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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H16N2O2.H2O4S
Molecular Weight 342.368
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETOMIDATE SULFATE

SMILES

OS(O)(=O)=O.CCOC(=O)C1=CN=CN1[C@H](C)C2=CC=CC=C2

InChI

InChIKey=YCUUCSZGTWIJDW-RFVHGSKJSA-N
InChI=1S/C14H16N2O2.H2O4S/c1-3-18-14(17)13-9-15-10-16(13)11(2)12-7-5-4-6-8-12;1-5(2,3)4/h4-11H,3H2,1-2H3;(H2,1,2,3,4)/t11-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C14H16N2O2
Molecular Weight 244.289
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1982
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
Total intravenous anesthesia with etomidate. III. Some observations in adults.
1977
Respiratory effects of etomidate.
1977 Mar
Etomidate in a new solvent. A clinical evaluation.
1977 Nov-Dec
Effect of premedication on etomidate anaesthesia.
1979 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
Epileptiform seizures during prolonged etomidate sedation.
1983 Aug 27
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
Venous reactions following etomidate.
1984 Aug
Alfentanil in minor gynaecological surgery: use with etomidate and a comparison with halothane.
1984 Aug
Venous sequelae following the injection of etomidate or thiopentone i.v.
1984 Feb
The prevention of etomidate-induced myoclonus.
1984 Jan
Prolonged myoclonus after etomidate anesthesia.
1985 Jan
[Alfentanil in routine clinical use. A study of 50 patients].
1985 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
Hypertension during anaesthesia with monoamine oxidase inhibitors.
1987 Jun
Angioneurotic oedema following etomidate/lignocaine.
1987 Mar
[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
Vecuronium induced bradycardia following induction of anaesthesia with etomidate or thiopentone, with or without fentanyl.
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
Cardiovascular instability following bolus dose of etomidate.
1989 May
[The modification of injection pain and the incidence of thrombophlebitis following etomidate].
1990 Jan
[Anesthesia for cardioversion. A comparison of propofol and etomidate].
1990 May-Jun
[Etomidate using a new solubilizer. Experimental clinical studies on venous tolerance and bioavailability].
1990 Oct
Excitatory effects and electroencephalographic correlation of etomidate, thiopental, methohexital, and propofol.
1993 Nov
Acute toxicosis in two dogs associated with etomidate-propylene glycol infusion.
1994 Dec
Propylene glycol toxicity following continuous etomidate infusion for the control of refractory cerebral edema.
1995 Aug
Total intravenous anesthesia for children undergoing brief diagnostic or therapeutic procedures.
1995 Jun
Propylene glycol toxicity caused by prolonged infusion of etomidate.
1995 Oct
Focal cerebral ischemia during anesthesia with etomidate, isoflurane, or thiopental: a comparison of the extent of cerebral injury.
1995 Oct
Cerebral hypoxia after etomidate administration and temporary cerebral artery occlusion.
1997 Oct
An unexpected arousal effect of etomidate in a patient on high-dose steroids.
1998 Dec
Anesthesia sensitivity in mice that lack the beta3 subunit of the gamma-aminobutyric acid type A receptor.
1998 Mar
Vascular effects of etomidate administered for electroencephalographic burst suppression in humans.
1998 Oct
Reducing myoclonus after etomidate.
1999 Jan
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:48:10 GMT 2023
Edited
by admin
on Fri Dec 15 15:48:10 GMT 2023
Record UNII
Y26131IQZI
Record Status Validated (UNII)
Record Version
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Name Type Language
ETOMIDATE SULFATE
WHO-DD  
Common Name English
1H-IMIDAZOLE-5-CARBOXYLIC ACID, 1-((1R)-1-PHENYLETHYL)-, ETHYL ESTER, SULFATE (1:1)
Common Name English
Etomidate sulfate [WHO-DD]
Common Name English
R-26490
Code English
R 26490
Code English
ETOMIDATE SULPHATE
Common Name English
Code System Code Type Description
EVMPD
SUB02047MIG
Created by admin on Fri Dec 15 15:48:10 GMT 2023 , Edited by admin on Fri Dec 15 15:48:10 GMT 2023
PRIMARY
SMS_ID
100000087479
Created by admin on Fri Dec 15 15:48:10 GMT 2023 , Edited by admin on Fri Dec 15 15:48:10 GMT 2023
PRIMARY
CAS
51919-80-3
Created by admin on Fri Dec 15 15:48:10 GMT 2023 , Edited by admin on Fri Dec 15 15:48:10 GMT 2023
PRIMARY
FDA UNII
Y26131IQZI
Created by admin on Fri Dec 15 15:48:10 GMT 2023 , Edited by admin on Fri Dec 15 15:48:10 GMT 2023
PRIMARY
PUBCHEM
22794265
Created by admin on Fri Dec 15 15:48:10 GMT 2023 , Edited by admin on Fri Dec 15 15:48:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID40966237
Created by admin on Fri Dec 15 15:48:10 GMT 2023 , Edited by admin on Fri Dec 15 15:48:10 GMT 2023
PRIMARY
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