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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
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
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. Also, for use with USP monographs such as:
- Miconazole Nitrate Cream
- Miconazole Nitrate Topical Powder
- Miconazole Nitrate Vaginal Suppositories
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 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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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Skin Sens. 1
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
S Gebremedhin et al.
Journal of physiology and pharmacology : an official journal of the Polish Physiological Society, 65(4), 593-600 (2014-09-03)
Oral candidiasis in the form of Candida-associated denture stomatitis (CaDS) is associated with Candida adhesion and biofilm formation on the fitting surface of poly (methyl methacrylate) (PMMA) dentures. Candida biofilms show considerable resistance to most conventional antifungal agents, a phenomenon
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 1443500-200MG | 04061838735577 |