QuickView for amprenavir (compound)

Summary
General Info

PubChem

PubChem Compound 10885665

Name:	amprenavir
PubChem Compound ID:	10885665
Molecular formula:	C₂₅H₃₅N₃O₆S
Molecular weight:	505.628 g/mol

DrugBank

Identification

Name:	amprenavir
Name (isomeric):	DB00701
Drug Type:	small molecule
Synonyms:	VX-478; AMP; APV; AMV
Brand:	Prozei, Agenerase, Vertex
Category:	HIV Protease Inhibitors, Anti-HIV Agents, Antibiotics, Antitubercular
CAS number:	161814-49-9

Pharmacology

Indication:	For the treatment of HIV-1 infection in combination with other antiretroviral agents.
Pharmacology:	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 ... show more » 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 the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs. show less «
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 (T_max) 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

Interactions

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:

Metronidazole	Increased risk of side effects (oral solution)
St. John's Wort	St. John's Wort decreases the effect of indinavir
Dihydroergotamine	Amprenavir may increase the serum concentration of dihydroergotamine. Concomitant therapy is contraindicated.
Zopiclone	Amprenavir, 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.
Tramadol	Amprenavir may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.

Metronidazole	Increased risk of side effects (oral solution)
St. John's Wort	St. John's Wort decreases the effect of indinavir
Dihydroergotamine	Amprenavir may increase the serum concentration of dihydroergotamine. Concomitant therapy is contraindicated.
Zopiclone	Amprenavir, 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.
Tramadol	Amprenavir may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
Disulfiram	Increased irsk of side effects (oral solution)
Dihydroxyaluminium	The antiacid decreases the absorption of amprenavir
Sildenafil	The protease inhibitor, amprenavir, may increase the effect and toxicity of sildenafil.
Flurazepam	Amprenavir may increase the effect and toxicity of the benzodiazepine, flurazepam.
Clorazepate	Amprenavir may increase the effect and toxicity of the benzodiazepine, clorazepate.
Lovastatin	Amprenavir may increase the serum concentration of the lovastatin. Concomitant therapy is contraindicated.
Pimozide	Amprenavir may increase the effect and toxicity of pimozide.
Cyclosporine	The protease inhibitor, amprenavir, may increase the effect of cyclosporine.
Vinorelbine	Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Vinorelbine by decreasing its metabolism. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Amprenavir is initiated, discontinued or dose changed.
Simvastatin	Amprenavir may increase the effect and toxicity of simvastatin. Concomitant therapy is contraindicated.
Bismuth Subsalicylate	The antiacid decreases the absorption of amprenavir
Magnesium oxide	The antiacid decreases the absorption of amprenavir
Tamoxifen	Amprenavir may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
Tamsulosin	Amprenavir, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Amprenavir is initiated, discontinued, or dose changed.
Rifabutin	Amprenavir may increase the effect and toxicity of rifabutin.
Anisindione	Amprenavir may increase the anticoagulant effect of anisindione by increasing its serum concentration.
Dicumarol	Amprenavir may increase the anticoagulant effect of dicumarol by increasing its serum concentration.
Triazolam	Amprenavir may increase the effect and toxicity of the benzodiazepine, triazolam.
Diazepam	Amprenavir may increase the effect and toxicity of the benzodiazepine, diazepam.
Methadone	The protease inhibitor, amprenavir, may decrease the effect of methadone.
Atorvastatin	Amprenavir may increase the serum concentration of atorvastatin by decreasing its metabolism. Concomitant therapy is contraindicated.
Calcium	The antiacid decreases the absorption of amprenavir
Astemizole	Increased risk of cardiotoxicity and arrhythmias
Zonisamide	Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zonisamide by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zonisamide if amprenavir is initiated, discontinued or dose changed.
Vardenafil	Amprenavir, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
Tolterodine	Amprenavir may decrease the metabolism and clearance of Tolterodine. Adjust the Tolterodine dose and monitor for efficacy and toxicity.
