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Miconazole is an imidazole antifungal compound that inhibits ergosterol synthesis and fungal cell wall formation. Miconazole is clinically used to treat fungal infections and is especially active against Candida. Miconazole also exhibits anti-angiogenic activities, decreasing expression of HIF-1α and VEGF in breast cancer and glioma cells. Additionally, this compound may inhibit glucocorticoid receptors.
| Cas No. | 22916-47-8 |
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| Purity | ≥98% |
| Formula | C18H14Cl4N2O |
| Formula Wt. | 416.14 |
| Chemical Name | 1-[2-(2,4-Dichlorophenyl)-2-[(2,4-dichlorophenyl)- methoxy]ethyl]-1H-imidazole |
| IUPAC Name | 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole |
| Synonym | Monistat IV |
| Melting Point | 84.3°C |
| Solubility | Practically insoluble in water. Soluble in ethanol (105 mg/mL), methanol (66 mg/mL). |
| Appearance | White to yellowish powder |
| Store Temp | Ambient |
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| Ship Temp | Ambient |
| MSDS | |
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| Info Sheet |
Park JY, Jung HJ, Seo I, et al. Translational suppression of HIF-1α by miconazole through the mTOR signaling pathway. Cell Oncol (Dordr). 2014 Jul 29. [Epub ahead of print]. PMID: 25070654.
Niimi M, Firth NA, Cannon RD. Antifungal drug resistance of oral fungi. Odontology. 2010 Feb;98(1):15-25. PMID: 20155503.
Duret C, Daujat-Chavanieu M, Pascussi JM, et al. 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. 2006 Jul;70(1):329-39. PMID: 16608920.
Tatsumi Y, Nagashima M, Shibanushi T, et al. Mechanism of action of efinaconazole, a novel triazole antifungal agent. Antimicrob Agents Chemother. 2013 May;57(5):2405-2409. PMID: 23459486.