M3512

(±)-Miconazole nitrate salt

imidazole antibiotic

• Synonym(s): 1-(2,4-Dichloro-β-[(2,4-dichlorobenzyl)oxy]phenethyl)imidazole
• Empirical Formula (Hill Notation): C₁₈H₁₄Cl₄N₂O · HNO₃
• CAS Number: 22832-87-7
• Molecular Weight: 479.14
• PubChem Substance ID: 24896848
• eCl@ss: 39161001
• UNSPSC Code: 51102829
• NACRES: NA.85
• EC Number: 245-256-6
• MDL number: MFCD00058161

Properties

• Quality Segment: 200
• optical activity: [α]/D ±0.10° (Specific Rotation (BP))
• color: white to off-white
• antibiotic activity spectrum: fungi, mycobacteria
• mode of action: enzyme | inhibits
• SMILES string: ClC1=CC(Cl)=CC=C1C(OCC2=CC=C(Cl)C=C2Cl)CN3C=CN=C3.[O-][N+](O)=O
• InChI: 1S/C18H14Cl4N2O.HNO3/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22;2-1(3)4/h1-8,11,18H,9-10H2;(H,2,3,4)
• InChI key: MCCACAIVAXEFAL-UHFFFAOYSA-N

Description

General description

Chemical structure: imidazole

Application

Miconazole is an imidazole antifungal agent that is used topically and by intravenous infusion. It is used to inhibit cytochrome P450 and to study automated luminescence-based cytochrome P450 profiling.

Biochem/physiol Actions

Antifungal azole. Mode of action: Inhibits cytochrome P450-dependent 14α-demethylase, which is critical to ergosterol biosynthesis. The accumulated 14α-methylated sterols change the membrane structure of sensitive fungi, resulting in an altered cell membrane permeability. Also inhibits peroxidases, which results in accumulation of peroxide within the cell.

Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for ergosterol biosynthesis. The inhibition of ergosterol results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with phospholipids in the cell membrane, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and interfere with triglyceride and phospholipid biosynthesis.

Preparation Note

Sparingly soluble in methanol, slightly soluble in ethanol. Very slightly soluble in water.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Codes: H302,H317
• Precautionary Statements: P280 - P301 + P312 + P330 - P302 + P352
• Hazard Classifications: Acute Tox. 4 Oral - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): dust mask type N95 (US), Eyeshields, Faceshields, Gloves