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Showing drug card for Etomidate (DB00292)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:07:34
Primary Accession Number DB00292
Secondary Accession Number
  • APRD00965
Name Etomidate
Drug Type
  • Approved
  • Small Molecule
Description Imidazole derivative anesthetic and hypnotic with little effect on blood gases, ventilation, or the cardiovascular system. It has been proposed as an induction anesthetic. [PubChem]
Synonyms
  1. Etomidic acid
Brand Names
  1. Amidate
  2. Hypnomidate
Brand Mixtures Not Available
Chemical IUPAC Name ethyl 3-(1-phenylethyl)imidazole-4-carboxylate
Chemical Formula C14H16N2O2
Chemical Structure Structure
CAS Registry Number 33125-97-2
InChI Identifier InChI=1/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
InChI Key NPUKDXXFDDZOKR-UHFFFAOYAF
KEGG Drug D00548 Link Image
KEGG Compound C07522 Link Image
PubChem Compound 36339 Link Image
PubChem Substance 9725 Link Image
ChEBI ID Not Available
PharmGKB ID PA449551 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Etomidate Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 244.2890
Monoisotopic Molecular Weight 244.1212
State Solid
Melting Point 67 oC
Experimental Water Solubility 63.2 mg/L Source: PhysProp
Predicted Water Solubility 4.77e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 2.9 Source: PhysProp
Predicted LogP 2.66 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.71 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCOC(=O)C1=CN=CN1[C@@H](C)C1=CC=CC=C1
Canonical SMILES CCOC(=O)C1=CN=CN1C(C)C1=CC=CC=C1
Drug Category
  • Anesthetics, Intravenous
  • Hypnotics and Sedatives
ATC Codes
AHFS Codes Not Available
Indication Used in the induction of general anesthesia.
Pharmacology 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.
Absorption Not Available
Toxicity 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.
Protein Binding 76%, primarily to serum albumin.
Biotransformation Hepatic. Metabolized rapidly by ester hydrolysis to inactive metabolites.
Half Life 75 minutes.
Dosage Forms
Form Route
Solution Intravenous
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cholinesterase
Targets
  1. Gamma-aminobutyric-acid receptor subunit alpha-1
  2. Solute carrier family 2, facilitated glucose transporter member 1
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cholinesterase
Enzyme 1 Gene Name BCHE
Enzyme 1 SwissProt ID P06276 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >Cholinesterase 
MHSKVTIICIRFLFWFLLLCMLIGKSHTEDDIIIATKNGKVRGMNLTVFGGTVTAFLGIP
YAQPPLGRLRFKKPQSLTKWSDIWNATKYANSCCQNIDQSFPGFHGSEMWNPNTDLSEDC
LYLNVWIPAPKPKNATVLIWIYGGGFQTGTSSLHVYDGKFLARVERVIVVSMNYRVGALG
FLALPGNPEAPGNMGLFDQQLALQWVQKNIAAFGGNPKSVTLFGESAGAASVSLHLLSPG
SHSLFTRAILQSGSFNAPWAVTSLYEARNRTLNLAKLTGCSRENETEIIKCLRNKDPQEI
LLNEAFVVPYGTPLSVNFGPTVDGDFLTDMPDILLELGQFKKTQILVGVNKDEGTAFLVY
GAPGFSKDNNSIITRKEFQEGLKIFFPGVSEFGKESILFHYTDWVDDQRPENYREALGDV
VGDYNFICPALEFTKKFSEWGNNAFFYYFEHRSSKLPWPEWMGVMHGYEIEFVFGLPLER
RDNYTKAEEILSRSIVKRWANFAKYGNPNETQNNSTSWPVFKSTEQKYLTLNTESTRIMT
KLRAQQCRFWTSFFPKVLEMTGNIDEAEWEWKAGFHRWNNYMMDWKNQFNDYTSKKESCV
GL
Drug Target 1 [top]
Target 1 ID 872
Target 1 Name Gamma-aminobutyric-acid receptor subunit alpha-1
