Atazanavir | CAS #198904-31-3 | HIV Protease Inhibitor | Antiretroviral Drug

MedKoo Cat#: 317254 | Name: Atazanavir

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Description:

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

Atazanavir is an antiretroviral drug of the protease inhibitor (PI) class. It is sold under the trade name Reyataz. Like other antiretrovirals, it is used to treat infection of human immunodeficiency virus. Atazanavir is distinguished from other PIs in that it can be given once-daily and has lesser effects on the patient's lipid profile. Like other protease inhibitors, it is used only in combination with other HIV medications.

Chemical Structure

Atazanavir

CAS#198904-31-3 (free base)

Theoretical Analysis

MedKoo Cat#: 317254

Name: Atazanavir

CAS#: 198904-31-3 (free base)

Chemical Formula: C38H52N6O7

Exact Mass: 704.3898

Molecular Weight: 704.86

Elemental Analysis: C, 64.75; H, 7.44; N, 11.92; O, 15.89

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
200mg	USD 450.00	2 Weeks
500mg	USD 850.00	2 Weeks
1g	USD 1,450.00	2 Weeks
2g	USD 2,250.00	2 Weeks
5g	USD 4,050.00	2 Weeks

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Related CAS #

229975-97-7 (sulfate) 198904-31-3 (free base)

Synonym

Atazanavir; Latazanavir; Zrivada; Reyataz; BMS-232632; BMS232632; BMS 232632; CGP 73547; CGP73547; CGP-73547

IUPAC/Chemical Name

methyl N-[(2S)-1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-4-phenylbutyl]-2-[(4-pyridin-2-ylphenyl)methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate

InChi Key

AXRYRYVKAWYZBR-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

CC(C)(C)C(C(=O)NC(CC1=CC=CC=C1)C(CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)C(C(C)(C)C)NC(=O)OC)O)NC(=O)OC

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, not in water

Shelf Life

>2 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

2934.99.9001

More Info

Related: 198904-31-3(Atazanavir) 229975-97-7(Atazanavir sulfate).

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Atazanavir (BMS-232632) is a highly selective HIV-1 protease inhibitor, inhibitor of CYP3A4, and an inhibitor and inducer of P-glycoprotein (P-gp).

In vitro activity:

After CoCl2-induced hypoxia, HLF-1 cell proliferation increased compared with the control group (p < 0.01) (fig. 4), but was significantly inhibited in a concentration-dependent manner after atazanavir sulphate treatment at concentrations between 1 and 10 μM compared with the CoCl2 group (p < 0.05). To further characterize this inhibitory effect, atazanavir sulphate treatment was combined with HCQ, a TLR-9 antagonist. However, this study found no further decline in HLF-1 proliferation compared with the HCQ group (p > 0.05) (fig. 4). Reference: Basic Clin Pharmacol Toxicol. 2018 Feb;122(2):199-207. https://pubmed.ncbi.nlm.nih.gov/28816009/

In vivo activity:

This study evaluated the effect of atazanavir on LVSP and ± dp/dtmax of the left ventricle after MI 28 days. Compared with vehicle-treated animals, rats treated with atazanavir had significantly improved LVSP, + dp/dtmax and − dp/dtmax 28 days after MI as shown in Table 2. In addition, this study found no further change in SP, DP and HR compared with the HCQ group (P > 0.05). It is clear that continuous atazanavir treatment 28 days provided long-term benefits for the myocardial function recovery after MI. Reference: Eur J Pharmacol. 2018 Jun 5;828:97-102. https://pubmed.ncbi.nlm.nih.gov/29605419/

	Solvent	mg/mL	mM
Solubility
	DMSO	38.0	53.91
	DMF	0.0	35.47
	DMF:PBS (pH 7.2) (1:8)	0.1	0.14
	Ethanol	13.0	18.44

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 704.86 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.

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

Formulation protocol:

1. Song S, Ji Y, Zhang G, Zhang X, Li B, Li D, Jiang W. Protective Effect of Atazanavir Sulphate Against Pulmonary Fibrosis In Vivo and In Vitro. Basic Clin Pharmacol Toxicol. 2018 Feb;122(2):199-207. doi: 10.1111/bcpt.12871. Epub 2017 Sep 6. PMID: 28816009. 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. PMID: 29605419.

In vitro protocol:

In vivo protocol:

1. 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. PMID: 29605419. 2. Song S, Ji Y, Zhang G, Zhang X, Li B, Li D, Jiang W. Protective Effect of Atazanavir Sulphate Against Pulmonary Fibrosis In Vivo and In Vitro. Basic Clin Pharmacol Toxicol. 2018 Feb;122(2):199-207. doi: 10.1111/bcpt.12871. Epub 2017 Sep 6. PMID: 28816009.

