Apronal

Apronal
Clinical data
Routes of
administration		Oral
ATC code
Pharmacokinetic data
ExcretionRenal
Identifiers
  • (±)-N-Carbamoyl-2-propan-2-ylpent-4-enamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.677 Edit this at Wikidata
Chemical and physical data
FormulaC9H16N2O2
Molar mass184.239 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=C(NC(=O)N)C(C(C)C)C\C=C
  • InChI=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) checkY
  • Key:KSUUMAWCGDNLFK-UHFFFAOYSA-N checkY
  (verify)

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[1] by Hoffmann-La Roche. Though it is not a barbiturate, apronalide is similar in structure to the barbiturates (being an open-chain carbamide instead of having a heterocyclic ring).[2] 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every 3 to 4 hours).[2] Upon the finding that it caused patients to develop thrombocytopenic purpura, apronalide was withdrawn from clinical use.[3]

Medicines with allylisopropylacetylurea are no longer used except in Japan and South Korea.[3] 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[4] due to its dangerous side effects.

  1. ^ DE 459903, "Verfahren zur Darstellung von Ureiden der Dialkylessigsaeuren", issued 15 May 1928, assigned to Hoffmann-La Roche 
  2. ^ a b Roche Review ... Hoffman-La Roche, and Roche-organon. 1938. p. 164.
  3. ^ a b Vollum RL, Jamison DG, Cummins CS (20 May 2014). Fairbrother's Textbook of Bacteriology. Elsevier Science. pp. 152–. ISBN 978-1-4831-4178-7.
  4. ^ "EVE Allylisopropylacetylurea tablets". Therapeutic Goods Administration (TGA). Retrieved 31 May 2023.