econazole   Click here for help

GtoPdb Ligand ID: 2446

Synonyms: R-14827 | Spectazole®
Approved drug
econazole is an approved drug (FDA (1982))
Compound class: Synthetic organic
Comment: Econazole topical is an antifungal agent. The preparation of econazole specified by the INN document is a racemic mixture of an (R)- and an (S)- isomer. The structure shown here does not specify stereochemistry and represents the mixture.
Marketed formulations may contain econazole nitrate (PubChem CID 68589).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 27.05
Molecular weight 380.02
XLogP 5.46
No. Lipinski's rules broken 1
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Canonical SMILES Clc1ccc(cc1)COC(c1ccc(cc1Cl)Cl)Cn1cncc1
Isomeric SMILES Clc1ccc(cc1)COC(c1ccc(cc1Cl)Cl)Cn1cncc1
InChI InChI=1S/C18H15Cl3N2O/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21/h1-9,12,18H,10-11H2
No information available.
Summary of Clinical Use Click here for help
Topically applied econazole is used to treat fungal skin infections such as athlete's foot, ringworm, tinea versicolor, and yeast infections.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Econazole interacts with 14-α demethylase (cytochrome P450 51 ), an enzyme required to convert lanosterol to ergosterol, an essential component of the fungal cell membrane. This disrupts fungal cell wall formation and results in cell death.