Identification
- Summary
Etomidate is a short-acting intravenous anesthetic indicated for the induction of anesthesia and supplementation of subpotent anesthesia during short operative procedures.
- Brand Names
- Amidate
- Generic Name
- Etomidate
- DrugBank Accession Number
- DB00292
- Background
Imidazole derivative anesthetic and hypnotic with little effect on blood gases, ventilation, or the cardiovascular system. It has been proposed as an induction anesthetic.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Etomidate (DB00292)
- Weight
- Average: 244.289
Monoisotopic: 244.121177766 - Chemical Formula
- C14H16N2O2
- Synonyms
- (+)-ethyl 1-(α-methylbenzyl)imidazole-5-carboxylate
- (+)-etomidate
- (R)-(+)-1-(α-methylbenzyl)imidazole-5-carboxylic acid ethyl ester
- (R)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid ethyl ester
- 3-((R)-1-Phenyl-ethyl)-3H-imidazole-4-carboxylic acid ethyl ester
- Etomidate
- Etomidato
- Etomidatum
- R-(+)-ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate
Pharmacology
- Indication
Used in the induction of general anesthesia.
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- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Etomidate is a non-barbiturate hypnotic that acts at the level of the reticular-activating system to produce anesthesia. Etomidate is an imidazole compound that appears to depress CNS function via GABA. Duration of action is intermediate between thiopental and methohexital, and recovery from a single dose is rapid with little residual depression. Like the barbiturates and propofol, etomidate is does not induce analgesia. Etomidate induces unconsciousness within one circulation time. Recovery is rapid as a result of extensive redistribution and rapid metabolism.
- Mechanism of action
Etomidate binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Target Actions Organism AGamma-aminobutyric acid receptor subunit alpha-1 agonistHumans AAlpha-2B adrenergic receptor agonistHumans AGABA(A) Receptor positive allosteric modulatorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
76%, primarily to serum albumin.
- Metabolism
Hepatic. Metabolized rapidly by ester hydrolysis to inactive metabolites.
- Route of elimination
Approximately 75% of the administered dose is excreted in the urine during the first day after injection.
- Half-life
75 minutes.
- Clearance
Not Available
- Adverse Effects
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Undesirable side effects of etomidate that may limit its use include pain on injection, myoclonus and adrenocortical suppression lasting 4-6 hours following an induction dose.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Etomidate is combined with 1,2-Benzodiazepine. Abacavir Etomidate may decrease the excretion rate of Abacavir which could result in a higher serum level. Acebutolol The therapeutic efficacy of Etomidate can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Etomidate is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Etomidate is combined with Acemetacin. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Hypnomidate (Janssen)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Amidate Injection, solution 2 mg/1mL Intravenous General Injectables & Vaccines 2010-03-10 2017-06-19 US 
Amidate Injection, solution 2 mg/1mL Intravenous Hospira, Inc. 2005-10-07 2017-05-01 US Amidate Injection, solution 2 mg/1mL Intravenous Hospira, Inc. 2006-11-07 2006-11-07 US Amidate Injection, solution 2 mg/1mL Intravenous Henry Schein, Inc. 2022-01-06 Not applicable US Amidate Injection, solution 2 mg/1mL Intravenous General Injectables & Vaccines, Inc 2010-08-01 2023-05-01 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Etomidate Injection, solution 2 mg/1mL Intravenous REMEDYREPACK INC. 2018-02-06 2020-05-07 US Etomidate Injection, solution 2 mg/1mL Intravenous Bedford Pharmaceuticals 1996-12-01 2012-02-29 US Etomidate Injection 2 mg/1mL Intravenous Hikma Pharmaceuticals USA Inc. 2016-02-25 Not applicable US Etomidate Injection, solution 2 mg/1mL Intravenous Mylan Institutional LLC 2012-02-03 2018-03-31 US Etomidate Injection, solution 2 mg/1mL Intravenous Sandoz 2009-04-01 2011-09-27 US
Categories
- ATC Codes
- N01AX07 — Etomidate
- Drug Categories
- Adrenergic Agonists
- Adrenergic alpha-2 Receptor Agonists
- Adrenergic alpha-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Anesthetics
- Anesthetics, General
- Anesthetics, Intravenous
- Central Nervous System Agents
- Central Nervous System Depressants
- Drugs that are Mainly Renally Excreted
- Hypnotics and Sedatives
- Imidazoles
- Nervous System
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as carbonylimidazoles. These are substituted imidazoles in which the imidazole ring bears a carbonyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azoles
- Sub Class
- Imidazoles
- Direct Parent
- Carbonylimidazoles
- Alternative Parents
- N-substituted imidazoles / Benzene and substituted derivatives / Heteroaromatic compounds / Carboxylic acid esters / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides show 1 more
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carboxylic acid derivative / Carboxylic acid ester / Heteroaromatic compound / Hydrocarbon derivative / Imidazole-4-carbonyl group / Monocarboxylic acid or derivatives / Monocyclic benzene moiety show 7 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- ethyl ester, imidazoles (CHEBI:4910)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- Z22628B598
- CAS number
- 33125-97-2
- InChI Key
- NPUKDXXFDDZOKR-LLVKDONJSA-N
- InChI
- 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
- IUPAC Name
- ethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate
- SMILES
- CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1
References
- Synthesis Reference
Douglas E. Raines, "ETOMIDATE ANALOGUES THAT DO NOT INHIBIT ADRENOCORTICAL STEROID SYNTHESIS." U.S. Patent US20130079381, issued March 28, 2013.
