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MedKoo Cat#: 593009 | Name: Atazanavir sulfate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Atazanavir sulfate is an azapeptide and HIV-PROTEASE INHIBITOR that is used in the treatment of HIV INFECTIONS and AIDS in combination with other ANTI-HIV AGENTS.

Chemical Structure

Atazanavir sulfate
Atazanavir sulfate
CAS#229975-97-7 (sulfate)

Theoretical Analysis

MedKoo Cat#: 593009

Name: Atazanavir sulfate

CAS#: 229975-97-7 (sulfate)

Chemical Formula: C38H54N6O11S

Exact Mass: 0.0000

Molecular Weight: 802.94

Elemental Analysis: C, 56.84; H, 6.78; N, 10.47; O, 21.92; S, 3.99

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
50mg USD 400.00 2 Weeks
100mg USD 650.00 2 Weeks
250mg USD 1,250.00 2 Weeks
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Related CAS #
229975-97-7 (sulfate) 198904-31-3 (free base)
Synonym
Atazanavir sulfate
IUPAC/Chemical Name
2,5,6,10,13-Pentaazatetradecanedioic acid, 3,12-bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-((4-(2-pyridinyl)phenyl)methyl)-, dimethyl ester, (3S,8S,9S,12S)-, sulfate (1:1) (salt)
InChi Key
DQSGVVGOPRWTKI-QVFAWCHISA-N
InChi Code
InChI=1S/C38H52N6O7.H2O4S/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;1-5(2,3)4/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47);(H2,1,2,3,4)/t29-,30-,31+,32+;/m0./s1
SMILES Code
O=C(OC)N[C@@H](C(C)(C)C)C(NN(CC1=CC=C(C2=NC=CC=C2)C=C1)C[C@H](O)[C@H](CC3=CC=CC=C3)NC([C@H](C(C)(C)C)NC(OC)=O)=O)=O.O=S(O)(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 802.94 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kim B, Kim KS. Monomorphic ventricular tachycardia due to protease inhibitor intoxication by atazanavir. Clin Exp Emerg Med. 2018 Jun;5(2):131-134. doi: 10.15441/ceem.17.229. Epub 2018 Apr 30. PubMed PMID: 29706057; PubMed Central PMCID: PMC6039367. 2: Zhang G, Zhang X, Li D, Tian J, Jiang W. Long-term oral atazanavir attenuates myocardial infarction-induced cardiac fibrosis. Eur J Pharmacol. 2018 Jun 5;828:97-102. doi: 10.1016/j.ejphar.2018.03.041. Epub 2018 Mar 29. PubMed PMID: 29605419. 3: Pilalas D, Skoura L, Margariti A, Chatzopoulou F, Chatzidimitriou D, Tsachouridou O, Zebekakis P, Metallidis S, Papaioannou M. Prevalence and correlates of persistent intracellular HIV transcription in individuals on efavirenz versus atazanavir-based regimens: A prospective cohort study. PLoS One. 2018 Mar 13;13(3):e0194262. doi: 10.1371/journal.pone.0194262. eCollection 2018. PubMed PMID: 29534103; PubMed Central PMCID: PMC5849343. 4: Colella E, Cattaneo D, Galli L, Baldelli S, Clementi E, Galli M, Lazzarin A, Castagna A, Rusconi S, Spagnuolo V. Potential associations between atazanavir exposure and clinical outcome: a pharmacokinetic sub-study from the MODAt randomized trial. New Microbiol. 2018 Apr;41(2):106-111. Epub 2018 Mar 2. PubMed PMID: 29498742. 5: Dey S, Subhasis Patro S, Suresh Babu N, Murthy PN, Panda SK. Development and validation of a stability-indicating RP-HPLC method for estimation of atazanavir sulfate in bulk. J Pharm Anal. 2017 Apr;7(2):134-140. doi: 10.1016/j.jpha.2013.12.002. Epub 2013 Dec 31. PubMed PMID: 29404029; PubMed Central PMCID: PMC5686860. 6: Mantripragada MKVVN, Rao SV, Nutulapati VVS, Mantena BPV. Simultaneous Determination of Impurities of Atazanavir and Ritonavir in Tablet Dosage Form by Using Reversed-Phase Ultra Performance Liquid Chromatographic Method. J Chromatogr Sci. 2018 Mar 1;56(3):270-284. doi: 10.1093/chromsci/bmx110. PubMed PMID: 29300835. 7: Nzuza S, Zondi S, Owira PMO. Naringin prevents HIV-1 protease inhibitors-induced metabolic complications in vivo. PLoS One. 2017 Nov 9;12(11):e0183355. doi: 10.1371/journal.pone.0183355. eCollection 2017. PubMed PMID: 29121676; PubMed Central PMCID: PMC5679664. 8: Leger P, Chirwa S, Nwogu JN, Turner M, Richardson DM, Baker P, Leonard M, Erdem H, Olson L, Haas DW. Race/ethnicity difference in the pharmacogenetics of bilirubin-related atazanavir discontinuation. Pharmacogenet Genomics. 2018 Jan;28(1):1-6. doi: 10.1097/FPC.0000000000000316. PubMed PMID: 29117017; PubMed Central PMCID: PMC5726942. 9: Perrier M, Visseaux B, Landman R, Joly V, Todesco E, Yazdanpanah Y, Calvez V, Marcelin AG, Descamps D, Charpentier C. No impact of HIV-1 protease minority resistant variants on the virological response to a first-line PI-based regimen containing darunavir or atazanavir. J Antimicrob Chemother. 