Entecavir

Not to be confused with Emtricitabine.

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
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityn/a (≥70)[3]
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 Edit this at Wikidata
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[5]
  • 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
 ☒NcheckY (what is this?)  (verify)

Entecavir, sold under the brand name Baraclude, is an antiviral medication used in the treatment of hepatitis B virus infection.[6] In those with both HIV/AIDS and hepatitis B virus antiretroviral medication should also be used.[6] Entecavir is taken by mouth as a tablet or solution.[6]

Common side effects include headache, nausea, high blood sugar, and decreased kidney function.[6] Severe side effects include enlargement of the liver, high blood lactate levels, and liver inflammation if the medication is stopped.[6] While there appears to be no harm from use during pregnancy, this use has not been well studied.[1] Entecavir is in the nucleoside reverse transcriptase inhibitors (NRTIs) family of medications.[6][7] It prevents the hepatitis B virus from multiplying by blocking reverse transcriptase.[6]

Entecavir was approved for medical use in 2005.[6] It is on the World Health Organization's List of Essential Medicines.[8] It is available as a generic medication.

  1. ^ a b "Entecavir (Baraclude) Use During Pregnancy". Drugs.com. 3 December 2019. Archived from the original on 7 November 2016. Retrieved 24 January 2021.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ a b Cite error: The named reference Baraclude FDA label was invoked but never defined (see the help page).
  4. ^ "Baraclude EPAR". European Medicines Agency. 26 June 2006. Archived from the original on 6 March 2024. Retrieved 5 July 2024.
  5. ^ O'Neil MJ (2006). "The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals". The Merck Index (14th ed.). p. 613. ISBN 978-0-911910-00-1.
  6. ^ a b c d e f g h "Entecavir". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 28 November 2016.
  7. ^ Shetty K, Wu GY (2009). Chronic Viral Hepatitis: Diagnosis and Therapeutics. Springer Science & Business Media. p. 34. ISBN 9781597455657.
  8. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.