Bucindolol
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| ECHA InfoCard | 100.114.291 |
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| Formula | C22H25N3O2 |
| Molar mass | 363.461g·mol−1 |
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Bucindololis anon-selectivebeta blockerwith additional weakAlpha -blockingproperties andintrinsic sympathomimetic activityin some model systems[1][2]but not in human hearts.[3][4]It was under review by theFDAin theUnited Statesfor the treatment ofheart failurein 2009, but was rejected due to issues pertaining to integrity of data submitted.[5]
Synthesis
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The displacement of the dimethylamino group ingramine(1) by the anion from2-nitropropanegives 3-(2-methyl-2-nitropropyl)indole (2), which isreducedto theamineAlpha, Alpha -dimethyltryptamine (3). Separately, the reaction of 2-hydroxybenzonitrile (4) withepichlorohydringives theepoxide(5). Combination of the two intermediates (3) and (5) gives bucindolol.[6][7]
See also
[edit]References
[edit]- ^Reinhart KM, White CM (June 2009)."Bucindolol: a beta-blocker for the treatment of heart failure".Formulary.44(6): 166. Archived fromthe originalon 2012-03-04.
- ^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.PMID9467185.S2CID46848815.
- ^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.PMC6656140.PMID9853189.
- ^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.PMID1694919.
- ^Husten L (2 June 2009)."FDA rejects bucindolol and questions trial integrity".CardioBrief.
- ^US 4234595,Kreighbaum WE, Comer WT, "3-Indolyl-tertiary butylaminopropanols", issued 18 November 1980, assigned to Mead Johnson & Company
- ^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.PMID6102605.
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