2018 Jan 1;73(1):173-176. doi: 10.1093/jac/dkx366. PubMed PMID: 29077926. 10: Beckman JA, Wood BR, Ard KL, Price CN, Solomon DA, Zuflacht JP, Milian J, Prenner JC, Sax PE. Conflicting effects of atazanavir therapy on atherosclerotic risk factors in stable HIV patients: A randomized trial of regimen switch to atazanavir. PLoS One. 2017 Oct 12;12(10):e0181993. doi: 10.1371/journal.pone.0181993. eCollection 2017. PubMed PMID: 29023508; PubMed Central PMCID: PMC5638209. 11: Caniglia EC, Phillips A, Porter K, Sabin CA, Winston A, Logan R, Gill J, Vandenhende MA, Barger D, Lodi S, Moreno S, Arribas JR, Pacheco A, Cardoso SW, Chrysos G, Gogos C, Abgrall S, Costagliola D, Meyer L, Seng R, van Sighem A, Reiss P, Muga R, Hoyos SP, Braun D, Hauser C, Barrufet P, Leyes M, Tate J, Justice A, Hernán MA. Commonly Prescribed Antiretroviral Therapy Regimens and Incidence of AIDS-Defining Neurological Conditions. J Acquir Immune Defic Syndr. 2018 Jan 1;77(1):102-109. doi: 10.1097/QAI.0000000000001562. PubMed PMID: 28991888; PubMed Central PMCID: PMC5720915. 12: Focà E, Calcagno A, Bonito A, Simiele M, Domenighini E, D'Avolio A, Quiros Roldan E, Trentini L, Casari S, Di Perri G, Castelli F, Bonora S. Atazanavir intracellular concentrations remain stable during pregnancy in HIV-infected patients. J Antimicrob Chemother. 2017 Nov 1;72(11):3163-3166. doi: 10.1093/jac/dkx274. PubMed PMID: 28961777. 13: Pearson-Leary J, Jahagirdar V, Sage J, McNay EC. Insulin modulates hippocampally-mediated spatial working memory via glucose transporter-4. Behav Brain Res. 2018 Feb 15;338:32-39. doi: 10.1016/j.bbr.2017.09.033. Epub 2017 Sep 21. PubMed PMID: 28943428; PubMed Central PMCID: PMC5681878. 14: Patel S, Leibrand CR, Palasuberniam P, Couraud PO, Weksler B, Jahr FM, McClay JL, Hauser KF, McRae M. Effects of HIV-1 Tat and Methamphetamine on Blood-Brain Barrier Integrity and Function In Vitro. Antimicrob Agents Chemother. 2017 Nov 22;61(12). pii: e01307-17. doi: 10.1128/AAC.01307-17. Print 2017 Dec. PubMed PMID: 28893794; PubMed Central PMCID: PMC5700307. 15: LaFleur J, Bress AP, Rosenblatt L, Crook J, Sax PE, Myers J, Ritchings C. Cardiovascular outcomes among HIV-infected veterans receiving atazanavir. AIDS. 2017 Sep 24;31(15):2095-2106. doi: 10.1097/QAD.0000000000001594. PubMed PMID: 28692532; PubMed Central PMCID: PMC5603981. 16: Ongubo DM, Lim R, Tweya H, Stanley CC, Tembo P, Broadhurst R, Gugsa S, Ngongondo M, Speight C, Heller T, Phiri S, Hosseinipour MC. A cross-sectional study to evaluate second line virological failure and elevated bilirubin as a surrogate for adherence to atazanavir/ritonavir in two urban HIV clinics in Lilongwe, Malawi. BMC Infect Dis. 2017 Jul 3;17(1):461. doi: 10.1186/s12879-017-2528-0. PubMed PMID: 28673254; PubMed Central PMCID: PMC5496231. 17: Barzi M, Pankowicz FP, Zorman B, Liu X, Legras X, Yang D, Borowiak M, Bissig-Choisat B, Sumazin P, Li F, Bissig KD. A novel humanized mouse lacking murine P450 oxidoreductase for studying human drug metabolism. Nat Commun. 2017 Jun 28;8(1):39. doi: 10.1038/s41467-017-00049-x. Erratum in: Nat Commun. 2017 Oct 17;8(1):984. PubMed PMID: 28659616; PubMed Central PMCID: PMC5489481. 18: Tseng A, Hughes CA, Wu J, Seet J, Phillips EJ. Cobicistat Versus Ritonavir: Similar Pharmacokinetic Enhancers But Some Important Differences. Ann Pharmacother. 2017 Nov;51(11):1008-1022. doi: 10.1177/1060028017717018. Epub 2017 Jun 19. Review. PubMed PMID: 28627229; PubMed Central PMCID: PMC5702580. 19: Metsu D, Toutain PL, Chatelut E, Delobel P, Gandia P. Antiretroviral unbound concentration during pregnancy: piece of interest in the puzzle? J Antimicrob Chemother. 2017 Sep 1;72(9):2407-2409. doi: 10.1093/jac/dkx176. PubMed PMID: 28595364. 20: Svärd J, Mugusi S, Mloka D, Neogi U, Meini G, Mugusi F, Incardona F, Zazzi M, Sönnerborg A. Drug resistance testing through remote genotyping and predicted treatment options in human immunodeficiency virus type 1 infected Tanzanian subjects failing first or second line antiretroviral therapy. PLoS One. 2017 Jun 5;12(6):e0178942. doi: 10.1371/journal.pone.0178942. eCollection 2017. PubMed PMID: 28582463; PubMed Central PMCID: PMC5459473.