Atazanavir A highly potent HIV-1 protease inhibitor

Atazanavir (CAS 198904-31-3)

Atazanavir | CAS 198904-31-3 is rated 5.0 out of 5 by 1.
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Synonym: BMS-232632; CGP-73547
Application: A highly potent HIV-1 protease inhibitor
CAS Number: 198904-31-3
Purity: ≥99%
Molecular Weight: 704.86
Molecular Formula: C38H52N6O7
* Refer to Certificate of Analysis for lot specific data (including water content).
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Atazanavir is a highly potent HIV-1 protease inhibitor. Has shown to be generally more potent than the five currently approved HIV-1 Prt inhibitors. Atazanavir (BMS-232632) inhibited the proteolytic cleavage of the viral gag precursor p55 polyprotein in a dose-dependent manner, with a EC 50 of approximately 47 nM. Also highly selective for HIV-1 Prt and exhibits cytotoxicity only at concentrations 6,500- to 23,000-fold higher than that required for anti-HIV activity. Atazanavir (BMS-232632) may be an effective HIV-1 inhibitor that may be utilized in a variety of different drug combinations.


References

Palella, F.J. Jr., et al.: N. Engl. J. Med., 338(13), 853 (1998), Nolan, D., et al.: Drugs, 63(23), 2555 (2003), Musial, B.L., et al.: Am. J. Health Syst. Pharm., 61, 1365 (2004), Wood, R., et al.: J. Acquir. Immune Defic. Syndr., 36, 684 (2004),

Physical State :
Solid
Solubility :
Soluble in methanol, ethanol (~2 mg/ml), DMSO (~16 mg/ml), DMF (~25 mg/ml), and DMF:PBS(pH 7.2) 1: 8 (~0.1 mg/ml).
Storage :
Store at -20° C
Melting Point :
207-209° C
Density :
~1.2 g/cm3 (Predicted)
Refractive Index :
n20D 1.56 (Predicted)
Optical Activity :
α20/D -47°, c = 1 in ethanol
IC50 :
HIV-1 protease: EC5050 = 2.6 nM; Human immunodeficiency virus 1: IC50 = 3 nM; MT4: IC50 = 25 nM (human); Human immunodeficiency virus type 1 reverse transcriptase: IC50 = 26 nM; Human immunodeficiency virus 2: IC50 = 30 nM; OATP8: IC50 = 0.4 µM (human)
pK Values :
pKa: 11.11 (Predicted), pKb: 4.65 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
148192
MDL Number :
MFCD08435966
SMILES :
CC(C)(C)[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)[C@H](C(C)(C)C)NC(=O)OC)O)NC(=O)OC

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Certificate of Analysis

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Atazanavir  Product Citations

See how others have used Atazanavir. Click on the entry to view the PubMed entry .

Citations 1 to 5 of 5 total

PMID: # 26189431  Mendonza, A. et al. 2016. J Clin Pharmacol. 56: 355-64.

PMID: # 27249967  Costa, S. et al. 2016. Parasitology research.

PMID: # 25815168  Hara, M. et al. 2015. Clin Kidney J. 8: 137-42.

PMID: # 23750830  Chang, JH. et al. 2013. Mol. Pharm. 10: 3067-75.

PMID: # 21068005  Leroyer, S. et al. 2011. J. Lipid Res. 52: 207-20.

Citations 1 to 5 of 5 total

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. Atazanavir, sc-207305, is a white crystalline powder.
Answered by: TechService7
Date published: 2017-12-08
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Rated 5 out of 5 by from Hresko Hresko, RC. et al. (PubMed 21966466) found that HIV protease inhibitors, such as Atazanavir, act as competitive inhibitors of the cytoplasmic glucose binding site of GLUTs with differing affinities for GLUT1 and GLUT4. -SCBT Publication Review
Date published: 2015-07-06
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