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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H16N2O2
Molecular Weight 244.2896
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETOMIDATE

SMILES

CCOC(=O)c1cncn1[C@]([H])(C)c2ccccc2

InChI

InChIKey=NPUKDXXFDDZOKR-LLVKDONJSA-N
InChI=1S/C14H16N2O2/c1-3-18-14(17)13-9-15-10-16(13)11(2)12-7-5-4-6-8-12/h4-11H,3H2,1-2H3/t11-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68005045 | https://www.ncbi.nlm.nih.gov/pubmed/21263301 | https://academic.oup.com/bjaed/article/6/2/49/305039/The-molecular-mechanisms-of-general-anaesthesia

Etomidate (AMIDATE®) is an imidazole derivative anesthetic and hypnotic with little effect on blood gases, ventilation, or the cardiovascular system. It is intended for the induction of general anesthesia by intravenous injection. Etomidate (AMIDATE®) is also indicated for the supplementation of subpotent anesthetic agents, such as nitrous oxide in oxygen, during maintenance of anesthesia for short operative procedures such as dilation and curettage or cervical conization. It also produces a unique toxicity among anesthetic drugs - inhibition of adrenal steroid synthesis that far outlasts its hypnotic action and that may reduce survival of critically ill patients. The major molecular targets mediating anesthetic effects of etomidate (AMIDATE®) in the central nervous system are specific gamma-aminobutyric acid (GABA) type A receptor subtypes. The R(+) isomer of etomidate is 10 times more potent than its S(-) isomer at potentiating GABA-A receptor activity.

CNS Activity

Curator's Comment:: Etomidate is supposed to be neuroprotective.

Originator

Curator's Comment:: # Janssen Pharmaceuticals, a division of Ortho-McNeil-Jannsen Pharmaceuticals

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMIDATE

Approved Use

Etomidate injection, USP is indicated by intravenous injection for the induction of general anesthesia. When considering use of etomidate, the usefulness of its hemodynamic properties (see CLINICAL PHARMACOLOGY) should be weighed against the high frequency of transient skeletal muscle movements (see ADVERSE REACTIONS). Intravenous etomidate is also indicated for the supplementation of subpotent anesthetic agents, such as nitrous oxide in oxygen, during maintenance of anesthesia for short operative procedures such as dilation and curettage or cervical conization.

Launch Date

4.00204792E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
87 ng/mL
25 mg 1 times / day multiple, oral
dose: 25 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ETOMIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3263 ng × min/mL
25 mg 1 times / day multiple, oral
dose: 25 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ETOMIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
75 min
25 mg 1 times / day multiple, oral
dose: 25 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ETOMIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Respiratory effects of etomidate.
1977 Mar
Etomidate in a new solvent. A clinical evaluation.
1977 Nov-Dec
Comparison of etomidate in combination with fentanyl or diazepam, with thiopentone as an induction agent for general anaesthesia.
1979 Dec
Venous complications after intravenous injection of diazepam, flunitrazepam, thiopentone and etomidate.
1980 Jun
Etomidate: a foreshortened clinical trial.
1980 Nov
Pain and myoclonus during induction with etomidate. A double-blind, controlled evaluation of the influence of droperidol and fentanyl.
1981
Cardiac complications during use of etomidate.
1983 Dec
The safety of etomidate: a new intravenous anaesthetic induction agent.
1983 Jun
[Etomidate in Intralipid. A solution for pain-free injection].
1983 Oct
Alfentanil in minor gynaecological surgery: use with etomidate and a comparison with halothane.
1984 Aug
The prevention of etomidate-induced myoclonus.
1984 Jan
[Increased tendency to seizures as affected by long-term infusions of etomidate in delirium tremens].
1985 Sep
Myoclonus on recovery from etomidate.
1985 Sep
Etomidate versus thiopental for induction of anesthesia.
1985 Sep
[Increase in somatosensory evoked potentials during anesthesia induction with etomidate].
1986 Jun
[Fentanyl in the prevention of etomidate-induced myoclonus].
1987 May-Jun
Use of etomidate for elective cardioversion.
1988 Apr
Respiratory disturbance during recovery from etomidate anaesthesia.
1988 Jan
Generalised seizures after etomidate anaesthesia.
1988 Sep
Etomidate infusions for the control of refractory status epilepticus.
1989
[A new formulation of etomidate in lipid emulsion--bioavailability and venous provocation].
1989 Aug
[The modification of injection pain and the incidence of thrombophlebitis following etomidate].
1990 Jan
Excitatory effects and electroencephalographic correlation of etomidate, thiopental, methohexital, and propofol.
1993 Nov
Total intravenous anesthesia for children undergoing brief diagnostic or therapeutic procedures.
1995 Jun
Propylene glycol toxicity caused by prolonged infusion of etomidate.
1995 Oct
Cerebral hypoxia after etomidate administration and temporary cerebral artery occlusion.
1997 Oct
Anesthesia sensitivity in mice that lack the beta3 subunit of the gamma-aminobutyric acid type A receptor.
1998 Mar
Pretreatment with sufentanil reduces myoclonus after etomidate.
2003 Apr
A single M1 residue in the beta2 subunit alters channel gating of GABAA receptor in anesthetic modulation and direct activation.
2003 Oct 31
Double-blind placebo controlled study of the effects of etomidate-alfentanil anesthesia in electroconvulsive therapy.
2004 Jun
Midazolam is more likely to cause hypotension than etomidate in emergency department rapid sequence intubation.
2004 Nov
Contrasting anesthetic sensitivities of T-type Ca2+ channels of reticular thalamic neurons and recombinant Ca(v)3.3 channels.
2005 Jan
Magnesium sulfate pretreatment reduces myoclonus after etomidate.
2005 Sep
BIS during etomidate-induced myoclonus.
2006 Apr
Alpha5GABAA receptors mediate the amnestic but not sedative-hypnotic effects of the general anesthetic etomidate.
2006 Apr 5
Remifentanil pretreatment reduces myoclonus after etomidate.
2006 Mar
[Prevention of myoclonus after etomidate using a priming dose].
2006 Oct
Etomidate-Lipuro is associated with considerably less injection pain in children compared with propofol with added lidocaine.
2006 Oct
Complete atrioventricular block following etomidate.
2007 Dec
Randomized clinical trial of etomidate versus propofol for procedural sedation in the emergency department.
2007 Jan
Etomidate-induced pacemaker-mediated ventricular tachycardia.
2007 May
Fatal outcome during anaesthesia induction in a patient with amiodarone-induced thyrotoxicosis.
2008 Apr
Cardiovascular manifestations of sedatives and analgesics in the critical care unit.
2009 Jul-Aug
Lidocaine pretreatment reduces the frequency and severity of myoclonus induced by etomidate.
2010 Apr
Epileptic seizure during anaesthesia induction with etomidate.
2010 Jun
Pretreatment with dexmedetomidine or thiopental decreases myoclonus after etomidate: a randomized, double-blind controlled trial.
2010 Mar
Does lidocaine more effectively prevent pain upon induction with propofol or etomidate when given preemptively than when mixed with the drug?
2010 Nov
GABAA receptor open-state conformation determines non-competitive antagonist binding.
2011 Feb 1
Etomidate deteriorates the toxicity of advanced glycation end products to human endothelial Eahy926 cells.
2014
Prevention of etomidate-induced myoclonus: which is superior: Fentanyl, midazolam, or a combination? A Retrospective comparative study.
2014 Feb 16
Patents

