Oxiconazole - 64211-45-6

Oxiconazole

Catalog Number: EVT-277976
CAS Number: 64211-45-6
Molecular Formula: C18H13Cl4N3O
Molecular Weight: 429.1 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.

Product Introduction

Description
Oxiconazole is a synthetic imidazole antifungal agent that is used to treat various fungal infections. It is a broad-spectrum antifungal drug that is effective against a wide range of fungi, including dermatophytes, yeasts, and molds. Oxiconazole is available in various forms, including creams, lotions, and solutions, and is used to treat skin infections such as athlete's foot, jock itch, and ringworm.
Applications in Various Fields
In medical research, oxiconazole has been used in drug development and clinical trials to evaluate its efficacy and safety in treating fungal infections. Clinical trials have shown that oxiconazole is effective in treating various fungal infections and has a low risk of developing resistance.
In environmental research, oxiconazole has been studied for its effects on ecosystems and its role in pollution management. The drug has been found to have low toxicity to aquatic organisms and is considered to be environmentally safe.
In industrial research, oxiconazole has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations include the proper handling and disposal of hazardous chemicals and waste products.

Properties

CAS Number

64211-45-6

Product Name

Oxiconazole

IUPAC Name

(Z)-1-(2,4-dichlorophenyl)-N-[(2,4-dichlorophenyl)methoxy]-2-imidazol-1-ylethanimine

Molecular Formula

C18H13Cl4N3O

Molecular Weight

429.1 g/mol

InChI

InChI=1S/C18H13Cl4N3O/c19-13-2-1-12(16(21)7-13)10-26-24-18(9-25-6-5-23-11-25)15-4-3-14(20)8-17(15)22/h1-8,11H,9-10H2/b24-18+

InChI Key

QRJJEGAJXVEBNE-HKOYGPOVSA-N

SMILES

C1=CC(=C(C=C1Cl)Cl)CON=C(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl

Solubility

Soluble in DMSO

Synonyms

(Z)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-O-(2,4-dichlorobenzyl) ethanone oxime nitrate
2',4'-dichloro-2-imidazol-1-ylacetophenone (Z)-(O-(2,4-dichlorobenzyl)oxime), mononitrate
Fonx
Gyno-Myfungar
Myfungar
Oceral
oxiconazole
oxiconazole mononitrate, (Z)-isomer
oxiconazole nitrate
Oxistat
Oxizole
oxyconazole
RO-13-8996
Salongo
Sgd 301-76

Canonical SMILES

C1=CC(=C(C=C1Cl)Cl)CON=C(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl

Isomeric SMILES

C1=CC(=C(C=C1Cl)Cl)CO/N=C(\CN2C=CN=C2)/C3=C(C=C(C=C3)Cl)Cl
Method of Synthesis or Extraction
Oxiconazole is synthesized by reacting 2,4-dichlorobenzyl chloride with 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone in the presence of a base such as potassium carbonate. The reaction yields oxiconazole as a white crystalline solid with a melting point of 102-104°C. The yield of the synthesis process is typically around 70-80%, and the process is considered to be efficient and cost-effective.
Environmental and safety considerations of the synthesis process include the use of hazardous chemicals such as 2,4-dichlorobenzyl chloride, which is toxic and can cause skin and eye irritation. The process also generates waste products that must be disposed of properly to prevent environmental contamination.
Chemical Structure and Biological Activity
The chemical structure of oxiconazole consists of an imidazole ring attached to a dichlorophenyl group. The imidazole ring is responsible for the antifungal activity of the drug, as it inhibits the synthesis of ergosterol, a key component of fungal cell membranes.
Oxiconazole has a broad spectrum of activity against various fungi, including dermatophytes, yeasts, and molds. It is effective against both superficial and systemic fungal infections and has a low risk of developing resistance.
Biological Effects
Oxiconazole exerts its antifungal activity by inhibiting the synthesis of ergosterol, which is essential for fungal cell membrane integrity. This leads to the disruption of fungal cell membranes and ultimately results in fungal cell death.
Potential therapeutic effects of oxiconazole include the treatment of various fungal infections, including athlete's foot, jock itch, and ringworm. However, the drug may also have potential toxic effects, including skin irritation, allergic reactions, and liver toxicity.
Future Perspectives and Challenges
Current limitations in the use and study of oxiconazole include the potential for toxic effects and the development of resistance. Possible solutions and improvements include the development of new formulations and delivery methods to improve efficacy and reduce toxicity.
Future trends and prospects in the application of oxiconazole in scientific research include the development of new antifungal drugs with improved efficacy and safety profiles. The use of oxiconazole in combination with other antifungal agents may also be explored to improve treatment outcomes and reduce the risk of resistance.

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