Oxiconazole

Oxiconazole (trade names Oxistat in the US, Oxizole in Canada) is an antifungal medication typically administered in a cream or lotion to treat skin infections, such as athlete's foot, jock itch and ringworm. It can also be prescribed to treat the skin rash known as tinea versicolor, caused by systemic yeast overgrowth (Candida spp.).

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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H13Cl4N3O
Molar mass429.12 g·mol−1
3D model (JSmol)
  • 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- Y
  • Key:QRJJEGAJXVEBNE-MOHJPFBDSA-N Y
 NY (what is this?)  (verify)

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

Synthesis

The condensation of 1-(2,4-dichlorophenyl)-2-imidazol-1-ylethanone [46503-52-0] (1) with hydroxylamine [7803-49-8] gave 1-(2,4-dichlorophenyl)-2-imidazol-1-yl-ethanone oxime [64211-06-9] (2). Treatment with 2,4-Dichlorobenzyl chloride [94-99-5] (3) in the presence of strong base completed the synthesis of oxiconazole (4).

See also

References
  1. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 9783527607495.
  2. Serradell, MN; Blancafort, P.; Hillier, K.; Castaer, J.; Oxiconazole nitrate. Drugs Fut 1981, 6, 2, 99.
  3. Mixich G, Thiele K. Ein Beitrag zur stereospezifischen Synthese von antimykotisch wirksamen Imidazolyloximäthern. Oxiconazol-nitrat (Sgd 301-76), ein neues Breitbandantimykotikum [A contribution to the stereospecific synthesis of antifungal imidazolyloxime-ethers/Oxiconazole nitrate (Sgd 301-76), a new broadspectrum antifungal agent (author's transl)]. Arzneimittelforschung. 1979;29(10):1510-3. German. PMID: 583212.
  4. Georg Mixich, Kurt Thiele, U.S. patent 4,550,175 (1985 to Siegfried Aktiengesellschaft).
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