Oxiconazole

Last updated
Oxiconazole
Oxiconazol.svg
Clinical data
Trade names Oxistat, Oxizole
AHFS/Drugs.com Monograph
MedlinePlus a689004
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
Formula C18H13Cl4N3O
Molar mass 429.12 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- Yes check.svgY
  • Key:QRJJEGAJXVEBNE-MOHJPFBDSA-N Yes check.svgY

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.).

Contents

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

Synthesis

Oxiconazole synthesis.svg

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

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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.