基本情報
- CAS
27220-47-9- 標準SMILES
Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)cc1- InChIKey
LEZWWPYKPKIXLL-UHFFFAOYSA-N- 分子式
- C18H15Cl3N2O
- 平均分子量
- 381.7 g/mol
- 単同位体質量
- 380.024996
概要
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.
名称と識別子
- 優先名称
- Econazole
- IUPAC
- 1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
- 現地名
- エコナゾール
- 英語名
- Econazole
- 分子式
- C18H15Cl3N2O
- 分子量
- 381.68
名称と別名
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
名称をさらに表示
1-[β-[(4-クロロベンジル)オキシ]-2,4-ジクロロフェネチル]-1H-イミダゾール1-[2-[(4-クロロフェニル)メトキシ]-2-(2,4-ジクロロフェニル)エチル]-1H-イミダゾール(-)-1-[2-[(4-クロロフェニル)メトキシ]-2-(2,4-ジクロロフェニル)エチル]-1H-イミダゾール(+)-1-[2-[(4-クロロフェニル)メトキシ]-2-(2,4-ジクロロフェニル)エチル]-1H-イミダゾール1-(1H-イミダゾール-1-イル)-2-(2,4-ジクロロフェニル)-2-(4-クロロベンジルオキシ)エタンエコナゾール1-[2,4-ジクロロ-β-(p-クロロベンジルオキシ)フェネチル]-1H-イミダゾール1-(2,4-ジクロロフェニル)-2-(1H-イミダゾール-1-イル)エチル4-クロロベンジルエーテルNSC 187789(±)-EconazolEconazole CRSEconazole USP/EP/BPEconazole (Standard)Econazole, 10 mM in DMSOEconazole Solution, 100ppmMiconazole EP Impurity B HCl
物性
構造計算による物性
- XLogP
- 5.3
- 極性表面積
- 27.1 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 6
- 重原子数
- 24
- 形式電荷
- 0
- 複雑度
- 379
実験および物理化学的性質
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]
物理化学的性質
- 融点
- 86.8 °C · 86.8°C
- 沸点
- 533.8 · 533.8±50.0 °C(Predicted)
- 比重(密度)
- 1.33 · 1.33±0.1 g/cm3(Predicted)
- 貯蔵温度
- Sealed in dry,Room Temperature
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (97.4%)
毒性情報
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
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
econazole
化学と産業
薬理情報
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
関連反応
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