{{Short description|Chemical compound}} {{Infobox drug | Watchedfields = changed | verifiedrevid = 443395760 | IUPAC_name = (''±'')-''N''-Carbamoyl-2-propan-2-ylpent-4-enamide | image = Apronal.svg | image_class = skin-invert-image | width = 180px | caption = Above: molecular structure of apronal Below: 3D representation of an apronal molecule | image2 = Apronal 3D.png | image_class2 = bg-transparent | chirality = Racemic mixture <!--Clinical data-->| tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration = Oral
<!--Pharmacokinetic data-->| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = Renal
<!--Identifiers-->| 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
<!--Chemical data-->| 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<ref>{{cite patent | country = DE | number = 459903 | title = Verfahren zur Darstellung von Ureiden der Dialkylessigsaeuren | assign1 = Hoffmann-La Roche | gdate = 15 May 1928 }}</ref> 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).<ref name="Roche1938">{{cite book|title=Roche Review ...|url=https://books.google.com/books?id=D20zAQAAIAAJ |year=1938|publisher=Hoffman-La Roche, and Roche-organon |page=164 }}</ref> 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).<ref name="Roche1938" /> Upon the finding that it caused patients to develop thrombocytopenic purpura, apronal was withdrawn from clinical use.<ref name="VollumJamison2014">{{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–}}</ref>
Medicines with apronal are no longer used except in Japan and South Korea.<ref name="VollumJamison2014" /><ref>{{Cite web |title=약학정보원 |url=https://www.health.kr/searchDrug/result_drug.asp?drug_cd=2009071505656 |access-date=2025-10-05 |website=www.health.kr}}</ref> 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<ref>{{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}}</ref> due to its dangerous side effects.
==See also== * Bromoureide * {{langx|ja|アリルイソプロピルアセチル尿素}}
==References== {{Reflist|2}}
{{Hypnotics and sedatives}} {{GABAAergics}}
Category:Alkene derivatives Category:GABAA receptor positive allosteric modulators Category:Hypnotics Category:Sedatives Category:Ureas Category:Withdrawn drugs