# Apronal

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Apronal
> Markdown URL: https://mediated.wiki/source/Apronal.md
> Source: https://en.wikipedia.org/wiki/Apronal
> Source revision: 1329964541
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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](/source/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](/source/Kidney)

<!--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](/source/hypnotic)/[sedative](/source/sedative) [drug](/source/drug) of the [ureide](/source/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](/source/Hoffmann-La_Roche). Though it is not a [barbiturate](/source/barbiturate), apronal is similar in [structure](/source/chemical_structure) to the barbiturates (being an open-chain [carbamide](/source/carbamide) instead of having a [heterocyclic ring](/source/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](/source/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](/source/Japan) and [South Korea](/source/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](/source/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](/source/Bromoureide)
* {{langx|ja|[アリルイソプロピルアセチル尿素](/source/%3Aja%3A%E3%82%A2%E3%83%AA%E3%83%AB%E3%82%A4%E3%82%BD%E3%83%97%E3%83%AD%E3%83%94%E3%83%AB%E3%82%A2%E3%82%BB%E3%83%81%E3%83%AB%E5%B0%BF%E7%B4%A0)}}

==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

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Adapted from the Wikipedia article [Apronal](https://en.wikipedia.org/wiki/Apronal) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Apronal?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.