Apronal
Chemical compound
- N05CM12 (WHO)
- (±)-N-Carbamoyl-2-propan-2-ylpent-4-enamide
- 528-92-7
Y
- 10715
- 10264 Y
- V18J24E25E
- D03975 Y
- ChEMBL509282 Y
- DTXSID00862125
- Interactive image
- O=C(NC(=O)N)C(C(C)C)C\C=C
InChI
- 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)Y
- Key:KSUUMAWCGDNLFK-UHFFFAOYSA-NY
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every 3 to 4 hours).[2] Upon the finding that it caused patients to develop thrombocytopenic purpura, apronalide was withdrawn from clinical use.[3]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.[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.
See also
- Bromoureide
- Japanese: アリルイソプロピルアセチル尿素
References
- ^ DE 459903, "Verfahren zur Darstellung von Ureiden der Dialkylessigsaeuren", issued 15 May 1928, assigned to Hoffmann-La Roche
- ^ a b Roche Review ... Hoffman-La Roche, and Roche-organon. 1938. p. 164.
- ^ 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.
- ^ "EVE Allylisopropylacetylurea tablets". Therapeutic Goods Administration (TGA). Retrieved 31 May 2023.
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