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1443500

USP

Miconazole nitrate

Name: Miconazole nitrate
Brand: USP

United States Pharmacopeia (USP) Reference Standard

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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

MDL number:

MFCD00058161

PubChem Substance ID:

329750464

NACRES:

NA.24

grade

pharmaceutical primary standard

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

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Analytical Reference Standards

Pharmacopeia & Metrological Institute Standards

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.

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.

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.

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Pricing

1443431

1443464

1443497

BP253

Miconazole nitrate, British Pharmacopoeia (BP) Reference Standard

BP884

Miconazole impurity A, British Pharmacopoeia (BP) Reference Standard

PHR9002

1-[(2RS)-2-(Benzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazolium nitrate, certified reference material, TraceCERT^®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

Pictograms

GHS07

Signal Word

Warning

Hazard Statements

H302 - H317

Precautionary Statements

P280 - P301 + P312 + P330 - P302 + P352

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

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Miconazole activity against Candida biofilms developed on acrylic discs.

S Gebremedhin et al.

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Multicenter, double-blind, parallel group study investigating the non-inferiority of efficacy and safety of a 2% miconazole nitrate shampoo in comparison with a 2% ketoconazole shampoo in the treatment of seborrhoeic dermatitis of the scalp.

Stanislaw A Buechner

The Journal of dermatological treatment, 25(3), 226-231 (2013-04-06)

This study investigated the non-inferiority of efficacy and tolerance of 2% miconazole nitrate shampoo in comparison with 2% ketoconazole shampoo in the treatment of scalp seborrheic dermatitis. A randomized, double-blind, comparative, parallel group, multicenter study was done. A total of

NO-donating oximes relax corpora cavernosa through mechanisms other than those involved in arterial relaxation.

Bart Pauwels et al.

The journal of sexual medicine, 11(7), 1664-1674 (2014-05-21)

Erectile dysfunction (ED), as well as many cardiovascular diseases, is associated with impaired nitric oxide (NO) bioavailability. Recently, oxime derivatives have emerged as vasodilators due to their NO-donating capacities. However, whether these oximes offer therapeutic perspectives as an alternative NO

Antimicrobial activity of ibuprofen: new perspectives on an "Old" non-antibiotic drug.

Jelena Obad et al.

European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 71, 93-98 (2015-02-25)

Pharmaceutical industry has been encountering antimicrobial activity of non-antibiotics during suitability tests carried out prior to routine pharmacopoeial microbiological purity analysis of finished dosage forms. These properties are usually ignored or perceived as a nuisance during pharmaceutical analysis. The aim

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