Oxiconazole

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 ;
PubChem CID	5361463;
DrugBank	DB00239 ;
ChemSpider	4514745 ;
UNII	RQ8UL4C17S;
KEGG	D00885 ;
ChEBI	CHEBI:7825 ;
ChEMBL	ChEMBL1262 ;
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- ; Key:QRJJEGAJXVEBNE-MOHJPFBDSA-N ;

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]

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

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