ContaminantDB: Econazole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:25 UTC

Update Date

2026-05-14 16:58:03 UTC

Accession Number

CHEM002353

Identification

Common Name

Econazole

Class

Small 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Spectazole	ChEMBL, HMDB
gyno Pevaryl	MeSH, HMDB
gyno-Pervaryl 150	MeSH, HMDB
gyno-Pevaryl	MeSH, HMDB
Econazole nitrate	MeSH, HMDB
gyno Pevaril	MeSH, HMDB
gyno-Pevaril	MeSH, HMDB
Nitrate, econazole	MeSH, HMDB
Pevaryl	MeSH, HMDB
Ekonazole	MeSH, HMDB
gyno Pervaryl 150	MeSH, HMDB
GynoPevaril	MeSH, HMDB
Econazole	MeSH

Chemical Formula

C₁₈H₁₅Cl₃N₂O

Average Molecular Mass

381.684 g/mol

Monoisotopic Mass

380.025 g/mol

CAS Registry Number

27220-47-9

IUPAC Name

1-{2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole

Traditional Name

econazole

SMILES

ClC1=CC=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1

InChI Identifier

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

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).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:82873 )
ether (CHEBI:82873 )
dichlorobenzene (CHEBI:82873 )
monochlorobenzenes (CHEBI:82873 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antifungal agent

Biological Roles

antifungal agent

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	162°C
Boiling Point	Not Available
Solubility	1.48e-03 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
logP	4.67	ALOGPS
logP	5.35	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	6.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.05 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	98.26 m³·mol⁻¹	ChemAxon
Polarizability	37.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9341000000-4ffb0473a31cea3f8c18	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-0209000000-dd9a7887032ba981630f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-004i-1900000000-28f4c0046949a5e27ab1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-004i-0900000000-f00842704123db9b0465	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0903000000-6c5549ea79b88c593f2e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-0009000000-0e20351a1183f50f888e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-004i-5900000000-bb76504dc81de5c3b579	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-004i-0900000000-a667527ad6d687e25400	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0019000000-e4e35751739b91041ba8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00m0-5169000000-ef3cb4a26c4fda6ee25d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9310000000-88884e5d802b100711cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1009000000-cef44f57a37b6b00c969	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9001000000-7c677fea699efb1a72f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9310000000-1d15b5e04ae4eb7ad414	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2039000000-17f63aee73e32a973719	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9551000000-33222b3a25a12499d2cb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00lr-9000000000-cd84e8c432915c9cc869	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-7996a613e7d9dea8ceba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1219000000-1878634d92d58865370e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00or-6910000000-84c9b556f80d88764610	Spectrum

Toxicity Profile

Route of Exposure

After 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 Toxicity

Econazole 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.

Metabolism

Hepatic.

Toxicity Values

LD50: 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 Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For 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 Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01127

HMDB ID

HMDB0257074

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Econazole

Chemspider ID

3086

ChEBI ID

82873

PubChem Compound ID

Not Available

Kegg Compound ID

C08068

YMDB ID

Not Available

ECMDB ID

Not 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.

MSDS

Link

General References

Not Available

Econazole (CHEM002353)

Structure for CHEM002353: Econazole