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Apronal

Chemical compound

Apronal

Apronal, or apronalide, also known as allylisopropylacetylurea or allylisopropylacetylcarbamide, is a hypnotic/sedative drug of the ureide (acylurea) group synthesized in 1926 by Hoffmann-La Roche. Though it is not a barbiturate, apronal is similar in structure to the barbiturates. In accordance, it is similar in action to the barbiturates, although considerably milder in comparison. Upon the finding that it caused patients to develop thrombocytopenic purpura, apronal was withdrawn from clinical use.

Apronal
Apronal
Molecular structure of apronal
3D representation of an (R)-apronal molecule
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, apronal 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grams every 3 to 4 hours).[2] Upon the finding that it caused patients to develop thrombocytopenic purpura, apronal was withdrawn from clinical use.[3]

Medicines with apronal are no longer used except in Japan and South Korea.[3][4] 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[5] due to its dangerous side effects.

See also

References

  1. ↑ DE 459903, "Verfahren zur Darstellung von Ureiden der Dialkylessigsaeuren", issued 15 May 1928, assigned to Hoffmann-La Roche
  2. 1 2 Roche Review ... Hoffman-La Roche, and Roche-organon. 1938. p. 164.
  3. 1 2 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. ↑ "약학정보원". www.health.kr. Retrieved 2025-10-05.
  5. ↑ "EVE Apronal tablets". Therapeutic Goods Administration (TGA). Retrieved 31 May 2023.