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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.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Ethotoin
    		p-Hydroxyl-ethotoin Details
    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