Miconazole Nitrate

For research use only.

Catalog No.S1956 Synonyms: NSC 169434 Nitrate

5 publications

Miconazole Nitrate Chemical Structure

CAS No. 22832-87-7

Miconazole (NSC 169434) Nitrate is an imidazole antifungal agent by inhibiting ergosterol biosynthesis and inducing ROS, used to treat vaginal yeast infections.

Selleck's Miconazole Nitrate has been cited by 5 publications

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Biological Activity

Description Miconazole (NSC 169434) Nitrate is an imidazole antifungal agent by inhibiting ergosterol biosynthesis and inducing ROS, used to treat vaginal yeast infections.
In vitro

Miconazole induces changes in the actin cytoskeleton, indicative of increased filament stability, prior to ROS induction. [1] Miconazole disrupts steroidogenesis in Leydig and adrenal cells by inhibiting 17alpha-hydroxylase/17,20-lyase (P450c17) enzyme activity, thus reducing the conversion of progesterone to androstenedione. Miconazole reversibly inhibits (Bu)(2)cAMP-stimulated progesterone production in a dose- and time-dependent manner in MA-10 cells without affecting total protein synthesis or P450(scc) and 3beta-hydroxysteroid dehydrogenase (3beta-HSD) enzyme expression or activity. [2] Miconazole is known to interfere with the synthesis of fungal and bacterial lipid membranes as it restrains the synthesis of Ergosterol which results in accumulation of toxic methylated sterol intermediates in membranes and subsequently in fungal cell growth arrests. [3] Miconazole induces actin cytoskeleton stabilization in Saccharomyces cerevisiae prior to induction of reactive oxygen species, pointing to an ancillary mode of action. [4] Miconazole treatment releases Ca(2+) from the thapsigargin (TG)-sensitive ER pool of WEHI7.2 cells. Miconazole induces apoptosis, based on morphological and biochemical criteria, and on inhibition by the Bcl-2 oncogene. Miconazole–induced intracellular Ca(2+) changes is inhibited by overexpression of Bcl-2. Miconazole induces apoptosis in the glucocorticoid sensitive and resistant human T-cell leukemia lines, CEM-C7 and CEM-C1 respectively, in normal thymocytes and in normal lymphocytes, in addition to inducing cell death in WEHI7.2 cells. [5]

Protocol

Solubility (25°C)

In vitro DMSO 96 mg/mL (200.35 mM)
Water Insoluble
Ethanol '1 mg/mL

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 479.14
Formula

C18H14Cl4N2O.HNO3

CAS No. 22832-87-7
Storage powder
in solvent
Synonyms NSC 169434 Nitrate
Smiles C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl.[N+](=O)(O)[O-]

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Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT00668538 Completed Drug: Brentan (miconazole) Healthy University of Southern Denmark|Odense University Hospital April 2008 Not Applicable
NCT00390780 Completed Drug: miconazole Lauriad|Drug: Clotrimazole HIV Infections Onxeo July 2006 Phase 3

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID