Adefovir

From Wikipedia, the free encyclopedia
(Redirected from Hepsera)

Template:Short description Template:Short description Page Template:Infobox drug/styles.css has no content.

Page Module:Infobox/styles.css has no content.

Adefovir
Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found.
Clinical data
Trade namesHepsera
AHFS/Drugs.comMonograph
Pregnancy
category		Page Template:Plainlist/styles.css has no content.
  • AU: B3
Routes of
administration		Oral
ATC codePage Template:Plainlist/styles.css has no content.
Legal status
Legal statusPage Template:Plainlist/styles.css has no content.
Pharmacokinetic data
Bioavailability59%
Protein binding<4%
Elimination half-life7.5 hours
ExcretionUrine
Identifiers
  • {[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonic acid
CAS NumberPage Template:Plainlist/styles.css has no content.
PubChem CIDPage Template:Plainlist/styles.css has no content.
PubChem SIDPage Template:Plainlist/styles.css has no content.
IUPHAR/BPSPage Template:Plainlist/styles.css has no content.
DrugBankPage Template:Plainlist/styles.css has no content.
ChemSpiderPage Template:Plainlist/styles.css has no content.
UNIIPage Template:Plainlist/styles.css has no content.
KEGGPage Template:Plainlist/styles.css has no content.
ChEBIPage Template:Plainlist/styles.css has no content.
ChEMBLPage Template:Plainlist/styles.css has no content.
NIAID ChemDBPage Template:Plainlist/styles.css has no content.
PDB ligandPage Template:Plainlist/styles.css has no content.
CompTox Dashboard (EPA)Page Template:Plainlist/styles.css has no content.
Chemical and physical data
FormulaC8H12N5O4P
Molar mass273.189 g·mol−1
3D model (JSmol)Page Template:Plainlist/styles.css has no content.
  • O=P(O)(O)COCCn1c2ncnc(c2nc1)N
  • InChI=1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16) checkY
  • Key:SUPKOOSCJHTBAH-UHFFFAOYSA-N checkY
Data page
Template:Infobox drug/data page link
Page Template:Nobold/styles.css has no content. ☒NcheckY (what is this?)Page Template:Nobold/styles.css has no content.  (verify)

Adefovir is a prescription medicine used to treat (chronic) infections with hepatitis B virus. A prodrug form of adefovir was previously called bis-POM PMEA, with trade names Preveon and Hepsera. It is an orally administered nucleotide analog reverse-transcriptase inhibitor (ntRTI). It can be formulated as the pivoxil prodrug adefovir dipivoxil.

Uses

It is used for treatment of hepatitis B.[1][2][3][4]

Trials of adefovir in patients with HIV have not shown any clear benefits.[3][5]

History

Adefovir was invented in the Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic by Antonín Holý, and the drug was developed by Gilead Sciences for HIV with the brand name Preveon. However, in November 1999, an expert panel advised the U.S. Food and Drug Administration (FDA) not to approve the drug due to concerns about the severity and frequency of kidney toxicity when dosed at 60 or 120 mg. The FDA followed that advice, refusing to approve adefovir as a treatment for HIV.[6]

Gilead Sciences discontinued its development for HIV treatment in December 1999, but continued to develop the drug for hepatitis B (HBV), where it is effective with a much lower dose of 10 mg. FDA approval for use in the treatment of hepatitis B was granted on September 20, 2002, and adefovir is sold for this indication under the brand name Hepsera. Adefovir became an approved treatment for HBV in the European Union in March 2003.[citation needed][7]

Mechanism of action

File:Adefovir dipivoxil structure.svg
Adefovir dipivoxil

Adefovir works by blocking reverse transcriptase, an enzyme crucial for the HBV to reproduce in the body. It is approved for the treatment of chronic hepatitis B in adults with evidence of active viral replication and either evidence of persistent elevations in serum aminotransferases (primarily ALT) or histologically active disease.

The main benefit of adefovir over lamivudine (the first NRTI approved for the treatment of HBV) is that it takes a much longer period of time for the virus to develop resistance to it.

Adefovir dipivoxil contains two pivaloyloxymethyl units, making it a prodrug form of adefovir.

References

Page Template:Reflist/styles.css has no content.

  1. ^ Page Module:Citation/CS1/styles.css has no content.Marcellin P, Chang TT, Lim SG, Tong MJ, Sievert W, Shiffman ML, et al. (February 2003). "Adefovir dipivoxil for the treatment of hepatitis B e antigen-positive chronic hepatitis B". The New England Journal of Medicine. 348 (9): 808–16. doi:10.1056/NEJMoa020681. PMID 12606735.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Manolakopoulos S, Bethanis S, Koutsounas S, Goulis J, Vlachogiannakos J, Christias E, et al. (February 2008). "Long-term therapy with adefovir dipivoxil in hepatitis B e antigen-negative patients developing resistance to lamivudine". Alimentary Pharmacology & Therapeutics. 27 (3): 266–73. doi:10.1111/j.1365-2036.2007.03567.x. PMID 17988233.
  3. ^ a b Page Module:Citation/CS1/styles.css has no content.ADHOC International Steering Committee (October 2002). "A randomized placebo-controlled trial of adefovir dipivoxil in advanced HIV infection: the ADHOC trial". HIV Medicine. 3 (4): 229–38. doi:10.1046/j.1468-1293.2002.00111.x. PMID 12444940.
  4. ^ Page Module:Citation/CS1/styles.css has no content."US Adefovir Dipivoxil label" (PDF). FDA. April 2013. Retrieved 12 February 2017.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Fisher EJ, Chaloner K, Cohn DL, Grant LB, Alston B, Brosgart CL, et al. (September 2001). "The safety and efficacy of adefovir dipivoxil in patients with advanced HIV disease: a randomized, placebo-controlled trial". AIDS. 15 (13): 1695–700. doi:10.1097/00002030-200109070-00013. PMID 11546945. S2CID 9425407.
  6. ^ Page Module:Citation/CS1/styles.css has no content."Gilead Sciences Announces Termination of Its US Development Program for Adefovir Dipivoxil for HIV". www.gilead.com. Retrieved 2025-11-14.
  7. ^ Page Module:Citation/CS1/styles.css has no content."COMMISSION IMPLEMENTING DECISION" (PDF). www.ec.europa.eu. 18 November 2022. Retrieved 2 December 2025.

Lua error in package.lua at line 80: module 'Module:Navbox/configuration' not found.

Retrieved from "https://cosmopedia.co/index.php?title=Adefovir&oldid=730400"