1-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

• ChemBase ID: 105234
• Molecular Formular: C26H28Cl2N4O4
• Molecular Mass: 531.43092
• Monoisotopic Mass: 530.14876076
• SMILES: CC(=O)N1CCN(CC1)c1ccc(OCC2COC(Cn3ccnc3)(O2)c2ccc(Cl)cc2Cl)cc1
• Canonical SMILES: Clc1ccc(c(c1)Cl)C1(OCC(O1)COc1ccc(cc1)N1CCN(CC1)C(=O)C)Cn1cncc1
• InChI: InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3
• InChIKey: XMAYWYJOQHXEEK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one; 1-[4-(4-{[2-(2,4-dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
• IUPAC Traditional name: @ketoconazole; ketoconazole
• Synonyms: cis-1-Acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H-1M-idazol-1-ylmethyl)-1,3-dioxolan-4-yl) methoxy) phenyl)-piperazine; Fungarest; Fungoral; Ketoconazol; Ketoderm; Ketoisdin; KW-1414; Nizoral; R 41400; KETOCONAZOLE; cis-1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine

Database IDs

• CAS Number: 65277-42-1
• EC Number: 265-667-4
• PubChem SID: 162092001
• PubChem CID: 3823

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.6516864
• LogD (pH = 7.4): 4.128518
• Log P: 4.191598
• Molar Refractivity: 138.0672 cm^3
• Polarizability: 53.26531 Å^3
• Polar Surface Area: 69.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 148-150°C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: TK7912300
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: R:25
• Safety Statements: S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154

Product Information

• Purity: 98%; 99%

DETAILS

MP Biomedicals - 02159158

Purity: 99% Cytochrome P^450 inhibitor and demonstrates anti-psoriatic activity

REFERENCES

• Lambert, A., et al., Biochem. Pharmacol., 35 : 3999 (1986).
• Van Wauwe, J.P. and Janssen, P.A.J., J. Med. Chem., 32: 2231 (1989).
• Tucker, W.F.G., et al., Br. Med. J., 293: 882 (1986).