Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Ethotoin: Difference between pages
(Difference between pages)
Content deleted Content added
Saving copy of the {{drugbox}} taken from revid 447436081 of page Ethotoin for the Chem/Drugbox validation project (updated: 'DrugBank'). |
m Dating maintenance tags: {{Cn}} |
||
| Line 1: | Line 1: | ||
{{Short description|Chemical compound}} |
|||
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Ethotoin|oldid=447436081}} 447436081] of page [[Ethotoin]] with values updated to verified values.}} |
|||
{{Drugbox |
{{Drugbox |
||
| Watchedfields = changed |
|||
| verifiedrevid = |
| verifiedrevid = 461096712 |
||
| IUPAC_name = 3- |
| IUPAC_name = 3-Ethyl-5-phenyl-imidazolidine-2,4-dione |
||
| image = Ethotoin structure.png |
|||
| |
| image = Ethotoin.svg |
||
| alt = Skeletal formula of ethotoin |
|||
| width = 105 |
|||
<!--Clinical data--> |
<!--Clinical data--> |
||
| tradename = |
| tradename = |
||
| Drugs.com = {{drugs.com|CDI|ethotoin}} |
| Drugs.com = {{drugs.com|CDI|ethotoin}} |
||
| MedlinePlus = a682022 |
| MedlinePlus = a682022 |
||
| pregnancy_category = C |
| pregnancy_category = C |
||
| legal_status = |
| legal_status = |
||
| routes_of_administration = Oral |
| routes_of_administration = [[Oral administration|By mouth]] ([[Tablet (pharmacy)|tablets]]) |
||
<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
||
| bioavailability = |
| bioavailability = |
||
| protein_bound = |
| protein_bound = |
||
| metabolism = |
| metabolism = |
||
| elimination_half-life = |
| elimination_half-life = 3–9 hours |
||
<!--Identifiers--> |
<!--Identifiers--> |
||
| IUPHAR_ligand = 7183 |
|||
| |
| CAS_number_Ref = {{cascite|correct|??}} |
||
| CAS_number = 86-35-1 |
| CAS_number = 86-35-1 |
||
| ATC_prefix = N03 |
| ATC_prefix = N03 |
||
| Line 41: | Line 44: | ||
<!--Chemical data--> |
<!--Chemical data--> |
||
| C=11 | H=12 | N=2 | O=2 |
| C=11 | H=12 | N=2 | O=2 |
||
| molecular_weight = 204.225 g/mol |
|||
| smiles = O=C2NC(c1ccccc1)C(=O)N2CC |
| smiles = O=C2NC(c1ccccc1)C(=O)N2CC |
||
| 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) |
|||
| InChIKey = SZQIFWWUIBRPBZ-UHFFFAOYAG |
|||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| 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) |
| 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) |
||
| Line 51: | Line 51: | ||
| StdInChIKey = SZQIFWWUIBRPBZ-UHFFFAOYSA-N |
| StdInChIKey = SZQIFWWUIBRPBZ-UHFFFAOYSA-N |
||
}} |
}} |
||
'''Ethotoin''' (previously marketed as '''Peganone''') is an [[anticonvulsant]] drug used in the treatment of [[epilepsy]].<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 [[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.<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> |
|||
==Dosing== |
|||
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. |
|||
==Side effects== |
|||
Side effects include [[ataxia]], visual disturbances, rash, and [[Gastrointestinal tract|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''').<ref>A. Pinner, Chem. Ber., 21, 2324 (1888); W.J. Close, {{US Patent|2793157}} (1946)</ref> Alkylation of this product using [[ethyl iodide]] leads to the formation |
|||
of ethotoin ('''5'''). |
|||
:[[File:Ethotoin synthesis.png|thumb|left|800px|Synthesis of ethotoin]] |
|||
{{clear left}} |
|||
==References== |
|||
{{reflist}} |
|||
{{Anticonvulsants}} |
|||
[[Category:Anticonvulsants]] |
|||
[[Category:Hydantoins]] |
|||
[[Category:Drugs developed by AbbVie]] |
|||