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Home > Indoles and Oxindole > 71119-11-4
71119-11-4 | Bucindolol
CAS No: 71119-11-4 Catalog No: AG005NYX MDL No:MFCD00865898
Product Description
Catalog Number:
AG005NYX
Chemical Name:
Bucindolol
CAS Number:
71119-11-4
Molecular Formula:
C22H25N3O2
Molecular Weight:
363.4528
MDL Number:
MFCD00865898
IUPAC Name:
2-[2-hydroxy-3-[[1-(1H-indol-3-yl)-2-methylpropan-2-yl]amino]propoxy]benzonitrile
InChI:
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
InChI Key:
FBMYKMYQHCBIGU-UHFFFAOYSA-N
SMILES:
N#Cc1ccccc1OCC(CNC(Cc1c[nH]c2c1cccc2)(C)C)O
EC Number:
615-251-7
Properties
Complexity:
515
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
363.195g/mol
Formal Charge:
0
Heavy Atom Count:
27
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
363.461g/mol
Monoisotopic Mass:
363.195g/mol
Rotatable Bond Count:
8
Topological Polar Surface Area:
81.1A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
3.3
Literature
| Title | Journal |
|---|---|
| Crystal structures of a stabilized β1-adrenoceptor bound to the biased agonists bucindolol and carvedilol. | Structure (London, England : 1993) 20120509 |
| β-blockers in stage B: a precursor of heart failure. | Heart failure clinics 20120401 |
| Combinatorial pharmacogenetic interactions of bucindolol and β1, α2C adrenergic receptor polymorphisms. | PloS one 20120101 |
| Predicting in vivo cardiovascular properties of β-blockers from cellular assays: a quantitative comparison of cellular and cardiovascular pharmacological responses. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20111201 |
| Which beta-blocker is most effective in heart failure? | Cardiovascular drugs and therapy 20100801 |
| An alpha2C-adrenergic receptor polymorphism alters the norepinephrine-lowering effects and therapeutic response of the beta-blocker bucindolol in chronic heart failure. | Circulation. Heart failure 20100101 |
| Pharmacogenetic effect of an endothelin-1 haplotype on response to bucindolol therapy in chronic heart failure. | Pharmacogenetics and genomics 20090101 |
| Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1. | Journal of medicinal chemistry 20081009 |
| A polymorphism within a conserved beta(1)-adrenergic receptor motif alters cardiac function and beta-blocker response in human heart failure. | Proceedings of the National Academy of Sciences of the United States of America 20060725 |
| Beta-adrenoceptor antagonists in elderly patients with chronic heart failure: therapeutic potential of third-generation agents. | Drugs & aging 20060101 |
| American Association for the Advancement of Science meeting. DNA tells story of heart drug failure. | Science (New York, N.Y.) 20050225 |
| Clinical trials update from the Heart Failure Society of America: EMOTE, HERB-CHF, BEST genetic sub-study and RHYTHM-ICD. | European journal of heart failure 20041201 |
| Effect of baseline or changes in adrenergic activity on clinical outcomes in the beta-blocker evaluation of survival trial. | Circulation 20040914 |
| Adverse effects of beta-blocker therapy for patients with heart failure: a quantitative overview of randomized trials. | Archives of internal medicine 20040712 |
| Beta blockers as anti-arrhythmic agents. | Heart failure reviews 20040401 |
| Myocardial contractile reserve by dobutamine stress echocardiography predicts improvement in ejection fraction with beta-blockade in patients with heart failure: the Beta-Blocker Evaluation of Survival Trial (BEST). | Circulation 20031111 |
| How should subgroup analyses affect clinical practice? Insights from the Metoprolol Succinate Controlled-Release/Extended-Release Randomized Intervention Trial in Heart Failure (MERIT-HF). | Cardiac electrophysiology review 20030901 |
| Failure of benefit and early hazard of bucindolol for Class IV heart failure. | Journal of cardiac failure 20030801 |
| Partial agonist activity of bucindolol is dependent on the activation state of the human beta1-adrenergic receptor. | Circulation 20030722 |
| Catecholamine release in human heart by bupropion. | European journal of pharmacology 20030425 |
| Beta-blockers in heart failure: how far have we progressed? | Postgraduate medicine 20021101 |
| [Treatment of heart failure: an update]. | Italian heart journal. Supplement : official journal of the Italian Federation of Cardiology 20020701 |
| Bucindolol displays intrinsic sympathomimetic activity in human myocardium. | Circulation 20020521 |
| Differential effects of bucindolol and carvedilol on noradenaline-induced hypertrophic response in ventricular cardiomyocytes of adult rats. | The Journal of pharmacology and experimental therapeutics 20020401 |
| Bucindolol exerts agonistic activity on the propranolol-insensitive state of beta1-adrenoceptors in human myocardium. | The Journal of pharmacology and experimental therapeutics 20020301 |
| Effects of beta-blocker therapy in severe chronic heart failure. | The New England journal of medicine 20010927 |
| [Role of beta-blockers in the treatment of chronic heart heart failure]. | Orvosi hetilap 20010916 |
| Nebivolol, bucindolol, metoprolol and carvedilol are devoid of intrinsic sympathomimetic activity in human myocardium. | British journal of pharmacology 20010801 |
| [Effect of carvedilol on survival in severe chronic heart failure. A trial of the beta-blocker bucindolol in patient with advanced heart failure]. | Italian heart journal. Supplement : official journal of the Italian Federation of Cardiology 20010801 |
| Beta-blocker trials seem to be in conflict. | Circulation 20010612 |
| Bucindolol, a nonselective beta 1- and beta 2-adrenergic receptor antagonist, decreases beta-adrenergic receptor density in cultured embryonic chick cardiac myocyte membranes. | Journal of cardiovascular pharmacology 20010601 |
| Expanding indications for beta-blockers in heart failure. | The New England journal of medicine 20010531 |
| [Adrenergic beta inhibitors in heart insufficiency: which and when?]. | Revista portuguesa de cardiologia : orgao oficial da Sociedade Portuguesa de Cardiologia = Portuguese journal of cardiology : an official journal of the Portuguese Society of Cardiology 20010301 |
| Receptor pharmacology of carvedilol in the human heart. | Journal of cardiovascular pharmacology 19920101 |
| Comparison of the haemodynamic effects of bucindolol, propranolol and pindolol in healthy volunteers. | British journal of clinical pharmacology 19851201 |
| Differential cardioprotective properties of the l- and d- enantiomers of bucindolol in a canine model of heart failure. | Archives internationales de pharmacodynamie et de therapie 19850501 |
| Beneficial effects of bucindolol in a canine model of pentobarbital-induced heart failure. | Archives internationales de pharmacodynamie et de therapie 19810301 |
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