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EntityQ1095009· pop 10· linked from 591 articles

Also known as allylisopropylacetylurea, allylisopropylacetylcarbamide, apronalide, Sedormid, (±)-N-carbamoyl-2-propan-2-ylpent-4-enamide

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. 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). 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 patient

Key facts

Drug.Watchedfields
changed
Drug.verifiedrevid
443395760
Drug.IUPAC_name
(±)-N-Carbamoyl-2-propan-2-ylpent-4-enamide
Drug.image
Apronal.svg
Drug.image_class
skin-invert-image
Drug.width
180px
Drug.caption
Above: molecular structure of apronal Below: 3D representation of an apronal molecule
Drug.image2
Apronal 3D.png
Drug.image_class2
bg-transparent
Drug.chirality
Racemic mixture
Drug.routes_of_administration
Oral
Drug.excretion
Renal
Drug.CAS_number
528-92-7
Drug.ATC_prefix
N05
Drug.ATC_suffix
CM12
Drug.PubChem
10715
Drug.ChemSpiderID
10264
Drug.UNII
V18J24E25E

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Wikidata facts

Mass
184.121
Show 3 more facts
chemical formula
C₉H₁₆N₂O₂
canonical SMILES
CC(C)C(CC=C)C(=O)NC(=O)N
Commons category
Apronal
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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 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). 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 Upon the finding that it caused patients to develop thrombocytopenic purpura, apronal was withdrawn from clinical use.

Medicines with apronal are no longer used except in Japan and South Korea. 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 due to its dangerous side effects.

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