Bucindolol | CAS# 71119-11-4 | beta blocker

MedKoo Cat#: 574603 | Name: Bucindolol

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bucindolol is a high-affinity, competitive beta blocker used in the treatment of congestive heart failure and hypertension.

Chemical Structure

Bucindolol

CAS#71119-11-4 (free base)

Theoretical Analysis

MedKoo Cat#: 574603

Name: Bucindolol

CAS#: 71119-11-4 (free base)

Chemical Formula: C22H25N3O2

Exact Mass: 363.1947

Molecular Weight: 363.46

Elemental Analysis: C, 72.70; H, 6.93; N, 11.56; O, 8.80

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 450.00	2 Weeks
25mg	USD 850.00	2 Weeks

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Related CAS #

71119-11-4 (free base) 91548-61-7 (free base S-isomer) 70369-47-0 (HCl)

Synonym

Bucindolol; MJ 13105-1; DL-Bucindolol

IUPAC/Chemical Name

2-[2-Hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethylethyl]amino]propoxy]benzonitrile

InChi Key

FBMYKMYQHCBIGU-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H25N3O2/c1-22(2,11-17-13-24-20-9-5-4-8-19(17)20)25-14-18(26)15-27-21-10-6-3-7-16(21)12-23/h3-10,13,18,24-26H,11,14-15H2,1-2H3

SMILES Code

N#CC1=CC=CC=C1OCC(O)CNC(C)(C)CC2=CNC3=C2C=CC=C3

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Bucindolol is a β1-adrenergic receptor blocker, with intrinsic sympathomimetic activity, used in the research of heart failure.

In vitro activity:

Cell death was assessed by measuring caspase3/7 activity and by PI staining. A significant increase in active caspase-3/7, a direct indicator of apoptosis, was evident in the NE condition in comparison to the CTL condition. Bucindolol was able to reduce (66%) this activity in the NE+BCD condition when compared to the NE condition (Figures 2(a) and 2(b)). Reference: Oxid Med Cell Longev. 2019; 2019: 6325424. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6652037/

In vivo activity:

After two weeks, animals were treated for seven days with bucindolol (2mg/kg/day i.p.) or vehicle. Bucindolol treatment also reduced RV pleomorphism, necrosis, fibrosis and infiltration of inflammatory cells. In addition, bucindolol promoted a decrease in the cardiac sympathovagal balance (93%) by reducing sympathetic drive (70%) and increasing parasympathetic drive (142%). Bucindolol also reduced blood pressure variability (75%). Reference: Eur J Pharmacol. 2017 Mar 5;798:57-65. https://pubmed.ncbi.nlm.nih.gov/28011346/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	55.03
	DMF	30.0	82.54

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 363.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. de Lima-Seolin BG, Nemec-Bakk A, Forsyth H, Kirk S, da Rosa Araujo AS, Schenkel PC, Belló-Klein A, Khaper N. Bucindolol Modulates Cardiac Remodeling by Attenuating Oxidative Stress in H9c2 Cardiac Cells Exposed to Norepinephrine. Oxid Med Cell Longev. 2019 Jul 10;2019:6325424. doi: 10.1155/2019/6325424. PMID: 31360296; PMCID: PMC6652037. 2. Lima-Seolin BG, Colombo R, Bonetto JHP, Teixeira RB, Donatti LM, Casali KR, Godoy AEG, Litvin IE, Schenkel PC, Rosa Araujo ASD, Belló-Klein A. Bucindolol improves right ventricle function in rats with pulmonary arterial hypertension through the reversal of autonomic imbalance. Eur J Pharmacol. 2017 Mar 5;798:57-65. doi: 10.1016/j.ejphar.2016.12.028. Epub 2016 Dec 21. PMID: 28011346.

In vitro protocol:

In vivo protocol:

1. Lima-Seolin BG, Colombo R, Bonetto JHP, Teixeira RB, Donatti LM, Casali KR, Godoy AEG, Litvin IE, Schenkel PC, Rosa Araujo ASD, Belló-Klein A. Bucindolol improves right ventricle function in rats with pulmonary arterial hypertension through the reversal of autonomic imbalance. Eur J Pharmacol. 2017 Mar 5;798:57-65. doi: 10.1016/j.ejphar.2016.12.028. Epub 2016 Dec 21. PMID: 28011346.

