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-hydroxybutan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one

• ChemBase ID: 170605
• Molecular Formular: C35H38Cl2N8O5
• Molecular Mass: 721.63282
• Monoisotopic Mass: 720.23422172
• 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(C)O)C
• Canonical SMILES: CC(C(n1ncn(c1=O)c1ccc(cc1)N1CCN(CC1)c1ccc(cc1)OC[C@H]1CO[C@](O1)(Cn1cncn1)c1ccc(cc1Cl)Cl)C)O
• InChI: InChI=1S/C35H38Cl2N8O5/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/h3-12,17,21-25,31,46H,13-16,18-20H2,1-2H3/t24?,25?,31-,35-/m0/s1
• InChIKey: ISJVOEOJQLKSJU-QURBUZHQSA-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-hydroxybutan-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-hydroxybutan-2-yl)-1,2,4-triazol-3-one
• Synonyms: 4-[4-[4-[4-[[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-(2-hydroxy-1-methylpropyl)-3H-1,2,4-triazol-3-one; R 63373; Hydroxy Itraconazole

Database IDs

• CAS Number: 112559-91-8
• PubChem SID: 164226515
• PubChem CID: 9831719

CALCULATED PROPERTIES

• Acid pKa: 14.834891
• H Acceptors: 10
• H Donor: 1
• LogD (pH = 5.5): 6.1472983
• LogD (pH = 7.4): 6.158371
• Log P: 6.1585135
• Molar Refractivity: 201.8385 cm^3
• Polarizability: 72.25019 Å^3
• Polar Surface Area: 121.02 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 87-90°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H943600

A metabolite of Itraconazole, an orally active antimycotic structurally related to Ketoconazole.

REFERENCES

• Saag, M., et al.: Antimicrob. Agents Chemother., 32, 1 (1988)
• Haria, M., et al.: Drugs, 51, 585 (1988)
• Kousoulos, C., et al.: Anal. Bioanal. Chem., 384,199 (1988)