Article · Wikipedia archive · Last revised Jul 26, 2026

Bucindolol

Bucindolol is a non-selective beta blocker with additional weak alpha-blocking properties and intrinsic sympathomimetic activity in some model systems but not in human hearts. It was under review by the FDA in the United States for the treatment of heart failure in 2009, but was rejected due to issues pertaining to integrity of data submitted.

Last revised
Jul 26, 2026
Read time
≈ 1 min
Length
323 w
Citations
7
Source
Wikipedia ↗
Bucindolol
Clinical data
ATC code
  • none
Identifiers
  • 2-[2-hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethyl-ethyl]amino]propoxy]benzonitrile
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.114.291
Chemical and physical data
FormulaC22H25N3O2
Molar mass363.461 g·mol−1
3D model (JSmol)
  • N#Cc0ccccc0OCC(O)CNC(C)(C)Cc1c[nH]c2c1cccc2

Bucindolol is a non-selective beta blocker with additional weak alpha-blocking properties and intrinsic sympathomimetic activity in some model systems12 but not in human hearts.34 It was under review by the FDA in the United States for the treatment of heart failure in 2009, but was rejected due to issues pertaining to integrity of data submitted.5

Synthesis

The displacement of the dimethylamino group in gramine (1) by the anion from 2-nitropropane gives 3-(2-methyl-2-nitropropyl)indole (2), which is reduced to the amine alpha,alpha-dimethyltryptamine (3). Separately, the reaction of 2-hydroxybenzonitrile (4) with epichlorohydrin gives the epoxide (5). Combination of the two intermediates (3) and (5) gives bucindolol.67

See also

See also

References

References

  1. Reinhart KM, White CM (June 2009). "Bucindolol: a beta-blocker for the treatment of heart failure". Formulary. 44 (6): 166. Archived from the original on 2012-03-04.
  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): 30–36. doi:10.1159/000028179. PMID 9467185. S2CID 46848815.
  3. Bristow MR, Roden RL, Lowes BD, Gilbert EM, Eichhorn EJ (December 1998). "The role of third-generation beta-blocking agents in chronic heart failure". Clinical Cardiology. 21 (12 Suppl 1): I3-13. doi:10.1002/clc.4960211303. PMC 6656140. PMID 9853189.
  4. Hershberger RE, Wynn JR, Sundberg L, Bristow MR (June 1990). "Mechanism of action of bucindolol in human ventricular myocardium". Journal of Cardiovascular Pharmacology. 15 (6): 959–967. doi:10.1097/00005344-199006000-00014. PMID 1694919.
  5. Husten L (2 June 2009). "FDA rejects bucindolol and questions trial integrity". CardioBrief.
  6. US 4234595, Kreighbaum WE, Comer WT, "3-Indolyl-tertiary butylaminopropanols", issued 18 November 1980, assigned to Mead Johnson & Company 
  7. Kreighbaum WE, Matier WL, Dennis RD, Minielli JL, Deitchman D, Perhach JL, et al. (March 1980). "Antihypertensive indole derivatives of phenoxypropanolamines with beta-adrenergic receptor antagonist and vasodilating activity". Journal of Medicinal Chemistry. 23 (3): 285–289. doi:10.1021/jm00177a015. PMID 6102605.