Atazanavir

atazanavir
IUPAC name: see chemistry section Synonyms: AZT Formula: C38H52N6O7
Uses:	HIV
Properties:	protease inhibitor
Hazards:	see drug interactions
Mass (g/mol): CAS #: 704.8555 198904-31-3

Atazanavir, widely known as ATZ, and also called ATV and formerly called BMS-232632, is an antiretroviral protease inhibitor (PI) used to treat HIV/AIDS. Unlike most protease inhibitors, atazanavir can be given once a day and hence has fewer effects on patient lipid profiles. Like most protease inhibitors, it is used in combination with other HIV medications. It is sold under the brand names Latazanavir®, Reyataz® and Zrivada®.

Mechanism of action

It inhibits the proteolytic cleavage of the viral polyprotein precursors (Gag and Gag-Pol) so that the individual active proteins of HIV cannot be made, thus stopping the formation of mature, infectious viral particles. This and other protease inhibitors are almost always used in combination with at least two other anti-HIV drugs.

Chemistry

Its IUPAC chemical name is methyl N-[(2S)-1-[[(2S,3S)-3-hydroxy-4-[[[(2S)-2-(methoxycarbonylamino)- 3,3-dimethylbutanoyl]amino]-[(4-pyridin-2-ylphenyl)methyl]amino]-1-phenylbutan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]carbamate, and its chemical formula is C₃₈H₅₂N₆O₇ (MW 704.8555 g/mol).

Drug interactions

The absorption of indinavir is decreased by St. John's Wort, antacids and other gastric pH modifiers, such as aluminum, bismuth, calcium, cimetidine, dihydroxyaluminium, famotidine, magnesium, magnesium oxide, magnesium sulfide, nizatidine, ranitidine and sodium bicarbonate, by efavirenz, omeprazole and related compounds (esomeprazole, lansoprazole, pantoprazole and rabeprazole) and by rifampin and its derivitive rifabutin. It is also decreased when taking nevirapine or tenofovir.

Atazanavir increases the anticoagulant effect of anisindione, acenocoumarol, dicumarol, and warfarin and also increases the effect of benzodiazepine when taken with midazolam or triazolam. An increased risk of cardiotoxicity and arrhythmias occurs when taken with amiodarone, cisapride, dihydroquinidine barbiturate, lidocaine, quinidine, and quinidine barbiturate.

The effects and toxicity of some statins, such as atorvastatin, lovastatin and simvastatin, is increased when taking atazanavir. The effects of cyclosporine, pimozide, sildenafil and tacrolimus are increased when taken with atazanavir. The effect and toxicity of ergot derivatives, such as ergotamine, dihydroergotamine and methylergonovine, and the drugs erlotinib and ranolazine are also increased. The effects and toxicity of tricyclic compounds are increased when atazanavir is taken with amitriptyline, amoxapine, clomipramine, desipramine, doxepin, imipramine, nortriptyline, protriptyline, or trimipramine. The effects or levels of the following are also increased: bepridil, clarithromycin, diltiazem, irinotecan, sirolimus and sunitinib. Increased risk of hyperbilirubinemia exists when indinavir and atazanavir are taken together.

External Links

• Atazanavir - FDA approved drug information (drug label) from DailyMed (U.S. National Library of Medicine).
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