Isoconazole

Isoconazole
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	D01AC05 (WHO) G01AF07 (WHO);
Identifiers
	IUPAC name (RS)-1-[2-[(2,6-Dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole;
CAS Number	27523-40-6;
PubChem CID	3760;
DrugBank	DB08943 N;
ChemSpider	3629;
UNII	GRI7WFR424;
KEGG	D04624;
ChEBI	CHEBI:82865 Y;
ChEMBL	ChEMBL1571863;
CompTox Dashboard (EPA)	DTXSID7045447 ;
ECHA InfoCard	100.044.084
Chemical and physical data
Formula	C18H14Cl4N2O
Molar mass	416.12 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(c(Cl)c1)C(OCc2c(Cl)cccc2Cl)Cn3ccnc3;

Isoconazole is an azole antifungal drug and could inhibit gram positive bacteria.¹² For foot and vaginal infections, isoconazole has a similar effectiveness to clotrimazole.³⁴ Isoconazole nitrate may be used in combination with corticosteroid diflucortolone to increase its bioavailability.¹

It was patented in 1968 and approved for medical use in 1979.⁵

Isoconazole is also known to bind to tubulin and inhibit its polymerization. ⁶

References

Veraldi S (May 2013). "Isoconazole nitrate: a unique broad-spectrum antimicrobial azole effective in the treatment of dermatomycoses, both as monotherapy and in combination with corticosteroids". Mycoses. 56 (Suppl 1): 3–15. doi:10.1111/myc.12054. PMID 23574019. S2CID 1881151.
Budavari S, O'Neil M, Smith A, Heckelman P, Obenchain J (1996). "Isoconazole". In Budavari S (ed.). The Merck Index (12th ed.). Taylor & Francis. p. 5176. ISBN 0-911910-12-3.
Oyeka CA, Gugnani HC (1992). "Isoconazole nitrate versus clotrimazole in foot and nail infections due to Hendersonula toruloidea, Scytalidium hyalinum and dermatophytes". Mycoses. 35 (11–12): 357–361. doi:10.1111/j.1439-0507.1992.tb00894.x. PMID 1302811. S2CID 6764090.
Cohen L (February 1984). "Single dose treatment of vaginal candidosis: comparison of clotrimazole and isoconazole". The British Journal of Venereal Diseases. 60 (1): 42–44. doi:10.1136/sti.60.1.42. PMC 1046268. PMID 6365236.
Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 502. ISBN 9783527607495.
Baksheeva VE, La Rocca R, Allegro D, Derviaux C, Pasquier E, Roche P, Morelli X, Devred F, Golovin AV, Tsvetkov PO (2025). "NanoDSF Screening for Anti-tubulin Agents Uncovers New Structure–Activity Insights". Journal of Medicinal Chemistry. doi:10.1021/acs.jmedchem.5c01008.