QuickView for Atazanavir (compound)

Summary
General Info

PubChem

PubChem Compound 11520467

Name:	atazanavir
PubChem Compound ID:	11520467
Molecular formula:	C₃₈H₅₂N₆O₇
Molecular weight:	707.874 g/mol

DrugBank

Identification

Name:	atazanavir
Name (isomeric):	DB01072
Drug Type:	small molecule
Synonyms:	Atazanavir sulfate; ATV; ATZ; BMS-232632
Brand:	Reyataz, Latazanavir, Zrivada
Category:	HIV Protease Inhibitors, Anti-HIV Agents, Protease Inhibitors
CAS number:	198904-31-3

Pharmacology

Indication:	Used in combination with other antiretroviral agents for the treatment of HIV-1 infection, as well as postexposure prophylaxis of HIV infection in individuals who have had occupational or nonoccupational exposure to potentially infectious body fluids of a person known to be infected with HIV when that exposure represents a substantial risk for HIV transmission.
Pharmacology:	Atazanavir (ATV) is an azapeptide HIV-1 protease inhibitor (PI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). 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. Atazanavir binds to the protease active site and i... show more » Atazanavir (ATV) is an azapeptide HIV-1 protease inhibitor (PI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). 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. Atazanavir 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. Atazanivir is pharmacologically related but structurally different from other protease inhibitors and other currently available antiretrovirals. show less «
Mechanism of Action:	Atazanavir selectively inhibits the virus-specific processing of viral Gag and Gag-Pol polyproteins in HIV-1 infected cells by binding to the active site of HIV-1 protease, thus preventing the formation of mature virions. Atazanavir is not active against HIV-2.
Absorption:	Atazanavir is rapidly absorbed with a T_max of approximately 2.5 hours. Administration of atazanavir with food enhances bioavailability and reduces pharmacokinetic variability. Oral bioavailability is 60-68%.
Protein binding:	86% bound to human serum proteins (alpha-1-acid glycoprotein and albumin). Protein binding is independent of concentration.
Biotransformation:	Atazanavir is extensively metabolized in humans, primarily by the liver. The major biotransformation pathways of atazanavir in humans consisted of monooxygenation and dioxygenation. Other minor biotransformation pathways for atazanavir or its metabolites consisted of glucuronidation, N-dealkylation, hydrolysis, and oxygenation with dehydrogenation. In vitro studies using human liver microsomes suggested that atazanavir is metabolized by CYP3A.
Half Life:	Elimination half-life in adults (healthy and HIV infected) is approximately 7 hours (following a 400 mg daily dose with a light meal). Elimination half-life in hepatically impaired is 12.1 hours (following a single 400 mg dose).
Affected organisms:	Human Immunodeficiency Virus

Interactions

Food interaction:

Administration with food reduces pharmacokinetic variability.

Food increases product absorption.

Drug interaction:

Teniposide	The strong CYP3A4 inhibitor, Atazanavir, 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 Atazanavir is initiated, discontinued or dose changed.
Bromazepam	Atazanavir, a strong CYP3A4 inhibitor, may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bromazepam if atazanavir is initiated, discontinued or dose changed. Dosage adjustments may be required.
Erlotinib	This CYP3A4 inhibitor increases levels/toxicity of erlotinib
Atorvastatin	Atazanavir may increase the serum concentration of atorvastatin by decreasing its metabolism. Concomitant therapy is contraindicated.
Sodium bicarbonate	This gastric pH modifier decreases the levels/effect of atazanavir

