etomidate
Trade name: amidate
Approved
Sep 7, 1982
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. — NCATS
Clinical trial activity
80 trials · 68 clinical orgs · 17 marketing orgs
Earliest trial started Oct 1, 2002 (NCT00248729)
Timeline
1980s
1990s
- Nov 4, 1996
West-Ward Pharmaceutical — Marketing Organization
2000s
- Jan 1, 2002
Earliest Phase 2 Sponsor(trial)
- Jan 2, 2009
Rising Pharmaceuticals — Marketing Organization
- Jan 2, 2009
Mylan — Marketing Organization
- Dec 22, 2009
Lutipold — Marketing Organization
- Dec 22, 2009
Daiichi Sankyo — Marketing Organization
2010s
- Jan 1, 2012
Earliest Phase 3 Sponsor(trial)
- Jun 20, 2012
Par Pharmaceuticals — Marketing Organization
- Jun 20, 2012
Endo Pharmaceuticals — Marketing Organization
- Jun 20, 2012
PH HEALTH — Marketing Organization
- Jul 18, 2014
Zydus Discovery DMCC — Marketing Organization
- Aug 13, 2014
Emcure — Marketing Organization
- Aug 13, 2014
Avet Lifesciences — Marketing Organization
- Jan 1, 2016
Earliest Phase 1 Sponsor(trial)
- Feb 25, 2016
Hikma — Marketing Organization
- Feb 24, 2017
Aurobindo Pharma — Marketing Organization
- Feb 24, 2017
Eugia Pharma — Marketing Organization
- Apr 18, 2017
Gland Pharma Ltd — Marketing Organization
2020s
- Dec 18, 2020
Caplin Point Laboratories — Marketing Organization
Indications
Approved for
Studied for
- Abortion, Induced · Phase 4
- Acne Vulgaris · Phase 4
- Airway Management · Phase 4
- Anesthesia · Phase 4
- Anesthesia, General · Phase 4
- Anesthetics, General · Phase 1
- Bipolar Disorder · Phase 4
- Cholangiocarcinoma · Phase 4
- Choledochal Cyst · Phase 4
- Choledocholithiasis · Phase 4
- Colonoscopy · Phase 3
- Congenital Abnormalities · Phase 4
- Coronary Artery Bypass · Phase 4
- Coronary Artery Disease · Phase 4
- Coronary Disease · Phase 4
- Critical Illness · Phase 2/Phase 3
- Delirium · Phase 4
- Depression · Phase 4
- Drug Interactions · Phase 1
- Drug-Related Side Effects and Adverse Reactions · Phase 4
- Electroconvulsive Therapy · Phase 4
- Etomidate · Phase 4
- Fractures, Bone · Phase 4
- Gastroscopy · Phase 3
- General Surgery · Phase 4
- Healthy Volunteers · Phase 1
- Heart · Phase 1
- Heart Arrest · Phase 4
- Heart Valve Diseases · Phase 4
- Hemodynamics · Phase 4
- Hepatic Insufficiency · Phase 1
- Hypertension · Phase 3
- Hypoadrenocorticism, Familial · Phase 4
- Hysteroscopy · Phase 4
- Infusions, Intravenous · Phase 4
- Intubation · Phase 4
- Lung Diseases · Phase 4
- Magnetic Resonance Spectroscopy · Phase 4
- Major Depressive Disorder · Phase 4
- Mitral Valve Insufficiency · Phase 4
- Myoclonus · Phase 4
- Oxidative Stress · Phase 4
- Pancreatic Neoplasms · Phase 4
- Pancreatitis · Phase 4
- Pharmacokinetics · Phase 1
- Pharmacological and Toxicological Phenomena · Phase 4
- Postoperative Cognitive Complications · Phase 4
- Postoperative Complications · Phase 4
- Procedural Sedation · Phase 4
- Psychotic Disorders · Phase 4
- Renal Insufficiency · Phase 1
- Respiratory Insufficiency · Phase 2
