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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
Structure of BUCINDOLOL HYDROCHLORIDE

SMILES

Cl.CC(C)(CC1=CNC2=C1C=CC=C2)NCC(O)COC3=CC=CC=C3C#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

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
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.
Name Type Language
GENCARO
Preferred Name English
BUCINDOLOL HYDROCHLORIDE
DASH   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
Bucindolol hydrochloride [WHO-DD]
Common Name English
BUCINDOLOL HYDROCHLORIDE [USAN]
Common Name English
BUCINDOLOL HCL
Common Name English
BUCINDOLOL HYDROCHLORIDE [MART.]
Common Name English
MJ-13105-1
Code English
O-[2-Hydroxy-3-[(2-indol-3-yl-1,1-dimethylethyl)amino]propoxy]benzonitrile monohydrochloride
Common Name English
BENZONITRILE, 2-(2-HYDROXY-3-((2-(1H-INDOL-3-YL)-1,1-DIMETHYLETHYL)AMINO)PROPOXY)-, MONOHYDROCHLORIDE
Common Name English
BUCINDOLOL HYDROCHLORIDE [MI]
Common Name English
MJ 13,105-1
Code English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Mon Mar 31 19:25:38 GMT 2025 , Edited by admin on Mon Mar 31 19:25:38 GMT 2025
Code System Code Type Description
PUBCHEM
51044
Created by admin on Mon Mar 31 19:25:38 GMT 2025 , Edited by admin on Mon Mar 31 19:25:38 GMT 2025
PRIMARY
NCI_THESAURUS
C142971
Created by admin on Mon Mar 31 19:25:38 GMT 2025 , Edited by admin on Mon Mar 31 19:25:38 GMT 2025
PRIMARY
MESH
C024307
Created by admin on Mon Mar 31 19:25:38 GMT 2025 , Edited by admin on Mon Mar 31 19:25:38 GMT 2025
PRIMARY
MERCK INDEX
m2741
Created by admin on Mon Mar 31 19:25:38 GMT 2025 , Edited by admin on Mon Mar 31 19:25:38 GMT 2025
PRIMARY Merck Index
CAS
70369-47-0
Created by admin on Mon Mar 31 19:25:38 GMT 2025 , Edited by admin on Mon Mar 31 19:25:38 GMT 2025
PRIMARY
SMS_ID
100000085126
Created by admin on Mon Mar 31 19:25:38 GMT 2025 , Edited by admin on Mon Mar 31 19:25:38 GMT 2025
PRIMARY
EVMPD
SUB00886MIG
Created by admin on Mon Mar 31 19:25:38 GMT 2025 , Edited by admin on Mon Mar 31 19:25:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID50990563
Created by admin on Mon Mar 31 19:25:38 GMT 2025 , Edited by admin on Mon Mar 31 19:25:38 GMT 2025
PRIMARY
FDA UNII
SH683G4QII
Created by admin on Mon Mar 31 19:25:38 GMT 2025 , Edited by admin on Mon Mar 31 19:25:38 GMT 2025
PRIMARY
ChEMBL
CHEMBL321582
Created by admin on Mon Mar 31 19:25:38 GMT 2025 , Edited by admin on Mon Mar 31 19:25:38 GMT 2025
PRIMARY