Teniposide	The strong CYP3A4 inhibitor, Atazanavir, 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 Atazanavir is initiated, discontinued or dose changed.
Bromazepam	Atazanavir, a strong CYP3A4 inhibitor, may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bromazepam if atazanavir is initiated, discontinued or dose changed. Dosage adjustments may be required.
Erlotinib	This CYP3A4 inhibitor increases levels/toxicity of erlotinib
Atorvastatin	Atazanavir may increase the serum concentration of atorvastatin by decreasing its metabolism. Concomitant therapy is contraindicated.
Sodium bicarbonate	This gastric pH modifier decreases the levels/effect of atazanavir
Sirolimus	Increases the effect and toxicity of immunosuppressant
Dihydroxyaluminium	This gastric pH modifier decreases the levels/effects of atazanavir
Quinidine	Increased risk of cardiotoxicity and arrhythmias.
St. John's Wort	St. John's Wort decreases the levels/effects of atazanavir
Acenocoumarol	The protease inhibitor, atazanavir, may increase the anticoagulant effect of acenocoumarol.
Lansoprazole	This gastric pH modifier decreases the levels/effects of atazanavir
Tipranavir	Tipranavir, co-administered with Ritonavir, may decrease the plasma concentration of Atazanavir. Consider alternate therapy.
Trazodone	The protease inhibitor, Atazanavir, may increase the efficacy/toxicity of Trazodone by inhibiting Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Atazanavir is initiated, discontinued or dose changed.
Ritonavir	Association with dose adjustment
Dihydroergotamine	Atazanavir may increase the therapeutic and adverse effects of dihydroergotamine.
Anisindione	The protease inhibitor, atazanavir, may increase the anticoagulant effect of anisindione.
Simvastatin	Increased risk of myopathy/rhabdomyolysis
Methylergonovine	Increases the effect and toxicity of ergot derivative
Telithromycin	Co-administration may result in altered plasma concentrations of Atazanavir and/or Telithromycin. Consider alternate therapy or monitor the therapeutic/adverse effects of both agents.
Vinorelbine	Atazanavir, 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 Atazanavir is initiated, discontinued or dose changed.
Vilazodone	CYP3A4 Inhibitors (Strong) may increase the serum concentration of Vilazodone. imit maximum adult vilazodone dose to 20 mg/day in patients receiving strong CYP3A4 inhibitors.
Zonisamide	Atazanavir, 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 atazanavir is initiated, discontinued or dose changed.
Rabeprazole	Rabeprazole may decrease the serum levels and therapeutic effects of atazanavir.
Irinotecan	Increases levels/effect of irinotecan
Protriptyline	Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, protriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of protriptyline if atazanavir if initiated, discontinued or dose changed.
Tadalafil	Atazanavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
Pimozide	The protease inhibitor, atazanavir, may increase the effect and toxicity of pimozide.
Quinidine barbiturate	Increased risk of cardiotoxicity and arrhythmias
Indinavir	Increased risk of hyperbilirubinemia with this association
Tamoxifen	Atazanavir may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
Trimipramine	The strong CYP3A4 inhibitor, Atazanavir, 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 Atazanavir is initiated, discontinued or dose changed.
Lovastatin	Atazanavir may increase the effect and toxicity of lovastatin. Concomitant therapy is contraindicated.
Tramadol	Atazanavir may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
Tolterodine	Atazanavir may decrease the metabolism and clearance of Tolterodine. Adjust the Tolterodine dose and monitor for efficacy and toxicity.
Sildenafil	Increases the effect and toxicity of sildenafil
Sunitinib	Possible increase in sunitinib levels
Abacavir	The serum concentration of Abacavir may be decreased by protease inhibitors such as Atazanavir. The antiviral response should be closely monitored.
Triazolam	Atazanavir may increase the effect and toxicity of the benzodiazepine, triazolam.
Ranolazine	Atazanavir, a strong CYP3A4 inhibitor, may increase the serum level of ranolazine. Concomitant therapy is contraindicated.
Doxepin	Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if atazanavir if initiated, discontinued or dose changed.
Efavirenz	Efavirenz decreases the levels/effects of atazanavir
Zolpidem	Atazanavir, 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 atazanavir is initiated, discontinued or dose changed.
Rifampin	Rifampin reduces levels and efficacy of atazanavir
Vardenafil	Atazanavir, 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.
Ramelteon	Atazanavir increases levels/toxicity of ramelteon
Magnesium Sulfate	This gastric pH modifier decreases the levels/effects of atazanavir
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of atazanavir by decreasing its metabolism. The serum concentration of voriconazole may be increased by atazanavir. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if doses are changed.
Clarithromycin	Atazanavir may increase serum level of clarithromycin.
Nortriptyline	Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, nortriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of nortriptyline if atazanavir if initiated, discontinued or dose changed.
Amitriptyline	Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, amitriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of amitriptyline if atazanavir if initiated, discontinued or dose changed.
