Completing data — usually done within a minute
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
Show more names
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
- Formal charge
- 0
- Complexity
- 277
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Depressants and Tranquilizers
Pharmaceuticals -> Listed in ZINC15
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anesthetics, Intravenous; Hypnotics and Sedatives
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
142-142.8
67 °C
Safety & regulation
GHS classification
GHS Classification
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
Toxicology
Adverse Effects
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
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
Drug Induced Liver Injury Rank (DILIrank 2.0)
Etomidate
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Pharmacodynamics
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
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.
FDA Pharmacological Classification
Z22628B598
ETOMIDATE
Physiologic Effects [PE] - General Anesthesia
Established Pharmacologic Class [EPC] - General Anesthetic
Etomidate is a General Anesthetic. The physiologic effect of etomidate is by means of General Anesthesia.
AMIDATE(TM) ETOMIDATE
MeSH Pharmacological Classification
Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174)
Uses & manufacturing
Related reactions
No reaction records under the current filter.
Compound notes
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