Clear Search sequence regions
Bookmark Forward

QuickView for Ketoconazole (compound)


PubChem
Name: Ketoconazole
PubChem Compound ID: 3823
Description: Broad spectrum antifungal agent used for long periods at high doses, especially in immunosuppressed patients.
Molecular formula: C26H28Cl2N4O4
Molecular weight: 531.43 g/mol
Synonyms:
(+-)-cis-1-acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1- ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine; ketoconazol; ketoisdin; 79156-75-5; Ketoconazole; CPD-4503; fungarest; orifungal M; NSC317629; fungoral.
show more »
DrugBank
Identification
Name: Ketoconazole
Name (isomeric): DB01026
Drug Type: small molecule
Description: Broad spectrum antifungal agent used for long periods at high doses, especially in immunosuppressed patients.
Synonyms:
2%; Ketoconazol [INN-Spanish]; Ketoconazolum [INN-Latin]; Ketocanazole; Ketoconazol; Ketoconazole [Usan:Ban:Inn:Jan]
Brand: Fungoral, Ketoderm, Nizoral, Nizoral a-D Shampoo, Nizoral Cream, Orifungal M, Sebazole, Orifungal, Fungarest, Extina, Ketoisdin, Nizoral a-D, Nizoral Shampoo, Panfungol, Ketozole
Category: Antifungal Agents, Antifungals
CAS number: 65277-42-1
Pharmacology
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.
Mechanism of Action:
Ketoconazole interacts with 14-α 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, inhibit...
show more »
Absorption: Moderate
Protein binding: 99% (in vitro, plasma protein binding)
Biotransformation: Hepatic
Half Life: 2 hours
Toxicity: Hepatotoxicity, LD50=86 mg/kg (orally in rat)
Affected organisms: Fungi
Interactions
Food interaction:
Avoid alcohol.
Avoid milk, calcium containing dairy products, iron, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication.
Take with food.
Drug interaction:
EstazolamKetoconazole may increase the effect of the benzodiazepine, estazolam.
HalazepamKetoconazole may increase the effect of the benzodiazepine, halazepam.
BudesonideKetoconazole may increase levels/effect of budesonide.
ConivaptanAntifungal Agents (Azole Derivatives, Systemic) may decrease the metabolism of Conivaptan. Concomitant use of conivaptan with strong CYP3A4 inhibitors (e.g., azole antifungals) is contraindicated.
TolbutamideKetoconazole, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Ketoconazole is initiated, discontinued or dose changed.
show more »

Targets


Enzymes


Transporters