Ethotoin
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| Systematic (IUPAC) name | |
|---|---|
| 3-ethyl-5-phenyl-imidazolidine-2,4-dione | |
| Clinical data | |
| AHFS/Drugs.com | Consumer Drug Information |
| MedlinePlus | a682022 |
| |
| Oral | |
| Pharmacokinetic data | |
| Half-life | 3 to 9 hours |
| Identifiers | |
86-35-1  | |
| N03AB01 | |
| PubChem | CID 3292 |
| DrugBank |
DB00754 |
| ChemSpider |
3176 |
| UNII |
46QG38NC4U |
| KEGG |
D00708 |
| ChEBI |
CHEBI:4888 |
| ChEMBL |
CHEMBL1095 |
| Chemical data | |
| Formula | C11H12N2O2 |
| 204.225 g/mol | |
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SMILES
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| (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
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
- Schwade ED, Richards RK, Everett GM (May 1956). "Peganone, a new antiepileptic drug". Dis Nerv Syst 17 (5): 155–8. PMID 13317788.
- Shorvon, S.D.; Fish, David R.; Perucca, Emilio; Dodson, W. Edwin, ed. (2004). The Treatment of Epilepsy. Blackwell Publishing. ISBN 0-632-06046-8.
- Drugs.com: Ethotoin
- PEGANONE 250 mg Ethotoin Tablets, USP (PDF)