Ethotoin

Ethotoin

Ethotoin
Structural formula of ethotoin
Ball-and-stick model of the ethotoin molecule
Systematic (IUPAC) name
3-ethyl-5-phenyl-imidazolidine-2,4-dione
Clinical data
AHFS/Drugs.com
MedlinePlus
Pregnancy
category
  • C
Routes of
administration
Oral
Pharmacokinetic data
Biological half-life 3 to 9 hours
Identifiers
CAS Registry Number  YesY
ATC code N03
PubChem CID:
IUPHAR/BPS
DrugBank  YesY
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEBI  YesY
ChEMBL  YesY
Chemical data
Formula C11H12N2O2
Molecular mass
Documentation

 YesY   

Ethotoin (marketed as Peganone by Ovation) is an anticonvulsant drug used in the treatment of epilepsy. It is a hydantoin, similar to phenytoin. Ethotoin lacks phenytoin's side effects of gingival hyperplasia and hirsutism; however, it is less effective. This, combined with the need for frequent dosing has limited its usefulness. Ethotoin is no longer widely used.

Contents

  • Mechanism of action 1
  • Approval history 2
  • Indications and usage 3
  • Dosing 4
  • Side effects 5
  • Chemistry 6
  • References 7
  • External links 8

Mechanism of action

Similar to phenytoin.

Approval history

  • 1957 Peganone was granted Food and Drug Administration (FDA) approval to Abbott Laboratories for treatment of grand mal (tonic clonic) and partial complex (psychomotor) seizures.
  • 2003 Peganone was acquired from Abbott Laboratories by Ovation Pharmaceuticals (specialty pharmaceutical company who acquire underpromoted branded pharmaceutical products).

Indications and usage

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

Dosing

Ethotoin is available in 250mg 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).

References

  • Drugs.com: Ethotoin
  • PEGANONE 250 mg Ethotoin Tablets, USP (PDF)

External links

  • Ovation Pharmaceuticals