Atazanavir

Atazanavir
Clinical data
Pronunciation/ˌætəˈzænəvɪər/ AT-ə-ZAN-ə-veer[1]
Trade namesReyataz, Evotaz, others[2]
AHFS/Drugs.comMonograph
MedlinePlusa603019
License data
Pregnancy
category
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60-68%
Protein binding86%
MetabolismLiver (CYP3A4-mediated)
Elimination half-life6.5 hours
ExcretionFecal and kidney
Identifiers
  • 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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.243.594 Edit this at Wikidata
Chemical and physical data
FormulaC38H52N6O7
Molar mass704.869 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:AXRYRYVKAWYZBR-GASGPIRDSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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] As of 2017 there is a generic version available in the United States manufactured by Teva Pharmaceuticals[9]

  1. ^ "Atazanavir". MedlinePlus. National Institutes of Health. 15 October 2012. Archived from the original on 2 August 2013. Retrieved 3 August 2013.
  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.
  3. ^ "Atazanavir (Reyataz) Use During Pregnancy". Drugs.com. 27 February 2020. Archived from the original on 1 October 2022. Retrieved 15 September 2020.
  4. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  5. ^ "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.
  6. ^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Archived from the original on 29 March 2024. Retrieved 3 April 2024.
  7. ^ "Reyataz EPAR". European Medicines Agency (EMA). 2 March 2004. Archived from the original on 3 December 2023. Retrieved 25 May 2024.
  8. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  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.