Acecarbromal

Acecarbromal (INN) (brand names Sedamyl, Abasin, Carbased, Paxarel, Sedacetyl, numerous others), also known as acetylcarbromal and acetyladalin, is a hypnotic and sedative drug of the ureide (acylurea) group discovered by Bayer in 1917[1] that was formerly marketed in the United States and Europe.[2][3] It is also used in combination with extract of quebracho and vitamin E as a treatment for erectile dysfunction under the brand name Afrodor in Europe.[4][5][6] Acecarbromal is structurally related to the barbiturates, which are basically cyclized ureas.[7] Prolonged use is not recommended as it can cause bromine poisoning.[7]

Acecarbromal
Names
Preferred IUPAC name
N-(Acetylcarbamoyl)-2-bromo-2-ethylbutanamide
Other names
1-Acetyl-3-(2-bromo-2-ethylbutyryl)urea
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.953
EC Number
  • 201-047-1
KEGG
MeSH acecarbromal
PubChem CID
UNII
InChI
  • InChI=1S/C9H15BrN2O3/c1-4-9(10,5-2)7(14)12-8(15)11-6(3)13/h4-5H2,1-3H3,(H2,11,12,13,14,15) Y
    Key: SAZUGELZHZOXHB-UHFFFAOYSA-N Y
SMILES
  • CCC(Br)(CC)C(=O)NC(=O)NC(C)=O
Properties
Chemical formula
 C9H15BrN2O3
Molar mass 279.134 g·mol−1
Pharmacology
Oral
Legal status
  • In general: ℞ (Prescription only)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. DE 327129, "Verfahren zur Darstellung von Derivaten bromacylierter Harnstoffe (Procedures for the preparation of derivatives of bromoacylated urea)", issued 5 October 1920, assigned to Bayer AG
  2. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 2–. ISBN 978-1-4757-2085-3.
  3. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 4–. ISBN 978-3-88763-075-1.
  4. Muller NF, Dessing RP, eds. (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 36–. ISBN 978-3-7692-2114-5.
  5. Baumbusch F, Papp GK, Kopa ZS (1995). "Treatment for potency problems with Afrodor 2000". Acta Chirurgica Hungarica. 35 (1–2): 87–92. PMID 8659243.
  6. Sperling H, Lümmen G, Luboldt HJ, Rübben H (January 1999). "[Secondary erectile dysfunction. Is oral medication in the diagnostic phase indicated?]". Der Urologe. Ausg. A. 38 (1): 56–9. doi:10.1007/s001200050246. PMID 10081103. S2CID 24907635.
  7. Williams DA, Foye WO, Lemke TL (January 2002). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 380–. ISBN 978-0-683-30737-5.
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