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E4632

Sigma-Aldrich

Econazole nitrate salt

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C18H15Cl3N2O · HNO3
CAS Number:
24169-02-6
Molecular Weight:
444.70
EC Number:
246-053-5
MDL number:
MFCD00058160
UNSPSC Code:
51102829
PubChem Substance ID:
24894567
NACRES:
NA.85

form

powder or crystals

Quality Level

200

color

white to off-white

antibiotic activity spectrum

Gram-positive bacteria
fungi

Mode of action

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

SMILES string

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)

InChI key

DDXORDQKGIZAME-UHFFFAOYSA-N

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General description

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.

Biochem/physiol Actions

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
Núria Daranas et al.
Applied and environmental microbiology, 84(10) (2018-03-11)
A viability quantitative PCR (v-qPCR) assay was developed for the unambiguous detection and quantification of Lactobacillus plantarum PM411 viable cells in aerial plant surfaces. A 972-bp region of a PM411 predicted prophage with mosaic architecture enabled the identification of a
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