• Clotrimazole packaged and labeled.

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SKU: C037

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Description

Clotrimazole is a broad-spectrum antifungal.  It falls into the imidazole subclass of azole compounds, which interfere with the biosynthesis of ergosterol, a major membrane component of the fungal cytoplasmic membrane.  It was discovered in 1969 and was developed by Schering Plough.  It inhibits Ca2+-activated potassium channels.  The compound has promising anti-cancer effects. It is an CYP450 enzyme inhibitor.  It is freely soluble in water.

    CAS Number

    23593-75-1

    Molecular Formula

    C22H17ClN2

    Molecular Weight

    344.84

    Mechanism of Action

    Clotrimazole increases fungal cell permeability by inhibiting ergosterol synthesis, a major cell membrane component found exclusively in fungi, thus is fungistatic and inhibits fungal growth. Specifically, it inhibits the microsomal cytochrome P450-dependent 14α-demethylase, which is critical to ergosterol biosynthesis.

    Storage Conditions

    2-8°C

    Tariff Code

    2933.29.2000

    Spectrum

    Clotrimazole is broad-spectrum, targeting a broad range of fungi including Candida and Aspergillus species.

Applications

    Application

    Clotrimazole is a reversible inhibitor of cytochrome P450 (CYP450). Metabolism by cytochrome P450s is a principal mechanism for metabolism-based drug-drug interactions and in vitro CYP450 inhibition screening has been used to evaluate drug-drug interactions (Yan et al, 2002).

    Cancer Applications

    Clotrimazole has promising anti-cancer effects, interfering with glycolytic enzymes, specifically their cellular distribution and their activity. Cell lines from human breast tissue (MCF10A, MCF-7 and MDA-MB-231) were used, and Clotrimazole induced a dose-dependent decrease in glucose uptake in all three cell lines, affecting the metabolism, growth, and migration of human breast cancer cell lines. It was non-toxic to non-tumor human breast cell lines (Furtado et al, 2012).

    Eukaryotic Cell Culture Applications

    Clotrimazole can be used to inhibit CYP450 in cell cultures.

Specifications

    Form

    Powder

    Appearance

    White crystalline powder

    Source

    Synthetic

    Melting Point

    141- 145°C

    Assay

    (On Dried Basis): 98.5-100.5%

    Loss on Drying

    ≤0.5%

    Residue On Ignition

    ≤0.1%

    Heavy Metals

    Not more than 10ppm

    Impurities

    Clotrimazole A: ≤0.5%

References

    References

    Crowley PD and Gallagher HC (2014)  Clotrimazole as a pharmaceutical: Past, present, and future. J. Appl. Microbiol. 117(3):611-617

    Furtado CM, Marcondes MC, Sola-Penna M, de Souza MLS, and Zancan P (2012) Clotrimazole preferentially inhibits human breast cancer cell proliferation, viability and glycolysis. PLoS ONE 7(2): e30462

    Jensen BS, Strøbaek D, Olesen SP, Christophersen P (2001)  The Ca2+-activated K+ channel of intermediate conductance: a molecular target for novel treatments? Curr Drug Targets. 2(4):401-422  PMID 11732639

    Rice LB and Ghannoum MA (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

    Yan Z, Rafferty B, Caldwell GW and MAsucci JA (2002)  Rapidly distinguishing reversible and irreversible CYP450 inhibitors by using fluorometric kinetic analyses. E. J. Drug Metab. And Pharmacokin. 27(4):281-287

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