Basic information
- CAS
27220-47-9- Standard SMILES
Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)cc1- InChIKey
LEZWWPYKPKIXLL-UHFFFAOYSA-N- Molecular formula
- C18H15Cl3N2O
- Average molar mass
- 381.7 g/mol
- Monoisotopic mass
- 380.024996
Overview
1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 4-chlorobenzyl group. It is a dichlorobenzene, a member of imidazoles, an ether and a member of monochlorobenzenes.
Names & identifiers
- Preferred name
- Econazole
- IUPAC
- 1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
- English name
- Econazole
- Molecular formula
- C18H15Cl3N2O
- Molecular weight
- 381.68
Names & synonyms
econazole27220-47-9EconazolEconazolum(+-)-Econazole1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole1-[2-[(4-Chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazoleeconazoloEkonazoleGynoPevarilNSC-1877896Z1Y2V4A7M
Show more names
NSC 187789(±)-EconazolEconazole CRSEconazole USP/EP/BPEconazole (Standard)Econazole, 10 mM in DMSOEconazole Solution, 100ppmMiconazole EP Impurity B HCl
DTXSID20298721-(2,4-Dichloro-beta-((p-chlorobenzyl)oxy)phenethyl)imidazole1-{2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole1H-Imidazole, 1-(2-((4-chlorophenyl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-Imidazole, 1-(2,4-dichloro-beta-((p-chlorobenzyl)oxy)phenethyl)-1H-Imidazole, 1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-Gyno PevarilGyno Pevaryl
Database identifiers
- CAS
27220-47-9
Properties
Computed structural properties
- XLogP
- 5.3
- Topological polar surface area
- 27.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 6
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 379
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals
LogP5.5
Solubility1.48e-03 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antifungal Agents; Anti-Infective Agents
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid
Collision Cross Section
185.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID6025226]
182.89 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 86.8 °C · 86.8°C
- Boiling point
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2.6% (1 of 39) of reports.
Warning
H302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (97.4%)
Toxicology
Exposure Routes
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.
Toxicity Summary
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.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Chemistry & industry
Pharmacology
ATC Code
D01AC03
D - Dermatologicals
G - Genito urinary system and sex hormones
QD - Dermatologicals
QG - Genito urinary system and sex hormones
Pharmacodynamics
Econazole is an antifungal medication related to fluconazole (Diflucan), ketoconazole (Nizoral), itraconazole (Sporanox), and clotrimazole (Lotrimin, Mycelex). Econazole prevents fungal organisms from producing vital substances required for growth and function. This medication is effective only for infections caused by fungal organisms. It will not work for bacterial or viral infections.
Mechanism of Action
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/Metabolites
Hepatic.
Hepatic.
FDA Pharmacological Classification
6Z1Y2V4A7M
ECONAZOLE
Established Pharmacologic Class [EPC] - Azole Antifungal
Chemical Structure [CS] - Azoles
Econazole is an Azole Antifungal.
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism.
Absorption, Distribution and Excretion
Related reactions
1 records
Compound notes
Loading…