1: Black-Maier E, Steinberg BA, Piccini JP. Bucindolol hydrochloride in atrial fibrillation and concomitant heart failure. Expert Rev Cardiovasc Ther. 2015 Jun;13(6):627-36. doi: 10.1586/14779072.2015.1031111. Epub 2015 May 11. PMID: 25959096. 2: Parikh KS, Piccini JP. Pharmacogenomics of Bucindolol in Atrial Fibrillation and Heart Failure. Curr Heart Fail Rep. 2017 Dec;14(6):529-535. doi: 10.1007/s11897-017-0364-6. PMID: 28975475. 3: Fiuzat M, O'Connor CM. Bucindolol: new hopes from reviewing past data. Drugs Today (Barc). 2011 May;47(5):347-51. doi: 10.1358/dot.2011.47.5.1579112. PMID: 22013565. 4: Rosa GM, Meliota G, Brunelli C, Ferrero S. Pharmacokinetic drug evaluation of bucindolol for the treatment of atrial fibrillation in heart failure patients. Expert Opin Drug Metab Toxicol. 2017 Apr;13(4):473-481. doi: 10.1080/17425255.2017.1291631. Epub 2017 Feb 15. PMID: 28162002. 5: Piccini JP, Abraham WT, Dufton C, Carroll IA, Healey JS, van Veldhuisen DJ, Sauer WH, Anand IS, White M, Wilton SB, Aleong R, Rienstra M, Krueger SK, Ayala- Paredes F, Khaykin Y, Merkely B, Miloradović V, Wranicz JK, Ilkhanoff L, Ziegler PD, Davis G, Emery LL, Marshall D, Kao DP, Bristow MR, Connolly SJ; GENETIC-AF Trial Investigators. Bucindolol for the Maintenance of Sinus Rhythm in a Genotype-Defined HF Population: The GENETIC-AF Trial. JACC Heart Fail. 2019 Jul;7(7):586-598. doi: 10.1016/j.jchf.2019.04.004. Epub 2019 Apr 29. PMID: 31042551; PMCID: PMC7205445. 6: Gill JS, Beevers DG. Bucindolol. Am J Cardiol. 1985 Oct 1;56(10):704. doi: 10.1016/0002-9149(85)91045-8. PMID: 2864842. 7: Lima-Seolin BG, Colombo R, Bonetto JHP, Teixeira RB, Donatti LM, Casali KR, Godoy AEG, Litvin IE, Schenkel PC, Rosa Araujo ASD, Belló-Klein A. Bucindolol improves right ventricle function in rats with pulmonary arterial hypertension through the reversal of autonomic imbalance. Eur J Pharmacol. 2017 Mar 5;798:57-65. doi: 10.1016/j.ejphar.2016.12.028. Epub 2016 Dec 21. PMID: 28011346. 8: Piccini JP, Dufton C, Carroll IA, Healey JS, Abraham WT, Khaykin Y, Aleong R, Krueger SK, Sauer WH, Wilton SB, Rienstra M, van Veldhuisen DJ, Anand IS, White M, Camm AJ, Ziegler PD, Marshall D, Bristow MR, Connolly SJ; Genotype-Directed Comparative Effectiveness Trial of Bucindolol and Toprol-XL for Prevention of Atrial Fibrillation/Atrial Flutter in Patients with Heart Failure Trial Investigators*. Bucindolol Decreases Atrial Fibrillation Burden in Patients With Heart Failure and the ADRB1 Arg389Arg Genotype. Circ Arrhythm Electrophysiol. 2021 Aug;14(8):e009591. doi: 10.1161/CIRCEP.120.009591. Epub 2021 Jul 16. PMID: 34270905. 9: Smart NA, Kwok N, Holland DJ, Jayasighe R, Giallauria F. Bucindolol: a pharmacogenomic perspective on its use in chronic heart failure. Clin Med Insights Cardiol. 2011;5:55-66. doi: 10.4137/CMC.S4309. Epub 2011 Jun 28. PMID: 21792345; PMCID: PMC3140276. 