Ethotoin

Ethotoin
Clinical data

AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a682022
Pregnancy category	C
Routes of administration	By mouth (tablets)
ATC code	N03AB01 (WHO)
Pharmacokinetic data
Biological half-life	3–9 hours
Identifiers
IUPAC name 3-Ethyl-5-phenyl-imidazolidine-2,4-dione
CAS Number	86-35-1^Y
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
ECHA InfoCard	100.001.514
Chemical and physical data
Formula	C₁₁H₁₂N₂O₂
Molar mass	204.225 g/mol
3D model (Jmol)	Interactive image
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
(verify)

Ethotoin (marketed as Peganone by Ovation) is an anticonvulsant drug used in the treatment of epilepsy. It is a hydantoin, similar to phenytoin.

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 250 mg 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, eds. (2004). The Treatment of Epilepsy. Blackwell Publishing. ISBN 0-632-06046-8.
Drugs.com: Ethotoin
PEGANONE 250 mg Ethotoin Tablets, USP (PDF)

External links

Ovation Pharmaceuticals

Anticonvulsants (N03)

GABAergics

GABA_AR PAMs	Barbiturates: Barbexaclone Metharbital Methylphenobarbital Pentobarbital Phenobarbital^# Primidone; Carbamates: Felbamate; Benzodiazepines: Clobazam Clonazepam Clorazepate Diazepam^# Lorazepam^# Midazolam Nimetazepam Nitrazepam Temazepam; Others: Bromide (potassium bromide, sodium bromide) Paraldehyde Stiripentol

GABA-T inhibitors	Fatty acids: Valproate Valpromide Valproate pivoxil; Others: Ethanolamine-O-sulfate Vigabatrin

Others	GABAR agonists: Progabide; GAT-1 inhibitors: Tiagabine

Channelergics

Sodium blockers	Hydantoins: Ethotoin Fosphenytoin Mephenytoin Phenytoin^#; Ureides: Acetylpheneturide Chlorphenacemide Phenacemide^‡ Pheneturide; Fatty acids: Valproate Valpromide Valproate pivoxil; Carboxamides: Carbamazepine^# Eslicarbazepine acetate Oxcarbazepine; Others: Lacosamide Lamotrigine Rufinamide Topiramate Zonisamide

Calcium blockers	Oxazolidinediones: Ethadione Paramethadione Trimethadione; Succinimides: Ethosuximide^# Mesuximide Phensuximide; Gabapentinoids: Gabapentin Pregabalin; Others: Lamotrigine Topiramate Zonisamide

Potassium openers	Retigabine

Others

CA inhibitors	Sulfonamides: Acetazolamide Ethoxzolamide Sultiame Topiramate Zonisamide

Others	Beclamide Brivaracetam Levetiracetam Perampanel

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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