Description
Oxiconazole nitrate is a broad-spectrum antifungal agent indicated for the
treatment of skin infections due to yeasts, dermatophytes, yeast-like fungi and
molds, and gram positive organisms.
Chemical Properties
Crystalline Solid
Originator
Siegfried (Switzerland)
Uses
Topical antimycotic agent
Definition
ChEBI: An organic nitrate salt resulting from the reaction of equimolar amounts of oxiconazole and nitric acid. An antifungal agent, it is used in creams and powders for the topical treatment of fungal skin infections.
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.
Brand name
Oxistat (Altana);OCERAL;MYFUNGAR.
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.
