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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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IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: econazole

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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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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
InChI Key LEZWWPYKPKIXLL-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

References
1. Hill K, McNulty S, Randall AD. (2004)
Inhibition of TRPM2 channels by the antifungal agents clotrimazole and econazole.
Naunyn Schmiedebergs Arch Pharmacol, 370 (4): 227-37. [PMID:15549272]
2. Ishida H, Noshiro M, Okuda K, Coon MJ. (1992)
Purification and characterization of 7 alpha-hydroxy-4-cholesten-3-one 12 alpha-hydroxylase.
J Biol Chem, 267 (30): 21319-23. [PMID:1400444]
3. Liu J, Carlson HA, Scott EE. (2022)
The structure and characterization of human cytochrome P450 8B1 supports future drug design for nonalcoholic fatty liver disease and diabetes.
J Biol Chem, 298 (9): 102344. [PMID:35944583]