Bucindolol HCl | 71119-11-4 | 70369-47-0 | beta-adrenergic receptor antagonist

MedKoo Cat#: 326854 | Name: Bucindolol HCl

Description:

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

Bucindolol, also known as MJ-13105-1 or MJ-131051, is a beta-adrenergic receptor antagonist potentially for the treatment of chronic heart failure and atrial. Bucindolol is a fourth-generation β-blocker in development for the treatment of CHF. Bucindolol prevented new-onset AF; β₁ and α(2c) polymorphisms predicted therapeutic response; and the 47% of patients who were β₁389 Arg homozygotes had an enhanced effect size of 74%.

Chemical Structure

Bucindolol HCl

CAS#70369-47-0 (HCl)

Theoretical Analysis

MedKoo Cat#: 326854

Name: Bucindolol HCl

CAS#: 70369-47-0 (HCl)

Chemical Formula: C22H26ClN3O2

Exact Mass: 0.0000

Molecular Weight: 399.92

Elemental Analysis: C, 66.07; H, 6.55; Cl, 8.86; N, 10.51; O, 8.00

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

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

Synonym

MJ-131051; MJ 131051; MJ131051; MJ-13105-1; Bucindolol hydrochloride; Bucindolol HCl.

IUPAC/Chemical Name

2-(2-Hydroxy-3-((2-(3-indolyl)-1,1-dimethylethyl)amino)propoxy)benzonitrile hydrochloride

InChi Key

NCEAPFRHADKEHP-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H25N3O2.ClH/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;1H

SMILES Code

N#CC1=CC=CC=C1OCC(O)CNC(C)(C)CC2=CNC3=C2C=CC=C3.[H]Cl

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

>2 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 399.92 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

