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M3512

(±)-Miconazole nitrate salt

Name: (±)-Miconazole nitrate salt
Brand: SIGMA

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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Propiedades

Quality Segment

200

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

Descripción

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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pictograms

GHS07

signalword

Warning

hcodes

H302,H317

pcodes

P280 - P301 + P312 + P330 - P302 + P352

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