Structure via PubChem · Public domain (PubChem)
apronal
Sign in to saveAlso 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
via Wikipedia infobox
Chemical data
- Formula
- C9H16N2O2
- Molecular weight
- 184.24 g/mol
- IUPAC name
- N-carbamoyl-2-propan-2-ylpent-4-enamide
- SMILES
- CC(C)C(CC=C)C(=O)NC(=O)N
- InChIKey
- KSUUMAWCGDNLFK-UHFFFAOYSA-N
- XLogP
- 1.7
- Polar surface area
- 72.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- 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
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
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.
Excerpted from Wikipedia’s “apronal” article, available under the CC BY-SA 4.0 licence.
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via Wikidata sitelinks · CC0