Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

M3512

Sigma-Aldrich

(±)-Miconazole nitrate salt

imidazole antibiotic

Synonym(s):

1-(2,4-Dichloro-β-[(2,4-dichlorobenzyl)oxy]phenethyl)imidazole

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C18H14Cl4N2O · HNO3
CAS Number:
22832-87-7
Molecular Weight:
479.14
EC Number:
245-256-6
MDL number:
MFCD00058161
UNSPSC Code:
51102829
eCl@ss:
39161001
PubChem Substance ID:
24896848
NACRES:
NA.85

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Automated Luminescence-Based Cytochrome P450 Profiling Using a Simple, Elegant Robotic Platform
Brad Larson, Peter Banks, et al.
Journal of the Association for Laboratory Automation, 16, 47-55 (2011)
Francis X Cunningham et al.
Eukaryotic cell, 6(3), 533-545 (2006-11-07)
Cyanidioschyzon merolae is considered to be one of the most primitive of eukaryotic photosynthetic organisms. To obtain insights into the origin and evolution of the pathway of carotenoid biosynthesis in eukaryotic plants, the carotenoid content of C. merolae was ascertained
Michele Tonelli et al.
Bioorganic & medicinal chemistry, 16(18), 8447-8465 (2008-09-02)
Eighty-five arylazoenamines, characterized by different types of aryl and basic moieties, have been synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against a panel of ten RNA and DNA viruses. The most commonly affected viruses were, in
Ali Reza Khosravi et al.
Foodborne pathogens and disease, 9(7), 674-679 (2012-06-14)
The purpose of the present study was to evaluate and assess the capability of Zataria multiflora, Geranium herbarium, and Eucalyptus camaldolensis essential oils in treating Saprolegnia parasitica-infected rainbow (Oncorhynchus mykiss) trout eggs. A total of 150 infected eggs were collected
Sónia P M Ventura et al.
Ecotoxicology and environmental safety, 83, 55-62 (2012-06-30)
A wide range of ionic liquids (ILs), containing a diverse set of cations, anions and alkyl chain lengths, was screened for their antimicrobial activity toward four microorganisms, Escherichia coli CCT-0355, Staphylococcus aureus ATCC-6533, Fusarium sp. LM03 and Candida albicans ATCC-76645.
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service