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 names	Oxistat, Oxizole
AHFS/Drugs.com	Monograph
MedlinePlus	a689004
ATC code	D01AC11 (WHO) G01AF17 (WHO)
Identifiers
IUPAC name (E)-[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethylidene] [(2,4-dichlorophenyl)methoxy]amine
CAS Number	64211-46-7 Y
PubChem CID	5361463
DrugBank	DB00239 Y
ChemSpider	4514745 Y
UNII	RQ8UL4C17S
KEGG	D00885 Y
ChEBI	CHEBI:7825 N
ChEMBL	ChEMBL1262 N
CompTox Dashboard (EPA)	DTXSID8040690
Chemical and physical data
Formula	C18H13Cl4N3O
Molar mass	429.12 g·mol−1
3D model (JSmol)	Interactive image
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- Y Key:QRJJEGAJXVEBNE-MOHJPFBDSA-N Y

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

• Fluconazole