Target 1 Synonyms
  1. Gamma-aminobutyric-acid receptor subunit alpha-1 precursor
Target 1 Gene Name GABRA1
Target 1 Protein Sequence >Gamma-aminobutyric-acid receptor subunit alpha-1 precursor 
MRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLLDGYDNRLRPG
LGERVTEVKTDIFVTSFGPVSDHDMEYTIDVFFRQSWKDERLKFKGPMTVLRLNNLMASK
IWTPDTFFHNGKKSVAHNMTMPNKLLRITEDGTLLYTMRLTVRAECPMHLEDFPMDAHAC
PLKFGSYAYTRAEVVYEWTREPARSVVVAEDGSRLNQYDLLGQTVDSGIVQSSTGEYVVM
TTHFHLKRKIGYFVIQTYLPCIMTVILSQVSFWLNRESVPARTVFGVTTVLTMTTLSISA
RNSLPKVAYATAMDWFIAVCYAFVFSALIEFATVNYFTKRGYAWDGKSVVPEKPKKVKDP
LIKKNNTYAPTATSYTPNLARGDPGLATIAKSATIEPKEVKPETKPPEPKKTFNSVSKID
RLSRIAFPLLFGIFNLVYWATYLNREPQLKAPTPHQ
Target 1 Number of Residues 463
Target 1 Molecular Weight 51802
Target 1 Theoretical pI 9.61
Target 1 GO Classification
Function
neurotransmitter receptor activity
transporter activity
ion transporter activity
ion channel activity
ligand-gated ion channel activity
extracellular ligand-gated ion channel activity
signal transducer activity
receptor activity
transmembrane receptor activity
GABA receptor activity
GABA-A receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
gamma-aminobutyric acid signaling pathway
anion transport
inorganic anion transport
chloride transport
physiological process
cellular physiological process
transport
ion transport
Component
postsynaptic membrane
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in GABA-A receptor activity
Target 1 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
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-27
Target 1 Transmembrane Regions
  • 252-273
  • 279-300
  • 313-334
  • 422-443
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 31631 Link Image
Target 1 UniProtKB/Swiss-Prot ID P14867 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name GBRA1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1371 bp 
ATGAGGAAAAGTCCAGGTCTGTCTGACTGTCTTTGGGCCTGGATCCTCCTTCTGAGCACA
CTGACTGGAAGAAGCTATGGACAGCCGTCATTACAAGATGAACTTAAAGACAATACCACT
GTCTTCACCAGGATTTTGGACAGACTCCTAGATGGTTATGACAATCGCCTGAGACCAGGA
TTGGGAGAGCGTGTAACCGAAGTGAAGACTGATATCTTCGTCACCAGTTTCGGACCCGTT
TCAGACCATGATATGGAATATACAATAGATGTATTTTTCCGTCAAAGCTGGAAGGATGAA
AGGTTAAAATTTAAAGGACCTATGACAGTCCTCCGGTTAAATAACCTAATGGCAAGTAAA
ATCTGGACTCCGGACACATTTTTCCACAATGGAAAGAAGTCAGTGGCCCACAACATGACC
ATGCCCAACAAACTCCTGCGGATCACAGAGGATGGCACCTTGCTGTACACCATGAGGCTG
ACAGTGAGAGCTGAATGTCCGATGCATTTGGAGGACTTCCCTATGGATGCCCATGCTTGC
CCACTAAAATTTGGAAGTTATGCTTATACAAGAGCAGAAGTTGTTTATGAATGGACCAGA
GAGCCAGCACGCTCAGTGGTTGTAGCAGAAGATGGATCACGTCTAAACCAGTATGACCTT
CTTGGACAAACAGTAGACTCTGGAATTGTCCAGTCAAGTACAGGAGAATATGTTGTTATG
ACCACTCATTTCCACTTGAAGAGAAAGATTGGCTACTTTGTTATTCAAACATACCTGCCA
TGCATAATGACAGTGATTCTCTCACAAGTCTCCTTCTGGCTCAACAGAGAGTCTGTACCA
GCAAGAACTGTCTTTGGAGTAACAACTGTGCTCACCATGACAACATTGAGCATCAGTGCC
AGAAACTCCCTCCCTAAGGTGGCTTATGCAACAGCTATGGATTGGTTTATTGCCGTGTGC
TATGCCTTTGTGTTCTCAGCTCTGATTGAGTTTGCCACAGTAAACTATTTCACTAAGAGA
GGTTATGCATGGGATGGCAAAAGTGTGGTTCCAGAAAAGCCAAAGAAAGTAAAGGATCCT
CTTATTAAGAAAAACAACACTTACGCTCCAACAGCAACCAGCTACACCCCTAATTTGGCC
AGGGGCGACCCGGGCTTAGCCACCATTGCTAAAAGTGCAACCATAGAACCTAAAGAGGTC
AAGCCCGAAACAAAACCACCAGAACCCAAGAAAACCTTTAACAGTGTCAGCAAAATTGAC
