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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=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

HIDE SMILES / InChI

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.

Originator

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Evaluation of intrinsic sympathomimetic activity of bucindolol and carvedilol in rat heart.
1998 Jan
Bucindolol: a pharmacogenomic perspective on its use in chronic heart failure.
2011
Adrenergic receptor polymorphisms and prevention of ventricular arrhythmias with bucindolol in patients with chronic heart failure.
2013 Feb
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 Fri Dec 15 18:54:29 GMT 2023
Edited
by admin
on Fri Dec 15 18:54:29 GMT 2023
Record UNII
SH683G4QII
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
GENCARO
Brand 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 Fri Dec 15 18:54:30 GMT 2023 , Edited by admin on Fri Dec 15 18:54:30 GMT 2023
Code System Code Type Description
PUBCHEM
51044
Created by admin on Fri Dec 15 18:54:30 GMT 2023 , Edited by admin on Fri Dec 15 18:54:30 GMT 2023
PRIMARY
NCI_THESAURUS
C142971
Created by admin on Fri Dec 15 18:54:30 GMT 2023 , Edited by admin on Fri Dec 15 18:54:30 GMT 2023
PRIMARY
MESH
C024307
Created by admin on Fri Dec 15 18:54:30 GMT 2023 , Edited by admin on Fri Dec 15 18:54:30 GMT 2023
PRIMARY
MERCK INDEX
m2741
Created by admin on Fri Dec 15 18:54:30 GMT 2023 , Edited by admin on Fri Dec 15 18:54:30 GMT 2023
PRIMARY Merck Index
CAS
70369-47-0
Created by admin on Fri Dec 15 18:54:30 GMT 2023 , Edited by admin on Fri Dec 15 18:54:30 GMT 2023
PRIMARY
SMS_ID
100000085126
Created by admin on Fri Dec 15 18:54:30 GMT 2023 , Edited by admin on Fri Dec 15 18:54:30 GMT 2023
PRIMARY
EVMPD
SUB00886MIG
Created by admin on Fri Dec 15 18:54:30 GMT 2023 , Edited by admin on Fri Dec 15 18:54:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID50990563
Created by admin on Fri Dec 15 18:54:30 GMT 2023 , Edited by admin on Fri Dec 15 18:54:30 GMT 2023
PRIMARY
FDA UNII
SH683G4QII
Created by admin on Fri Dec 15 18:54:30 GMT 2023 , Edited by admin on Fri Dec 15 18:54:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL321582
Created by admin on Fri Dec 15 18:54:30 GMT 2023 , Edited by admin on Fri Dec 15 18:54:30 GMT 2023
PRIMARY
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