| Systematic (IUPAC) name | |
|---|---|
| methyl N-[(1S)-1-{[(2S,3S)-3-hydroxy-4-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-N'-{[4-(pyridin-2-yl)phenyl]methyl}butanehydrazido]-1-phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate | |
| Clinical data | |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a603019 |
| Pregnancy cat. | B2(AU) B(US) |
| Legal status | POM (UK) ℞-only (US) |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | 60-68% |
| Protein binding | 86% |
| Metabolism | Hepatic (CYP3A4-mediated) |
| Half-life | 6.5 hours |
| Excretion | Fecal and renal |
| Identifiers | |
| CAS number | 198904-31-3 |
| ATC code | J05AE08 |
| PubChem | CID 148192 |
| DrugBank | APRD00804 |
| ChemSpider | 130642 |
| UNII | QZU4H47A3S |
| KEGG | D01276 |
| ChEBI | CHEBI:37924 |
| ChEMBL | CHEMBL1163 |
| Chemical data | |
| Formula | C38H52N6O7 |
| Mol. mass | 704.856 g/mol |
| SMILES | eMolecules & PubChem |
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Atazanavir, marketed under the trade name Reyataz by Bristol Myers, (formerly known as BMS-232632) is an antiretroviral drug of the protease inhibitor (PI) class. Like other antiretrovirals, it is used to treat infection of human immunodeficiency virus (HIV).
Atazanavir is distinguished from other PIs in that it can be given once-daily (rather than requiring multiple doses per day) and has lesser effects on the patient's lipid profile (the amounts of cholesterol and other fatty substances in the blood). Like other protease inhibitors, it is used only in combination with other HIV medications.
The U.S. Food and Drug Administration (FDA) approved atazanavir on June 20, 2003. Atazanavir is the first PI approved for once-daily dosing, and also appears to be less likely to cause lipodystrophy and elevated cholesterol as side effects. It may also not be cross-resistant with other PIs. When boosted with ritonavir it is of equivalent potency to lopinavir for use in salvage therapy in patients with a degree of drug resistance; although boosting with ritonavir reduces the metabolic advantages of atazanavir.
On October 20, 2006, the FDA approved a new formulation of atazanavir (300 mg capsules) to be taken as part of combination drug therapy.[1] This formulation should reduce pill burden, as one 300 mg capsule may replace two 150 mg capsules.
Newer research has been investigating the potential anticancer effects of atazanavir. For example, laboratory studies have found that this drug can inhibit the growth of brain tumor cells in culture.[2]
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The efficacy of atazanavir has been assessed in a number of well designed trials in ART-naive and ART-experienced adults.[3]
Bilirubin levels in the blood are normally asymptomatically raised with atazanavir. A single case of torsades de pointes attributable to atazanavir therapy has been described.[4]
CONTRAINDICATIONS: In April 2009, the FDA issued a warning: Atazanavir should not be used with proton pump inhibitors, such as omeprazole (Prilosec), esomeprazole (Nexium), or rabeprazole (Aciphex). According to the FDA, "A 76% reduction in atazanavir area under the concentration-time curve (AUC) and a 78% reduction in atazanavir trough plasma concentration (Cmin) were observed when REYATAZ/ritonavir [a protease inhibitor, the same class as Azatanavir] 300/100 mg was coadministered with omeprazole 40 mg." In other words, proton pump inhibitors reduce the effects of atazanavir.
For more information, visit: http://www.fda.gov/ForConsumers/ByAudience/ForPatientAdvocates/HIVandAIDSActivities/ucm124940.htm
Bold, Guido; Fässler, Alexander; Capraro, Hans-Georg; Cozens, Robert; Klimkait, Thomas; Lazdins, Janis; Mestan, JüRgen; Poncioni, Bernard et al. (1998). "New Aza-Dipeptide Analogues as Potent and Orally Absorbed HIV-1 Protease Inhibitors: Candidates for Clinical Development". Journal of Medicinal Chemistry 41 (18): 3387. doi:10.1021/jm970873c. PMID 9719591.