M3512
(±)-Miconazole nitrate salt
imidazole antibiotic
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
PubChem Substance ID:
eCl@ss:
39161001
UNSPSC Code:
51102829
NACRES:
NA.85
EC Number:
245-256-6
MDL number:
Quality Level
optical activity
[α]/D ±0.10° (Specific Rotation (BP))
color
white to off-white
antibiotic activity spectrum
fungi, mycobacteria
mode of action
enzyme | inhibits
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
Chemical structure: imidazole
Application
Miconazole is an imidazole antifungal agent that is used topically and by intravenous infusion. It is used to inhibit cytochrome P450 and to study automated luminescence-based cytochrome P450 profiling.
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.
Preparation Note
Sparingly soluble in methanol, slightly soluble in ethanol. Very slightly soluble in water.
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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
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Automated Luminescence-Based Cytochrome P450 Profiling Using a Simple, Elegant Robotic Platform
Brad Larson, Peter Banks, et al.
Journal of the Association for Laboratory Automation, 16, 47-55 (2011)
Francis X Cunningham et al.
Eukaryotic cell, 6(3), 533-545 (2006-11-07)
Cyanidioschyzon merolae is considered to be one of the most primitive of eukaryotic photosynthetic organisms. To obtain insights into the origin and evolution of the pathway of carotenoid biosynthesis in eukaryotic plants, the carotenoid content of C. merolae was ascertained
Ali Reza Khosravi et al.
Foodborne pathogens and disease, 9(7), 674-679 (2012-06-14)
The purpose of the present study was to evaluate and assess the capability of Zataria multiflora, Geranium herbarium, and Eucalyptus camaldolensis essential oils in treating Saprolegnia parasitica-infected rainbow (Oncorhynchus mykiss) trout eggs. A total of 150 infected eggs were collected
Global Trade Item Number
| SKU | GTIN |
|---|---|
| M3512-25G | 04061834050285 |
| M3512-5G | 04061834050292 |
| M3512-1G | 04061835546756 |