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Ethotoin
Skeletal formula of ethotoin
Clinical data
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682022
Pregnancy
category
  • C
Routes of
administration		By mouth (tablets)
ATC code
Pharmacokinetic data
Elimination half-life3–9 hours
Identifiers
  • 3-Ethyl-5-phenyl-imidazolidine-2,4-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.514 Edit this at Wikidata
Chemical and physical data
FormulaC11H12N2O2
Molar mass204.229 g·mol−1
3D model (JSmol)
  • O=C2NC(c1ccccc1)C(=O)N2CC
  • 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) checkY
  • Key:SZQIFWWUIBRPBZ-UHFFFAOYSA-N checkY
  (verify)

Ethotoin (previously marketed as Peganone) is an anticonvulsant drug used in the treatment of epilepsy. It is a hydantoin, similar to phenytoin. It is not available in the United States.

Mechanism of action

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Similar to phenytoin.

Approval history

Indications and usage

Ethotoin is indicated for tonic-clonic and partial complex seizures.

Dosing

Ethotoin is available in 250 mg tablets. It is taken orally in 4 to 6 divided doses per day, preferably after food.

Side effects

Ataxia, visual disturbances, rash and gastrointestinal problems.

Chemistry

Ethotoin, 3-ethyl-5-phenylimidazolidine-2,4-dione, is synthesized by the reaction of benzaldehyde oxynitrile, with urea or ammonium hydrocarbonate, which forms an intermediate urea derivative which on acidic conditions cyclizes to 5-phenylhydantoin. Alkylation of this product using ethyliodide leads to the formation of ethotoin.

A. Pinner, Chem. Ber., 21, 2324 (1888); W.J. Close, U.S. Patent 2,793,157 (1946).
A. Pinner, Chem. Ber., 21, 2324 (1888); W.J. Close, U.S. Patent 2,793,157 (1946).

References

External links

Anticonvulsants (N03)
Categories