sulfuric acid 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

• ChemBase ID: 72896
• Molecular Formular: C38H54N6O11S
• Molecular Mass: 802.93396
• Monoisotopic Mass: 802.35712758
• SMILES: O(C(=O)N[C@H](C(=O)N[C@H]([C@H](CN(NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)Cc1ccc(cc1)c1ncccc1)O)Cc1ccccc1)C(C)(C)C)C.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.COC(=O)N[C@@H](C(C)(C)C)C(=O)NN(Cc1ccc(cc1)c1ccccn1)C[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)(C)C)NC(=O)OC)O
• InChI: 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
• InChIKey: DQSGVVGOPRWTKI-QVFAWCHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid 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; sulfuric acid methyl N-[(1S)-1-{N'-[(2S,3S)-2-hydroxy-3-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanamido]-4-phenylbutyl]-N'-{[4-(pyridin-2-yl)phenyl]methyl}hydrazinecarbonyl}-2,2-dimethylpropyl]carbamate
• IUPAC Traditional name: atazanavir; sulfuric acid; sulfuric acid methyl N-[(1S)-1-{N'-[(2S,3S)-2-hydroxy-3-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanamido]-4-phenylbutyl]-N'-{[4-(pyridin-2-yl)phenyl]methyl}hydrazinecarbonyl}-2,2-dimethylpropyl]carbamate
• Synonyms: BMS-232632-05; CGP-73547; Reyataz; Zrivada; Atazanavir sulfate

Database IDs

• CAS Number: 229975-97-7
• MDL Number: MFCD08067748
• PubChem SID: 162037816
• PubChem CID: 158550

CALCULATED PROPERTIES

• Acid pKa: 11.919422
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 4.5060835
• LogD (pH = 7.4): 4.5393934
• Log P: 4.5398483
• Molar Refractivity: 191.8025 cm^3
• Polarizability: 76.91037 Å^3
• Polar Surface Area: 171.22 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: HIV protease

Product Information

• Purity: 95+%
• Salt Data: Sulfate

DETAILS

Selleck Chemicals - S2204

Research Area: Cancer
Biological Activity:
Atazanavir is an antiretroviral drug of the protease inhibitor (PI) class. Like other antiretrovirals, it is used to treat infection of human immunodeficiency virus (HIV). Atazanavir is distinguished from other PIs in that it can be given once-daily (rather than requiring multiple doses per day) and has lesser effects on the patient’s lipid profile (the amounts of cholesterol and other fatty substances in the blood). Like other protease inhibitors, it is used only in combination with other HIV medications. [1]

REFERENCES

• Xu et al. Org Proc Res Dev, 2002, 6 (3): 323–328