SKU: M005

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Description

Miconazole Nitrate is the nitrate salt of Miconazole, an imidazole antimycotic compound patented in 1968 (Janssen Pharmaceutica).  It targets the fungi that cause tinea (ringworm) and athlete’s foot.  It inhibits ergosterol synthesis, and a variety of cytochrome P450 enzymes.   Miconazole can act as a chemopreventive agent in a mammary cancer cell model.  

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  • Miconazole (M041)

    CAS Number

    22832-87-7

    Molecular Formula

    C18H14Cl4N2O

    Molecular Weight

    479.14

    Mechanism of Action

    Miconazole Nitrate increases cell permeability by inhibiting enzymes involved in ergosterol synthesis, including a variety of cytochrome P450 enzymes including cytochrome P450-dependent 14-alpha-demethylase. Increased permeability has a toxic effect on the fungi and leads to cell death. Miconazole can also act as an antagonist of the glucocorticoid receptor (GR) and can inhibit aromatase.

    Storage Conditions

    2-8 °C

    Tariff Code

    2933.29.2000

    Spectrum

    Active against fungi including yeast (Candida) and fungi that cause tinea (ringworm) ie.  Trichophyton species

Applications

    Application

    Miconazole can be used for cytochrome P450 profiling.

    Microbiology Applications

    Miconazole is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against fungal isolates.  Medical microbiologists use AST results to recommend antibiotic treatment options.  Representative MIC values include:

    • Candida albicans (ATCC 28366) (2 µg/ml)
    • Candida krusei (1 - 4 µg/ml)
    • Chrysosporium spp. (0.5 - 4 µg/ml)
    • Trichophyton rubrum (0.01 - 8 µg/ml)

    For a representative list of Miconazole MIC values, click here.

Specifications

    Form

    Powder

    Appearance

    White or off-white powder

    Source

    synthetic

    Melting Point

    178 - 183°C

    Loss on Drying

    Not more than 0.5%

References

    References

    Ghannoum MA and Rice LB (1999)  Antifungal agents: Mode of action, mechanisms of resistance, and correlation of these mechanisms with bacterial resistance. Clin. Microbiol. Rev. 12(4):501-517  PMID 10515900

    Duret C et al (2006)  Ketoconazole and Miconazole are antagonists of the human glucocorticoid receptor: Consequences on the expression and function of the constitutive androstane receptor and the pregnane X receptor. Mol Pharmacol. 70(1):329–339 PMID 16608920

    Lubet et al (1997)  Chemopreventive efficacy of anethole trithione, N-acetyl-L-cysteine, Miconazole and phenethylisothiocyanate in the DMBA-induced rat mammary cancer model. Int. J. Cancer 72(1):95-101  PMID 9212229

    Sreedhara KH, Sirsi M and Ramananda RGR (1974)  Studies on the mechanism of action of Miconazole: Effect of Miconazole on respiration and cell permeability of Candida albicans.  Antimicrob. Agents and Chemother. 5(4):420-425  PMID 15825399

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