatment of chronic hepatitis B. It has a role as an antiviral drug and an EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor. It is a primary alcohol, a member of 2-aminopurines, an oxopurine and a secondary alcohol.
2D Structure
Properties
C12H15N5O3
Molecular Formula
277.28
Molecular Weight
g/mol
277.1175
Exact Mass
Da
-1.3
XLogP
Drug-like (Lipinski: < 5)
126
TPSA
Good oral absorption (< 140 A²)
4
H-Bond Donors
5
H-Bond Acceptors
480
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Entecavir142217-69-4Baracludeanhydrous entecavirEntecavir anhydrousBMS 200475BMS-200475entecavir (anhydrous)NNU2O4609DDTXSID4046446CHEBI:4739906H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-DTXCID2026446SQ-346762-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one
Data from PubChem (NCBI)
This platform is for informational purposes only and does not constitute medical advice. Always consult a qualified healthcare professional.
Drug Network
Trials and conditions connected to Entecavir
Loading drug network...