Etomidate

HCID 667484CAS 33125-97-2

基本情報

標準SMILES
CCOC(=O)c1cncn1[C@H](C)c1ccccc1
InChIKey
NPUKDXXFDDZOKR-LLVKDONJSA-N
分子式
C14H16N2O2
平均分子量
244.29 g/mol
単同位体質量
244.12117775

概要

Etomidate is the ethyl ester of 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylic acid. It is an intravenous general anaesthetic with no analgesic activity. It has a role as a sedative and an intravenous anaesthetic. It is an ethyl ester and a member of imidazoles. It is functionally related to a 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylic acid.

名称と識別子

優先名称
Etomidate
IUPAC
ethyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylate

名称と別名

Etomidate33125-97-2HypnomidateAmidate(+)-EtomidateD-EtomidateEtomidatoEtomidatumethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate(+)-Ethyl 1-(alpha-methylbenzyl)imidazole-5-carboxylateethyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylateR-(+)-Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate
名称をさらに表示
R 16659(R)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid ethyl ester(R)-(+)-1-(alpha-Methylbenzyl)imidazole-5-carboxylic acid ethyl esterNSC-7591601H-Imidazole-5-carboxylic acid, 1-[(1R)-1-phenylethyl]-, ethyl esterCHEBI:4910Z22628B5983-((R)-1-Phenyl-ethyl)-3H-imidazole-4-carboxylic acid ethyl ester

データベース識別子

CAS
33125-97-2
PubChem CID
667484
DTXSID
DTXSID5023033
ChEMBL
CHEMBL23731、CHEMBL681
ChEBI
CHEBI:4910
UNII
Z22628B598
EC Number
251-385-9
Nikkaji
J17.549H

物性

構造計算による物性

XLogP
3
極性表面積
44.1 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
5
重原子数
18

実験および物理化学的性質

Drugs · 2 件

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

Pharmaceuticals -> Listed in ZINC15

LogP2.9
Solubility4.77e-01 g/L
Human Drugs · 3 件

Breast Feeding; Lactation; Milk, Human; Anesthetics, Intravenous; Hypnotics and Sedatives

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point · 2 件

142-142.8

67 °C

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 62 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationChemical: 1H-Imidazole-5-carboxylic acid, 1-(1-phenylethyl)-, ethyl ester, (R)-
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Adverse Effects · 1 件

Transient inhibition of adrenal steroid synthesis is considered etomidate's most significant adverse effect. A single bolus dose causes a dose-dependent inhibition of 11-beta-hydroxylase lasting 6 to 12 hours. This enzyme is responsible for converting 11-deoxycortisol to cortisol, which results in adrenocortical suppression. Hence, it poses a theoretical risk of impairing a patient's ability to produce an adequate stress response. 80% of patients were found to have etomidate-induced adrenal inhibition at 12 hours, and most patients' suppression had resolved by 48 hours. Etomidate is no longer administered by continuous infusion because of the risks of sustained suppression of endogenous cortisol and aldosterone production.

Toxicity Summary · 1 件

According to manufacturer labeling, overdose can occur from too rapid and repeated injections. In addition, the administration of rapid injections is followed by a fall in blood pressure. There is no antidote for etomidate. In a suspected case of overdosage, etomidate should be discontinued, a patent airway established (intubate, if necessary) or maintained, and oxygen administered with assisted ventilation.

Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Etomidate

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

化学と産業

薬理情報

ATC Code · 2 件

N - Nervous system

QN - Nervous system

Protein Binding76%, primarily to serum albumin.
Pharmacodynamics · 1 件

Etomidate is a non-barbiturate hypnotic that acts at the level of the reticular-activating system to produce anesthesia. Etomidate is an imidazole compound that appears to depress CNS function via GABA. Duration of action is intermediate between thiopental and methohexital, and recovery from a single dose is rapid with little residual depression. Like the barbiturates and propofol, etomidate is does not induce analgesia. Etomidate induces unconsciousness within one circulation time. Recovery is rapid as a result of extensive redistribution and rapid metabolism.

Mechanism of Action · 1 件

Etomidate binds at a distinct binding site associated with a Cl<sup>-</sup> ionopore at the GABA<sub>A</sub> receptor, increasing the duration of time for which the Cl<sup>-</sup> ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.

Biological Half-Life75 minutes.
Metabolism/MetabolitesHepatic. Metabolized rapidly by ester hydrolysis to inactive metabolites.

用途と製造

UsesUse (kg; approx.) in Germany (2009): >10

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