(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

• ChemBase ID: 154598
• Molecular Formular: C16H14F3N5O
• Molecular Mass: 349.3104696
• Monoisotopic Mass: 349.11504475
• SMILES: C[C@@H](c1c(cncn1)F)[C@](Cn1cncn1)(c1ccc(cc1F)F)O
• Canonical SMILES: Fc1ccc(c(c1)F)[C@]([C@H](c1ncncc1F)C)(Cn1cncn1)O
• InChI: InChI=1S/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/m0/s1
• InChIKey: BCEHBSKCWLPMDN-MGPLVRAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
• IUPAC Traditional name: voriconazole
• Synonyms: 2R,3S-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol; UK-109496; Voriconazole; (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Database IDs

• CAS Number: 137234-62-9
• MDL Number: MFCD00905717
• PubChem SID: 162248736
• PubChem CID: 71616

CALCULATED PROPERTIES

• Acid pKa: 12.708208
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.8227984
• LogD (pH = 7.4): 1.8230275
• Log P: 1.8230326
• Molar Refractivity: 95.278 cm^3
• Polarizability: 30.730742 Å^3
• Polar Surface Area: 76.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white powder
• Hydrophobicity(logP): 0.523

Safety Information

• RTECS: UV9145000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 61-25-40-48/22-52/53
• Safety Statements: 53-22-36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H351-H361-H373-H412
• GHS Precautionary statements: P273-P281-P301 + P310
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC); 95%
• Empirical Formula (Hill Notation): C16H14F3N5O

DETAILS

Sigma Aldrich - PZ0005

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Voriconazole is an antifungal used to treat serious fungal infections. Voriconazole inhibits ergosterol synthesis by inhibiting CYP450-dependent 14-α sterol demethylase resulting in a depletion of ergosterol in fungal cell membranes.