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| Clinical data | |
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| Trade names | Hepsera |
| AHFS/Drugs.com | Monograph |
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| Routes of administration | Oral |
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| Pharmacokinetic data | |
| Bioavailability | 59% |
| Protein binding | <4% |
| Eliminationhalf-life | 7.5 hours |
| Excretion | Urine |
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| CAS Number | |
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| DrugBank |
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| ChemSpider |
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| UNII | |
| KEGG |
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| ChEBI | |
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| NIAID ChemDB | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.106.235 |
| Chemical and physical data | |
| Formula | C8H12N5O4P |
| Molar mass | 273.189 g·mol−1 |
| 3D model (JSmol) | |
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Adefovir is a prescription medicine used to treat (chronic) infections with hepatitis B virus. A prodrug form of adefovir was previously calledbis-POM PMEA, with trade namesPreveon andHepsera. It is an orally administered nucleotide analogreverse-transcriptase inhibitor (ntRTI). It can be formulated as thepivoxilprodrugadefovir dipivoxil.
It is used for treatment ofhepatitis B.[1][2][3][4]
Trials of adefovir in patients withHIV have not shown any clear benefits.[3][5]
Adefovir was invented in the Institute of Organic Chemistry and Biochemistry,Academy of Sciences of the Czech Republic byAntonín Holý, and the drug was developed byGilead 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]
Adefovir works by blockingreverse 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 serumaminotransferases (primarily ALT) or histologically active disease.
The main benefit of adefovir overlamivudine (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 twopivaloyloxymethyl units, making it aprodrug form of adefovir.
- Adefovir dipivoxil