Atazanavir

Atazanavir
Clinical data
Pronunciation	/ˌætəˈzænəvɪər/ AT-ə-ZAN-ə-veer
Trade names	Reyataz, Evotaz, others
AHFS/Drugs.com	Monograph
MedlinePlus	a603019
License data	US DailyMed: Atazanavir;
Pregnancy; category	AU: B2;
Routes of; administration	By mouth
ATC code	J05AE08 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	60-68%
Protein binding	86%
Metabolism	Liver (CYP3A4-mediated)
Elimination 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 ;
PubChem CID	148192;
DrugBank	DB01072 ;
ChemSpider	130642 ;
UNII	QZU4H47A3S;
KEGG	D01276 ; D07471 ;
ChEBI	CHEBI:37924 ;
ChEMBL	ChEMBL1163 ;
NIAID ChemDB	057755;
CompTox Dashboard (EPA)	DTXSID9048691 ;
ECHA InfoCard	100.243.594
Chemical and physical data
Formula	C38H52N6O7
Molar mass	704.869 g·mol−1
3D model (JSmol)	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 ; Key:AXRYRYVKAWYZBR-GASGPIRDSA-N ;
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Atazanavir, sold under the brand name Reyataz among others, is an antiretroviral medication used to treat 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 (postexposure prophylaxis (PEP)). It is taken by mouth.

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. It is available as a generic medication.

Clinical data


Pronunciation	/ˌætəˈzænəvɪər/ AT-ə-ZAN-ə-veer
Trade names	Reyataz, Evotaz, others
AHFS/Drugs.com	Monograph
MedlinePlus	a603019
License data	US DailyMed: Atazanavir
Pregnancy category	AU: B2
Routes of administration	By mouth
ATC code	J05AE08 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only EU: Rx-only
Pharmacokinetic data
Bioavailability	60-68%
Protein binding	86%
Metabolism	Liver (CYP3A4-mediated)
Elimination 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
KEGG	D01276^N D07471^N
ChEBI	CHEBI:37924^Y
ChEMBL	ChEMBL1163^Y
NIAID ChemDB	057755
CompTox Dashboard (EPA)	DTXSID9048691
ECHA InfoCard	100.243.594
Chemical and physical data
Formula	C₃₈H₅₂N₆O₇
Molar mass	704.869 g·mol⁻¹
3D model (JSmol)	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
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