Miconazole Nitrate

Synonyms: NSC 169434 Nitrate

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

Miconazole Nitrate Chemical Structure

Miconazole Nitrate Chemical Structure

CAS No. 22832-87-7

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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
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]
NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT00668538 Completed
Healthy
University of Southern Denmark|Odense University Hospital
April 2008 Not Applicable
NCT00390780 Completed
HIV Infections
Valerio Therapeutics
July 2006 Phase 3

Chemical Information & Solubility

Molecular Weight 479.14 Formula

C18H14Cl4N2O.HNO3

CAS No. 22832-87-7 SDF Download Miconazole Nitrate SDF
Smiles C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl.[N+](=O)(O)[O-]
Storage (From the date of receipt)

In vitro
Batch:

DMSO : 96 mg/mL ( (200.35 mM) Moisture-absorbing DMSO reduces solubility. Please use fresh DMSO.)

Ethanol : 1 mg/mL

Water : Insoluble


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