Apronal

Apronal
Clinical data

Routes of administration	Oral
ATC code	N05CM12 (WHO)
Pharmacokinetic data
Excretion	Renal
Identifiers
IUPAC name (±)-N-Carbamoyl-2-propan-2-ylpent-4-enamide
CAS Number	528-92-7^Y
PubChem CID	10715
ChemSpider	10264^Y
UNII	V18J24E25E
KEGG	D03975^Y
ChEMBL	CHEMBL509282^Y
ECHA InfoCard	100.007.677
Chemical and physical data
Formula	C₉H₁₆N₂O₂
Molar mass	184.236 g/mol
3D model (JSmol)	Interactive image
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)^Y Key:KSUUMAWCGDNLFK-UHFFFAOYSA-N^Y

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 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). 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). Upon the finding that it caused patients to develop thrombocytopenic purpura, apronalide was withdrawn from clinical use.

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