- Schizophrenia · Phase 4
- Shoulder Dislocation · Phase 4
- Stroke · Phase 3
- Thoracic Surgery · Phase 4
Mechanism of action
- GABA-A receptor; anion channelPOSITIVE MODULATOR
GABA-A receptor; anion channel positive modulator
selectivity for beta-3 containing complexes
Likely allosteric but unclear whether benzodiazepine or barbiturate site involved
- Gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1) ↗
- Gamma-aminobutyric acid receptor subunit beta-2 (GABRB2) ↗
- Gamma-aminobutyric acid receptor subunit gamma-2 (GABRG2) ↗
- Gamma-aminobutyric acid receptor subunit beta-3 (GABRB3) ↗
- Gamma-aminobutyric acid receptor subunit alpha-4 (GABRA4) ↗
- Gamma-aminobutyric acid receptor subunit gamma-3 (GABRG3) ↗
- Gamma-aminobutyric acid receptor subunit theta (GABRQ) ↗
- Gamma-aminobutyric acid receptor subunit alpha-3 (GABRA3) ↗
- Gamma-aminobutyric acid receptor subunit pi (GABRP) ↗
- Gamma-aminobutyric acid receptor subunit delta (GABRD) ↗
- Gamma-aminobutyric acid receptor subunit gamma-1 (GABRG1) ↗
- Gamma-aminobutyric acid receptor subunit beta-1 (GABRB1) ↗
- Gamma-aminobutyric acid receptor subunit epsilon (GABRE) ↗
- Gamma-aminobutyric acid receptor subunit alpha-2 (GABRA2) ↗
- Gamma-aminobutyric acid receptor subunit alpha-5 (GABRA5) ↗
- Gamma-aminobutyric acid receptor subunit alpha-6 (GABRA6) ↗
- GABA receptor alpha-1 subunit
- GABA receptor beta-2 subunit
- GABA receptor alpha-4 subunit
- GABA receptor delta subunit
- GABA receptor alpha-5 subunit
- GABA receptor alpha-6 subunit
- GABA receptor beta-3 subunit
- GABA receptor alpha-3 subunit
- GABA receptor alpha-2 subunit
- GABA-A receptor; GABA-A site (alpha1/beta2 interface)
- GABA-A receptor; alpha-3/beta-3/gamma-2
- GABA-A receptor; alpha-1/beta-3/gamma-2
- GABA-A receptor; alpha-5/beta-3/gamma-2
- GABA-A receptor; alpha-2/beta-3/gamma-2
- GABA-A receptor; alpha-1/beta-2/gamma-2
- GABA-A receptor; alpha-6/beta-3/gamma-2
- GABA-A receptor; benzodiazepine site
- GABA-A receptor; agonist GABA site
- GABA A receptor alpha-2/beta-2/gamma-2
- GABA A receptor alpha-3/beta-2/gamma-2
- GABA A receptor alpha-6/beta-2/gamma-2
- GABA A receptor alpha-1/beta-1/gamma-2
- GABA A receptor alpha-4/beta-3/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-4/beta3/delta
- Gamma-aminobutyric acid receptor subunit alpha-1/ beta-1
- Gamma-aminobutyric acid receptor subunit alpha-2/beta-2
- Gamma-aminobutyric acid receptor subunit alpha-3/ beta-2
- Gamma-aminobutyric acid receptor subunit alpha-3/ beta-3/gamma-3
- Gamma-aminobutyric acid receptor subunit alpha-3/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-3/beta-3/theta
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-2
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-3/gamma-3
- Gamma-aminobutyric acid receptor subunit alpha-6/beta-3
- GABA-A receptor alpha-1/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-1/beta-2/delta
- Gamma-aminobutyric acid receptor subunit alpha-4/beta-2/delta
