4-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)(1,1,1-2H3)butan-2-yl]-5-fluoropyrimidin-1-ium-1-olate

• ChemBase ID: 179564
• Molecular Formular: C16H14F3N5O2
• Molecular Mass: 365.3098696
• Monoisotopic Mass: 365.10995937
• SMILES: C(C([C@@H](c1nc[n+](cc1F)[O-])C)(c1c(cc(cc1)F)F)O)n1cncn1
• Canonical SMILES: [O-][n+]1cnc(c(c1)F)[C@H](C(c1ccc(cc1F)F)(Cn1cncn1)O)C
• InChI: InChI=1S/C16H14F3N5O2/c1-10(15-14(19)5-24(26)9-21-15)16(25,6-23-8-20-7-22-23)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16-/m1/s1
• InChIKey: KPLFPLUCFPRUHU-QLJPJBMISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)(1,1,1-^2H₃)butan-2-yl]-5-fluoropyrimidin-1-ium-1-olate
• IUPAC Traditional name: 4-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)(1,1,1-^2H₃)butan-2-yl]-5-fluoropyrimidin-1-ium-1-olate
• Synonyms: (αR,βS)-α-(2,4-Difluorophenyl)-5-fluoro-β-methyl-d3-α-(1H-1,2,4-triazol-1-ylmethyl)-1-oxide-4-pyrimidineethanol; UK 121265-d3; Voriconazole-d3 N-Oxide

Database IDs

• PubChem SID: 164235474
• PubChem CID: 71752988

CALCULATED PROPERTIES

• Acid pKa: 12.681942
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.507465
• LogD (pH = 7.4): 0.5076904
• Log P: 0.50769556
• Molar Refractivity: 98.2788 cm^3
• Polarizability: 31.294016 Å^3
• Polar Surface Area: 89.29 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White Solid
• Melting Point: 67-69°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - V760012

A labelled metabolite of Voriconazole (V760000).

REFERENCES

• Sanati, H., et al.: Antimicrob. Ag. Chemother., 41, 2492 (1997)
• Geist, M., et al.: Antimicrob. Agents. Chemother., 50, 3227 (1997)
• Yamazaki, H., et al.: Drug. Metab. Dispos., 34, 1803 (1997)
• Yamazaki, H., et al.: Xenobiotica, 36, 1201 (1997)