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QuickView for adefovir dipivoxil (compound)
PubChem
| Name: | adefovir dipivoxil |
|---|---|
| PubChem Compound ID: | 60871 |
| Molecular formula: | C20H32N5O8P |
| Molecular weight: | 501.471 g/mol |
| Synonyms: |
Piv2PMEA; Adefovir pivoxil; LS-173141; Adefovir dipivoxil (USAN); Adefovir pivoxil (JAN); Bis(pivaloyloxymethyl)-9-(2-phosphonylmethoxyethyl)adenine; GS-0840; GS 840; Hepsera; GS 0840.
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DrugBank
Identification
| Name: | adefovir dipivoxil |
|---|---|
| Name (isomeric): | DB00718 |
| Drug Type: | small molecule |
| Synonyms: |
Adefovir pivoxil; Adefovirdipivoxl; Adefovir; ADV; bis-POM PMEA; GS-840; PMEA
|
| Brand: | Hepsera, Preveon |
| Category: | Antiviral Agents, Reverse Transcriptase Inhibitors |
| CAS number: | 142340-99-6 |
Pharmacology
| Indication: | For the treatment of chronic hepatitis B in adults with evidence of active viral replication and either evidence of persistent elevations in serum aminotransferases (ALT or AST) or histologically active disease. |
|---|---|
| Pharmacology: |
Adefovir dipivoxil a diester prodrug of adefovir. Adefovir is an acyclic nucleotide analog with activity against human hepatitis B virus (HBV). The concentration of adefovir that inhibited 50% of viral DNA synthesis (IC50) in vitro ranged from 0.2 to 2.5 μM in HBV transfected human hepatoma cell lines. The combination of adefovir with lamivudine...
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| Mechanism of Action: |
Adefovir dipivoxil is a prodrug of adefovir. Adefovir is an acyclic nucleotide analog of adenosine monophosphate which is phosphorylated to the active metabolite adefovir diphosphate by cellular kinases. Adefovir diphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate deoxyadenosine triphosphate and b...
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| Absorption: | Approximate oral bioavailability is 59%. |
| Protein binding: | ≤4% over the adefovir concentration range of 0.1 to 25 μg/mL |
| Biotransformation: | Following oral administration, adefovir dipivoxil is rapidly converted to adefovir. Forty-five percent of the dose is recovered as adefovir in the urine over 24 hours at steady state following 10 mg oral doses. Adefovir is not a substrate of the cytochrome P450 enzymes. |
| Route of elimination: | Adefovir is renally excreted by a combination of glomerular filtration and active tubular secretion. |
| Half Life: | Terminal elimination half-life of 7.48 ± 1.65 hours |
| Clearance: | 469 +/- 99.0 mL/min [Patients with Unimpaired renal Function receiving a 10 mg single dose] 356 +/- 85.6 mL/min [Patients with mild renal impairement receiving a 10 mg single dose] 237 +/- 118 mL/min [Patients with moderate renal impairement receiving a 10 mg single dose] 91.7+/- 51.3 mL/min [Patients with severe renal impairement receiving a 10 mg single dose] |
| Toxicity: | Renal tubular nephropathy characterized by histological alterations and/or increases in BUN and serum creatinine was the primary dose-limiting toxicity associated with administration of adefovir dipivoxil in animals. Nephrotoxicity was observed in animals at systemic exposures approximately 3–10 times higher than those in humans at the recommended therapeutic dose of 10 mg/day. |
| Affected organisms: | Hepatitis B virus |
Interactions
| Food interaction: |
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Targets
Transporters
