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Identification
Name Ethotoin
Accession Number DB00754 (APRD00962)
Type small molecule
Groups approved
Description

Ethotoin is a hydantoin derivative and anticonvulsant. Ethotoin exerts an antiepileptic effect without causing general central nervous system depression. The mechanism of action is probably very similar to that of phenytoin. The latter drug appears to stabilize rather than to raise the normal seizure threshold, and to prevent the spread of seizure activity rather than to abolish the primary focus of seizure discharges.
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
  • Ethotoine [INN-French]
  • Ethotoinum [INN-Latin]
  • Etotoina [INN-Spanish]
Brand names
  • Accenon
  • Peganone
  • Pegoanone
Brand name mixtures Not Available
Categories
  • Anticonvulsants
CAS number 86-35-1
Weight Average: 204.2252
Monoisotopic: 204.089877638
Chemical Formula C11H12N2O2
InChI Key InChIKey=SZQIFWWUIBRPBZ-UHFFFAOYSA-N
InChI
InChI=1S/C11H12N2O2/c1-2-13-10(14)9(12-11(13)15)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,15)
Plain Text
IUPAC Name
3-ethyl-5-phenylimidazolidine-2,4-dione
SMILES
CCN1C(=O)NC(C1=O)C1=CC=CC=C1
Plain Text
Mass Spec show (8.5 KB)
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
Substructures
  • Imidazolidinediones
  • Amino Ketones
  • Benzene and Derivatives
  • Ureas and Derivatives
  • Imidazolidines
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Carboxylic Acids and Derivatives
Pharmacology
Indication For the control of tonic-clonic (grand mal) and complex partial (psychomotor) seizures.
Pharmacodynamics Ethotoin is a hydantoin derivative and anticonvulsant. Ethotoin exerts an antiepileptic effect without causing general central nervous system depression. The mechanism of action is probably very similar to that of phenytoin. The latter drug appears to stabilize rather than to raise the normal seizure threshold, and to prevent the spread of seizure activity rather than to abolish the primary focus of seizure discharges.
Mechanism of action The mechanism of action is probably very similar to that of phenytoin. The latter drug appears to stabilize rather than to raise the normal seizure threshold, and to prevent the spread of seizure activity rather than to abolish the primary focus of seizure discharges. Ethotoin inhibits nerve impulses in the motor cortex by lowering sodium ion influx, limiting tetanic stimulation.
Absorption Fairly rapidly absorbed, however, the extent of oral absorption is not known.
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Hepatic. The drug exhibits saturable metabolism with respect to the formation of N-deethyl and p-hydroxyl-ethotoin, the major metabolites.
Route of elimination Not Available
Half life 3 to 9 hours
Clearance Not Available
Toxicity Symptoms of overdose include drowsiness, loss of or impaired muscle coordination, nausea, visual disturbance, and, at very high doses, coma.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Lundbeck inc
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Peganone 250 mg tablet 1.33 USD tablet
Patents Not Available
Properties
State solid
Melting point 94 oC
Experimental Properties
Property Value Source
water solubility 5280 mg/L PhysProp
logP 0.8 PhysProp
Predicted Properties
Property Value Source
water solubility 2.38e+00 g/l ALOGPS
logP 1.11 ALOGPS
logP 1.07 ChemAxon Molconvert
logS -1.93 ALOGPS
pKa 16.23 ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 49.41 ChemAxon Molconvert
rotatable bond count 2 ChemAxon Molconvert
refractivity 55.05 ChemAxon Molconvert
polarizability 20.68 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. SCHWADE ED, RICHARDS RK, EVERETT GM: Peganone, a new antiepileptic drug. Dis Nerv Syst. 1956 May;17(5):155-8. Pubmed
External Links
Resource Link
KEGG Drug D00708 Link_out
KEGG Compound C07839 Link_out
PubChem Compound 3292 Link_out
PubChem Substance 46504521 Link_out
ChemSpider 3176 Link_out
ChEBI 4888 Link_out
ChEMBL 4888 Link_out
Therapeutic Targets Database DAP000512 Link_out
PharmGKB PA449534 Link_out
Drug Product Database 0 Link_out
RxList http://www.rxlist.com/cgi/generic3/peganone.htm Link_out
Drugs.com http://www.drugs.com/cdi/ethotoin.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/peg1665.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Ethotoin Link_out
ATC Codes
  • N03AB01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Sodium channel protein type 5 subunit alpha

Pharmacological action: yes
Actions: inhibitor

This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram

Organism class: human
UniProt ID: Q14524 Link_out
Gene: SCN5A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  3. Lenkowski PW, Ko SH, Anderson JD, Brown ML, Patel MK: Block of human NaV1.5 sodium channels by novel alpha-hydroxyphenylamide analogues of phenytoin. Eur J Pharm Sci. 2004 Apr;21(5):635-44. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. Cytochrome P450 2C19

Actions: inhibitor

Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:06

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.