Ethotoin (previously marketed as Peganone) is an

anticonvulsant Anticonvulsants (also known as antiepileptic drugs, antiseizure drugs, or anti-seizure medications (ASM)) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also used in the treatme ...

drug used in the treatment of

epilepsy Epilepsy is a group of Non-communicable disease, non-communicable Neurological disorder, neurological disorders characterized by a tendency for recurrent, unprovoked Seizure, seizures. A seizure is a sudden burst of abnormal electrical activit ...

. It is a

hydantoin Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sen ...

, similar to

phenytoin Phenytoin (PHT), sold under the brand name Dilantin among others, is an anticonvulsant, anti-seizure medication. It is useful for the prevention of tonic-clonic seizures (also known as grand mal seizures) and focal seizures, but not absence se ...

. It is not available in the United States.

Mechanism of action

The

mechanism of action In pharmacology, the term mechanism of action (MOA) refers to the specific biochemical Drug interaction, interaction through which a Medication, drug substance produces its pharmacological effect. A mechanism of action usually includes mention o ...

of ethotoin is similar to that of phenytoin.

Approval history

*1957 Peganone was granted

Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respo ...

(FDA) approval to

Abbott Laboratories Abbott Laboratories is an American multinational medical devices and health care company with headquarters in Abbott Park, Illinois, in the United States. The company was founded by Chicago physician Wallace Calvin Abbott in 1888 to formulate k ...

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). *2018 It was announced by Recordati Rare Diseases Inc. that due to a combination of low product demand and complex manufacturing difficulties, product manufacturing, distribution and sale was being discontinued.

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

Side effects include

ataxia Ataxia (from Greek α- negative prefix+ -τάξις rder= "lack of order") is a neurological sign consisting of lack of voluntary coordination of muscle movements that can include gait abnormality, speech changes, and abnormalities in e ...

, visual disturbances, rash, and

gastrointestinal The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The tract is the largest of the body's systems, after the cardiovascular system. ...

problems.

Chemistry

Ethotoin is synthesized by the reaction of benzaldehyde oxynitrile (2) with

urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...

ammonium bicarbonate Ammonium bicarbonate is an inorganic compound with formula (NH4)HCO3. The compound has many names, reflecting its long history. Chemically speaking, it is the bicarbonate salt of the ammonium ion. It is a colourless solid that degrades readily to ...

, which forms an intermediate urea derivative (3) which on acidic conditions cyclizes to 5-phenylhydantoin (4).A. Pinner, Chem. Ber., 21, 2324 (1888); W.J. Close, (1946) Alkylation of this product using

ethyl iodide Ethyl iodide (also iodoethane) is a transparency and translucency, colorless flammable chemical compound. It has the chemical formula C2H5I and is prepared by heating ethanol with iodine and phosphorus.''Merck Index of Chemicals and Drugs'', 9th e ...

leads to the formation of ethotoin (5). : Ethotoin synthesis

References

{{Anticonvulsants Anticonvulsants Hydantoins Drugs developed by AbbVie