CGACTGTCAAGAATAGCCTTCCCGCTGCTATTTGGAATCTTTAACTTAGTCTACTGGGCT
ACGTATTTAAACAGAGAGCCTCAGCTAAAAGCCCCCACACCACATCAATAG
Target 1 GenBank Gene ID
Target 1 GeneCard ID GABRA1 Link Image
Target 1 GenAtlas ID GABRA1 Link Image
Target 1 HGNC ID HGNC:4075 Link Image
Target 1 Chromosome Location 5
Target 1 Locus 5q34-q35
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Cossette P, Liu L, Brisebois K, Dong H, Lortie A, Vanasse M, Saint-Hilaire JM, Carmant L, Verner A, Lu WY, Wang YT, Rouleau GA: Mutation of GABRA1 in an autosomal dominant form of juvenile myoclonic epilepsy. Nat Genet. 2002 Jun;31(2):184-9. Epub 2002 May 6. [PubMed Link Image]
  2. Schofield PR, Pritchett DB, Sontheimer H, Kettenmann H, Seeburg PH: Sequence and expression of human GABAA receptor alpha 1 and beta 1 subunits. FEBS Lett. 1989 Feb 27;244(2):361-4. [PubMed Link Image]
  3. Garrett KM, Duman RS, Saito N, Blume AJ, Vitek MP, Tallman JF: Isolation of a cDNA clone for the alpha subunit of the human GABA-A receptor. Biochem Biophys Res Commun. 1988 Oct 31;156(2):1039-45. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 1680
Target 2 Name Solute carrier family 2, facilitated glucose transporter member 1
Target 2 Synonyms
  1. Glucose transporter type 1, erythrocyte/brain
  2. HepG2 glucose transporter
Target 2 Gene Name SLC2A1
Target 2 Protein Sequence >Solute carrier family 2, facilitated glucose transporter member 1 
MEPSSKKLTGRLMLAVGGAVLGSLQFGYNTGVINAPQKVIEEFYNQTWVHRYGESILPTT
LTTLWSLSVAIFSVGGMIGSFSVGLFVNRFGRRNSMLMMNLLAFVSAVLMGFSKLGKSFE
MLILGRFIIGVYCGLTTGFVPMYVGEVSPTALRGALGTLHQLGIVVGILIAQVFGLDSIM
GNKDLWPLLLSIIFIPALLQCIVLPFCPESPRFLLINRNEENRAKSVLKKLRGTADVTHD
LQEMKEESRQMMREKKVTILELFRSPAYRQPILIAVVLQLSQQLSGINAVFYYSTSIFEK
AGVQQPVYATIGSGIVNTAFTVVSLFVVERAGRRTLHLIGLAGMAGCAILMTIALALLEQ
LPWMSYLSIVAIFGFVAFFEVGPGPIPWFIVAELFSQGPRPAAIAVAGFSNWTSNFIVGM
CFQYVEQLCGPYVFIIFTVLLVLFFIFTYFKVPETKGRTFDEIASGFRQGGASQSDKTPE
ELFHPLGADSQV
Target 2 Number of Residues 500
Target 2 Molecular Weight 54085
Target 2 Theoretical pI 8.91
Target 2 GO Classification
Function
carrier activity
electrochemical potential-driven transporter activity
porter activity
sugar porter activity
transporter activity
carbohydrate transporter activity
sugar transporter activity
monosaccharide transporter activity
hexose transporter activity
glucose transporter activity
Process
carbohydrate transport
physiological process
cellular physiological process
transport
Component
intrinsic to membrane
integral to membrane
cell
membrane
Target 2 General Function Carbohydrate transport and metabolism
Target 2 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 both pentoses and hexoses
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • 13-33
  • 67-87
  • 96-116
  • 127-147
  • 156-176
  • 186-206
  • 272-292
  • 308-328
  • 338-358
  • 372-392
  • 402-422
  • 430-450
Target 2 Essentiality Non-Essential
Target 2 GenBank ID Protein 183303 Link Image
Target 2 UniProtKB/Swiss-Prot ID P11166 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name GTR1_HUMAN Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location
  • Cell membrane
  • multi-pass membrane protein. Melanosome. Note=Localizes primarily at the cell surface
Target 2 Gene Sequence >1479 bp 
