methyl N-[(1S)-1-{N'-[(2S,3S)-2-hydroxy-3-[(2S)-2-[(methoxycarbonyl)amino]-3,3-bis(2H3)methyl(4,4,4-2H3)butanamido]-4-phenylbutyl]-N'-{[4-(pyridin-2-yl)phenyl]methyl}hydrazinecarbonyl}-2,2-bis(2H3)methyl(3,3,3-2H3)propyl]carbamate

• ChemBase ID: 73297
• Molecular Formular: C38H52N6O7
• Molecular Mass: 704.85548
• Monoisotopic Mass: 704.38974803
• SMILES: C(=O)(N[C@H](C(=O)NN(C[C@@H]([C@@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)Cc1ccccc1)O)Cc1ccc(cc1)c1ccccn1)C(C)(C)C)OC
• Canonical SMILES: 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/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
• InChIKey: AXRYRYVKAWYZBR-GASGPIRDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl N-[(1S)-1-{N'-[(2S,3S)-2-hydroxy-3-[(2S)-2-[(methoxycarbonyl)amino]-3,3-bis(^2H₃)methyl(4,4,4-^2H₃)butanamido]-4-phenylbutyl]-N'-{[4-(pyridin-2-yl)phenyl]methyl}hydrazinecarbonyl}-2,2-bis(^2H₃)methyl(3,3,3-^2H₃)propyl]carbamate
• IUPAC Traditional name: methyl N-[(1S)-1-{N'-[(2S,3S)-2-hydroxy-3-[(2S)-2-[(methoxycarbonyl)amino]-3,3-bis(^2H₃)methyl(4,4,4-^2H₃)butanamido]-4-phenylbutyl]-N'-{[4-(pyridin-2-yl)phenyl]methyl}hydrazinecarbonyl}-2,2-bis(^2H₃)methyl(3,3,3-^2H₃)propyl]carbamate
• Synonyms: Deuterated Atazanivir-D3-3

Database IDs

• CAS Number: 1092540-52-7
• PubChem SID: 162038217
• PubChem CID: 25145277

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

DETAILS

Selleck Chemicals - S3011

Research Area

• Description: Infection

Biological Activity

• Description: Atazanivir-D3-3 is a azapeptide derivative and inhibits HIV protease.
• Targets: HIV protease
• In Vitro: Atazanivir-D3-3 is an azapeptide derivative and a HIV protease inhibitor. Atazanivir-D3-3 is a deuterium-containing agent with ameliorated ADME properties. ^[1] Atazanivir-D3-3 displays a significantly longer half life, at almost 46% than atazanavir when co-dosed in chimps. Atazanavir sulfate prevents the formation of mature HIV virions in HIV-1 infected cells by selectively inhibiting the virus-specific processing of certain polyproteins (viral Gag and Gag-Pol). Atazanavir sulfate is currently approved for the treatment of HIV infection.^[1] Atazanavir is contraindicated for co-administration with medicines that are highly dependent on CYP3A for clearance and for which elevated plasma concentrations are associated with serious and/or life-threatening events. Due to inhibitory effects of atazanavir on CYP3A, CYP2C8, and UGTIAl, caution is advised when prescribing. Common adverse events associated with atazanavir include hyperbilirubinemia, rash, nausea, headache, mid jaundice/sclcral icterus. ^[1]

References

• References: [1] Harbeson, S.L., et al. Eur. Pat. Appl. 2008, 59 pp. EP 2003120 A1 20081217.

REFERENCES

• Harbeson, S.L., et al. Eur. Pat. Appl. 2008, 59 pp. EP 2003120 A1 20081217.