Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H16N2O2 |
Molecular Weight | 244.289 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)C1=CN=CN1[C@H](C)C2=CC=CC=C2
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
DescriptionCurator'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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17013247
Curator's Comment: Etomidate is supposed to be neuroprotective.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21263301
Curator's Comment: # Janssen Pharmaceuticals, a division of Ortho-McNeil-Jannsen Pharmaceuticals
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095190 |
23.0 µM [EC50] | ||
Target ID: CHEMBL2095190 |
0.7 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AMIDATE Approved UseEtomidate 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 Date4.00204792E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
87 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9447861/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3263 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9447861/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
75 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9447861/ |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/20352599/ |
no | |||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/20352599/ |
yes | |||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Some experience of the use of etomidate in children. | 1976 |
|
A comparative study of etomidate and methohexital as induction agents for analgesic anesthesia. | 1976 |
|
Total intravenous anesthesia with etomidate. III. Some observations in adults. | 1977 |
|
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 |
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Venous complications after intravenous injection of diazepam, flunitrazepam, thiopentone and etomidate. | 1980 Jun |
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Etomidate: a foreshortened clinical trial. | 1980 Nov |
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Pain and myoclonus during induction with etomidate. A double-blind, controlled evaluation of the influence of droperidol and fentanyl. | 1981 |
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Epileptiform seizures during prolonged etomidate sedation. | 1983 Aug 27 |
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Cardiac complications during use of etomidate. | 1983 Dec |
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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 |
|
[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 |
|
Respiratory disturbance during recovery from etomidate anaesthesia. | 1988 Jan |
|
Cardiovascular instability following bolus dose of etomidate. | 1989 May |
|
[Anesthesia for cardioversion. A comparison of propofol and etomidate]. | 1990 May-Jun |
|
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 |
|
Pretreatment with sufentanil reduces myoclonus after etomidate. | 2003 Apr |
|
Deletion of the alpha1 or beta2 subunit of GABAA receptors reduces actions of alcohol and other drugs. | 2003 Jan |
|
Myoclonus associated with etomidate for ED procedural sedation and analgesia. | 2003 Nov |
|
Etomidate versus pentobarbital for sedation of children for head and neck CT imaging. | 2004 Aug |
|
Midazolam is more likely to cause hypotension than etomidate in emergency department rapid sequence intubation. | 2004 Nov |
|
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 |
|
Etomidate versus midazolam for procedural sedation in pediatric outpatients: a randomized controlled trial. | 2006 Oct |
|
Etomidate-Lipuro is associated with considerably less injection pain in children compared with propofol with added lidocaine. | 2006 Oct |
|
Randomized clinical trial of etomidate versus propofol for procedural sedation in the emergency department. | 2007 Jan |
|
Etomidate-induced pacemaker-mediated ventricular tachycardia. | 2007 May |
|
Etomidate and unpredicted seizures during electroconvulsive therapy. | 2007 Sep |
|
Cytotoxicity and decreased corticosterone production in adrenocortical Y-1 cells by 3-methylsulfonyl-DDE and structurally related molecules. | 2009 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 |
|
Prevention of etomidate-induced myoclonus: which is superior: Fentanyl, midazolam, or a combination? A Retrospective comparative study. | 2014 Feb 16 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8783230
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.
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WHO-ATC |
N01AX07
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WHO-VATC |
QN01AX07
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NDF-RT |
N0000175681
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NCI_THESAURUS |
C245
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NDF-RT |
N0000175975
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DTXSID5023033
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4177
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33125-97-2
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5463
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M5196
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C47527
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1268750
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251-385-9
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667484
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D005045
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CHEMBL681
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SUB07330MIG
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ETOMIDATE
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759160
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1926
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DB00292
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Etomidate
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)