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 |
| Pregnancy category |
|
| Routes of administration | Oral |
| Pharmacokinetic data | |
| Biological half-life | 3 to 9 hours |
| Identifiers | |
| CAS Number |
86-35-1  |
| ATC code | N03AB01 (WHO) |
| PubChem | CID 3292 |
| IUPHAR/BPS | 7183 |
| DrugBank |
DB00754 |
| ChemSpider |
3176 |
| UNII |
46QG38NC4U |
| KEGG |
D00708 |
| ChEBI |
CHEBI:4888 |
| ChEMBL |
CHEMBL1095 |
| Chemical data | |
| Formula | C11H12N2O2 |
| Molar mass | 204.225 g/mol |
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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)