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Apronal

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Apronal
Clinical data
Routes of
administration
Oral
ATC code
Pharmacokinetic data
ExcretionRenal
Identifiers
  • (±)-N-Carbamoyl-2-propan-2-ylpent-4-enamide
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.007.677Edit 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 nameSedormid), orapronalide, also known asallylisopropylacetylurea orallylisopropylacetylcarbamide, is ahypnotic/sedativedrug of theureide (acylurea) group synthesized in 1926[1] byHoffmann-La Roche. Though it is not abarbiturate, apronal is similar instructure to the barbiturates (being an open-chaincarbamide instead of having aheterocyclic 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grams every 3 to 4 hours).[2] Upon the finding that it caused patients to developthrombocytopenic purpura, apronal was withdrawn from clinical use.[3]

Medicines with apronal are no longer used except inJapan andSouth Korea.[3] Notably AustralianTherapeutic 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.

See also

[edit]

References

[edit]
  1. ^DE 459903, "Verfahren zur Darstellung von Ureiden der Dialkylessigsaeuren", issued 15 May 1928, assigned to Hoffmann-La Roche 
  2. ^abRoche Review ... Hoffman-La Roche, and Roche-organon. 1938. p. 164.
  3. ^abVollum 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 Apronal tablets". Therapeutic Goods Administration (TGA). Retrieved31 May 2023.
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