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.[1] It is a hydantoin, similar to phenytoin. It is not available in the United States.

Mechanism of action

The mechanism of action of ethotoin is similar to that of phenytoin.[citation needed]

Approval history

Indications and usage

Ethotoin is indicated for tonic-clonic and partial complex seizures.[2]

Dosing

Ethotoin is available in 250 mg tablets.[3][4] It is taken orally in 4 to 6 divided doses per day, preferably after food.

Side effects

Side effects include ataxia, visual disturbances, rash, and gastrointestinal problems.[citation needed]

Chemistry

Ethotoin is synthesized by the reaction of benzaldehyde oxynitrile (2) with urea or ammonium bicarbonate, which forms an intermediate urea derivative (3) which on acidic conditions cyclizes to 5-phenylhydantoin (4).[5] Alkylation of this product using ethyl iodide leads to the formation of ethotoin (5).

Synthesis of ethotoin

References

  1. ^ Schwade ED, Richards RK, Everett GM (May 1956). "Peganone, a new antiepileptic drug". Dis Nerv Syst. 17 (5): 155–8. PMID 13317788.
  2. ^ Shorvon, S.D.; Fish, David R.; Perucca, Emilio; Dodson, W. Edwin, eds. (2004). The Treatment of Epilepsy. Blackwell Publishing. ISBN 0-632-06046-8.
  3. ^ "Ethotoin". drugs.com.
  4. ^ "PEGANONE 250 mg Ethotoin Tablets, USP" (PDF).
  5. ^ A. Pinner, Chem. Ber., 21, 2324 (1888); W.J. Close, U.S. patent 2,793,157 (1946)