4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-1-(3-oxobutan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one

• ChemBase ID: 172080
• Molecular Formular: C35H36Cl2N8O5
• Molecular Mass: 719.61694
• Monoisotopic Mass: 718.21857165
• SMILES: C1N(CCN(C1)c1ccc(cc1)OC[C@@H]1O[C@@](OC1)(Cn1ncnc1)c1c(cc(cc1)Cl)Cl)c1ccc(cc1)n1c(=O)n(nc1)C(C(=O)C)C
• Canonical SMILES: CC(=O)C(n1ncn(c1=O)c1ccc(cc1)N1CCN(CC1)c1ccc(cc1)OC[C@H]1CO[C@](O1)(Cn1cncn1)c1ccc(cc1Cl)Cl)C
• InChI: InChI=1S/C35H36Cl2N8O5/c1-24(25(2)46)45-34(47)44(23-40-45)29-6-4-27(5-7-29)41-13-15-42(16-14-41)28-8-10-30(11-9-28)48-18-31-19-49-35(50-31,20-43-22-38-21-39-43)32-12-3-26(36)17-33(32)37/h3-12,17,21-24,31H,13-16,18-20H2,1-2H3/t24?,31-,35-/m0/s1
• InChIKey: GZEZATDDANETAV-QQPVTLCMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-1-(3-oxobutan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: 4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2-(3-oxobutan-2-yl)-1,2,4-triazol-3-one
• Synonyms: rel-4-[4-[4-[4-[[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methyl-2-oxopropyl)-3H-1,2,4-triazol-3-one; keto-ITZ; Keto Itraconazole

Database IDs

• CAS Number: 112560-33-5
• PubChem SID: 164227990
• PubChem CID: 45039625

CALCULATED PROPERTIES

• Acid pKa: 18.479332
• H Acceptors: 10
• H Donor: 0
• LogD (pH = 5.5): 6.380625
• LogD (pH = 7.4): 6.391696
• Log P: 6.391839
• Molar Refractivity: 200.8382 cm^3
• Polarizability: 71.7092 Å^3
• Polar Surface Area: 117.86 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Off-White Solid
• Melting Point: 151-154°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - K195000

A new metabolite of Itraconazole.

REFERENCES

• Back, D., et al.: Br. J. Clin. Pharmacol., 32, 624 (1991)
• Barone, J., et al.: Antimicrob. Agents Chemother., 37, 778 (1991)
• Haria, M., et al.: Drugs, 51, 585 (1991)
• Kivisto, K., et al.: Pharmacol. Toxicol., 84, 94 (1991)
• Lin, Y., et al.: Mol. Pharmacol