Ketoconazole

• Catalog No.: DB01026
• CAS Number: 65277-42-1
• M. F.: C26H28Cl2N4O4
• M. W.: 531.43092

SYNONYMS

• 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: Nizoral a-D; Nizoral; Extina; Fungoral; Ketoderm; Ketoisdin; Ketozole; Nizoral Cream; Nizoral Shampoo; Nizoral a-D Shampoo; Orifungal; Orifungal M; Sebazole; Fungarest; Panfungol
• Synonyms: Ketoconazol [INN-Spanish]; Ketoconazolum [INN-Latin]; Ketoconazole [Usan:Ban:Inn:Jan]; ketoconazole; Ketoconazol; Ketocanazole; 2%

DATABASE IDS

• CAS Number: 65277-42-1

PROPERTIES

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

DETAILS

Description (English)

• 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