Oxiconazole

Oxiconazole
Clinical data
Trade names	Oxistat, Oxizole
AHFS/Drugs	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;
PubChemCID	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	429.12g·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 namesOxistatin the US,Oxizolein Canada) is anantifungal medicationtypically administered in a cream or lotion to treatskin infections,such asathlete's foot,jock itchandringworm.It can also be prescribed to treat theskin rashknown astinea versicolor,caused by systemic yeast overgrowth (Candidaspp.).

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

Synthesis

Treatment of theketone(1) withhydroxylaminegives theoxime(2), which isalkylatedwith 2,4-dichlorobenzyl chloride (3) in the presence of the strong basesodium hydrideto 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.Retrieved2024-06-30.

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