Etomidate

HCID 667484

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Basic information

CAS
33125-97-2
Standard SMILES
CCOC(=O)c1cncn1[C@H](C)c1ccccc1
InChIKey
NPUKDXXFDDZOKR-LLVKDONJSA-N
Molecular formula
C14H16N2O2
Average molar mass
244.29 g/mol
Monoisotopic mass
244.12117775

Overview

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.

Names & identifiers

Preferred name
Etomidate
IUPAC
ethyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylate

Names & synonyms

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
Show more names
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

Database identifiers

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

Properties

Computed structural propertiesFilling in

XLogP
3
Topological polar surface area
44.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
5
Heavy atoms
18

Experimental & physicochemical properties

Drugs · 2 items

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

Pharmaceuticals -> Listed in ZINC15

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

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 items

142-142.8

67 °C

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

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%)

Toxicology

Adverse Effects · 1 item

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 item

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 items

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

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

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

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 item

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.

Uses & manufacturing

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

Related reactions

0 records

No reaction records under the current filter.

Compound notes

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