SKU: M041  / 
    CAS Number: 22916-47-8

    Miconazole

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    Miconazole

    Miconazole is an imidazole antimycotic compound patented in 1968 by Janssen Pharmaceutica.  It inhibits ergosterol synthesis, and a variety of cytochrome P450 enzymes.   It can act as a chemopreventive agent in a mammary cancer cell model.  Miconazole is freely soluble in alcohol, acetone, DMF and chloroform but is practically insoluble in water. 

    We also offer:

    • Miconazole Nitrate (M005)
    Mechanism of Action Miconazole increases cell permeability by inhibiting enzymes involved in ergosterol synthesis, including a variety of cytochrome P450 enzymes including cytochrome P450-dependent 14-alpha-demethylase. The increase of 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.
    Spectrum Miconazole has activity against fungi including Candida and Trichophyton.  It can also be used for select Leishmania protozoa.
    Microbioogy 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.
    Eukaryotic Cell Culture Applications Miconazole tested on transcriptional activity of human GR in HeLa and HepG2 cells, and primary human hepatocytes.  It behaved similarly to Ketoconazole and inhibited expression of: 1) GR-responsive genes tyrosine aminotransferase, PXR, CAR.  2) cytochromes P450 (P450) CYP2B6, CYP2C9, and CYP3A4; 3) UDP-glucuronosyltransferase 1A1, glutathione S-transferases A1 and A2, thus its mechanism of action may influence drug metabolism (Duret et al, 2006).
    Cancer Applications Miconazole can act as a chemopreventive agent in a mammary cancer cell model, and increased tumor latency, decreased incidence at the highest dose, and decreased tumor multiplicity up to 60% (Lubet et al, 1997).
    Impurity Profile Impurity C| (2RS)-2-[(2,4-dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethanamine||||
    Molecular Formula C18H14Cl4N2O
    References

    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

    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

    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