ATGGAGCCCAGCAGCAAGAAGCTGACGGGTCGCCTCATGCTGGCTGTGGGAGGAGCAGTG
CTTGGCTCCCTGCAGTTTGGCTACAACACTGGAGTCATCAATGCCCCCCAGAAGGTGATC
GAGGAGTTCTACAACCAGACATGGGTCCACCGCTATGGGGAGAGCATCCTGCCCACCACG
CTCACCACGCTCTGGTCCCTCTCAGTGGCCATCTTTTCTGTTGGGGGCATGATTGGCTCC
TTCTCTGTGGGCCTTTTCGTTAACCGCTTTGGCCGGCGGAATTCAATGCTGATGATGAAC
CTGCTGGCCTTCGTGTCCGCCGTGCTCATGGGCTTCTCGAAACTGGGCAAGTCCTTTGAG
ATGCTGATCCTGGGCCGCTTCATCATCGGTGTGTACTGCGGCCTGACCACAGGCTTCGTG
CCCATGTATGTGGGTGAAGTGTCACCCACAGCCTTTCGTGGGGCCCTGGGCACCCTGCAC
CAGCTGGGCATCGTCGTCGGCATCCTCATCGCCCAGGTGTTCGGCCTGGACTCCATCATG
GGCAACAAGGACCTGTGGCCCCTGCTGCTGAGCATCATCTTCATCCCGGCCCTGCTGCAG
TGCATCGTGCTGCCCTTCTGCCCCGAGAGTCCCCGCTTCCTGCTCATCAACCGCAACGAG
GAGAACCGGGCCAAGAGTGTGCTAAAGAAGCTGCGCGGGACAGCTGACGTGACCCATGAC
CTGCAGGAGATGAAGGAAGAGAGTCGGCAGATGATGCGGGAGAAGAAGGTCACCATCCTG
GAGCTGTTCCGCTCCCCCGCCTACCGCCAGCCCATCCTCATCGCTGTGGTGCTGCAGCTG
TCCCAGCAGCTGTCTGGCATCAACGCTGTCTTCTATTACTCCACGAGCATCTTCGAGAAG
GCGGGGGTGCAGCAGCCTGTGTATGCCACCATTGGCTCCGGTATCGTCAACACGGCCTTC
ACTGTCGTGTCGCTGTTTGTGGTGGAGCGAGCAGGCCGGCGGACCCTGCACCTCATAGGC
CTCGCTGGCATGGCGGGTTGTGCCATACTCATGACCATCGCGCTAGCACTGCTGGAGCAG
CTACCCTGGATGTCCTATCTGAGCATCGTGGCCATCTTTGGCTTTGTGGCCTTCTTTGAA
GTGGGTCCTGGCCCCATCCCATGGTTCATCGTGGCTGAACTCTTCAGCCAGGGTCCACGT
CCAGCTGCCATTGCCGTTGCAGGCTTCTCCAACTGGACCTCAAATTTCATTGTGGGCATG
TGCTTCCAGTATGTGGAGCAACTGTGTGGTCCCTACGTCTTCATCATCTTCACTGTGCTC
CTGGTTCTGTTCTTCATCTTCACCTACTTCAAAGTTCCTGAGACTAAAGGCCGGACCTTC
GATGAGATCGCTTCCGGCTTCCGGCAGGGGGGAGCCAGCCAAAGTGATAAGACACCCGAG
GAGCTGTTCCATCCCCTGGGGGCTGATTCCCAAGTGTGA
Target 2 GenBank Gene ID
Target 2 GeneCard ID SLC2A1 Link Image
Target 2 GenAtlas ID SLC2A1 Link Image
Target 2 HGNC ID HGNC:11005 Link Image
Target 2 Chromosome Location 1
Target 2 Locus 1p35-p31.3
Target 2 SNPs SNPJam Report Link Image
Target 2 General References
  1. Klepper J, Wang D, Fischbarg J, Vera JC, Jarjour IT, O'Driscoll KR, De Vivo DC: Defective glucose transport across brain tissue barriers: a newly recognized neurological syndrome. Neurochem Res. 1999 Apr;24(4):587-94. [PubMed Link Image]
  2. Wang D, Kranz-Eble P, De Vivo DC: Mutational analysis of GLUT1 (SLC2A1) in Glut-1 deficiency syndrome. Hum Mutat. 2000 Sep;16(3):224-31. [PubMed Link Image]
  3. Klepper J, Willemsen M, Verrips A, Guertsen E, Herrmann R, Kutzick C, Florcken A, Voit T: Autosomal dominant transmission of GLUT1 deficiency. Hum Mol Genet. 2001 Jan 1;10(1):63-8. [PubMed Link Image]
  4. Brockmann K, Wang D, Korenke CG, von Moers A, Ho YY, Pascual JM, Kuang K, Yang H, Ma L, Kranz-Eble P, Fischbarg J, Hanefeld F, De Vivo DC: Autosomal dominant glut-1 deficiency syndrome and familial epilepsy. Ann Neurol. 2001 Oct;50(4):476-85. [PubMed Link Image]
  5. Fukumoto H, Seino S, Imura H, Seino Y, Bell GI: Characterization and expression of human HepG2/erythrocyte glucose-transporter gene. Diabetes. 1988 May;37(5):657-61. [PubMed Link Image]
  6. Mueckler M, Caruso C, Baldwin SA, Panico M, Blench I, Morris HR, Allard WJ, Lienhard GE, Lodish HF: Sequence and structure of a human glucose transporter. Science. 1985 Sep 6;229(4717):941-5. [PubMed Link Image]
Target 2 Drug References
  1. 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. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.