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=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
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 |
|---|---|---|---|
Target ID: CHEMBL2096974 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21792345 |
|||
Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21792345 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
88 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2859199/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
528 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2859199/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.58 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2859199/ |
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
| Dose | Population | Adverse events |
|---|---|---|
200 mg single, oral Highest studied dose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
Other AEs: Presyncope... |
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
| AE | Significance | Dose | Population |
|---|---|---|---|
| Presyncope | 50% | 200 mg single, oral Highest studied dose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 17.0 |
inconclusive [IC50 27.5404 uM] | |||
Page: 18.0 |
inconclusive [IC50 27.5404 uM] | |||
Page: 56.0 |
inconclusive | |||
Page: 103.0 |
no | |||
Page: 97.0 |
no | |||
Page: 7.0 |
yes [EC50 12.5893 uM] | |||
| yes [IC50 0.05 uM] | ||||
| yes [IC50 27.2 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 95.0 |
no |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 4.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
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.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
|---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY
SUBSTANCE RECORD