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Apronal
Chemical compound
Chemical compound
| Field | Value | |
|---|---|---|
| Watchedfields | changed | |
| verifiedrevid | 443395760 | |
| IUPAC_name | (±)-N-Carbamoyl-2-propan-2-ylpent-4-enamide | |
| image | Apronal.svg | |
| image_class | skin-invert-image | |
| width | 180px | |
| caption | Above: molecular structure of apronal | |
| image2 | Apronal 3D.png | |
| image_class2 | bg-transparent | |
| chirality | Racemic mixture | |
| pregnancy_AU | ||
| pregnancy_US | ||
| legal_AU | ||
| legal_CA | ||
| legal_UK | ||
| legal_US | ||
| routes_of_administration | Oral | |
| excretion | Renal | |
| <!--Identifiers--> | CAS_number_Ref | |
| CAS_number | 528-92-7 | |
| ATC_prefix | N05 | |
| ATC_suffix | CM12 | |
| PubChem | 10715 | |
| DrugBank_Ref | ||
| ChemSpiderID_Ref | ||
| ChemSpiderID | 10264 | |
| UNII_Ref | ||
| UNII | V18J24E25E | |
| KEGG_Ref | ||
| KEGG | D03975 | |
| ChEMBL_Ref | ||
| ChEMBL | 509282 | |
| <!--Chemical data--> | C | 9 |
| H | 16 | |
| N | 2 | |
| O | 2 | |
| smiles | O=C(NC(=O)N)C(C(C)C)C\C=C | |
| StdInChI_Ref | ||
| StdInChI | 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) | |
| StdInChIKey_Ref | ||
| StdInChIKey | KSUUMAWCGDNLFK-UHFFFAOYSA-N |
Below: 3D representation of an apronal molecule
| elimination_half-life =
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 Upon the finding that it caused patients to develop thrombocytopenic purpura, apronal was withdrawn from clinical use.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.
References
References
- "Verfahren zur Darstellung von Ureiden der Dialkylessigsaeuren".
- (1938). "Roche Review ...". Hoffman-La Roche, and Roche-organon.
- (20 May 2014). "Fairbrother's Textbook of Bacteriology". Elsevier Science.
- "약학정보원".
- "EVE Apronal tablets". Therapeutic Goods Administration (TGA).
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