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Ketoconazole

Ketoconazole

Product ID K1676
Cas No. 65277-42-1
Purity ≥98%
Product Unit SizeCostQuantityStock
1 g $68.30 In stock
5 g $144.20 In stock
25 g $444.70 In stock
Bulk Quote

Quicklinks

  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Custom Order

Description

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.

Product Info

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

Soluble in DMSO (3 mg/mL), ethanol (7 mg/mL).

Appearance

White Powder

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

K1676 MSDS PDF

Info Sheet

K1676 Info Sheet PDF

References

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.

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