Atazanavir
180px | |
220px | |
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 | |
Pronunciation | /ˌæ.tə.ˈzæ.nə.vɪər/, A-tə-ZA-nə-vir[1] |
AHFS/Drugs.com | monograph |
MedlinePlus | a603019 |
Pregnancy category |
|
Legal status | |
Routes of administration |
Oral |
Pharmacokinetic data | |
Bioavailability | 60-68% |
Protein binding | 86% |
Metabolism | Hepatic (CYP3A4-mediated) |
Biological half-life | 6.5 hours |
Excretion | Fecal and renal |
Identifiers | |
CAS Number | 198904-31-3 |
ATC code | J05AE08 (WHO) |
PubChem | CID: 148192 |
DrugBank | DB01072 |
ChemSpider | 130642 |
UNII | QZU4H47A3S |
KEGG | D01276 |
ChEBI | CHEBI:37924 |
ChEMBL | CHEMBL1163 |
NIAID ChemDB | 057755 |
Chemical data | |
Formula | C38H52N6O7 |
Molecular mass | 704.856 g/mol |
|
|
|
|
(what is this?) (verify) |
Atazanavir, sold under the trade name Reyataz, 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 equivalent in 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.
It is on the World Health Organization's List of Essential Medicines, the most important medication needed in a basic health system.[2]
Contents
Medical uses
Atazanavir is used in the treatment of HIV. The efficacy of atazanavir has been assessed in a number of well designed trials in ART-naive and ART-experienced adults.[3]
Adverse effects
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] Atazanavir has less effect on glucose levels than ritonavir.
Contraindications
In April 2009, the US 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 through plasma concentration (Cmin) were observed when Reyataz/ritonavir [another protease inhibitor, often prescribed with azatanavir] 300/100 mg was coadministered with omeprazole 40 mg."[5] In other words, proton pump inhibitors reduce the absorption and effects of atazanavir due to their effect in decreasing stomach acidity.
Chemistry
Lua error in package.lua at line 80: module 'strict' not found.
Society and culture
On October 20, 2006, the FDA approved a new formulation of atazanavir (300 mg capsules) to be taken as part of combination drug therapy.[6] This formulation should reduce pill burden, as one 300 mg capsule may replace two 150 mg capsules.
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.