Ethotoin

From Wikipedia, the free encyclopedia
Jump to: navigation, search
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 Consumer Drug Information
MedlinePlus a682022
  • C
Oral
Pharmacokinetic data
Half-life 3 to 9 hours
Identifiers
86-35-1 YesY
N03AB01
PubChem CID 3292
DrugBank DB00754 YesY
ChemSpider 3176 YesY
UNII 46QG38NC4U YesY
KEGG D00708 YesY
ChEBI CHEBI:4888 YesY
ChEMBL CHEMBL1095 YesY
Chemical data
Formula C11H12N2O2
204.225 g/mol
 YesY (what is this?)  (verify)

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.

Mechanism of action[edit]

Similar to phenytoin.

Approval history[edit]

  • 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[edit]

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

Dosing[edit]

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

Side effects[edit]

Ataxia, visual disturbances, rash and gastrointestinal problems.

Chemistry[edit]

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. Ethotoin synthesis.png

References[edit]

External links[edit]