US20130079381- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014437
- KEGG Drug
- D00548
- KEGG Compound
- C07522
- PubChem Compound
- 667484
- PubChem Substance
- 46507012
- ChemSpider
- 580864
- BindingDB
- 50125935
- 4177
- ChEBI
- 4910
- ChEMBL
- CHEMBL681
- ZINC
- ZINC000000001408
- Therapeutic Targets Database
- DAP000669
- PharmGKB
- PA164743987
- PDBe Ligand
- V8D
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Etomidate
- PDB Entries
- 6x3v / 8f6y / 8pvb
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Prevention Adrenocortical Deficiency / Hemodynamics Instability 1 4 Completed Prevention Induction of Anaesthesia 1 4 Completed Screening Hemodynamics / Side Effects 1 4 Completed Supportive Care Surgery 1 4 Completed Treatment Airway Control / Anesthesia therapy / Complications / Intubation 1
Pharmacoeconomics
- Manufacturers
- Hospira inc
- Bedford laboratories div ben venue laboratories inc
- Parenta pharmaceuticals inc
- Pharmaforce inc
- Packagers
- American Regent
- Bedford Labs
- Ben Venue Laboratories Inc.
- Ebewe Pharma
- General Injectables and Vaccines Inc.
- Hospira Inc.
- Dosage Forms
Form Route Strength Solution Intravenous 20.000 mg Solution Intravenous 20 mg Injection, emulsion Intravenous 2 mg/ml Injection Intravenous 2 mg/1mL Injection, solution Intravenous 2 mg/1mL Injection, solution Intravenous 20 mg/10mL Injection, solution Intravenous 40 mg/20mL Solution Intravenous 2 mg/1mL Emulsion 2 mg/1ml Injection, emulsion Intravenous Injection Intravenous 20 mg/10ml Emulsion Intravenous 20 mg Emulsion Parenteral 2 mg Injection Intravenous Injection, solution Intravenous 2 mg/ml Injection Intravenous 20 mg Solution Intravenous 2 mg / mL Emulsion Intravenous 2 mg - Prices
Unit description Cost Unit Amidate 2 mg/ml vial 1.55USD ml Amidate 2 mg/ml ampul 1.19USD ml Etomidate 2 mg/ml vial 1.18USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 142-142.8 Godefroi, E.F. and Van Der Eijcken, C.A.M.; U.S. Patent 3,354,173; November 21, 1967; assigned to Janssen Pharrnaceutica NV (Belgium). water solubility 63.2 mg/L Not Available logP 3.05 POMONA (1987) - Predicted Properties
Property Value Source Water Solubility 0.477 mg/mL ALOGPS logP 2.66 ALOGPS logP 2.5 Chemaxon logS -2.7 ALOGPS pKa (Strongest Basic) 4.25 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 44.12 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 69.59 m3·mol-1 Chemaxon Polarizability 26.43 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9908 Blood Brain Barrier + 0.95 Caco-2 permeable + 0.6275 P-glycoprotein substrate Non-substrate 0.7386 P-glycoprotein inhibitor I Non-inhibitor 0.8567 P-glycoprotein inhibitor II Non-inhibitor 0.8597 Renal organic cation transporter Non-inhibitor 0.7918 CYP450 2C9 substrate Non-substrate 0.7947 CYP450 2D6 substrate Non-substrate 0.9117 CYP450 3A4 substrate Non-substrate 0.7671 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Inhibitor 0.5432 CYP450 3A4 inhibitor Inhibitor 0.7959 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8357 Ames test Non AMES toxic 0.7989 Carcinogenicity Non-carcinogens 0.8795 Biodegradation Not ready biodegradable 0.5121 Rat acute toxicity 2.5459 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9622 hERG inhibition (predictor II) Non-inhibitor 0.8553
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a6r-2910000000-df43a9b83f023b0bb392 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0005-5910000000-e3e55142d021e58cf423 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0297-2970000000-ab1c97a95da9dcaa9899 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-052b-7900000000-49c3144b2769b573db82 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-6920000000-a474ce5287ce573c4d69 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4j-3910000000-ca3a936261938f9917a4 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-006w-7900000000-54ef843e8eb9687f7902 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 167.8104813 predictedDarkChem Lite v0.1.0 [M-H]- 157.00337 predictedDeepCCS 1.0 (2019) [M+H]+ 168.4249813 predictedDarkChem Lite v0.1.0 [M+H]+ 159.36137 predictedDeepCCS 1.0 (2019) [M+Na]+ 168.2031813 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.45451 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
