1-[(3,3,4,4,4-2H5)butan-2-yl]-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}-4,5-dihydro-1H-1,2,4-triazol-5-one

• ChemBase ID: 172001
• Molecular Formular: C35H38Cl2N8O4
• Molecular Mass: 705.63342
• Monoisotopic Mass: 704.2393071
• SMILES: c1(ccc(cc1Cl)Cl)[C@]1(OC[C@@H](O1)COc1ccc(cc1)N1CCN(CC1)c1ccc(cc1)n1cnn(c1=O)C(CC)C)Cn1cncn1
• Canonical SMILES: CCC(n1ncn(c1=O)c1ccc(cc1)N1CCN(CC1)c1ccc(cc1)OC[C@H]1CO[C@](O1)(Cn1cncn1)c1ccc(cc1Cl)Cl)C
• InChI: InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1
• InChIKey: VHVPQPYKVGDNFY-ZPGVKDDISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(3,3,4,4,4-^2H₅)butan-2-yl]-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}-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: 2-[(3,3,4,4,4-^2H₅)butan-2-yl]-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}-1,2,4-triazol-3-one
• Synonyms: (+/-)-4-[4-[4-[4-[[(2R,4S)-(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-methylpropyl-d5)-3H-1,2,4-triazol-3-one; Itrizole-d5; Oriconazole-d5; R-51211-d5; Sporamelt-d5; Sporanox-d5; Triasporin-d5; Itraconazole-d5

Database IDs

• PubChem SID: 164227911
• PubChem CID: 45039617

CALCULATED PROPERTIES

• H Acceptors: 9
• H Donor: 0
• LogD (pH = 5.5): 7.3001556
• LogD (pH = 7.4): 7.3112283
• Log P: 7.3113713
• Molar Refractivity: 200.4 cm^3
• Polarizability: 71.596016 Å^3
• Polar Surface Area: 100.79 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Off-White to Beige Solid
• Melting Point: 163-165°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I937502

An isotopically labelled, orally active antimycotic structurally related to Ketoconazole.A representative lot was 88% d5, 12% d4 with no d0.

REFERENCES

• Espinel-Ingroff, A., et al.: Antimicrob. Agents Chemother., 26, 5 (1984)
• Heykants, J., et al.: Mycoses, 32, Suppl 1, 67 (1984)
• Sugar, A.M., et al.: Curr. Clin. Top. Infect. Dis., 13, 74 (1984)