Bucindolol

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Bucindolol
Bucindolol.png
Systematic (IUPAC) name
2-[2-hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethyl-ethyl]amino]propoxy]benzonitrile
Clinical data
Legal status
?
Identifiers
CAS number 71119-11-4
ATC code None
PubChem CID 51045
ChemSpider 46266
UNII E9UO06K7CE YesY
ChEMBL CHEMBL2107546
Chemical data
Formula C22H25N3O2 
Mol. mass 363.45 g/mol

Bucindolol is a non-selective beta blocker with additional weak alpha-blocking properties and some intrinsic sympathomimetic activity.[1][2] It was under review by the FDA in the United States for the treatment of heart failure in 2009 .[1][3]

Synthesis[edit]

Preparation of the amine for this agent starts by displacement of the dimethylamino group gramine by the anion from 2-nitropropane. Reduction of the nitro group leads to the requisite intermediate.[4]

See also[edit]

References[edit]

  1. ^ a b "formularyjournal.modernmedicine.com". 
  2. ^ Willette RN, Mitchell MP, Ohlstein EH, Lukas MA, Ruffolo RR (January 1998). "Evaluation of intrinsic sympathomimetic activity of bucindolol and carvedilol in rat heart". Pharmacology 56 (1): 30–6. doi:10.1159/000028179. PMID 9467185. 
  3. ^ "FDA rejects bucindolol and questions trial integrity « CardioBrief". 
  4. ^ Kreighbaum, W. E.; Matier, W. L.; Dennis, R. D.; Minielli, J. L.; Deitchman, D.; Perhach, J. L.; Comer, W. T. (1980). "Antihypertensive indole derivatives of phenoxypropanolamines with .beta.-adrenergic receptor antagonist and vasodilating activity". Journal of Medicinal Chemistry 23 (3): 285. doi:10.1021/jm00177a015. PMID 6102605.  edit