Econazole (CHEM002353)

Record Information
Version1.0
Creation Date2009-07-21 20:28:25 UTC
Update Date2026-05-14 16:58:03 UTC
Accession NumberCHEM002353
Identification
Common NameEconazole
ClassSmall Molecule
Description
Econazole is only found in individuals that have used or taken this drug. It is a broad spectrum antimycotic with some action against Gram positive bacteria. It is used topically in dermatomycoses also orally and parenterally. [PubChem] Econazole interacts with 14-alpha demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Econazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Antifungal Agent
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SpectazoleChEMBL, HMDB
gyno PevarylMeSH, HMDB
gyno-Pervaryl 150MeSH, HMDB
gyno-PevarylMeSH, HMDB
Econazole nitrateMeSH, HMDB
gyno PevarilMeSH, HMDB
gyno-PevarilMeSH, HMDB
Nitrate, econazoleMeSH, HMDB
PevarylMeSH, HMDB
EkonazoleMeSH, HMDB
gyno Pervaryl 150MeSH, HMDB
GynoPevarilMeSH, HMDB
EconazoleMeSH
Chemical FormulaC18H15Cl3N2O
Average Molecular Mass381.684 g/mol
Monoisotopic Mass380.025 g/mol
CAS Registry Number27220-47-9
IUPAC Name1-{2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
Traditional Nameeconazole
SMILESClC1=CC=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1
InChI IdentifierInChI=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 KeyLEZWWPYKPKIXLL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzylethers
Direct ParentBenzylethers
Alternative Parents
Substituents
  • Benzylether
  • 1,3-dichlorobenzene
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • N-substituted imidazole
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point162°C
Boiling PointNot Available
Solubility1.48e-03 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP4.67ALOGPS
logP5.35ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)6.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.05 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.26 m³·mol⁻¹ChemAxon
Polarizability37.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureAfter topical application to the skin of normal subjects, systemic absorption of econazole nitrate is extremely low. Although most of the applied drug remains on the skin surface, drug concentrations were found in the stratum corneum which, by far, exceeded the minimum inhibitory concentration for dermatophytes.
Mechanism of ToxicityEconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Econazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
MetabolismHepatic.
Toxicity ValuesLD50: 462 mg/kg (Oral, Mouse) (1) LD50: 462 mg/kg (Oral, Rat) (1) LD50: 668 mg/kg (Oral, Guinea pig) (1) LD50: >160 mg/kg (Oral, Dog) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor topical application in the treatment of tinea pedis, tinea cruris, and tinea corporis caused by Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans, Microsporum canis, Microsporum audouini, Microsporum gypseum, and Epidermophyton floccosum, in the treatment of cutaneous candidiasis, and in the treatment of tinea versicolor.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB01127
HMDB IDHMDB0257074
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEconazole
Chemspider ID3086
ChEBI ID82873
PubChem Compound IDNot Available
Kegg Compound IDC08068
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Godefroi, E.F. and Heeres, J.; U.S. Patent 3,717,655; February 20,1973; assigned to Jansen Pharmaceutica NV, Belgium.

MSDSLink
General References