Chemistry:Ethotoin
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| AHFS/Drugs.com | Consumer Drug Information |
| MedlinePlus | a682022 |
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| Routes of administration | By mouth (tablets) |
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| Elimination half-life | 3–9 hours |
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| Formula | C11H12N2O2 |
| Molar mass | 204.229 g·mol−1 |
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Ethotoin (previously marketed as Peganone) is an anticonvulsant drug used in the treatment of epilepsy.[1] It is a hydantoin, similar to phenytoin. It is not available in the United States.
Mechanism of action
The mechanism of action of ethotoin is similar to that of phenytoin.[citation needed]
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).
- 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.[2]
Dosing
Ethotoin is available in 250 mg tablets.[3][4] It is taken orally in 4 to 6 divided doses per day, preferably after food.
Side effects
Side effects include ataxia, visual disturbances, rash, and gastrointestinal problems.[citation needed]
Chemistry
Ethotoin is synthesized by the reaction of benzaldehyde oxynitrile (2) with urea or ammonium bicarbonate, which forms an intermediate urea derivative (3) which on acidic conditions cyclizes to 5-phenylhydantoin (4).[5] Alkylation of this product using ethyl iodide leads to the formation of ethotoin (5).
Synthesis of ethotoin
References
- ↑ "Peganone, a new antiepileptic drug". Dis Nerv Syst 17 (5): 155–8. May 1956. PMID 13317788.
- ↑ Shorvon, S.D., ed (2004). The Treatment of Epilepsy. Blackwell Publishing. ISBN 0-632-06046-8.
- ↑ "Ethotoin". https://www.drugs.com/search.php?searchterm=ethotoin.
- ↑ "PEGANONE 250 mg Ethotoin Tablets, USP". http://ovationpharmaceuticals.com/images/products/pdf/peganone_pi.pdf.
- ↑ A. Pinner, Chem. Ber., 21, 2324 (1888); W.J. Close, U.S. Patent 2,793,157 (1946)
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