Ketoconazole
Ketoconazole is a synthetic imidazole antifungal that also exhibits anti-androgen, anti-inflammatory, neuromodulatory, and anticancer chemotherapeutic activities. Ketoconazole is clinically used to treat fungal infections; it inhibits 14-α demethylase, preventing ergosterol production and cell wall synthesis. In clinical models of prostate cancer, ketoconazole decreases testosterone and cortisol production and inhibits androgen receptors, displaying potential chemotherapeutic benefit. In cellular models, ketoconazole activates Nrf2 and decreases production of IL-8 and TNF-α.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18936564
| Cas No. |
65277-42-1 |
|---|---|
| Purity |
≥98% |
| Formula |
C26H28Cl2N4O4 |
| Formula Wt. |
531.44 |
| Chemical Name |
cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine |
| IUPAC Name |
1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone |
| Synonym |
Fungarest; Fungoral; Ketoderm. |
| Melting Point |
148-149°C |
| Solubility |
DMSO to 3mg/mL, Ethanol to 7mg/mL |
| Appearance |
White Powder |
Tsuji G, Takahara M, Uchi H, et al. Identification of ketoconazole as an AhR-Nrf2 activator in cultured human keratinocytes: the basis of its anti-inflammatory effect. J Invest Dermatol. 2012 Jan;132(1):59-68. PMID: 21753779.
Eil C. Ketoconazole binds to the human androgen receptor. Horm Metab Res. 1992 Aug;24(8):367-70. PMID: 1526623.
Witjes FJ, Debruyne FM, Fernandez del Moral P, et al. Ketoconazole high dose in management of hormonally pretreated patients with progressive metastatic prostate cancer. Dutch South-Eastern Urological Cooperative Group. Urology. 1989 May;33(5):411-5. PMID: 2652864.
Loose DS, Kan PB, Hirst MA, et al. Ketoconazole blocks adrenal steroidogenesis by inhibiting cytochrome P450-dependent enzymes. J Clin Invest. 1983 May;71(5):1495-9. PMID: 6304148.
Matsumoto Y, Miyazaki S, Fukunaga DH, et al. Quantitative evaluation of cryptococcal pathogenesis and antifungal drugs using a silkworm infection model with Cryptococcus neoformans. J Appl Microbiol. 2012 Jan;112(1):138-146. PMID: 22040451.
