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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=CC=CC=C3C#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

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.

Originator

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
88 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUCINDOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
528 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUCINDOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.58 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUCINDOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
Other AEs: Presyncope...
Other AEs:
Presyncope (50%)
Sources:
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
AEs

AEs

AESignificanceDosePopulation
Presyncope 50%
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive [IC50 27.5404 uM]
inconclusive [IC50 27.5404 uM]
inconclusive
no
no
yes [EC50 12.5893 uM]
yes [IC50 0.05 uM]
yes [IC50 27.2 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Adrenergic receptor polymorphisms and prevention of ventricular arrhythmias with bucindolol in patients with chronic heart failure.
2013-02
Bucindolol: a pharmacogenomic perspective on its use in chronic heart failure.
2011
beta-adrenergic receptor blockade in chronic heart failure.
2000-02-08
Evaluation of intrinsic sympathomimetic activity of bucindolol and carvedilol in rat heart.
1998-01
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:49:35 GMT 2025
Edited
by admin
on Mon Mar 31 18:49:35 GMT 2025
Record UNII
E9UO06K7CE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUCINDOLOL
INN   MI   WHO-DD  
INN  
Official Name English
(±)-O-(2-HYDROXY-3-((2-INDOL-3-YL-1,1-DIMETHYLETHYL)AMINO)PROPOXY)BENZONITRILE
Preferred 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
BUCINDOLOL [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID3046744
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
WIKIPEDIA
Bucindolol
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
EVMPD
SUB05945MIG
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
INN
4811
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
CAS
71119-11-4
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
SMS_ID
100000085864
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
MERCK INDEX
m2741
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY Merck Index
PUBCHEM
51045
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
NCI_THESAURUS
C79557
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
CAS
91476-02-7
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
SUPERSEDED
DRUG BANK
DB12752
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
ChEMBL
CHEMBL321582
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
CAS
111671-41-1
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
SUPERSEDED
FDA UNII
E9UO06K7CE
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
MESH
C024307
Created by admin on Mon Mar 31 18:49:35 GMT 2025 , Edited by admin on Mon Mar 31 18:49:35 GMT 2025
PRIMARY
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY