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Documentos Principais

M3512

Sigma-Aldrich

(±)-Miconazole nitrate salt

imidazole antibiotic

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C18H14Cl4N2O · HNO3
Número CAS:
Peso molecular:
479.14
Número CE:
Número MDL:
Código UNSPSC:
51102829
eCl@ss:
39161001
ID de substância PubChem:
NACRES:
NA.85

Nível de qualidade

atividade óptica

[α]/D ±0.10° (Specific Rotation (BP))

cor

white to off-white

espectro de atividade do antibiótico

fungi
mycobacteria

Modo de ação

enzyme | inhibits

cadeia de caracteres SMILES

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)

chave InChI

MCCACAIVAXEFAL-UHFFFAOYSA-N

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Descrição geral

Chemical structure: imidazole

Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Nota de preparo

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

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Declarações de precaução

Classificações de perigo

Acute Tox. 4 Oral - Skin Sens. 1

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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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
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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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