Econazole (CED0005931)

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 an exogenous solid compound with the formula C18H15Cl3N2O and an average molecular weight of 381.68 g/mol. Econazole belongs to the benzylethers, a subclass of benzene and substituted derivatives within the organic compounds. It serves as an antifungal agent for biological application. The compound is found in 17 recorded sources, including healthcare, pharmaceuticals, and veterinary products such as antibiotics, gynecologicals, and antifungals for dermatological use. It is also present in food preservation, floors, and various household cleaning and consumer products, including soap detergents, perfumes within detergents and soaps, bleaching agents, cigar cigarettes, and other smoking requisites. Additionally, it is found in electrical and electronic equipment, including electrodes, hybrid capacitors, electric hearing aids, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for the compound include oral, topical, vaginal, and inhalation. Econazole interacts with six recorded protein targets. These include lanosterol 14-alpha demethylase (CYP51A1), steroid 17-alpha-hydroxylase/17,20 lyase (CYP17A1), malate dehydrogenase, cytoplasmic (MDH1), and it acts as an antagonist/partial agonist of cytochrome P450 3A4 (CYP3A4), along with two other proteins.
Contaminant Type
  • Amine
  • Antifungal Agent
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
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
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot 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
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004i-9341000000-4ffb0473a31cea3f8c18Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0209000000-dd9a7887032ba981630fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-1900000000-28f4c0046949a5e27ab1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-f00842704123db9b0465Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0903000000-6c5549ea79b88c593f2eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0009000000-0e20351a1183f50f888eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-5900000000-bb76504dc81de5c3b579Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-a667527ad6d687e25400Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0019000000-e4e35751739b91041ba8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00m0-5169000000-ef3cb4a26c4fda6ee25dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-9310000000-88884e5d802b100711cdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1009000000-cef44f57a37b6b00c969Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-9001000000-7c677fea699efb1a72f3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-9310000000-1d15b5e04ae4eb7ad414Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-2039000000-17f63aee73e32a973719Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9551000000-33222b3a25a12499d2cbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-9000000000-cd84e8c432915c9cc869Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-7996a613e7d9dea8cebaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1219000000-1878634d92d58865370eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00or-6910000000-84c9b556f80d88764610Not AvailableView Spectrum
Toxicity Profile
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.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
462.0mg/kgNot AvailableMouseLD50OralexperimentalA308
462.0mg/kgNot AvailableRatLD50OralexperimentalA308
668.0mg/kgNot AvailableGuinea pigLD50OralexperimentalA308
160.0mg/kg>160DogLD50OralexperimentalA308
949.0Log mg/kg[530:1700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
299Antifungals for dermatological useHealthcare, pharmaceuticals & veterinary productsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
497FloorsBuilding & ConstructionNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Indoleamine 2,3-dioxygenase 1 structureClick to view 3D structureIndoleamine 2,3-dioxygenase 1P14902HumansPredicted (SEA)0.311397
Cysteine protease ATG4A structureClick to view 3D structureCysteine protease ATG4AQ8WYN0HumansPredicted (SEA)0.155698
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)4.28171
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)2.80257
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)3.65891
Click to view 3D structureThromboxane-A synthaseP24557HumansPredicted (SEA)0.0778492
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)4.51525
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)1.63483
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)2.88042
Substance-K receptor structureClick to view 3D structureSubstance-K receptorP21452HumansPredicted (SEA)0.700643
Steroid 17-alpha-hydroxylase/17,20 lyase structureClick to view 3D structureSteroid 17-alpha-hydroxylase/17,20 lyaseP05093HumansPredicted (SEA)0.155698
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)3.73676
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)3.73676
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)2.25763
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)11.8331
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)8.56341
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)2.72472
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)9.49761
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)2.02408
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)3.65891
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)4.04816
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)10.3539
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)2.10193
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)52.0033
Lanosterol 14-alpha demethylase structureClick to view 3D structureLanosterol 14-alpha demethylaseQ16850HumansPredicted (SEA)0.0778492
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansKnownNot Available
Lanosterol 14-alpha demethylase structureClick to view 3D structureLanosterol 14-alpha demethylaseQ16850HumansKnownNot Available
Malate dehydrogenase, cytoplasmic structureClick to view 3D structureMalate dehydrogenase, cytoplasmicP40925HumansKnownNot Available
Steroid 17-alpha-hydroxylase/17,20 lyase structureClick to view 3D structureSteroid 17-alpha-hydroxylase/17,20 lyaseP05093HumansKnownNot 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