- Gamma-aminobutyric acid receptor subunit beta-1/beta-2
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-2/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-1/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-4/beta-2/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-4/beta-1/delta
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-2/gamma-2
- GABA receptor beta-1 subunit
- Gamma-aminobutyric acid receptor subunit alpha-2/beta-1/gamma-2
Approval history
- approvedSep 7, 1982
Chemistry & pharmacology
SMILES
CCOC(=O)C1=CN=CN1[C@H](C)C2=CC=CC=C2- Mol. weight
- 244.289 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Availability
- Prescription Only
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaEtomidate ↗
- NCATSZ22628B598 ↗
- ChEMBLCHEMBL681 ↗
- ChEMBLCHEMBL23731 ↗
Also known as
- 3-((r)-1-phenyl-ethyl)-3h-imidazole-4-carboxylic acid ethyl ester
- 3-((r)-1-phenyl-ethyl)-3h-imidazole-4-carboxylic acid ethyl ester
- amidate
- amidate
- amidate
- amidate
- amidate
- d-etomidate
- (+)-ethyl 1-(alpha-methylbenzyl)imidazole-5-carboxylate
- (+)-ethyl 1-(alpha-methylbenzyl)imidazole-5-carboxylate
- (+)-ethyl 1-(α-methylbenzyl)imidazole-5-carboxylate
- (+)-ethyl 1-(α-methylbenzyl)imidazole-5-carboxylate
- etomidate
- etomidate
- etomidate
- etomidate
- etomidate
- etomidate
- etomidate
- etomidate
- etomidate
- etomidate
- etomidate
- (+)-etomidate
- (+)-etomidate
- (+)-etomidate
- etomidato
- etomidato
- etomidatum
- etomidatum
- hypnomidate
- (r)-1-(1-phenylethyl)-1h-imidazole-5-carboxylic acid ethyl ester
- (r)-1-(1-phenylethyl)-1h-imidazole-5-carboxylic acid ethyl ester
- (r)-(+)-1-(alpha-methylbenzyl)imidazole-5-carboxylic acid ethyl ester
- (r)-(+)-1-(alpha-methylbenzyl)imidazole-5-carboxylic acid ethyl ester
- r-(+)-ethyl 1-(1-phenylethyl)-1h-imidazole-5-carboxylate
- r-(+)-ethyl 1-(1-phenylethyl)-1h-imidazole-5-carboxylate
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07079176 | N/A | Aug 1, 2025 | Jiao Tong University |
| NCT07062601 | N/A | Jul 10, 2025 | Anqing Municipal Hospital |
| NCT07012902 | Early Phase 1 (Phase 1) | Jun 12, 2025 | Shanxi Medical University |
| NCT06858852 | Phase 3 | Mar 31, 2025 | Fosun, Sichuan University |
| NCT06976996 | N/A | Mar 16, 2025 | Nanjing Medical University |
| NCT06682546 | Phase 2 | Nov 15, 2024 | Fosun, Sichuan University |
| NCT06764147 | Phase 1 | Dec 25, 2023 | Fosun, Shandong Province Qianfoshan Hospital |
| NCT06176716 | Phase 1 | Dec 6, 2023 | Fosun, Jinlin University |
| NCT06068764 | Phase 4 | Dec 5, 2023 | University of Connecticut |
| NCT06822166 | Phase 1 | Dec 4, 2023 | Fosun, Shandong Province Qianfoshan Hospital |
| NCT06747520 | Phase 1 | Nov 30, 2023 | Fosun, Shandong Province Qianfoshan Hospital |
| NCT06822153 | Phase 1 | Nov 9, 2023 | Fosun, Jinan University |
| NCT06203431 | Phase 3 | Oct 11, 2023 | Fosun, Sichuan University |
| NCT05748665 | N/A | Aug 14, 2023 | Xijing Hospital |
| NCT06822114 | Phase 1 | Jul 17, 2023 | Fosun, Soochow University |
