Oxiconazole

Source: Wikipedia, the free encyclopedia.
Oxiconazole
Clinical data
Trade namesOxistat, Oxizole
AHFS/Drugs.comMonograph
MedlinePlusa689004
ATC code
Identifiers
  • (E)-[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethylidene] [(2,4-dichlorophenyl)methoxy]amine
JSmol)
SMILES
  • Clc3ccc(/C(=N\OCc1ccc(Cl)cc1Cl)Cn2ccnc2)c(Cl)c3
  • 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- checkY
  • Key:QRJJEGAJXVEBNE-MOHJPFBDSA-N checkY

Oxiconazole (trade names Oxistat in the US, Oxizole in Canada) is an

skin rash known as tinea versicolor, caused by systemic yeast overgrowth (Candida
spp.).

It was patented in 1975 and approved for medical use in 1983.[1]

Synthesis

Treatment of the ketone (1) with hydroxylamine gives the oxime (2), which is alkylated with 2,4-dichlorobenzyl chloride (3) in the presence of the strong base sodium hydride to give oxiconazole.[2][3]

See also

References

  1. .
  2. ^ Georg Mixich, Kurt Thiele, U.S. patent 4,550,175 (1985 to Siegfried Aktiengesellschaft).
  3. ^ "Oxiconazole". Thieme. Retrieved 2024-06-30.