Sample Use Guides

Etomidate (AMIDATE®) is intended for administration only by the intravenous route. The dose for induction of anesthesia in adult patients will vary between 0.2 and 0.6 mg/kg of body weight, and it must be individualized in each case. The usual dose for induction in these patients is 0.3 mg/kg, injected over a period of 30 to 60 seconds.
Route of Administration: Intravenous
In Vitro Use Guide
The effect of etomidate on GABA-A receptor function was studied in cultured rat hippocampal neurons. At a clinically relevant concentration of 4.1 microM, etomidate shifts the GABA dose response to the left (ED50 shift from 10.2 to 5.2 microM), with no change in the maximum current evoked by saturating concentrations of GABA. At a higher concentration of 82 microM, etomidate directly induces current in the absence of GABA. Analysis of single channels opened by GABA indicates that 8.2 microM etomidate increases the probability of channels being open 13-fold and increases the effective channel open time two-fold.
Name Type Language
ETOMIDATE
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
AMIDATE
Brand Name English
ETOMIDATE [WHO-DD]
Common Name English
(+)-ETHYL 1-(.ALPHA.-METHYLBENZYL)IMIDAZOLE-5-CARBOXYLATE
Systematic Name English
ETOMIDATE [INN]
Common Name English
IMIDAZOLE-5-CARBOXYLIC ACID, 1-(.ALPHA.-METHYLBENZYL)-, ETHYL ESTER, (R)-(+)-
Systematic Name English
ETOMIDATE [ORANGE BOOK]
Common Name English
ETOMIDATE [EP MONOGRAPH]
Common Name English
ETOMIDATE [USAN]
Common Name English
ETOMIDATE [VANDF]
Common Name English
NSC-759160
Code English
HYPNOMIDATE
Brand Name English
ETOMIDATE [USP MONOGRAPH]
Common Name English
1H-IMIDAZOLE-5-CARBOXYLIC ACID, 1-(1-PHENYLETHYL)-, ETHYL ESTER, (+)-
Common Name English
ETOMIDATE [MART.]
Common Name English
ETOMIDATE [USP-RS]
Common Name English
ETOMIDATE [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC N01AX07
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
WHO-VATC QN01AX07
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
NDF-RT N0000175681
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
NCI_THESAURUS C245
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
NDF-RT N0000175975
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
Code System Code Type Description
DRUG CENTRAL
1109
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
EPA CompTox
33125-97-2
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
RXCUI
4177
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY RxNorm
CAS
33125-97-2
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
IUPHAR
5463
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
FDA UNII
Z22628B598
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
MERCK INDEX
M5196
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C47527
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
ECHA (EC/EINECS)
251-385-9
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
PUBCHEM
667484
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
MESH
D005045
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
USP_CATALOG
1268750
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY USP-RS
ChEMBL
CHEMBL681
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
EVMPD
SUB07330MIG
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
WIKIPEDIA
ETOMIDATE
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
INN
1926
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
DRUG BANK
DB00292
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY
LACTMED
Etomidate
Created by admin on Fri Jun 25 21:10:53 UTC 2021 , Edited by admin on Fri Jun 25 21:10:53 UTC 2021
PRIMARY