| NCT05810363 | N/A | Jun 16, 2023 | Huazhong University of Science and Technology |
| NCT06664138 | Phase 4 | Apr 28, 2023 | Dankook University |
| NCT05259787 | Phase 4 | Sep 28, 2022 | Jiao Tong University |
| NCT05358535 | Phase 3 | Sep 19, 2022 | The University of Texas, Dallas, University of Texas, Galveston |
| NCT05520645 | N/A | Aug 25, 2022 | Peking University |
Organizations
Research & Development (68)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Fosun | For profit | 9 | 9 | 3 | 2023 |
| People's Liberation Army of China | Government | 7 | 6 | 2 | 2013 |
| Jiao Tong University | Academic/Hospital | 5 | 5 | 2 | 2013 |
| Shandong Province Qianfoshan Hospital | Academic/Hospital | 3 | 0 | 1 | 2023 |
| Sichuan University | Academic/Hospital | 3 | 0 | 2 | 2023 |
| Advocate Healthcare | Academic/Hospital | 2 | 2 | 1 | 2007 |
| Henan Medical University | Academic/Hospital | 2 | 2 | 1 | 2014 |
| Huazhong University of Science and Technology | Academic/Hospital | 2 | 1 | 1 | 2013 |
| Jiangsu Nhwa Pharmaceutical Co., Ltd. | For profit | 2 | 2 | 2 | 2012 |
| Nanjing Medical University | Academic/Hospital | 2 | 2 | 1 | 2015 |
| Peking University | Academic/Hospital | 2 | 2 | 1 | 2021 |
| The Cleveland Clinic | Academic/Hospital | 2 | 2 | 2 | 2021 |
| The University of Texas, Dallas | Academic/Hospital | 2 | 2 | 2 | 2016 |
| Tianjin Medical University | Academic/Hospital | 2 | 1 | 1 | 2015 |
| Ajou University | Academic/Hospital | 1 | 1 | 1 | 2019 |
| Anqing Municipal Hospital | Academic/Hospital | 1 | 1 | 1 | 2025 |
| Baskent University | Academic/Hospital | 1 | 1 | 1 | 2011 |
| Central South University | Academic/Hospital | 1 | 1 | 1 | 2016 |
| Cheju Halla General Hospital | Academic/Hospital | 1 | 1 | 1 | 2013 |
| Dankook University | Academic/Hospital | 1 | 1 | 1 | 2023 |
Marketing (20)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Aurobindo Pharma | For profit | MKTG | Feb 24, 2017 |
| Avet Lifesciences | For profit | MKTG | Aug 13, 2014 |
| Caplin Point Laboratories | For profit | MKTG | Dec 18, 2020 |
| Daiichi Sankyo | For profit | MKTG | Dec 22, 2009 |
| Emcure | For profit | MKTG | Aug 13, 2014 |
| Endo Pharmaceuticals | For profit | MKTG | Jun 20, 2012 |
| Eugia Pharma | For profit | MKTG | Feb 24, 2017 |
| Gland Pharma Ltd | For profit | MKTG | Apr 18, 2017 |
| Gland Pharma Ltd | For profit | SYN | Apr 18, 2017 |
| Hikma | For profit | MKTG | Feb 25, 2016 |
| Hospira | For profit | NDA | Sep 7, 1982 |
| Hospira | For profit | NDA2 | Sep 7, 1982 |
| Lutipold | For profit | MKTG | Dec 22, 2009 |
| Mylan | For profit | MKTG | Jan 2, 2009 |
| PH HEALTH | For profit | MKTG | Jun 20, 2012 |
| Par Pharmaceuticals | For profit | MKTG | Jun 20, 2012 |
| Rising Pharmaceuticals | For profit | MKTG | Jan 2, 2009 |
| Rising Pharmaceuticals | For profit | SYN | Jan 2, 2009 |
| West-Ward Pharmaceutical | For profit | MKTG | Nov 4, 1996 |
| Zydus Discovery DMCC | For profit | MKTG | Jul 18, 2014 |