1443500

Miconazole nitrate

United States Pharmacopeia (USP) Reference Standard

• Synonym(s): (±)-Miconazole nitrate salt, 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
• NACRES: NA.24
• PubChem Substance ID: 329750464
• UNSPSC Code: 41116107
• MDL number: MFCD00058161

Properties

• grade: pharmaceutical primary standard
• agency: USP
• API family: miconazole
• manufacturer/tradename: USP
• application(s): pharmaceutical (small molecule)
• format: neat
• 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

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Miconazole nitrate USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:

• Miconazole Nitrate Cream
• Miconazole Nitrate Topical Powder
• Miconazole Nitrate Vaginal Suppositories

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.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302,H317
• Hazard Classifications: Acute Tox. 4 Oral - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• pcodes: P261 - P264 - P272 - P280 - P301 + P312 - P302 + P352