Econazole - 27220-47-9

Econazole

Catalog Number: EVT-242563
CAS Number: 27220-47-9
Molecular Formula: C18H15Cl3N2O
Molecular Weight: 381.7g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.

Product Introduction

Description
Econazole is a synthetic antifungal agent that belongs to the imidazole class of compounds. It is used to treat a variety of fungal infections, including ringworm, athlete's foot, and jock itch. Econazole works by inhibiting the synthesis of ergosterol, a key component of fungal cell membranes, which leads to cell death.
Applications in Various Fields
In medical research, econazole has been used in drug development and clinical trials for the treatment of fungal infections. It has been shown to be effective in treating a variety of fungal infections, with few side effects. However, it may not be effective against all fungal species, and resistance can develop over time.
In environmental research, econazole has been shown to have negative effects on ecosystems, particularly aquatic organisms. It can also have negative impacts on soil microorganisms and plant growth. However, it may have potential applications in pollution management and sustainability, particularly in the treatment of contaminated soils and water.
In industrial research, econazole has been used in manufacturing processes to improve product quality and efficiency. It has also been used in the development of new materials, such as antifungal coatings for medical devices. However, health and safety considerations must be taken into account when using econazole in industrial settings.

Properties

CAS Number

27220-47-9

Product Name

Econazole

IUPAC Name

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

Molecular Formula

C18H15Cl3N2O

Molecular Weight

381.7g/mol

InChI

InChI=1S/C18H15Cl3N2O/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/h1-9,12,18H,10-11H2

InChI Key

LEZWWPYKPKIXLL-UHFFFAOYSA-N

SMILES

C1=CC(=CC=C1COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl)Cl

Solubility

1.48e-03 g/L

Synonyms

Econazole
Econazole Nitrate
Ekonazole
Gyno Pervaryl 150
Gyno Pevaril
Gyno Pevaryl
Gyno-Pervaryl 150
Gyno-Pevaril
Gyno-Pevaryl
GynoPevaril
Nitrate, Econazole
Pevaryl

Canonical SMILES

C1=CC(=CC=C1COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl)Cl
Method of Synthesis or Extraction
Econazole can be synthesized using a variety of methods, including the reaction of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone with 2,4-dichlorobenzylamine in the presence of a base. This method has been shown to be efficient, with yields of up to 80%. However, it also produces a significant amount of waste and requires the use of toxic solvents, which can have negative environmental and safety implications.
Another method of synthesis involves the reaction of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone with 2,4-dichlorobenzyl alcohol in the presence of a base. This method has been shown to be more environmentally friendly, with yields of up to 90%. However, it is also more complex and requires more steps than the previous method.
Chemical Structure and Biological Activity
The chemical structure of econazole consists of a imidazole ring and a dichlorophenyl group. Econazole has been shown to have potent antifungal activity against a variety of fungal species, including Candida albicans and Trichophyton mentagrophytes. Its mechanism of action involves inhibition of the synthesis of ergosterol, which is essential for fungal cell membrane integrity.
Biological Effects
Econazole has been shown to have a variety of effects on cell function and signal transduction. It has been shown to inhibit the growth and proliferation of cancer cells, and may have potential therapeutic effects in the treatment of certain types of cancer. However, it can also have toxic effects on cells, particularly at high concentrations.
Future Perspectives and Challenges
One of the main challenges in the use and study of econazole is the development of resistance in fungal species. This highlights the need for continued research into new antifungal agents and alternative treatment strategies. Additionally, more research is needed to fully understand the potential therapeutic and toxic effects of econazole on cells and organisms. Future trends and prospects in the application of econazole in scientific research may include the development of new formulations and delivery methods, as well as the exploration of its potential in the treatment of other diseases.

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