Apronal

Apronal

Systematic (IUPAC) name
(±)-N-Carbamoyl-2-propan-2-ylpent-4-enamide
Clinical data
Routes of administration	Oral
Pharmacokinetic data
Excretion	Renal
Identifiers
CAS Number	528-92-7
ATC code	N05CM12 (WHO)
PubChem	CID 10715
ChemSpider	10264
UNII	V18J24E25E
KEGG	D03975
ChEMBL	CHEMBL509282
Chemical data
Formula	C9H16N2O2
Molar mass	184.236 g/mol
Chirality	Racemic mixture
SMILES 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) Key:KSUUMAWCGDNLFK-UHFFFAOYSA-N
(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 that is no longer used. 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every 3 to 4 hours).^[2] Upon the finding that it caused patients to develop thrombocytopenic purpura, apronalide was withdrawn from clinical use.^[3]

See also

• Bromoureide

References

1. DE Patent 459903 - Verfahren zur Darstellung von Ureiden der Dialkylessigsaeuren
2. Roche Review ... Hoffman-La Roche, and Roche-organon. 1938. p. 164.
3. R. L. Vollum; D. G. Jamison; C. S. Cummins (20 May 2014). Fairbrother's Textbook of Bacteriology. Elsevier Science. pp. 152–. ISBN 978-1-4831-4178-7.