Telithromycin	Co-administration may result in altered plasma concentrations of Amprenavir and/or Telithromycin. Consider alternate therapy or monitor the therapeutic/adverse effects of both agents.
Fusidic Acid	The protease inhibitor, amprenavir, may increase the effect and toxicity of fusidic acid.
Amiodarone	The protease inhibitor, amprenavir, may increase the effect and toxicity of amiodarone.
Bepridil	Amprenavir may increase the effect and toxicity of bepridil.
Warfarin	Amprenavir may increase the anticoagulant effect of warfarin by increasing its serum concentration.
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of amprenavir by decreasing its metabolism. The serum concentration of voriconazole may be increased by amprenavir. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if doses are changed.
Ethinyl Estradiol	Ritonavir could decrease the contraceptive efficacy
Trimipramine	The strong CYP3A4 inhibitor, Amprenavir, may decrease the metabolism and clearance of Trimipramine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Amprenavir is initiated, discontinued or dose changed.
Fentanyl	The protease inhibitor, amprenavir, may increase the effect and toxicity of fentanyl.
Magnesium	The antiacid decreases the absorption of amprenavir
Temsirolimus	Amprenavir may inhibit the metabolism and clearance of Temsirolimus. Concomitant therapy should be avoided.
Mestranol	Ritonavir could decrease the contraceptive efficacy
Teniposide	The strong CYP3A4 inhibitor, Amprenavir, may decrease the metabolism and clearance of Teniposide, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Teniposide if Amprenavir is initiated, discontinued or dose changed.
Abacavir	The serum concentration of Abacavir may be decreased by protease inhibitors such as Amprenavir. The antiviral response should be closely monitored.
Tacrolimus	The protease inhibitor, Amprenavir, may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Amprenavir therapy is initiated, discontinued or altered.
Acenocoumarol	Amprenavir may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration.
Alprazolam	Amprenavir may increase the effect and toxicity of the benzodiazepine, alprazolam.
Cisapride	Amprenavir may increase the effect and toxicity of cisapride.
Vitamin E	Increased serum levels of vitamin E
Venlafaxine	Amprenavir, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Amprenavir is initiated, discontinued, or dose changed.
Zolpidem	Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zolpidem by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zolpidem if amprenavir is initiated, discontinued or dose changed.
Verapamil	Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Amprenavir is initiated, discontinued or dose changed.
Aluminium	The antiacid decreases the absorption of amprenavir
Vinblastine	Amprenavir, a strong CYP3A4 inhibitor, may decrease the metabolism of Vinblastine. Consider alternate therapy to avoid Vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of Vinblastine if Amprenavir is initiated, discontinued or dose changed.
Trazodone	The protease inhibitor, Amprenavir, may increase the efficacy/toxicity of Trazodone by inhibiting Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Amprenavir is initiated, discontinued or dose changed.
Midazolam	Amprenavir may increase the effect and toxicity of the benzodiazepine, midazolam.
Terfenadine	Increased risk of cardiotoxicity and arrhythmias
Vincristine	Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Vincristine by decreasing its metabolism. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Amprenavir is initiated, discontinued or dose changed.
Delavirdine	Decreased levels of delavirdine with increased levels of amprenavir
Ranolazine	Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentratin of ranolazine by inhibiting its metabolism. Concomitant therapy is contraindicated.
Tiagabine	The strong CYP3A4 inhibitor, Amprenavir, may decrease the metabolism and clearance of Tiagabine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Tiagabine if Amprenavir is initiated, discontinued or dose changed.
Tadalafil	Amprenavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
Ergotamine	Amprenavir may increase the effect and toxicity of ergotamine.
Rifampin	In presence of rifampin anticipate decrease of amprenavir efficiency

Targets

Enzymes

Transporters

Multidrug resistance protein 1

Multidrug resistance-associated protein 1