1: Goldsmith DR, Perry CM. Atazanavir. Drugs. 2003;63(16):1679-93; discussion 1694-5. doi: 10.2165/00003495-200363160-00003. PMID: 12904086. 2: Wood R. Atazanavir: its role in HIV treatment. Expert Rev Anti Infect Ther. 2008 Dec;6(6):785-96. doi: 10.1586/14787210.6.6.785. PMID: 19053892; PMCID: PMC3805961. 3: Antunes F. Atazanavir sulfate + cobicistat for the treatment of HIV infection. Expert Rev Anti Infect Ther. 2017 Jun;15(6):569-576. doi: 10.1080/14787210.2017.1323634. Epub 2017 May 9. PMID: 28443391. 4: Piliero PJ. Atazanavir: A novel once-daily protease inhibitor. Drugs Today (Barc). 2004 Nov;40(11):901-12. doi: 10.1358/dot.2004.40.11.872579. PMID: 15645003. 5: Santoriello D, Al-Nabulsi M, Reddy A, Salamera J, D'Agati VD, Markowitz GS. Atazanavir-Associated Crystalline Nephropathy. Am J Kidney Dis. 2017 Oct;70(4):576-580. doi: 10.1053/j.ajkd.2017.02.376. Epub 2017 Jun 2. PMID: 28579422. 6: Elgammal Y, Salama EA, Seleem MN. Atazanavir Resensitizes Candida auris to Azoles. Antimicrob Agents Chemother. 2023 May 17;67(5):e0163122. doi: 10.1128/aac.01631-22. Epub 2023 Apr 24. PMID: 37092991; PMCID: PMC10190639. 7: Busti AJ, Hall RG, Margolis DM. Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. doi: 10.1592/phco.24.17.1732.52347. PMID: 15585441. 8: Havlir DV, O'Marro SD. Atazanavir: new option for treatment of HIV infection. Clin Infect Dis. 2004 Jun 1;38(11):1599-604. doi: 10.1086/420932. Epub 2004 May 13. PMID: 15156449. 9: Becker S. Atazanavir: improving the HIV protease inhibitor class. Expert Rev Anti Infect Ther. 2003 Oct;1(3):403-13. doi: 10.1586/14787210.1.3.403. PMID: 15482137. 10: Raja A, Lebbos J, Kirkpatrick P. Atazanavir sulphate. Nat Rev Drug Discov. 2003 Nov;2(11):857-8. doi: 10.1038/nrd1232. PMID: 14702957. 11: Chang HR, Pella PM. Atazanavir urolithiasis. N Engl J Med. 2006 Nov 16;355(20):2158-9. doi: 10.1056/NEJMc061892. PMID: 17108352. 12: Paparizos VA, Kourkounti S, Leuow K, Kyriakis KP, Botsi C, Katsambas AD. Atazanavir-associated menorrhagia. Int J STD AIDS. 2007 Sep;18(9):651-2. doi: 10.1258/095646207781568637. PMID: 17785018. 13: Gammal RS, Court MH, Haidar CE, Iwuchukwu OF, Gaur AH, Alvarellos M, Guillemette C, Lennox JL, Whirl-Carrillo M, Brummel SS, Ratain MJ, Klein TE, Schackman BR, Caudle KE, Haas DW; Clinical Pharmacogenetics Implementation Consortium. Clinical Pharmacogenetics Implementation Consortium (CPIC) Guideline for UGT1A1 and Atazanavir Prescribing. Clin Pharmacol Ther. 2016 Apr;99(4):363-9. doi: 10.1002/cpt.269. Epub 2015 Nov 9. PMID: 26417955; PMCID: PMC4785051. 14: Momper JD, Wang J, Stek A, Shapiro DE, Powis KM, Paul ME, Badell ML, Browning R, Chakhtoura N, Denson K, Rungruengthanakit K, George K, Capparelli EV, Mirochnick M, Best BM; IMPAACT P1026s Protocol Team. Pharmacokinetics of Atazanavir Boosted With Cobicistat in Pregnant and Postpartum Women With HIV. J Acquir Immune Defic Syndr. 2022 Mar 1;89(3):303-309. doi: 10.1097/QAI.0000000000002856. PMID: 34732682; PMCID: PMC8837686. 15: Stephan C. Virological efficacy and safety of antiretroviral therapy-switch to atazanavir-based regimen: a review of the literature. Expert Opin Pharmacother. 2012 Nov;13(16):2355-67. doi: 10.1517/14656566.2012.734296. Epub 2012 Oct 10. PMID: 23050508. 16: Sethi S, Rana V. Atazanavir-Concentrate Loaded Soft Gelatin Capsule for Enhanced Concentration in Plasma, Brain, Spleen, and Lymphatics. AAPS PharmSciTech. 2022 Sep 28;23(7):270. doi: 10.1208/s12249-022-02428-0. PMID: 36171353. 17: Phillips M, Saxon C, Lee V. Atazanavir and chest pain. Int J STD AIDS. 2014 May;25(6):461-4. doi: 10.1177/0956462413506890. Epub 2013 Oct 9. PMID: 24108452. 18: Dorresteijn MJ, Dekker D, Zwaag J, Heemskerk S, Roelofs HMJ, Smits P, van der Hoeven JG, Wagener FADTG, Pickkers P. Atazanavir-induced unconjugated hyperbilirubinemia prevents vascular hyporeactivity during experimental human endotoxemia. Front Immunol. 2023 May 16;14:1176775. doi: 10.3389/fimmu.2023.1176775. PMID: 37261364; PMCID: PMC10228648. 19: Carey D, Amin J, Boyd M, Petoumenos K, Emery S. Lipid profiles in HIV- infected adults receiving atazanavir and atazanavir/ritonavir: systematic review and meta-analysis of randomized controlled trials. J Antimicrob Chemother. 2010 Sep;65(9):1878-88. doi: 10.1093/jac/dkq231. Epub 2010 Jun 16. PMID: 20554568. 20: Atazanavir: urolithiasis. Prescrire Int. 2014 Sep;23(152):214. PMID: 25325124.