Atazanavir

Atazanavir

Clinical data
Pronunciation	/ˌæ.tə.ˈzæ.nə.vɪər/, A-tə-ZA-nə-vir
Trade names	Reyataz, Evotaz, others
AHFS/Drugs.com	Monograph
MedlinePlus	a603019
Pregnancy category	AU: B2 US: B (No risk in non-human studies)
Routes of administration	By mouth
ATC code	J05AE08 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	60-68%
Protein binding	86%
Metabolism	Liver (CYP3A4-mediated)
Biological half-life	6.5 hours
Excretion	Fecal and kidney
Identifiers
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
CAS Number	198904-31-3 Y
PubChem (CID)	148192
DrugBank	DB01072 Y
ChemSpider	130642 Y
UNII	QZU4H47A3S Y
KEGG	D01276 N
ChEBI	CHEBI:37924 Y
ChEMBL	CHEMBL1163 Y
NIAID ChemDB	057755
Chemical and physical data
Formula	C38H52N6O7
Molar mass	704.856 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(OC)N[C@H](C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)Cc3ccc(c2ncccc2)cc3)C(C)(C)C
InChI InChI=1S/C38H52N6O7/c1-37(2,3)31(41-35(48)50-7)33(46)40-29(22-25-14-10-9-11-15-25)30(45)24-44(43-34(47)32(38(4,5)6)42-36(49)51-8)23-26-17-19-27(20-18-26)28-16-12-13-21-39-28/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47)/t29-,30-,31+,32+/m0/s1 Y Key:AXRYRYVKAWYZBR-GASGPIRDSA-N Y
NY (what is this?)

Atazanavir, sold under the trade name Reyataz among others, is an antiretroviral medication used to treat and prevent HIV/AIDS. It is generally recommended for use with other antiretrovirals. It may be used for prevention after a needlestick injury or other potential exposure. It is taken by mouth once a day.

Common side effects include headache, nausea, yellowish skin, abdominal pain, trouble sleeping, and fever. Severe side effects include rashes such as erythema multiforme and high blood sugar. Atazanavir appears to be safe to use during pregnancy. It is of the protease inhibitor (PI) class and works by blocking HIV protease.

Atazanavir was approved for medical use in the United States in 2003. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. In the United States it is not available as a generic medication. The wholesale cost in the developing world is about 15.72 USD per month. As of 2015, the cost for a typical month of medication in the United States was more than 200 USD.

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.

Atazanavir is distinguished from other PIs in that it has lesser effects on lipid profile and appears to be less likely to cause lipodystrophy. There may be some cross-resistant with other PIs. When boosted with ritonavir it is equivalent in potency to lopinavir for use in salvage therapy in people with a degree of drug resistance, although boosting with ritonavir reduces the metabolic advantages of atazanavir.