View source for 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
| caption = Above: molecular structure of apronal
Below: 3D representation of an apronal molecule
| image2 = Apronal 3D.png
| 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 = [[Kidney|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 [[chemical structure|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]].<ref name="VollumJamison2014" /> 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<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|[[:ja:アリルイソプロピルアセチル尿素|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]]