Ethotoin
{{Short description|Chemical compound}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 461096712
| IUPAC_name = 3-Ethyl-5-phenyl-imidazolidine-2,4-dione
| image = Ethotoin.svg
| alt = Skeletal formula of ethotoin
| width = 105
| tradename =
| Drugs.com = {{drugs.com|CDI|ethotoin}}
| MedlinePlus = a682022
| pregnancy_category = C
| legal_status =
| routes_of_administration = By mouth (tablets)
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life = 3–9 hours
| IUPHAR_ligand = 7183
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 86-35-1
| ATC_prefix = N03
| ATC_suffix = AB01
| ATC_supplemental =
| PubChem = 3292
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00754
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3176
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 46QG38NC4U
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00708
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4888
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1095
| C=11 | H=12 | N=2 | O=2
| smiles = O=C2NC(c1ccccc1)C(=O)N2CC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SZQIFWWUIBRPBZ-UHFFFAOYSA-N
}}
Ethotoin (previously marketed as Peganone) is an anticonvulsant drug used in the treatment of epilepsy.{{cite journal |vauthors=Schwade ED, Richards RK, Everett GM |title=Peganone, a new antiepileptic drug |journal=Dis Nerv Syst |volume=17 |issue=5 |pages=155–8 |date=May 1956 |pmid=13317788 }} 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.{{cn|date=January 2024}}
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.{{cite book |editor=Shorvon, S.D. |editor2=Fish, David R. |editor3=Perucca, Emilio |editor4=Dodson, W. Edwin |title=The Treatment of Epilepsy |publisher=Blackwell Publishing |year=2004 |isbn=0-632-06046-8 }}
Dosing
Ethotoin is available in 250 mg tablets.{{cite web | url = https://www.drugs.com/search.php?searchterm=ethotoin | title = Ethotoin | website = drugs.com }}{{cite web | url = http://ovationpharmaceuticals.com/images/products/pdf/peganone_pi.pdf | title = PEGANONE 250 mg Ethotoin Tablets, USP }} 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.{{cn|date=January 2024}}
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).A. Pinner, Chem. Ber., 21, 2324 (1888); W.J. Close, {{US Patent|2793157}} (1946) Alkylation of this product using ethyl iodide leads to the formation
of ethotoin (5).
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References
{{reflist}}
{{Anticonvulsants}}