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Details

Stereochemistry RACEMIC
Molecular Formula C22H25N3O2
Molecular Weight 363.4528
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUCINDOLOL

SMILES

CC(C)(CC1=CNC2=C1C=CC=C2)NCC(O)COC3=C(C=CC=C3)C#N

InChI

InChIKey=FBMYKMYQHCBIGU-UHFFFAOYSA-N
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

HIDE SMILES / InChI
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.

Originator

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

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
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.
Name Type Language
BUCINDOLOL
INN   MI   WHO-DD  
INN  
Official Name English
bucindolol [INN]
Common Name English
O-(2-HYDROXY-3-((2-INDOL-3-YL-1,1-DIMETHYLETHYL)AMINO)PROPOXY)BENZONITRILE
Common Name English
Bucindolol [WHO-DD]
Common Name English
BENZONITRILE, 2-(2-HYDROXY-3-((2-(1H-INDOL-3-YL)-1,1-DIMETHYLETHYL)AMINO)PROPOXY)-
Systematic Name English
(±)-O-(2-HYDROXY-3-((2-INDOL-3-YL-1,1-DIMETHYLETHYL)AMINO)PROPOXY)BENZONITRILE
Common Name English
BUCINDOLOL [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID3046744
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
PRIMARY
WIKIPEDIA
Bucindolol
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
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EVMPD
SUB05945MIG
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
PRIMARY
INN
4811
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
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CAS
71119-11-4
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
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SMS_ID
100000085864
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
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MERCK INDEX
m2741
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
PRIMARY Merck Index
PUBCHEM
51045
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
PRIMARY
NCI_THESAURUS
C79557
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
PRIMARY
CAS
91476-02-7
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
SUPERSEDED
DRUG BANK
DB12752
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
PRIMARY
ChEMBL
CHEMBL321582
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
PRIMARY
CAS
111671-41-1
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
SUPERSEDED
FDA UNII
E9UO06K7CE
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
PRIMARY
MESH
C024307
Created by admin on Fri Dec 15 17:37:18 GMT 2023 , Edited by admin on Fri Dec 15 17:37:18 GMT 2023
PRIMARY