| Revision as of 11:40, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 447436081 of page Ethotoin for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 16:27, 24 January 2024 edit AnomieBOT (talk | contribs)Bots6,571,359 editsm Dating maintenance tags: {{Cn}} |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Watchedfields = changed |
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| verifiedrevid = 443742864 |
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| verifiedrevid = 461096712 |
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| IUPAC_name = 3-ethyl-5-phenyl-imidazolidine-2,4-dione |
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| IUPAC_name = 3-Ethyl-5-phenyl-imidazolidine-2,4-dione |
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| image = Ethotoin structure.png |
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| width = 201 |
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| image = Ethotoin.svg |
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| alt = Skeletal formula of ethotoin |
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| width = 105 |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| Drugs.com = {{drugs.com|CDI|ethotoin}} |
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| Drugs.com = {{drugs.com|CDI|ethotoin}} |
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| MedlinePlus = a682022 |
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| MedlinePlus = a682022 |
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| pregnancy_category = C |
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| pregnancy_category = C |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = Oral |
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| routes_of_administration = ] (]) |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| protein_bound = |
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| protein_bound = |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = 3 to 9 hours |
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| elimination_half-life = 3–9 hours |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| IUPHAR_ligand = 7183 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 86-35-1 |
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| CAS_number = 86-35-1 |
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| ATC_prefix = N03 |
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| ATC_prefix = N03 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=11 | H=12 | N=2 | O=2 |
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| C=11 | H=12 | N=2 | O=2 |
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| molecular_weight = 204.225 g/mol |
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| smiles = O=C2NC(c1ccccc1)C(=O)N2CC |
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| smiles = O=C2NC(c1ccccc1)C(=O)N2CC |
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| InChI = 1/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) |
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| InChIKey = SZQIFWWUIBRPBZ-UHFFFAOYAG |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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) |
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| 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) |
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| StdInChIKey = SZQIFWWUIBRPBZ-UHFFFAOYSA-N |
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| StdInChIKey = SZQIFWWUIBRPBZ-UHFFFAOYSA-N |
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}} |
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}} |
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'''Ethotoin''' (previously marketed as '''Peganone''') is an ] drug used in the treatment of ].<ref>{{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 }}</ref> It is a ], similar to ]. It is not available in the United States. |
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==Mechanism of action== |
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The ] of ethotoin is similar to that of phenytoin.{{cn|date=January 2024}} |
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==Approval history== |
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*'''1957''' Peganone was granted ] (FDA) approval to ] for treatment of grand mal (tonic clonic) and partial complex (psychomotor) seizures. |
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*'''2003''' Peganone was acquired from Abbott Laboratories by Ovation Pharmaceuticals (specialty pharmaceutical company who acquire underpromoted branded pharmaceutical products). |
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*'''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. |
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==Indications and usage== |
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Ethotoin is indicated for tonic-clonic and partial complex seizures.<ref>{{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 }}</ref> |
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==Dosing== |
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Ethotoin is available in 250 mg tablets.<ref>{{cite web | url = https://www.drugs.com/search.php?searchterm=ethotoin | title = Ethotoin | website = drugs.com }}</ref><ref>{{cite web | url = http://ovationpharmaceuticals.com/images/products/pdf/peganone_pi.pdf | title = PEGANONE 250 mg Ethotoin Tablets, USP }}</ref> It is taken orally in 4 to 6 divided doses per day, preferably after food. |
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==Side effects== |
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Side effects include ], visual disturbances, rash, and ] problems.{{cn|date=January 2024}} |
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==Chemistry== |
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Ethotoin is synthesized by the reaction of benzaldehyde oxynitrile ('''2''') with ] or ], which forms an intermediate urea derivative ('''3''') which on acidic conditions cyclizes to 5-phenylhydantoin ('''4''').<ref>A. Pinner, Chem. Ber., 21, 2324 (1888); W.J. Close, {{US Patent|2793157}} (1946)</ref> Alkylation of this product using ] leads to the formation |
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of ethotoin ('''5'''). |
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:] |
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{{clear left}} |
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==References== |
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{{reflist}} |
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{{Anticonvulsants}} |
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] |
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] |
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] |