PHR1163
(±)-Miconazole nitrate salt
Pharmaceutical Secondary Standard; Certified Reference Material
Synonym(s):
1-(2,4-Dichloro-β-[(2,4-dichlorobenzyl)oxy]phenethyl)imidazole
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About This Item
Empirical Formula (Hill Notation):
C18H14Cl4N2O · HNO3
CAS Number:
Molecular Weight:
479.14
NACRES:
NA.24
PubChem Substance ID:
UNSPSC Code:
41116107
EC Number:
245-256-6
MDL number:
Quality Level
grade
certified reference material, pharmaceutical secondary standard
agency
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
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
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 secondary standards offer multi-traceability to the USP and EP (PhEur) primary standards, where they are available.
Other Notes
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.
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.
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.
Values of analytes vary lot to lot.
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Hazard Classifications
Acute Tox. 4 Oral - Skin Sens. 1
signalword
Warning
hcodes
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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’.
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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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| PHR1163-1G | 04061835237500 |