phenacemide

{{short description|Anticonvulsant}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 464199698

| IUPAC_name = N-Carbamoyl-2-phenyl-acetamide

| image = Phenacemide.svg

| width = 175

| tradename = Phenurone

| Drugs.com = {{drugs.com|CONS|phenacemide}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life = 22–25 hours

| excretion =

| 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

| 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.{{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–}} It is a congener and ring-opened analogue of phenytoin (a hydantoin),{{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–}}{{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 }} and is structurally related to the barbiturates and to other hydantoins.{{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–}} Phenacemide was introduced in 1949 for the treatment of epilepsy, but was eventually withdrawn due to toxicity.