Skip to Content
MilliporeSigma
All Photos(1)

Documents

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:
51101500
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

signalword

Warning

hcodes

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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

Customers Also Viewed

Slide 1 of 7

1 of 7

trans-2-Phenylcyclopropylamine hydrochloride

Sigma-Aldrich

P8511

trans-2-Phenylcyclopropylamine hydrochloride

Ketoconazole

Sigma-Aldrich

UC280

Ketoconazole

Moxalactam sodium salt

Supelco

M8158

Moxalactam sodium salt

Itraconazole ≥98% (HPLC)

Sigma-Aldrich

I6657

Itraconazole

α-Naphthoflavone ≥98%

Sigma-Aldrich

N5757

α-Naphthoflavone

Metronidazole VETRANAL®, analytical standard

Supelco

46461

Metronidazole

Quinidine anhydrous

Sigma-Aldrich

Q3625

Quinidine

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
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)
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
Janardhanan Saravanan et al.
European journal of medicinal chemistry, 45(9), 4365-4369 (2010-06-29)
A series of 3-substituted amino-4,5-tetramethylene thieno[2,3-d] [1,2,3]-triazine-4(3H)-ones have been synthesized and characterized by UV,IR, 1H NMR, elemental and mass spectral analysis. The title compounds were evaluated for their antimicrobial activity by agar diffusion method against four bacteria and three fungi
V M Litvinov et al.
Molecular pharmaceutics, 9(10), 2924-2932 (2012-08-22)
The use of hot-melt extrusion for preparing homogeneous API-excipient mixtures is studied for miconazole-PEG-g-PVA [poly(ethylene glycol)-poly(vinyl alcohol) graft copolymer] solid dispersions with a 5 cm(3) table-top, twin-screw corotating microcompounder (DSM Xplore). Phase behavior of PEG-g-PVA, miscibility of miconazole in PEG-g-PVA
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