4-{4-[4-(4-{[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy}phenyl)piperazin-1-yl](2H4)phenyl}-1-[(2S,3S)-2-hydroxypentan-3-yl]-4,5-dihydro-1H-1,2,4-triazol-5-one

• ChemBase ID: 176840
• Molecular Formular: C37H42F2N8O4
• Molecular Mass: 700.7773864
• Monoisotopic Mass: 700.3297083
• SMILES: c1c(ccc(c1)n1c(=O)n(nc1)[C@H]([C@@H](O)C)CC)N1CCN(CC1)c1ccc(cc1)OC[C@H]1C[C@](OC1)(Cn1ncnc1)c1c(cc(cc1)F)F
• Canonical SMILES: CC[C@H](n1ncn(c1=O)c1ccc(cc1)N1CCN(CC1)c1ccc(cc1)OC[C@@H]1CO[C@@](C1)(Cn1cncn1)c1ccc(cc1F)F)[C@@H](O)C
• InChI: InChI=1S/C37H42F2N8O4/c1-3-35(26(2)48)47-36(49)46(25-42-47)31-7-5-29(6-8-31)43-14-16-44(17-15-43)30-9-11-32(12-10-30)50-20-27-19-37(51-21-27,22-45-24-40-23-41-45)33-13-4-28(38)18-34(33)39/h4-13,18,23-27,35,48H,3,14-17,19-22H2,1-2H3/t26-,27+,35-,37-/m0/s1
• InChIKey: RAGOYPUPXAKGKH-XAKZXMRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{4-[4-(4-{[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy}phenyl)piperazin-1-yl](^2H₄)phenyl}-1-[(2S,3S)-2-hydroxypentan-3-yl]-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: 4-{4-[4-(4-{[(3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy}phenyl)piperazin-1-yl](^2H₄)phenyl}-2-[(2S,3S)-2-hydroxypentan-3-yl]-1,2,4-triazol-3-one
• Synonyms: 2,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-[[4-[4-[4-[1-[(1S,2S)-1-ethyl-2-hydroxypropyl]-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl]phenyl]-1-piperazinyl]phenoxy]methyl]-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol-d4; Noxafil-d4; Sch 56592-d4; Posaconazole-d4

Database IDs

• CAS Number: 1133712-26-1
• PubChem SID: 164232750
• PubChem CID: 25241315

CALCULATED PROPERTIES

• Acid pKa: 14.826501
• H Acceptors: 9
• H Donor: 1
• LogD (pH = 5.5): 5.394681
• LogD (pH = 7.4): 5.4060388
• Log P: 5.406185
• Molar Refractivity: 200.7058 cm^3
• Polarizability: 70.8201 Å^3
• Polar Surface Area: 111.79 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol (Sparingly)
• Apperance: Off-White Solid
• Melting Point: 164-167°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P689602

Orally active labelled triazole antifungal.

REFERENCES

• Cacciapuoti, A., et al.: Antimicrob. Agents Chemother., 44, 2017 (2000)
• Herbrecht, R., et al.: Int. J. Clin. Pract., 58, 612 (2000)
• Panackal, A., et al.: J. Clin. Microbiol., 44, 1740 (2000)