entecavir

Also known as BMS-200475-01, SQ-34676, Entecavir anhydrous, Entecavirum, Anhydrous entecavir, Entecavir (anhydrous)

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.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 464189683
Drug.image: Entecavir structure.svg
Drug.image_class: skin-invert-image
Drug.width: 240
Drug.image2: Entecavir ball-and-stick model.png
Drug.image_class2: bg-transparent
Drug.tradename: Baraclude, others
Drug.MedlinePlus: a605028
Drug.DailyMedID: Entecavir
Drug.pregnancy_AU: B3
Drug.routes_of_administration: By mouth
Drug.ATC_prefix: J05
Drug.ATC_suffix: AF10
Drug.legal_AU: S4
Drug.legal_CA: Rx-only
Drug.legal_UK: POM

via Wikipedia infobox

Chemical data

Formula: C12H15N5O3
Molecular weight: 277.28 g/mol
IUPAC name: 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one
SMILES: C=C1[C@H](C[C@@H]([C@H]1CO)O)N2C=NC3=C2NC(=NC3=O)N
InChIKey: QDGZDCVAUDNJFG-FXQIFTODSA-N
XLogP: -0.8
Polar surface area: 126 Å²
H-bond donors: 4
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

3,747 papers

Entecavir for children and adults with chronic hepatitis B.The Cochrane database of systematic reviews · 2025
Entecavir-associated thrombocytopenia.International journal of immunopathology and pharmacology · 2021
Lamivudine and Entecavir for Acute Hepatitis B: A Systematic Review and Meta-Analysis.Viruses · 2023
[Entecavir].Nihon rinsho. Japanese journal of clinical medicine · 2011
Entecavir (Bristol-Myers Squibb).Current opinion in investigational drugs (London, England : 2000) · 2001

via PubMed

Wikidata facts

Mass: 277.117489

Show 6 more facts

chemical formula: C₁₂H₁₅N₅O₃
canonical SMILES: C=C1C(CC(C1CO)O)N2C=NC3=C2NC(=NC3=O)N
isomeric SMILES: C=C1[C@H](C[C@@H]([C@H]1CO)O)N2C=NC3=C2NC(=NC3=O)N
World Health Organisation international non-proprietary name: entecavir
Commons category: Entecavir
defined daily dose: 0.5

Sources (8)

via Wikidata · CC0

~6 min read

Article

8 sections

Contents

Medical uses
Pregnancy and breastfeeding
Side effects
Mechanism of action
Administration
History
Patent information
References

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.