10: de Lima-Seolin BG, Hennemann MM, Fernandes RO, Colombo R, Bonetto JHP, Teixeira RB, Khaper N, Godoy AEG, Litvin IE, Sander da Rosa Araujo A, Schenkel PC, Belló-Klein A. Bucindolol attenuates the vascular remodeling of pulmonary arteries by modulating the expression of the endothelin-1 A receptor in rats with pulmonary arterial hypertension. Biomed Pharmacother. 2018 Mar;99:704-714. doi: 10.1016/j.biopha.2018.01.127. Epub 2018 Feb 20. PMID: 29710468. 11: White M, Desai RV, Guichard JL, Mujib M, Aban IB, Ahmed MI, Feller MA, de Denus S, Ahmed A. Bucindolol, systolic blood pressure, and outcomes in systolic heart failure: a prespecified post hoc analysis of BEST. Can J Cardiol. 2012 May;28(3):354-9. doi: 10.1016/j.cjca.2011.07.004. Epub 2011 Oct 7. PMID: 21982425; PMCID: PMC3769783. 12: de Lima-Seolin BG, Nemec-Bakk A, Forsyth H, Kirk S, da Rosa Araujo AS, Schenkel PC, Belló-Klein A, Khaper N. Bucindolol Modulates Cardiac Remodeling by Attenuating Oxidative Stress in H9c2 Cardiac Cells Exposed to Norepinephrine. Oxid Med Cell Longev. 2019 Jul 10;2019:6325424. doi: 10.1155/2019/6325424. PMID: 31360296; PMCID: PMC6652037. 13: Chatterjee S, Biondi-Zoccai G, Abbate A, D'Ascenzo F, Castagno D, Van Tassell B, Mukherjee D, Lichstein E. Benefits of β blockers in patients with heart failure and reduced ejection fraction: network meta-analysis. BMJ. 2013 Jan 16;346:f55. doi: 10.1136/bmj.f55. Erratum in: BMJ. 2013;346:f596. PMID: 23325883; PMCID: PMC3546627. 14: Asano K, Zisman LS, Yoshikawa T, Headley V, Bristow MR, Port JD. Bucindolol, a nonselective beta 1- and beta 2-adrenergic receptor antagonist, decreases beta-adrenergic receptor density in cultured embryonic chick cardiac myocyte membranes. J Cardiovasc Pharmacol. 2001 Jun;37(6):678-91. doi: 10.1097/00005344-200106000-00005. PMID: 11392464. 15: Bundkirchen A, Brixius K, Bölck B, Schwinger RH. Bucindolol exerts agonistic activity on the propranolol-insensitive state of beta1-adrenoceptors in human myocardium. J Pharmacol Exp Ther. 2002 Mar;300(3):794-801. doi: 10.1124/jpet.300.3.794. PMID: 11861783. 16: Andreka P, Aiyar N, Olson LC, Wei JQ, Turner MS, Webster KA, Ohlstein EH, Bishopric NH. Bucindolol displays intrinsic sympathomimetic activity in human myocardium. Circulation. 2002 May 21;105(20):2429-34. doi: 10.1161/01.cir.0000016050.79810.18. PMID: 12021232. 17: Rimele TJ, Aarhus LL, Lorenz RR, Rooke TW, Vanhoutte PM. Pharmacology of bucindolol in isolated canine vascular smooth muscle. J Pharmacol Exp Ther. 1984 Nov;231(2):317-25. PMID: 6149305. 18: Eichhorn EJ. Effects of bucindolol in heart failure. Am J Cardiol. 1993 Mar 25;71(9):65C-70C. doi: 10.1016/0002-9149(93)90089-u. PMID: 8096677. 19: Watts SW, Fink GD, Silver PJ, Cushing DJ. Interaction of the beta adrenergic receptor antagonist bucindolol with serotonergic receptors. J Cardiovasc Pharmacol. 2000 Jan;35(1):29-36. doi: 10.1097/00005344-200001000-00004. PMID: 10630730. 20: Torp-Pedersen C, Køber L, Ball S, Hall A, Brendorp B, Ottesen M, Berning J, Jensen G, Hampton J, Zilles P, Eberle S, Carlsen J. The incomplete bucindolol evaluation in acute myocardial infarction Trial (BEAT). Eur J Heart Fail. 2002 Aug;4(4):495-9. doi: 10.1016/s1388-9842(02)00032-6. PMID: 12167390.