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.^[2] It is generally recommended for use with other antiretrovirals.^[2] It may be used for prevention after a needlestick injury or other potential exposure (postexposure prophylaxis (PEP)).^[2] It is taken by mouth.^[2]

Common side effects include headache, nausea, yellowish skin, abdominal pain, trouble sleeping, and fever.^[2] Severe side effects include rashes such as erythema multiforme and high blood sugar.^[2] Atazanavir appears to be safe to use during pregnancy.^[2] It is of the protease inhibitor (PI) class and works by blocking HIV protease.^[2]

Atazanavir was approved for medical use in the United States in 2003.^[2] It is on the World Health Organization's List of Essential Medicines.^[8] It is available as a generic medication.^[9]

^ "Atazanavir". MedlinePlus. National Institutes of Health. 15 October 2012. Archived from the original on 2 August 2013. Retrieved 3 August 2013.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Atazanavir Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 28 November 2016.
^ "Atazanavir (Reyataz) Use During Pregnancy". Drugs.com. 27 February 2020. Archived from the original on 1 October 2022. Retrieved 15 September 2020.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 6 July 2023. Retrieved 30 March 2024.
^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Archived from the original on 29 March 2024. Retrieved 3 April 2024.
^ "Reyataz- atazanavir capsule, gelatin coated; Reyataz- atazanavir powder". DailyMed. 7 November 2023. Retrieved 17 October 2024.
^ "Reyataz EPAR". European Medicines Agency (EMA). 2 March 2004. Archived from the original on 3 December 2023. Retrieved 25 May 2024.
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
^ "Teva Announces Exclusive Launch of a Generic Version of Reyataz in the United States" (Press release). Teva. 27 December 2017. Archived from the original on 4 October 2022. Retrieved 29 September 2021 – via Business Wire.

[1] "Atazanavir". MedlinePlus. National Institutes of Health. 15 October 2012. Archived from the original on 2 August 2013. Retrieved 3 August 2013.

[AHFS2016-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Atazanavir Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 28 November 2016.

[Drugs.com_pregnancy-3] "Atazanavir (Reyataz) Use During Pregnancy". Drugs.com. 27 February 2020. Archived from the original on 1 October 2022. Retrieved 15 September 2020.

[4] "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 6 July 2023. Retrieved 30 March 2024.

[5] "Product monograph brand safety updates". Health Canada. 7 July 2016. Archived from the original on 29 March 2024. Retrieved 3 April 2024.

[Reyataz_FDA_label-6] "Reyataz- atazanavir capsule, gelatin coated; Reyataz- atazanavir powder". DailyMed. 7 November 2023. Retrieved 17 October 2024.

[7] "Reyataz EPAR". European Medicines Agency (EMA). 2 March 2004. Archived from the original on 3 December 2023. Retrieved 25 May 2024.

[WHO23rd-8] World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

[9] "Teva Announces Exclusive Launch of a Generic Version of Reyataz in the United States" (Press release). Teva. 27 December 2017. Archived from the original on 4 October 2022. Retrieved 29 September 2021 – via Business Wire.

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