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Ketoconazole

CAS No:
65277-42-1 Categories: , , ,
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Product Details:

  • Product Name: Ketoconazole
  • CAS #: 65277-42-1
  • Mode of Action:

    Ketoconazole interacts with 14-_ demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Other mechanisms may involve the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole can also inhibit the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone.

  • Pharmacodynamics:

    Ketoconazole, like clotrimazole, fluconazole, itraconazole, and miconazole, is an imidazole antifungal agent.

  • Metabolism:

    Hepatic

  • Toxicity:

    Hepatotoxicity, LD50=86 mg/kg (orally in rat)

  • IUPAC: 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
  • ATC: D01AC08 G01AF11 J02AB02
  • PubChem: 47576
  • DrugBank: DB01026 (APRD00401)
  • Formula: C9H7Cl2N5
  • Molecular Mass: 531.431
  • Synonyms: 2% Ketocanazole Ketoconazol Ketoconazol [INN-Spanish] Ketoconazole [Usan:Ban:Inn:Jan] Ketoconazolum [INN-Latin]
  • SMILES: CC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1
  • AHFS Code: 08:14.08 84:04.08.08
  • InChl: XMAYWYJOQHXEEK-UHFFFAOYSA-N
  • General Reference:

    1. 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
    2. Berwaerts J, Verhelst J, Mahler C, Abs R: Cushingês syndrome in pregnancy treated by ketoconazole: case report and review of the literature. Gynecol Endocrinol. 1999 Jun;13(3):175-82. Pubmed
    3. 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
    4. 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

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