M3512

Sigma-Aldrich

(±)-Miconazole nitrate salt

imidazole antibiotic

Sinônimo(s):
1-(2,4-Dichloro-β-[(2,4-dichlorobenzyl)oxy]phenethyl)imidazole
Empirical Formula (Hill Notation):
C18H14Cl4N2O · HNO3
Número CAS:
Peso molecular:
479.14
Número EC:
Número MDL:
eCl@ss:
39161001
ID de substância PubChem:
NACRES:
NA.85

Nível de qualidade

200

atividade óptica

[α]/D ±0.10° (Specific Rotation (BP))

cor

white to off-white

Modo de ação

enzyme | inhibits

espectro de atividade do antibiótico

fungi
mycobacteria

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

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Categorias relacionadas

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

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

Equipamento de proteção individual

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

RIDADR

NONH for all modes of transport

WGK Alemanha

WGK 3

Ponto de fulgor (ºF)

Not applicable

Ponto de fulgor (ºC)

Not applicable

Certificado de análise
Certificado de origem
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...
Yuan Cao et al.
Bioorganic & medicinal chemistry letters, 20(8), 2456-2460 (2010-03-26)
Six selaginellin derivatives, including three new analogues selaginellins D-F (1-3), were isolated from the EtOAc extract of the whole plant of Selaginella pulvinata (Hook. et Grev.) Maxim. Their structures were determined on the basis of extensive physical and chemical evidence....
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...
Kristy K Michael Miller et al.
Steroids, 78(1), 15-25 (2012-11-06)
Dehydroepiandrosterone (DHEA) levels were reported to associate with increased breast cancer risk in postmenopausal women, but some carcinogen-induced rat mammary tumor studies question this claim. The purpose of this study was to determine how DHEA and its metabolites affect estrogen...

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