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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
MDL number:
grade
pharmaceutical primary standard
API family
miconazole
manufacturer/tradename
EDQM
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
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 EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.
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.
Packaging
The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.
Other Notes
Sales restrictions may apply.
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Stefano Veraldi
Mycoses, 56 Suppl 1, 41-43 (2013-04-19)
A 43-year-old male, with intertrigo due to Candida albicans located at the inguinal folds and accompanied by severe pruritus, was treated with topical 1% isoconazole nitrate and 0.1% diflucortolone valerate (2 applications/day for 7 days). An improvement of pruritus was
Stefano Veraldi
Mycoses, 56 Suppl 1, 3-15 (2013-04-19)
Fungal skin infections, or dermatomycoses, are associated with a broad range of pathogens. Involvement of gram-positive bacteria is often suspected in dermatomycoses. Inflammation plays an important role in dermatomycoses, displaying a close association between frequent inflammation and reduced skin-related quality
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| M1900000 | 04061834041368 |