Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H25N3O2.ClH |
Molecular Weight | 399.914 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)(CC1=CNC2=C1C=CC=C2)NCC(O)COC3=C(C=CC=C3)C#N
InChI
InChIKey=NCEAPFRHADKEHP-UHFFFAOYSA-N
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
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C22H25N3O2 |
Molecular Weight | 363.4528 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Bucindolol is a third-generation, non-selective β-adrenergic receptor blocker, that acts on both β-1 and β-2 receptors. Bucindolol’s additional α-1 antagonistic activity contributes to its mild vasodilator effect. It was rejected by the FDA for the heart failure, because of the unreviewed submissions deal with comparative effectiveness, clinical pharmacology, some aspects of pharmacogenetic data, and toxicology/metabolism. In addition, bucindolol is in the phase II of clinical trial for the treatment of atrial fibrillation.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2096974 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21792345 |
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Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21792345 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Evaluation of intrinsic sympathomimetic activity of bucindolol and carvedilol in rat heart. | 1998 Jan |
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Bucindolol: a pharmacogenomic perspective on its use in chronic heart failure. | 2011 |
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Adrenergic receptor polymorphisms and prevention of ventricular arrhythmias with bucindolol in patients with chronic heart failure. | 2013 Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01970501
Capsules are available in the following dosage strengths to be taken twice daily (with or without food): 6.25mg, 12.5mg, 25mg, 50mg, and 100mg.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6149305
To determine the effects of bucindolol on isolated vascular smooth muscle, rings of canine coronary and femoral arteries and saphenous veins were suspended for isometric tension recording in organ chambers filled with physiological salt solution. Bucindolol (3 X 10(-10) to 1 X 10(-7) M) had a comparable inhibitory effect on relaxations induced by isoproterenol in coronary arteries (which contain postjunctional beta-1 adrenoceptors) and saphenous veins (which contain postjunctional beta-2 adrenoceptors). Bucindolol (1 X 10(-7) M) had no effect on relaxations induced by sodium nitroprusside during contractions evoked by prostaglandin F2 alpha in either saphenous veins or coronary arteries. Bucindolol also had weak (relative to its beta adrenoceptor effect) alpha adrenoceptor-antagonistic activity that was greater for postjunctional alpha-1 than alpha-2 adrenoceptors. In all tissues tested, bucindolol in concentrations greater than 1 X 10(-6) M caused relaxations of responses induced by various nonadrenergic agonists. In superfused saphenous vein strips, previously incubated with [3H]norepinephrine, bucindolol (3 X 10(-7) to 1 X 10(-5) M) increased the basal efflux of [3H]norepinephrine and its [3H] metabolites. Bucindolol at 1 X 10(-7) M inhibited prejunctional beta adrenoceptors without affecting prejunctional alpha adrenoceptors. These experiments indicate that bucindolol in decreasing orders of activity 1) has nonselective beta adrenoceptor-antagonistic properties, 2) has a selective alpha-1 adrenoceptor-inhibitory effect and 3) has a nonspecific direct relaxing action on vascular smooth muscle.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:54:29 GMT 2023
by
admin
on
Fri Dec 15 18:54:29 GMT 2023
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Record UNII |
SH683G4QII
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C29576
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |