Apronal

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Apronal
File:Apronal.svg
File:Apronal 3D.png
Above: molecular structure of apronal Below: 3D representation of an 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
E number{{#property:P628}}
CompTox Dashboard (EPA)
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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grams every 3 to 4 hours).[2] Upon the finding that it caused patients to develop thrombocytopenic purpura, apronal was withdrawn from clinical use.[3]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

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References

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  1. ^ DE 459903, "Verfahren zur Darstellung von Ureiden der Dialkylessigsaeuren", issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Hoffmann-La Roche 
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