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QuickView for Amprenavir (compound)

Name: amprenavir
PubChem Compound ID: 10885665
Molecular formula: C25H35N3O6S
Molecular weight: 505.628 g/mol
Name: amprenavir
Name (isomeric): DB00701
Drug Type: small molecule
Brand: Prozei, Agenerase, Vertex
Category: HIV Protease Inhibitors, Anti-HIV Agents, Antibiotics, Antitubercular
CAS number: 161814-49-9
Indication: For the treatment of HIV-1 infection in combination with other antiretroviral agents.
Amprenavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Amprenavir binds to ...
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Mechanism of Action: Amprenavir inhibits the HIV viral proteinase enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles.
Absorption: Rapidly absorbed after oral administration in HIV-1-infected patients with a time to peak concentration (Tmax) typically between 1 and 2 hours after a single oral dose. The absolute oral bioavailability of amprenavir in humans has not been established.
Protein binding: Very high (90%). Amprenavir has the highest affinity for alpha(1)-acid glycoprotein.
Biotransformation: Hepatic. Amprenavir is metabolized in the liver by the cytochrome P450 3A4 (CYP3A4) enzyme system. The 2 major metabolites result from oxidation of the tetrahydrofuran and aniline moieties. Glucuronide conjugates of oxidized metabolites have been identified as minor metabolites in urine and feces.
Half Life: 7.1-10.6 hours
Affected organisms: Human Immunodeficiency Virus
Food interaction:
Take with or without food, however avoid lipid-rich meals.
Avoid alcohol, especially with the oral solution since it contains propylene glycol which competes with alcohol for alcohol dehydrogenase metabolism.
Vitamin E increases amprenavir bioavailability.
Drug interaction:
MetronidazoleIncreased risk of side effects (oral solution)
St. John's WortSt. John's Wort decreases the effect of indinavir
DihydroergotamineAmprenavir may increase the serum concentration of dihydroergotamine. Concomitant therapy is contraindicated.
ZopicloneAmprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zopiclone by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if amprenavir is initiated, discontinued or dose changed.
TramadolAmprenavir may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
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