4-{2-[(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl}(2H4)benzonitrile

• ChemBase ID: 171755
• Molecular Formular: C22H17F2N5OS
• Molecular Mass: 437.4650864
• Monoisotopic Mass: 437.11218763
• SMILES: c1c(ccc(c1)c1csc(n1)[C@@H]([C@](Cn1cncn1)(c1c(ccc(c1)F)F)O)C)C#N
• Canonical SMILES: N#Cc1ccc(cc1)c1csc(n1)[C@@H]([C@@](c1cc(F)ccc1F)(Cn1cncn1)O)C
• InChI: InChI=1S/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-8-17(23)6-7-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1
• InChIKey: DDFOUSQFMYRUQK-RCDICMHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-[(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl}(^2H₄)benzonitrile
• IUPAC Traditional name: 4-{2-[(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl}(^2H₄)benzonitrile
• Synonyms: 4-[2-[(1R,2R)-2-(2,5-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile-d4; 2R,3R)-3-[4-(4-Cyanophenyl)thiazol-2-yl]-2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol-d4; BAL 4815-d4; RO 0094815-d4; Isavuconazole-d4

Database IDs

• PubChem SID: 164227665
• PubChem CID: 71749534

CALCULATED PROPERTIES

• Acid pKa: 12.6067095
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.143128
• LogD (pH = 7.4): 4.1434927
• Log P: 4.1435003
• Molar Refractivity: 123.9407 cm^3
• Polarizability: 43.196156 Å^3
• Polar Surface Area: 87.62 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I777832

Labelled Isavuconazole (I777832). It is a new triazole currently undergoing phase III clinical trials. This compound has shown in vitro activity against a large number of clinical important yeasts and molds including Aspergillus spp., Fusarium spp., Scedo

REFERENCES

• Ohwada, J., et al.: Bioorg. Med. Chem. Lett., 13, 191 (2003)
• Guinea, J., et al.: Antimicrob. Agents Chemother., 52, 1396 (2008)