Dantrolene	Atazanavir may increase the serum concentration of dantrolene by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of dantrolene if atazanavir is initiated, discontinued or dose changed.
Desipramine	Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, desipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of desipramine if atazanavir is initiated, discontinued or dose changed.
Calcium	This gastric pH modifier decreases the levels/effects of atazanavir
Lidocaine	Increased risk of cardiotoxicity and arrhythmias
Nizatidine	This gastric pH modifier decreases the levels/effects of atazanavir
Dihydroquinidine barbiturate	Increased risk of cardiotoxicity and arrhythmias
Aluminium	This gastric pH modifier decreases the levels/effects of atazanavir
Bismuth Subsalicylate	This gastric pH modifier decreases the levels/effects of atazanavir
Zopiclone	Atazanavir, 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 atazanavir is initiated, discontinued or dose changed.
Temsirolimus	Atazanavir may inhibit the metabolism and clearance of Temsirolimus. Concomitant therapy should be avoided.
Diltiazem	Atazanavir may increase the therapeutic and adverse effects of diltiazem resulting in increased risk of AV block. Consider alternate therapy, a 50% dose reduction of diltiazem and monitor for changes in the therapeutic and adverse effects of diltiazem if atazanavir is initiated, discontinued or dose changed.
Famotidine	This gastric pH modifier decreases the levels/effects of atazanavir
Warfarin	The protease inhibitor, atazanavir, may increase the anticoagulant effect of warfarin.
Tenofovir	Concomitant therapy may result in decreased serum levels of Atazanavir and increased levels of Tenofovir. Concomitant therapy should only be used with the inclusion of Ritonavir.
Amoxapine	Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, amoxapine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of amoxapine if atazanavir if initiated, discontinued or dose changed.
Tacrolimus	The protease inhibitor, Atazanavir, may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Atazanavir therapy is initiated, discontinued or altered.
Cimetidine	This gastric pH modifier decreases the levels/effects of atazanavir
Vincristine	Atazanavir, 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 Atazanavir is initiated, discontinued or dose changed.
Nevirapine	Nevirapine, a strong CYP3A4 inducer, may decrease the serum concentration of atazanavir by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of atazanavir if nevirapine is initiated, discontinued or dose changed.
Pantoprazole	This gastric pH modifier decreases the levels/effects of atazanavir
Vinblastine	Atazanavir, 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 Atazanavir is initiated, discontinued or dose changed.
Dicumarol	The protease inhibitor, atazanavir, may increase the anticoagulant effect of dicumarol.
Verapamil	Atazanavir, 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 Atazanavir is initiated, discontinued or dose changed.
Cyclosporine	Atazanavir may increase the therapeutic and adverse effects of cyclosporine.
Imipramine	Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, imipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of imipramine if atazanavir if initiated, discontinued or dose changed.
Bepridil	Atazanavir may increase the effect and toxicity of bepridil.
Esomeprazole	This gastric pH modifier decreases the levels/effects of atazanavir
Midazolam	Atazanavir may increase the effect and toxicity of the benzodiazepine, midazolam.
Ergotamine	Atazanavir may increase the effect and toxicity of ergotamine.
Rifabutin	Atazanavir may increase levels/toxicity of rifabutin.
Omeprazole	This gastric pH modifier decreases the levels/effects of atazanavir
Tretinoin	The strong CYP2C8 inhibitor, Atazanavir, may decrease the metabolism and clearance of oral Tretinoin. Consider alternate therapy or monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Atazanavir is initiated, discontinued to dose changed.
Amiodarone	Increased risk of cardiotoxicity and arrhythmias.
Magnesium oxide	This gastric pH modifier decreases the levels/effects of atazanavir
Tiagabine	The strong CYP3A4 inhibitor, Atazanavir, 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 Atazanavir is initiated, discontinued or dose changed.
Buprenorphine	Atazanavir may increase the serum concentration of Buprenorphine. Buprenorphine may decrease the serum concentration of Atazanavir. Avoid use of buprenorphine in patients receiving atazanavir without ritonavir boosting due to possible decreases in atazanavir exposure. In patients receiving buprenorphine with atazanavir/ritonavir, monitor for increased buprenorphine effects and consider dose reductions if patients experience adverse effects.
Magnesium	This gastric pH modifier decreases the levels/effects of atazanavir
Tamsulosin	Atazanvir, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Atazanavir is initiated, discontinued, or dose changed.
Venlafaxine	Atazanavir, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Atazanavir is initiated, discontinued, or dose changed.
Cisapride	Increased risk of cardiotoxicity and arrhythmias
Ranitidine	Ranitidine may decrease the levels/effects of atazanavir.
Clomipramine	Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, clomipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of clomipramine if atazanavir is initiated, discontinued or dose changed.

Targets

Enzymes

Transporters

Multidrug resistance protein 1

Multidrug resistance-associated protein 1