Entecavir

Entecavir
Clinical data
Pronunciation/ɛnˈtɛkəvɪər/ en-TEK-ə-veer
Trade namesBaraclude, others
Other namesETV, BMS-200475-01
AHFS/Drugs.comMonograph
MedlinePlusa605028
License data
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailabilityn/a (≥70)
Protein binding13% (in vitro)
Metabolismnegligible/nil
Elimination half-life128–149 hours
ExcretionKidney 62–73%
Identifiers
  • 2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1H-purin-6-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.111.234
Chemical and physical data
FormulaC12H15N5O3
Molar mass277.284 g·mol−1
3D model (JSmol)
Melting point220 °C (428 °F) value applies to entecavir monohydrate and is a minimum value
  • C=C1C(CC(C1CO)O)N2C=NC3=C2N=C(NC3=O)N
  • InChI=1S/C12H15N5O3/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)/t6-,7-,8-/m0/s1 N
  • Key:QDGZDCVAUDNJFG-FXQIFTODSA-N N
 NY (what is this?)  (verify)

Entecavir, sold under the brand name Baraclude, is an antiviral medication used in the treatment of hepatitis B virus infection. In those with both HIV/AIDS and hepatitis B virus antiretroviral medication should also be used. Entecavir is taken by mouth as a tablet or solution.

Common side effects include headache, nausea, high blood sugar, and decreased kidney function. Severe side effects include enlargement of the liver, high blood lactate levels, and liver inflammation if the medication is stopped. While there appears to be no harm from use during pregnancy, this use has not been well studied. Entecavir is in the nucleoside reverse transcriptase inhibitors (NRTIs) family of medications. It prevents the hepatitis B virus from multiplying by blocking reverse transcriptase.

Entecavir was approved for medical use in 2005. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.