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

• ChemBase ID: 899
• Molecular Formular: C26H28Cl2N4O4
• Molecular Mass: 531.43092
• Monoisotopic Mass: 530.14876076
• SMILES: Clc1c([C@]2(O[C@@H](CO2)COc2ccc(N3CCN(CC3)C(=O)C)cc2)Cn2ccnc2)ccc(Cl)c1
• Canonical SMILES: Clc1ccc(c(c1)Cl)[C@@]1(OC[C@H](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/t23-,26-/m1/s1
• InChIKey: XMAYWYJOQHXEEK-ZEQKJWHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
• IUPAC Traditional name: nizoral shampoo
• Brand Name: Extina; Fungarest; Fungoral; Ketoderm; Ketoisdin; Ketozole; Nizoral; Nizoral Cream; Nizoral Shampoo; Nizoral a-D; Nizoral a-D Shampoo; Orifungal; Orifungal M; Panfungol; Sebazole
• Synonyms: Ketoconazol [INN-Spanish]; Ketoconazole [Usan:Ban:Inn:Jan]; Ketoconazolum [INN-Latin]; Ketoconazol; Ketocanazole; ketoconazole; 2%; Ketoconazole

Database IDs

• CAS Number: 65277-42-1
• PubChem SID: 160964362
• PubChem CID: 47576

CALCULATED PROPERTIES

JChem

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.6516862
• 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

ALOGPS 2.1

• Log P: 4.3
• LOG S: -4.76
• Solubility (Water): 9.31e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.0866 mg/L
• Hydrophobicity(logP): 4

DETAILS

DrugBank - DB01026

• Drug Groups: approved; investigational
• Description: Broad spectrum antifungal agent used for long periods at high doses, especially in immunosuppressed patients. [PubChem]
• Indication: For the treatment of the following systemic fungal infections: candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis.
• Pharmacology: Ketoconazole, like clotrimazole, fluconazole, itraconazole, and miconazole, is an imidazole antifungal agent.
• Toxicity: Hepatotoxicity, LD₅₀=86 mg/kg (orally in rat)
• Affected Organisms: Fungi
• Biotransformation: Hepatic
• Absorption: Moderate
• Half Life: 2 hours
• Protein Binding: 99% (in vitro, plasma protein binding)
• References: Goeders NE, Peltier RL, Guerin GF: Ketoconazole reduces low dose cocaine self-administration in rats. Drug Alcohol Depend. 1998 Dec 1;53(1):67-77. [Pubmed] ; Berwaerts J, Verhelst J, Mahler C, Abs R: Cushing's syndrome in pregnancy treated by ketoconazole: case report and review of the literature. Gynecol Endocrinol. 1999 Jun;13(3):175-82. [Pubmed] ; Kazy Z, Puho E, Czeizel AE: Population-based case-control study of oral ketoconazole treatment for birth outcomes. Congenit Anom (Kyoto). 2005 Mar;45(1):5-8. [Pubmed] ; Pierard-Franchimont C, Goffin V, Decroix J, Pierard GE: A multicenter randomized trial of ketoconazole 2% and zinc pyrithione 1% shampoos in severe dandruff and seborrheic dermatitis. Skin Pharmacol Appl Skin Physiol. 2002 Nov-Dec;15(6):434-41. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Goeders NE, Peltier RL, Guerin GF: Ketoconazole reduces low dose cocaine self-administration in rats. Drug Alcohol Depend. 1998 Dec 1;53(1):67-77. Pubmed
• Berwaerts J, Verhelst J, Mahler C, Abs R: Cushing's syndrome in pregnancy treated by ketoconazole: case report and review of the literature. Gynecol Endocrinol. 1999 Jun;13(3):175-82. Pubmed
• Kazy Z, Puho E, Czeizel AE: Population-based case-control study of oral ketoconazole treatment for birth outcomes. Congenit Anom (Kyoto). 2005 Mar;45(1):5-8. Pubmed
• Pierard-Franchimont C, Goffin V, Decroix J, Pierard GE: A multicenter randomized trial of ketoconazole 2% and zinc pyrithione 1% shampoos in severe dandruff and seborrheic dermatitis. Skin Pharmacol Appl Skin Physiol. 2002 Nov-Dec;15(6):434-41. Pubmed