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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.

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Synonyms
Ethotoine [INN-French]
Ethotoinum [INN-Latin]
Etotoina [INN-Spanish]
Salts Not Available
Brand names
Name Company
Accenon
Peganone
Pegoanone
Brand 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
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 94 °C PhysProp
water solubility 5280 mg/L Not Available
logP 1.05 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 2.38e+00 g/l ALOGPS
logP 1.11 ALOGPS
logP 1.07 ChemAxon
logS -1.9 ALOGPS
pKa (strongest acidic) 11.29 ChemAxon
pKa (strongest basic) -8.4 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 49.41 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 55.05 ChemAxon
polarizability 20.68 ChemAxon
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 PA164768735 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
Drug Interaction
Alprazolam Ethotoin may increase the metabolism of alprazolam via CYP3A4.
Aminophylline Decreased effect of both products
Amiodarone Increases the effect of hydantoin
Aprepitant The CYP3A4 inducer, ethotoin, may decrease the effect of aprepitant.
Betamethasone The enzyme inducer, ethotoin, may decrease the effect of the corticosteroid, betamethasone.
Capecitabine Capecitabine increases the effect of hydantoin
Chloramphenicol Increases phenytoin, modifies chloramphenicol
Chlordiazepoxide Ethotoin may increase the metabolism of chlordiazepoxide via CYP3A4.
Chlorpheniramine The antihistamine increases the effect of hydantoin
Cimetidine Increases the effect of hydantoin
Ciprofloxacin Decreases the hydantoin effect
Clomifene The enzyme inducer, ethotoin, decreases the effect of the hormone agent, clomifene.
Clorazepate Ethotoin may increase the metabolism of clorazepate via CYP3A4.
Clozapine Hydantoin decreases the effect of clozapine
Conjugated Estrogens The enzyme inducer, ethotoin, decreases the effect of the hormone agent, conjugated estrogens.
Cyclosporine The hydantoin decreases the effect of cyclosporine
Dexamethasone The enzyme inducer, ethotoin, may decrease the effect of the corticosteroid, dexamethasone.
Diazepam Ethotoin may increase the metabolism of diazepam via CYP3A4.
Diethylstilbestrol The enzyme inducer, ethotoin, decreases the effect of the hormone agent, diethylstilbestrol.
Disopyramide The hydantoin decreases the effect of disopyramide
Disulfiram Increases the effect of phenytoin
Doxycycline The anticonvulsant, ethotoin, decreases the effect of doxycycline.
Estradiol The enzyme inducer, ethotoin, decreases the effect of the hormone agent, estradiol.
Ethinyl Estradiol This product may cause a slight decrease of contraceptive effect
Felbamate Increased phenytoin levels and decreased felbamate levels
Felodipine The hydantoin decreases the effect of felodipine
Fluconazole Increases the effect of hydantoin
Fludrocortisone The enzyme inducer, ethotoin, may decrease the effect of the corticosteroid, fludrocortisone.
Fluorouracil Fluorouracil increases the effect of hydantoin
Fluoxetine Fluoxetine increases the effect of phenytoin
Flurazepam Ethotoin may increase the metabolism of flurazepam via CYP3A4.
Fluvoxamine Increases the effect of hydantoin
Folic Acid Folic acid decreases the levels of hydantoin
Furosemide The hydantoin decreases the effect of furosemide
Gabapentin Increases the effect of hydantoin
Gefitinib The CYP3A4 inducer, ethotoin, may decrease the serum concentration and therapeutic effects of gefitinib.
Hydrocortisone The enzyme inducer, ethotoin, may decrease the effect of the corticosteroid, hydrocortisone.
Imatinib The hydantoin decreases the levels of imatinib
Isoniazid Isoniazid increases the effect of phenytoin in 20% of patients
Itraconazole Phenytoin decreases the effect of itraconazole
Lamotrigine Phenytoin may reduce levels of lamotrigine
Levonorgestrel Phenytoin decreases the contraceptive effect
Mebendazole The hydantoin decreases the efficiency of mebendazole
Medroxyprogesterone The enzyme inducer, ethotoin, decreases the effect of the hormone agent, medroxyprogesterone.
Megestrol The enzyme inducer, ethotoin, decreases the effect of the hormone agent, megestrol.
Methadone The hydantoin decreases the effect of methadone
Methotrexate The antineoplasic agent decreases the effect of hydantoin
Methoxsalen The hydantoin decreases the effect of psoralene
Mexiletine The hydantoin decreases the effect of mexiletine
Midazolam Ethotoin may increase the metabolism of midazolam via CYP3A4.
Mirtazapine The hydantoins may reduce mirtazapine plasma concentrations and pharmacological effects
Norethindrone This product may cause a slight decrease of contraceptive effect
Omeprazole Omeprazole increases the effect of hydantoin
Oxcarbazepine Oxcarbazepine increases the effect of hydantoin
Oxtriphylline Decreased effect of both products
Oxyphenbutazone The NSAID, oxyphenbutazone, may increase the hydantoin effect of ethotoin.
Phenylbutazone The NSAID, phenylbutazone, may increase the hydantoin effect of ethotoin.
Prednisolone The enzyme inducer, ethotoin, may decrease the effect of the corticosteroid, prednisolone.
Prednisone The enzyme inducer, ethotoin, may decrease the effect of the corticosteroid, prednisone.
Quetiapine Phenytoin decreases the effect of quetiapine
Rifampin Rifampin decreases the effect of the hydantoin
Theophylline Decreased effect of both products
Ticlopidine Ticlopidine increases the effect of hydantoin
Triamcinolone The enzyme inducer, ethotoin, may decrease the effect of the corticosteroid, triamcinolone.
Triazolam Ethotoin may increase the metabolism of triazolam via CYP3A4.
Triprolidine The CNS depressants, Triprolidine and Ethotoin, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
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 February 08, 2013 16:19