64211-46-7

Basic information

• Product Name: Oxiconazole nitrate
• Synonyms: (Z)-1-(2，4-Diehlorophenyl)-2-(1H-imidazol-1-y1)ethanone O-[(2，4-diehlorophenyl)methyl]oxime mononitrate;Gyno-Myfungar;(Z)-1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone;2',4'-Dichloro-2-imidazol-1-ylacetophenone (Z)-(o-(2,4-dichlorobenzyl))oxime nitrate;Ethanone, 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-, o-((2,4-dichlorophenyl)methyl)oxime, nitrate, (Z)-;O-[(2,4-Dichlorophenyl)methyl]oxime, (Z)-, mononitrate;Okiconale;Okiconale V
• CAS NO: 64211-46-7
• Molecular Formula: C18H13Cl4N3O
• Molecular Weight: 429.13
• EINECS: 264-730-3
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Oxiconazole;API;OXILAN
• Mol File: 64211-46-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 137-1380C
• Boiling Point: 576.8 °C at 760 mmHg
• Flash Point: 302.6 °C
• Appearance: Crystalline solid
• Vapor Pressure: 5.96E-17mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol (Sparingly)
• CAS DataBase Reference: Oxiconazole nitrate(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiconazole nitrate(64211-46-7)
• EPA Substance Registry System: Oxiconazole nitrate(64211-46-7)

Safety Data

• Hazardous Substances Data: 64211-46-7(Hazardous Substances Data)

Usage

Description

Oxiconazole nitrate is a broad-spectrum antifungal agent that belongs to the imidazole class. It is effective against a wide range of pathogenic yeasts, molds, and gram-positive organisms. Its antifungal action is attributed to the inhibition of ergosterol synthesis, which is a crucial component of the fungal cell membrane. Oxiconazole nitrate is available in the form of a crystalline solid and is commonly used in creams and powders for the topical treatment of fungal skin infections.

Uses

Used in Pharmaceutical Industry:
Oxiconazole nitrate is used as a topical antimycotic agent for the treatment of skin infections caused by yeasts, dermatophytes, yeast-like fungi, molds, and gram-positive organisms. Its broad-spectrum antifungal activity makes it a valuable asset in combating various fungal infections.
Used in Dermatology:
Oxiconazole nitrate is used as a therapeutic agent for treating skin infections, providing relief from symptoms such as itching, redness, and inflammation. Its ability to inhibit the growth of a wide range of pathogenic fungi makes it an effective treatment option for various skin conditions.
Used in Cosmetic Industry:
Oxiconazole nitrate is used as an active ingredient in antifungal creams and powders, targeting fungal skin infections and promoting skin health. Its incorporation into cosmetic products helps maintain skin hygiene and prevent the recurrence of fungal infections.
Brand Names:
Some of the brand names under which Oxiconazole nitrate is marketed include Oxistat (Altana), OCERAL, and MYFUNGAR. These products are widely available and are prescribed by healthcare professionals for the treatment of various fungal skin infections.

Originator

Siegfried (Switzerland)

Manufacturing Process

13.5 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanone oxime are dissolved in 100 ml dimethylformamide (DMF) and 1.2 g of sodium hydride are mixed in, whereupon an exothermic reaction is allowed to take place on its own with stirring. After cessation of evolution of hydrogen, a solution of 9.8 g of 2,4-dichlorobenzyl chloride in 10 cc DMF is added dropwise with continuous stirring and the stirring is carried on for 2 hours further. The reaction is then taken to completion at a bath temperature of 80°C, after which the reaction mixture is evaporated in a rotation evaporator under reduced pressure and the residue is dissolved in 100 ml ethanol. After filtering off of undissolved matter, the solution is stirred with 300 ml 2N nitric acid for the conversion of free base to the nitrate. The liquid standing over the heavy deposits which have separated out is separated off by decanting, whereupon an isomer is obtained which after recrystallization from ethanol is obtained in a yield of 5.2 g and having a melting point of 137°C to 138°C.

Therapeutic Function

Antifungal

Clinical Use

(Z)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone-O-[2,4-dichlorophenyl)methyl]oxime mononitrate (Oxistat)is a white crystalline nitric acid salt. It is used in cream andlotion dosage forms in 1% concentration for the treatment oftinea pedis, tinea corporis, and tinea capitis.

in vitro

oxiconazole is highly effective against many dermatophytes, including trichophyton rubrum, trichophyton mentagrophytes, trichophyton tonsurans, and epidermophyton floccosum. after application to the skin, oxiconazole is rapidly absorbed into the stratum corneum, maximum concentrations often being attained within 100 minutes. fungicidal concentrations are maintained in the epidermis, upper corium, and deeper corium for at least five hours, and levels exceeding the minimum inhibitory concentrations of susceptible fungi are present in the corneum, epidermis, upper corium, and the hair follicle for over 16 hours [2].

references

[1] polak a. oxiconazole, a new imidazole derivative. evaluation of antifungal activity in vitro and in vivo[j]. arzneimittel-forschung, 1981, 32(1): 17-24.[2] jegasothy b v, pakes g e. oxiconazole nitrate: pharmacology, efficacy, and safety of a new imidazole antifungal agent[j]. clinical therapeutics, 1990, 13(1): 126-141.

InChI:InChI=1/C17H11Cl4N3O.HNO3/c18-11-1-3-13(14(20)7-11)16(9-24-6-5-22-10-24)23-25-17-4-2-12(19)8-15(17)21;2-1(3)4/h1-8,10H,9H2;(H,2,3,4)/b23-16+;