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	Consumer Drug Information
MedlinePlus	a682022
Pregnancy category	C
Routes of administration	Oral
Pharmacokinetic data
Biological half-life	3 to 9 hours
Identifiers
CAS Number	86-35-1 Y
ATC code	N03AB01 (WHO)
PubChem	CID: 3292
IUPHAR/BPS	7183
DrugBank	DB00754 Y
ChemSpider	3176 Y
UNII	46QG38NC4U Y
KEGG	D00708 Y
ChEBI	CHEBI:4888 Y
ChEMBL	CHEMBL1095 Y
Chemical data
Formula	C11H12N2O2
Molecular mass	204.225 g/mol
SMILES O=C2NC(c1ccccc1)C(=O)N2CC
InChI 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) Y Key:SZQIFWWUIBRPBZ-UHFFFAOYSA-N Y
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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. 800px

• 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