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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:37 UTC
HMDB IDHMDB0014437
Secondary Accession Numbers
  • HMDB14437
Metabolite Identification
Common NameEtomidate
DescriptionEtomidate is only found in individuals that have used or taken this drug. It is an midazole derivative anesthetic and hypnotic with little effect on blood gases, ventilation, or the cardiovascular system. It has been proposed as an induction anesthetic. [PubChem]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.
Structure
Data?1582753179
Synonyms
ValueSource
(+)-Ethyl 1-(alpha-methylbenzyl)imidazole-5-carboxylateChEBI
(+)-EtomidateChEBI
(R)-(+)-1-(alpha-Methylbenzyl)imidazole-5-carboxylic acid ethyl esterChEBI
(R)-1-(1-Phenylethyl)-1H-imidazole-5-carboxylic acid ethyl esterChEBI
3-((R)-1-Phenyl-ethyl)-3H-imidazole-4-carboxylic acid ethyl esterChEBI
EtomidatoChEBI
EtomidatumChEBI
R-(+)-Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylateChEBI
(+)-Ethyl 1-(a-methylbenzyl)imidazole-5-carboxylateGenerator
(+)-Ethyl 1-(a-methylbenzyl)imidazole-5-carboxylic acidGenerator
(+)-Ethyl 1-(alpha-methylbenzyl)imidazole-5-carboxylic acidGenerator
(+)-Ethyl 1-(α-methylbenzyl)imidazole-5-carboxylateGenerator
(+)-Ethyl 1-(α-methylbenzyl)imidazole-5-carboxylic acidGenerator
(+)-Etomidic acidGenerator
(R)-(+)-1-(a-Methylbenzyl)imidazole-5-carboxylate ethyl esterGenerator
(R)-(+)-1-(a-Methylbenzyl)imidazole-5-carboxylic acid ethyl esterGenerator
(R)-(+)-1-(alpha-Methylbenzyl)imidazole-5-carboxylate ethyl esterGenerator
(R)-(+)-1-(Α-methylbenzyl)imidazole-5-carboxylate ethyl esterGenerator
(R)-(+)-1-(Α-methylbenzyl)imidazole-5-carboxylic acid ethyl esterGenerator
(R)-1-(1-Phenylethyl)-1H-imidazole-5-carboxylate ethyl esterGenerator
3-((R)-1-Phenyl-ethyl)-3H-imidazole-4-carboxylate ethyl esterGenerator
R-(+)-Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylic acidGenerator
Etomidic acidGenerator
EthomidateHMDB
RadenarkonHMDB
HypnomidateHMDB
Chemical FormulaC14H16N2O2
Average Molecular Weight244.289
Monoisotopic Molecular Weight244.121177766
IUPAC Nameethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate
Traditional Name(+)-etomidate
CAS Registry Number33125-97-2
SMILES
CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1
InChI Identifier
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
InChI KeyNPUKDXXFDDZOKR-LLVKDONJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carbonylimidazoles. These are substituted imidazoles in which the imidazole ring bears a carbonyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentCarbonylimidazoles
Alternative Parents
Substituents
  • Imidazole-4-carbonyl group
  • Monocyclic benzene moiety
  • Benzenoid
  • N-substituted imidazole
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point67 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.48 g/LNot Available
LogP2.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.48 g/LALOGPS
logP2.66ALOGPS
logP2.5ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)4.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.12 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.59 m³·mol⁻¹ChemAxon
Polarizability26.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.75431661259
DarkChem[M-H]-157.59731661259
DeepCCS[M+H]+159.36130932474
DeepCCS[M-H]-157.00330932474
DeepCCS[M-2H]-189.88930932474
DeepCCS[M+Na]+165.45530932474
AllCCS[M+H]+157.432859911
AllCCS[M+H-H2O]+153.532859911
AllCCS[M+NH4]+161.032859911
AllCCS[M+Na]+162.032859911
AllCCS[M-H]-160.832859911
AllCCS[M+Na-2H]-160.832859911
AllCCS[M+HCOO]-160.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EtomidateCCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C12524.5Standard polar33892256
EtomidateCCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C11794.8Standard non polar33892256
EtomidateCCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C11938.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Etomidate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-2910000000-df43a9b83f023b0bb3922017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etomidate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Etomidate 20V, Positive-QTOFsplash10-0002-9500000000-c04f55b6e6d0621886912021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etomidate 10V, Positive-QTOFsplash10-0006-2900000000-ed6163c539059d7b23912021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etomidate 40V, Positive-QTOFsplash10-0002-9200000000-20247fc7564af9bdab012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etomidate 20V, Positive-QTOFsplash10-0002-9500000000-895325978346e3ae96a82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etomidate 40V, Positive-QTOFsplash10-0002-9200000000-224f0be0f3472bdc799e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etomidate 35V, Positive-QTOFsplash10-052b-8900000000-f3e3257ccd9a87353f482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etomidate 10V, Positive-QTOFsplash10-0006-2900000000-6f0ad43e633434f014e82021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 10V, Positive-QTOFsplash10-0002-0290000000-733900e68c92323633532017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 20V, Positive-QTOFsplash10-0002-3930000000-fbc274f64b0d02f755a72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 40V, Positive-QTOFsplash10-0a4i-7900000000-485ad993bffaea25b5d32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 10V, Negative-QTOFsplash10-0007-2790000000-4b638d62f5e9c65a71952017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 20V, Negative-QTOFsplash10-006w-3920000000-0b29e1fde3fc264c376a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 40V, Negative-QTOFsplash10-014l-9100000000-75baf1004934a35dbe842017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 10V, Negative-QTOFsplash10-00kf-1690000000-74fc35bed6e521e6c00b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 20V, Negative-QTOFsplash10-00tg-8930000000-b1651ad0ac8257e2d1ba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 40V, Negative-QTOFsplash10-014l-9100000000-4704811d6e2b4a757f652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 10V, Positive-QTOFsplash10-0005-3920000000-ac9782ec40209043a3c32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 20V, Positive-QTOFsplash10-0002-9600000000-b3ee0327c056370deeea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etomidate 40V, Positive-QTOFsplash10-0002-9600000000-04f4f36e411030a8f3472021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00292 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00292 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00292
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID580864
KEGG Compound IDC07522
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEtomidate
METLIN IDNot Available
PubChem Compound667484
PDB IDNot Available
ChEBI ID4910
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in 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 cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular weight:
57572.44
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
References
  1. 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. [PubMed:20496522 ]
  2. 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. [PubMed:14508322 ]
General function:
Involved in monooxygenase activity
Specific function:
Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:
CYP11B2
Uniprot ID:
P19099
Molecular weight:
57559.62
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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. [PubMed:17016423 ]
  3. 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. [PubMed:19809285 ]
  4. 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. [PubMed:19741491 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]