Ethotoin is an anticonvulsant

Anticonvulsant

The anticonvulsants are a diverse group of pharmaceuticals used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of bipolar disorder, since many seem to act as mood stabilizers, and in the treatment of neuropathic pain. The goal of an...

 drug used in the treatment of epilepsy

Epilepsy

Epilepsy is a common chronic neurological disorder characterized by seizures. These seizures are transient signs and/or symptoms of abnormal, excessive or hypersynchronous neuronal activity in the brain.About 50 million people worldwide have epilepsy, and nearly two out of every three new cases...

. It is a hydantoin

Hydantoin

Hydantoin, which is also known as glycolylurea, is a heterocyclic organic compound that can be thought of as a cyclic "double-condensation reaction" product of glycolic acid and urea...

, similar to phenytoin

Phenytoin

Phenytoin sodium is a commonly used antiepileptic. Phenytoin acts to suppress the abnormal brain activity seen in seizure by reducing electrical conductance among brain cells by stabilizing the inactive state of voltage-gated sodium channels...

. Ethotoin lacks phenytoin's side effects of gingiva

Gingiva

The gingiva , or gums, consists of the mucosal tissue that lies over the mandible and maxilla inside the mouth.-General description:...

l hyperplasia

Hyperplasia

Hyperplasia means increase in number of cells/proliferation of cells. It may result in the gross enlargement of an organ and the term is sometimes mixed with benign neoplasia/ benign tumor....

 and hirsutism

Hirsutism

Hirsutism or frazonism is the excessive hairiness on women in those parts of the body where terminal hair does not normally occur or is minimal - for example, a beard or chest hair. It refers to a male pattern of body hair and it is therefore primarily of cosmetic and psychological concern...

, however it is less effective. This, combined with the need for frequent dosing has limited its usefulness. Ethotoin is no longer widely used.

Approval history

• 1957 Peganone was granted Food and Drug Administration
  Food and Drug Administration
  The Food and Drug Administration is an agency of the United States Department of Health and Human Services, one of the United States federal executive departments...
  
   (FDA) approval to Abbott Laboratories
  Abbott Laboratories
  Abbott Laboratories is an American-based global, diversified pharmaceuticals and health care products company. It has 90,000 employees and operates in over 130 countries. The company headquarters are in Abbott Park, North Chicago, Illinois. The company was founded by Chicago physician, Dr....
  
   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).

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

Ataxia

Ataxia is a neurological sign and symptom that consists of gross lack of coordination of muscle movements. Ataxia is a non-specific clinical manifestation implying dysfunction of the parts of the nervous system that coordinate movement, such as the cerebellum...

, visual disturbances, rash and gastrointestinal

Gastrointestinal tract

The human gastrointestinal tract refers to the stomach and intestine, and sometimes to all the structures from the mouth to the anus. ....

 problems.

Chemistry

Ethotoin, 3-ethyl-5-phenylimidazolidine-2,4-dione, is synthesized by the reaction of benzaldehyde oxynitrile, with urea

Urea

Urea or carbamide is an organic compound with the chemical formula CO2. The molecule has two —NH2 groups joined by a carbonyl functional group....

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, (1946).