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Key Documents

E4632

Sigma-Aldrich

Econazole nitrate salt

Synonyme(s) :

1-(2-[(4-Chlorophenyl)methoxy]-2-[2,4-dichlorophenyl]ethyl)-1H-imidazole

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About This Item

Formule empirique (notation de Hill):
C18H15Cl3N2O · HNO3
Numéro CAS:
Poids moléculaire :
444.70
Numéro CE :
Numéro MDL:
Code UNSPSC :
51102829
ID de substance PubChem :
Nomenclature NACRES :
NA.85

Forme

powder or crystals

Niveau de qualité

Couleur

white to off-white

Spectre d'activité de l'antibiotique

Gram-positive bacteria
fungi

Mode d’action

cell membrane | interferes
cell wall synthesis | interferes
enzyme | inhibits

Chaîne SMILES 

O[N+]([O-])=O.Clc1ccc(COC(Cn2ccnc2)c3ccc(Cl)cc3Cl)cc1

InChI

1S/C18H15Cl3N2O.HNO3/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21;2-1(3)4/h1-9,12,18H,10-11H2;(H,2,3,4)

Clé InChI

DDXORDQKGIZAME-UHFFFAOYSA-N

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Description générale

Chemical structure: imidazole

Application

Econazole is a broad spectrum antimycotic similar to ketoconazole. It has some action against Gram positive bacteria. It is used topically in dermatomycoses as well as orally and parenterally. It is used for studies on processes such as platelet serotonin uptake, prostanoid biosynthesis, EDHF-mediated relaxation, and Ca2+ transport pathways in thymic lymphocytes.

Actions biochimiques/physiologiques

Econazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. Inhibition of ergosterol results in increased cellular permeability causing leakage of cellular contents. Econazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and phospholipid biosynthesis.

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


Certificats d'analyse (COA)

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Inhibition of Ca2+ transport pathways in thymic lymphocytes by econazole, miconazole, and SKF 96365
M. J. Mason, B. Mayer, et al.
American Journal of Physiology. Cell Physiology, 264, C654-C662 (1993)
C J Jackson et al.
FEMS microbiology letters, 192(2), 159-162 (2000-11-07)
Azole antifungals are central to therapy and act by inhibiting a cytochrome P450, sterol 14-demethylase and blocking normal sterol synthesis. Our recent identification of a mycobacterial sterol biosynthetic pathway led us to probe the efficacy of a range of these
Alessandro Malara et al.
The Journal of biological chemistry, 292(8), 3239-3251 (2017-01-05)
Abscisic acid (ABA) is a phytohormone involved in pivotal physiological functions in higher plants. Recently, ABA has been proven to be also secreted and active in mammals, where it stimulates the activity of innate immune cells, mesenchymal and hematopoietic stem
M A Ghannoum et al.
Clinical microbiology reviews, 12(4), 501-517 (1999-10-09)
The increased use of antibacterial and antifungal agents in recent years has resulted in the development of resistance to these drugs. The significant clinical implication of resistance has led to heightened interest in the study of antimicrobial resistance from different
Núria Daranas et al.
PloS one, 13(1), e0190931-e0190931 (2018-01-06)
Lactobacillus plantarum strains PM411 and TC92 can efficiently control bacterial plant diseases, but their fitness on the plant surface is limited under unfavourable low relative humidity (RH) conditions. To increase tolerance of these strains to water stress, an adaptive strategy

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