Miconazole nitrate

SKU: orb1310702

Description

Miconazole nitrate is an imidazole antifungal agent that selectively disrupts fungal cell membranes by targeting ergosterol, a sterol not found in mammalian cells. It is widely used in research for studying antifungal mechanisms and efficacy in both in vitro assays and in vivo infection models.

Research Area

Infectious Disease & Virology

Key Properties

• CAS Number: 22832-87-7
• MW: 479.15
• Purity: >99.99% (May vary between batches)
• Formula: C₁₈H₁₅Cl₄N₃O₄
• SMILES: O[N+]([O-])=O.Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)c(Cl)c1
• Target: Antibiotic,Antibacterial,Antifungal
• Solubility: 10% DMSO+40% PEG300+5% Tween 80+45% Saline:2 mg/mL (4.17 mM);DMSO:60 mg/mL (125.22 mM);Ethanol:4.8 mg/mL (10.02 mM)

Bioactivity

• In Vitro:
  Miconazole induces changes in the actin cytoskeleton, indicative of increased filament stability, prior to ROS induction. 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. 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. Miconazole induces actin cytoskeleton stabilization in Saccharomyces cerevisiae prior to induction of reactive oxygen species, pointing to an ancillary mode of action. 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.

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Antifungal, Antibiotic, Bacterial, Inhibitor, Fungal, inhibit, NSC 169434 Nitrate, Miconazole, Miconazole nitrate, Miconazole Nitrate, NSC169434 Nitrate, NSC-169434 Nitrate, R18134, R-18134, R18134 Nitrate, R18134 nitrate, R-18134 Nitrate, R 18134, R 18134 Nitrate

Compound Identifiers

PubChem CID

68553