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
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
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 |
---|---|---|
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 |
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)