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PHR1163

(±)-Miconazole nitrate salt

Name: (±)-Miconazole nitrate salt
Brand: SIAL

Pharmaceutical Secondary Standard; Certified Reference Material

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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

EC Number:

245-256-6

MDL number:

MFCD00058161

PubChem Substance ID:

329823180

NACRES:

NA.24

grade

certified reference material
pharmaceutical secondary standard

Quality Level

300

Agency

traceable to BP 253
traceable to Ph. Eur. M1900000
traceable to USP 1443500

API family

miconazole

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-30°C

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

Sigma-Aldrich

Certified Reference Materials

General description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Miconazole nitrate is an imidazole derivative and a broad spectrum antifungal drug used in the management of fungal outbreak in humans and veterinary animals.

Application

Miconazole nitrate may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations by various techniques.

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

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 secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Values of analytes vary lot to lot.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAC3325 in the slot below. This is an example certificate only and may not be the lot that you receive.

Recommended products

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

related product

Product No.

Description

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

Certificates of Analysis (COA)

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Development of buccal adhesive tablet with prolonged antifungal activity: Optimization and ex vivo deposition studies.

Madgulkar A, et al.

Indian Journal of Pharmaceutical Sciences, 71(3), 290-290 (2009)

Development and validation of a simple stability-indicating high performance liquid chromatographic method for the determination of miconazole nitrate in bulk and cream formulations.

De Zan MM, et al.

Talanta, 79(3), 762-767 (2009)

Simultaneous determination of miconazole nitrate and metronidazole in different pharmaceutical dosage forms by gas chromatography and flame ionization detector (GC-FID).

Ashour S and Kattan N

International Journal of Biomedical Science : IJBS, 6(1), 13-13 (2010)

Solid state solubility of miconazole in poly[(ethylene glycol)-g-vinyl alcohol] using hot-melt extrusion.

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

Simple screening method to identify toxic/non-toxic ionic liquids: agar diffusion test adaptation.

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.

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