Apronal

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Apronal
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Above: molecular structure of apronal Below: 3D representation of an apronal molecule
Clinical data
Routes of
administration		Oral
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Pharmacokinetic data
ExcretionRenal
Identifiers
  • (±)-N-Carbamoyl-2-propan-2-ylpent-4-enamide
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Chemical and physical data
FormulaC9H16N2O2
Molar mass184.239 g·mol−1
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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
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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grams every 3 to 4 hours).[2] Upon the finding that it caused patients to develop thrombocytopenic purpura, apronal was withdrawn from clinical use.[3]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

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  1. ^ Page Template:Citation/styles.css has no content.DE 459903, "Verfahren zur Darstellung von Ureiden der Dialkylessigsaeuren", issued Script error: No such module "auto date formatter"., assigned to Hoffmann-La Roche 
  2. ^ a b Page Module:Citation/CS1/styles.css has no content.Roche Review ... Hoffman-La Roche, and Roche-organon. 1938. p. 164.
  3. ^ a b Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content."약학정보원". www.health.kr. Retrieved 2025-10-05.
  5. ^ Page Module:Citation/CS1/styles.css has no content."EVE Apronal tablets". Therapeutic Goods Administration (TGA). Retrieved 31 May 2023.

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