- Gene Name
- GABRA1
- Uniprot ID
- P14867
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-1
- Molecular Weight
- 51801.395 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Martin LJ, Oh GH, Orser BA: Etomidate targets alpha5 gamma-aminobutyric acid subtype A receptors to regulate synaptic plasticity and memory blockade. Anesthesiology. 2009 Nov;111(5):1025-35. doi: 10.1097/ALN.0b013e3181bbc961. [Article]
- Desai R, Ruesch D, Forman SA: Gamma-amino butyric acid type A receptor mutations at beta2N265 alter etomidate efficacy while preserving basal and agonist-dependent activity. Anesthesiology. 2009 Oct;111(4):774-84. doi: 10.1097/ALN.0b013e3181b55fae. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Epinephrine binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
- Gene Name
- ADRA2B
- Uniprot ID
- P18089
- Uniprot Name
- Alpha-2B adrenergic receptor
- Molecular Weight
- 49565.8 Da
References
- Creagh O, Torres H, Rodriguez N, Gatica SR: Alpha-2B adrenergic receptor mediated hemodynamic profile of etomidate. P R Health Sci J. 2010 Jun;29(2):91-5. [Article]
- Paris A, Philipp M, Tonner PH, Steinfath M, Lohse M, Scholz J, Hein L: Activation of alpha 2B-adrenoceptors mediates the cardiovascular effects of etomidate. Anesthesiology. 2003 Oct;99(4):889-95. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- ChEMBL Compound Report Card [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid 11-beta-monooxygenase activity
- Specific Function
- Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochro...
- Gene Name
- CYP11B1
- Uniprot ID
- P15538
- Uniprot Name
- Cytochrome P450 11B1, mitochondrial
- Molecular Weight
- 57572.44 Da
References
- Weber MM, Lang J, Abedinpour F, Zeilberger K, Adelmann B, Engelhardt D: Different inhibitory effect of etomidate and ketoconazole on the human adrenal steroid biosynthesis. Clin Investig. 1993 Nov;71(11):933-8. [Article]
- Hermansson V, Asp V, Bergman A, Bergstrom U, Brandt I: Comparative CYP-dependent binding of the adrenocortical toxicants 3-methylsulfonyl-DDE and o,p'-DDD in Y-1 adrenal cells. Arch Toxicol. 2007 Nov;81(11):793-801. Epub 2007 May 9. [Article]
- Hahner S, Sturmer A, Fassnacht M, Hartmann RW, Schewe K, Cochran S, Zink M, Schirbel A, Allolio B: Etomidate unmasks intraadrenal regulation of steroidogenesis and proliferation in adrenal cortical cell lines. Horm Metab Res. 2010 Jun;42(7):528-34. doi: 10.1055/s-0030-1249629. Epub 2010 Mar 29. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid 11-beta-monooxygenase activity
- Specific Function
- Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
- Gene Name
- CYP11B2
- Uniprot ID
- P19099
- Uniprot Name
- Cytochrome P450 11B2, mitochondrial
- Molecular Weight
- 57559.62 Da
References
- Hahner S, Sturmer A, Fassnacht M, Hartmann RW, Schewe K, Cochran S, Zink M, Schirbel A, Allolio B: Etomidate unmasks intraadrenal regulation of steroidogenesis and proliferation in adrenal cortical cell lines. Horm Metab Res. 2010 Jun;42(7):528-34. doi: 10.1055/s-0030-1249629. Epub 2010 Mar 29. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic transporter activity
- Specific Function
- Facilitative glucose transporter. This isoform may be responsible for constitutive or basal glucose uptake. Has a very broad substrate specificity; can transport a wide range of aldoses including b...
- Gene Name
- SLC2A1
- Uniprot ID
- P11166
- Uniprot Name
- Solute carrier family 2, facilitated glucose transporter member 1
- Molecular Weight
- 54083.325 Da
References
- Stephenson KN, Croxen RL, El-Barbary A, Fenstermacher JD, Haspel HC: Inhibition of glucose transport and direct interactions with type 1 facilitative glucose transporter (GLUT-1) by etomidate, ketamine, and propofol: a comparison with barbiturates. Biochem Pharmacol. 2000 Sep 1;60(5):651-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:39