Oxiconazole

Oxiconazole
Clinical data
Trade namesOxistat, Oxizole
AHFS/Drugs.comMonograph
MedlinePlusa689004
ATC code
Identifiers
IUPAC name
  • (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)
SMILES
  • Clc3ccc(/C(=N\OCc1ccc(Cl)cc1Cl)Cn2ccnc2)c(Cl)c3
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- checkY
  • Key:QRJJEGAJXVEBNE-MOHJPFBDSA-N checkY

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.).

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. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 9783527607495.
  2. ↑ Georg Mixich, Kurt Thiele, U.S. patent 4,550,175 (1985 to Siegfried Aktiengesellschaft).
  3. ↑ "Oxiconazole". Thieme. Retrieved 2024-06-30.
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