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. Review. PubMed PMID: 25959096. 2: Aleong RG, Sauer WH, Sauer WH, Murphy GA, Port JD, Anand IS, Fiuzat M, O'Connor CM, Abraham WT, Liggett SB, Bristow MR. Prevention of atrial fibrillation by bucindolol is dependent on the beta₁389 Arg/Gly adrenergic receptor polymorphism. JACC Heart Fail. 2013 Aug;1(4):338-44. PubMed PMID: 24159564; PubMed Central PMCID: PMC3804380. 3: Lymperopoulos A, Negussie S, Walklett K. β1- and α2C-adrenergic receptor polymorphisms and the antiarrhythmic effect of bucindolol in heart failure with reduced ejection fraction. Pharmacogenomics. 2013 Oct;14(13):1545-9. doi: 10.2217/pgs.13.137. PubMed PMID: 24088125. 4: Aleong RG, Sauer WH, Robertson AD, Liggett SB, Bristow MR. Adrenergic receptor polymorphisms and prevention of ventricular arrhythmias with bucindolol in patients with chronic heart failure. Circ Arrhythm Electrophysiol. 2013 Feb;6(1):137-43. doi: 10.1161/CIRCEP.111.969618. Epub 2012 Dec 30. PubMed PMID: 23275278. 5: Kao DP, Davis G, Aleong R, O'Connor CM, Fiuzat M, Carson PE, Anand IS, Plehn JF, Gottlieb SS, Silver MA, Lindenfeld J, Miller AB, White M, Murphy GA, Sauer W, Bristow MR. Effect of bucindolol on heart failure outcomes and heart rate response in patients with reduced ejection fraction heart failure and atrial fibrillation. Eur J Heart Fail. 2013 Mar;15(3):324-33. doi: 10.1093/eurjhf/hfs181. Epub 2012 Dec 7. PubMed PMID: 23223178; PubMed Central PMCID: PMC3576901. 6: Kao DP, Wagner BD, Robertson AD, Bristow MR, Lowes BD. A personalized BEST: characterization of latent clinical classes of nonischemic heart failure that predict outcomes and response to bucindolol. PLoS One. 2012;7(11):e48184. doi: 10.1371/journal.pone.0048184. Epub 2012 Nov 7. PubMed PMID: 23144856; PubMed Central PMCID: PMC3492337. 7: O'Connor CM, Fiuzat M, Carson PE, Anand IS, Plehn JF, Gottlieb SS, Silver MA, Lindenfeld J, Miller AB, White M, Walsh R, Nelson P, Medway A, Davis G, Robertson AD, Port JD, Carr J, Murphy GA, Lazzeroni LC, Abraham WT, Liggett SB, Bristow MR. Combinatorial pharmacogenetic interactions of bucindolol and β1, α2C adrenergic receptor polymorphisms. PLoS One. 2012;7(10):e44324. doi: 10.1371/journal.pone.0044324. Epub 2012 Oct 10. PubMed PMID: 23071495; PubMed Central PMCID: PMC3468617. 8: Warne T, Edwards PC, Leslie AG, Tate CG. Crystal structures of a stabilized β1-adrenoceptor bound to the biased agonists bucindolol and carvedilol. Structure. 2012 May 9;20(5):841-9. doi: 10.1016/j.str.2012.03.014. PubMed PMID: 22579251; PubMed Central PMCID: PMC3384003. 9: 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. Review. PubMed PMID: 22013565. 10: 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. PubMed PMID: 21982425; PubMed Central PMCID: PMC3769783. 11: 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. PubMed PMID: 21792345; PubMed Central PMCID: PMC3140276. 12: Bristow MR, Murphy GA, Krause-Steinrauf H, Anderson JL, Carlquist JF, Thaneemit-Chen S, Krishnan V, Abraham WT, Lowes BD, Port JD, Davis GW, Lazzeroni LC, Robertson AD, Lavori PW, Liggett SB. An alpha2C-adrenergic receptor polymorphism alters the norepinephrine-lowering effects and therapeutic response of the beta-blocker bucindolol in chronic heart failure. Circ Heart Fail. 2010 Jan;3(1):21-8. doi: 10.1161/CIRCHEARTFAILURE.109.885962. Epub 2009 Oct 30. PubMed PMID: 19880803. 13: Taylor MR, Slavov D, Humphrey K, Zhao L, Cockroft J, Zhu X, Lavori P, Bristow MR, Mestroni L, Lazzeroni LC. Pharmacogenetic effect of an endothelin-1 haplotype on response to bucindolol therapy in chronic heart failure. Pharmacogenet Genomics. 2009 Jan;19(1):35-43. doi: 10.1097/FPC.0b013e328317cc57. PubMed PMID: 18953265; PubMed Central PMCID: PMC3035051. 14: Frantz RP, Lowes BD, Grayburn PA, White M, Krause-Steinrauf H, Krishnan V, Uyeda L, Burnett JC; BEST Neurohumoral Substudy Investigators. Baseline and serial neurohormones in patients with congestive heart failure treated with and without bucindolol: results of the neurohumoral substudy of the Beta-Blocker Evaluation of Survival Study (BEST). J Card Fail. 2007 Aug;13(6):437-44. PubMed PMID: 17675057. 15: Scatena R. Bucindolol (Bristol-Myers Squibb Co). IDrugs. 1999 Feb;2(2):168-83. PubMed PMID: 16160951. 16: O'Connor CM, Gottlieb S, Bourque JM, Krause-Steinrauf H, Anand I, Anderson JL, Plehn JF, Silver MA, White M, Carson P; BEST Investigators. Impact of nonfatal myocardial infarction on outcomes in patients with advanced heart failure and the effect of bucindolol therapy. Am J Cardiol. 2005 Mar 1;95(5):558-64. PubMed PMID: 15721091. 17: Ali I, Akman D, Bruun NE, Køber L, Brendorp B, Ottesen M, Møller J, Torp-Pedersen C. Importance of a history of hypertension for the prognosis after acute myocardial infarction--for the Bucindolol Evaluation in Acute myocardial infarction Trial (BEAT) study group. Clin Cardiol. 2004 May;27(5):265-9. PubMed PMID: 15188939. 18: Anderson JL, Krause-Steinrauf H, Goldman S, Clemson BS, Domanski MJ, Hager WD, Murray DR, Mann DL, Massie BM, McNamara DM, Oren R, Rogers WJ; Beta-Blocker Evaluation of Survival Trial (BEST) Investigators. Failure of benefit and early hazard of bucindolol for Class IV heart failure. J Card Fail. 2003 Aug;9(4):266-77. PubMed PMID: 13680547. 19: Maack C, Böhm M, Vlaskin L, Dabew E, Lorenz K, Schäfers HJ, Lohse MJ, Engelhardt S. Partial agonist activity of bucindolol is dependent on the activation state of the human beta1-adrenergic receptor. Circulation. 2003 Jul 22;108(3):348-53. Epub 2003 Jul 7. PubMed PMID: 12847069. 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. PubMed PMID: 12167390.