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Merck

M3512

(±)-Miconazole nitrate salt

imidazole antibiotic

Sinónimos:

1-(2,4-Dichloro-β-[(2,4-dichlorobenzyl)oxy]phenethyl)imidazole

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Fórmula empírica (notación de Hill):
C18H14Cl4N2O · HNO3
Número CAS:
22832-87-7
Peso molecular:
479.14
PubChem Substance ID:
24896848
eCl@ss:
39161001
UNSPSC Code:
51102829
NACRES:
NA.85
EC Number:
245-256-6
MDL number:
MFCD00058161

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Nombre del producto

(±)-Miconazole nitrate salt, imidazole antibiotic

InChI key

MCCACAIVAXEFAL-UHFFFAOYSA-N

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)

SMILES string

ClC1=CC(Cl)=CC=C1C(OCC2=CC=C(Cl)C=C2Cl)CN3C=CN=C3.[O-][N+](O)=O

optical activity

[α]/D ±0.10° (Specific Rotation (BP))

color

white to off-white

antibiotic activity spectrum

fungi
mycobacteria

mode of action

enzyme | inhibits

Quality Level

200

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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.

General description

Chemical structure: imidazole

Preparation Note

Sparingly soluble in methanol, slightly soluble in ethanol. Very slightly soluble in water.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
127M4135V
068M4044V
049M4067V
096M4002V
085M4092V

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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
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)
Michele Tonelli et al.
Bioorganic & medicinal chemistry, 16(18), 8447-8465 (2008-09-02)
Eighty-five arylazoenamines, characterized by different types of aryl and basic moieties, have been synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against a panel of ten RNA and DNA viruses. The most commonly affected viruses were, in
Janardhanan Saravanan et al.
European journal of medicinal chemistry, 45(9), 4365-4369 (2010-06-29)
A series of 3-substituted amino-4,5-tetramethylene thieno[2,3-d] [1,2,3]-triazine-4(3H)-ones have been synthesized and characterized by UV,IR, 1H NMR, elemental and mass spectral analysis. The title compounds were evaluated for their antimicrobial activity by agar diffusion method against four bacteria and three fungi
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
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