apronal

{{Short description|Chemical compound}}

{{Infobox drug

| Watchedfields = changed

| verifiedrevid = 443395760

| IUPAC_name = (±)-N-Carbamoyl-2-propan-2-ylpent-4-enamide

| image = Apronal.svg

| width = 150px

| chirality = Racemic mixture

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion = Renal

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 528-92-7

| ATC_prefix = N05

| ATC_suffix = CM12

| PubChem = 10715

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10264

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = V18J24E25E

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D03975

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 509282

| C=9 | H=16 | N=2 | O=2

| smiles = O=C(NC(=O)N)C(C(C)C)C\C=C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C9H16N2O2/c1-4-5-7(6(2)3)8(12)11-9(10)13/h4,6-7H,1,5H2,2-3H3,(H3,10,11,12,13)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KSUUMAWCGDNLFK-UHFFFAOYSA-N

}}

Apronal (brand name Sedormid), or apronalide, also known as allylisopropylacetylurea or allylisopropylacetylcarbamide, is a hypnotic/sedative drug of the ureide (acylurea) group synthesized in 1926{{cite patent | country = DE | number = 459903 | title = Verfahren zur Darstellung von Ureiden der Dialkylessigsaeuren | assign1 = Hoffmann-La Roche | gdate = 15 May 1928 }} by Hoffmann-La Roche. Though it is not a barbiturate, apronal is similar in structure to the barbiturates (being an open-chain carbamide instead of having a heterocyclic ring).{{cite book|title=Roche Review ...|url=https://books.google.com/books?id=D20zAQAAIAAJ |year=1938|publisher=Hoffman-La Roche, and Roche-organon |page=164 }} In accordance, it is similar in action to the barbiturates, although considerably milder in comparison (formerly used as a daytime sedative at doses of 1 to 2 grams every 3 to 4 hours). Upon the finding that it caused patients to develop thrombocytopenic purpura, apronal was withdrawn from clinical use.{{cite book| vauthors = Vollum RL, Jamison DG, Cummins CS |title=Fairbrother's Textbook of Bacteriology |url=https://books.google.com/books?id=QnDiBQAAQBAJ&pg=PA152 |date=20 May 2014|publisher=Elsevier Science|isbn=978-1-4831-4178-7|pages=152–}}

Medicines with apronal are no longer used except in Japan. Notably Australian Therapeutic Goods Administration issued a safety alert in May 2023 which prohibits the sale, supply and use of Japanese EVE-branded products in Australia{{cite web |title=EVE Apronal tablets |url=https://www.tga.gov.au/news/safety-alerts/eve-allylisopropylacetylurea-tablets |publisher=Therapeutic Goods Administration (TGA) |access-date=31 May 2023}} due to its dangerous side effects.