Grundinformationen
- CAS
27220-47-9- Standard-SMILES
Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)cc1- InChIKey
LEZWWPYKPKIXLL-UHFFFAOYSA-N- Summenformel
- C18H15Cl3N2O
- Durchschnittliche Molmasse
- 381,7 g/mol
- Monoisotopische Masse
- 380,024996
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Econazole
- IUPAC
- 1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
- Lokaler Name
- Econazol
- Englischer Name
- Econazole
- Summenformel
- C18H15Cl3N2O
- Molmasse
- 381.68
Namen und Synonyme
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
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
27220-47-9
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,3
- Polarare Oberfläche (TPSA)
- 27,1 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 379
Experimentelle und physikochemische Eigenschaften
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]
Physikochemische Eigenschaften
- Schmelzpunkt
- 86.8 °C · 86.8°C
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (97.4%)
Toxikologische Informationen
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).
Chemie und Industrie
Pharmakologische Informationen
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.
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