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Ketoconazole is a broad-spectrum triazole antifungal agent that has activity against C. albicans, C. krusei, C. tropicalis, C. glabrata, C. parapsilosis, C. neoformans, and A. fumigatus strains (IC50s = 0.031-8 µg/ml). It inhibits the fungal cytochrome P450 isoform CYP51, also known as lanosterol 14α-demethylase, which arrests ergosterol biosynthesis at the fungal membrane. Ketoconazole also inhibits human CYP3A4 (IC50 = 0.54 µM). Formulations containing ketoconazole have been used in the treatment of fungal infections.
Ketoconazole is a broad-spectrum antifungal imidazole with commercially available product being under the trade name of Jindakening, Meikangling and keNing. It interferes with the activity of fungal cytochrome P-450 with a high selectivity, thus inhibiting the biosynthesis of ergosterol in fungal cell membrane. It is effective in treating both shallow, deep fungal infections and can inhibit both fungal growth and the transition from spores to mycelium to prevent the further infection. It has antifungal effect on Candida genus, Fonsecaea, Coccidioides, Histoplasma, Sporothrix spp and Trichophyton. Clinically, it is suitable for the treatment of ringworm, athlete's foot, and skin ringworm, tinea, jock itch, and thrush, tinea versicolor as well as cutaneous candidiasis.
Ketoconazole (65277-42-1) is a broad spectrum antifungal agent which acts via inhibition of a cytochrome P450, CYP51A1 which is a lanosterol 14α-demethylase. Also inhibits CYP3A and CYP1A1. Inhibits adrenal steroidogenesis. Downregulates cholesterol synthesis in drug-tolerant human lung cancer cell lines. Blocks the biosynthesis of leukotrienes (LT) via inhibition of 5-lipoxygenase and dose dependently inhibits LT-mediated bronchoconstriction in guinea pigs.
Catalogue Number | K186000 |
Chemical Name | Ketoconazole |
Synonyms | rel-1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]ethanone; cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine; (+/-)-Ketoconazole; Brizoral; Fungarest; Fungoral; Ketoderm; Ketoisdin; Ketozoral; Nizoral; Nizral; Onofin K; Orifungal M; Panfungol; R 41400; |
CAS Number | 65277-42-1 |
Molecular Formula | C??H??Cl?N?O? |
Appearance | White to Off-White Solid |
Melting Point | 144-146oC |
Molecular Weight | 531.43 |
Storage | -20°C Freezer |
Solubility | Chloroform (Slightly), Methanol (Slightly) |
Category | Standards; Enzyme Activators and Inhibitors; Pharmaceutical/API Drug Impurities/Metabolites; |
Applications | Inhibits cytochrome P-450 dependent steps in the biosynthesis of steroid hormones in vivo. Antimetastatic and antineoplastic activity. Orally active 5-lipoxygenase and thromboxane synthase inhibitor. Inhibitor of exosome secretion. |
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