{{short description|Anticonvulsant}} {{cs1 config|name-list-style=vanc}} {{Drugbox | Watchedfields = changed | verifiedrevid = 464199698 | IUPAC_name = ''N''-Carbamoyl-2-phenyl-acetamide | image = Phenacemide.svg | image_class = skin-invert-image | width = 175
<!--Clinical data--> | tradename = Phenurone | Drugs.com = {{drugs.com|CONS|phenacemide}} | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | legal_UK = <!-- GSL / P / POM / CD --> | legal_US = <!-- OTC / Rx-only --> | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = 22–25 hours | excretion =
<!--Identifiers--> | IUPHAR_ligand = 7265 | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 63-98-9 | ATC_prefix = N03 | ATC_suffix = AX07 | ATC_supplemental = | PubChem = 4753 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01121 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4589 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = PAI7J52V09 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D00504 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 918
<!--Chemical data--> | C=9 | H=10 | N=2 | O=2 | smiles = O=C(NC(=O)N)Cc1ccccc1 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C9H10N2O2/c10-9(13)11-8(12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,10,11,12,13) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = XPFRXWCVYUEORT-UHFFFAOYSA-N }}
'''Phenacemide''' (INN, BAN) (brand name '''Phenurone'''), also known as '''phenylacetylurea''', is an anticonvulsant of the ureide (acetylurea) class.<ref name="GanellinTriggle1996">{{cite book| vauthors = Ganellin CR, Triggle DJ |title=Dictionary of Pharmacological Agents|url=https://books.google.com/books?id=A0THacd46ZsC&pg=PA1578|date=21 November 1996|publisher=CRC Press|isbn=978-0-412-46630-4|pages=1578–}}</ref> It is a congener and ring-opened analogue of phenytoin (a hydantoin),<ref name="UniversitiesPress2010">{{cite book | vauthors = Prasad JP | chapter = Central Nervous System |title=Conceptual Pharmacology| chapter-url= https://books.google.com/books?id=s0e_FlM8LKYC&pg=PA236|year=2010|publisher=Universities Press|isbn=978-81-7371-679-9|pages=236–}}</ref><ref name="deStevensZingel2013">{{cite book | vauthors = Saxena AK, Saxena M | chapter = Developments in anticonvulsants | title = Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques | journal = Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progres des Recherches Pharmaceutiques | veditors = deStevens G, Zingel V, Leschke C, Hoeprich P, Schultz R, Mehrotra P, Batra S, Bhaduri A, Saxena A, Saxena M | display-editors = 6 | volume = 44 | issue = | pages = 185–291 | date = 1995 | pmid = 7644666 | doi = 10.1007/978-3-0348-7161-7_6 | publisher=Birkhäuser| location=Basel |isbn=978-3-0348-7161-7 }}</ref> and is structurally related to the barbiturates and to other hydantoins.<ref name="Kadam2007">{{cite book| vauthors = Kadam SS, Mahadik KR, Bothara KG | chapter = Central Nervous System Depresants |title = Principles of Medicinal Chemistry | volume = II |chapter-url=https://books.google.com/books?id=Z7Pb3lJuRksC&pg=PA147|date=1 July 2007|publisher=Pragati Books Pvt. Ltd.|isbn=978-81-85790-03-9|pages=147–}}</ref> Phenacemide was introduced in 1949 for the treatment of epilepsy, but was eventually withdrawn due to toxicity.<ref name="UniversitiesPress2010" /><ref name="deStevensZingel2013" />
== See also == * Pheneturide
== References == {{Reflist|2}}
== Further reading == {{refbegin}} * {{cite journal | vauthors = Coker SB | title = The use of phenacemide for intractable partial complex epilepsy in children | journal = Pediatric Neurology | volume = 2 | issue = 4 | pages = 230–232 | year = 1986 | pmid = 3508693 | doi = 10.1016/0887-8994(86)90053-6 }} * {{cite journal | vauthors = Coker SB, Holmes EW, Egel RT | title = Phenacemide therapy of complex partial epilepsy in children: determination of plasma drug concentrations | journal = Neurology | volume = 37 | issue = 12 | pages = 1861–1866 | date = December 1987 | pmid = 3683877 | doi = 10.1212/wnl.37.12.1861 | s2cid = 219205208 }} {{refend}}
== External links == * {{DiseasesDB|34078}} * {{MedlinePlusDrugInfo|uspdi|202454}}
{{Anticonvulsants}} {{Channel blockers}}
Category:Imides Category:Ureas Category:Withdrawn drugs
{{anticonvulsant-stub}}