U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C14H20N2O2.ClH
Molecular Weight 284.782
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUNITROLOL HYDROCHLORIDE

SMILES

Cl.CC(C)(C)NCC(O)COC1=C(C=CC=C1)C#N

InChI

InChIKey=RJPWESHPIMRNNM-UHFFFAOYSA-N
InChI=1S/C14H20N2O2.ClH/c1-14(2,3)16-9-12(17)10-18-13-7-5-4-6-11(13)8-15;/h4-7,12,16-17H,9-10H2,1-3H3;1H

HIDE SMILES / InChI

Description

Bunitrolol is a beta-adrenergic antagonist that can be used for treatment of coronary heart disease. It improves cardiac performance after beta-blockade in patients with coronary artery disease. Bunitrolol was found to have a greater beta 1 than beta 2 adrenergic activity and a weak alpha 1 blocking action.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Beta-1 adrenergic receptor
158
Target ID: P08588
Gene ID: 153.0
Gene Symbol: ADRB1
Target Organism: Homo sapiens (Human)
Antagonist
2778
 42.0 nM [Ki]
Beta-2 adrenergic receptor
203
Target ID: P07550|||Q53GA6|||Q9UCZ3
Gene ID: 154.0
Gene Symbol: ADRB2
Target Organism: Homo sapiens (Human)
Antagonist
2778
 3.55 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
504
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Haemodynamic observations with KO. 1366 (bunitrolol), a new beta-adrenergic blocking agent.
1977
Plasma catecholamines, plasma renin activity and haemodynamics during sodium nitroprusside-induced hypotension and additional beta-blockage with bunitrolol.
1981
Functional evaluation of cytochrome P450 2D6 with Gly42Arg substitution expressed in Saccharomyces cerevisiae.
2001 Nov
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].
2003 Oct-Dec
MetaSite: understanding metabolism in human cytochromes from the perspective of the chemist.
2005 Nov 3
Roles of phenylalanine at position 120 and glutamic acid at position 222 in the oxidation of chiral substrates by cytochrome P450 2D6.
2006 Feb
CYP2D-related metabolism in animals of the Canoidea superfamily - species differences.
2006 Jul
Extrapolating in vitro metabolic interactions to isolated perfused liver: predictions of metabolic interactions between R-bufuralol, bunitrolol, and debrisoquine.
2010 Oct
Patents

Patents

RU2414924C2
2

Sample Use Guides

In Vivo Use Guide
Bunitrolol 10 mg administered to patients with coronary artery disease
Route of Administration: Intravenous
In Vitro Use Guide
For assessments of pharmacological activities of bunitrolol the guinea pig trachea, left and right atria and aorta, and the rat aorta were used. Dose-response curves were obtained in the absence or presence of bunitrolol of the following concentrations: trachea, left and right atria 10(-8) M, guinea pig aorta 10(-4) M; rat aorta, 3x10(-6) M.
Name Type Language
BUNITROLOL HYDROCHLORIDE
JAN   MART.   MI   WHO-DD  
Common Name English
BENZONITRILE, 2-(3-((1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXY)-, HYDROCHLORIDE (1:1)
Systematic Name English
(±)-2-(3-TERT-BUTYLAMINO-2-HYDROXYPROPOXY)BENZONITRILE HYDROCHLORIDE
Systematic Name English
DL-O-(2-HYDROXY-3-(TERT-BUTYLAMINO)PROPOXY)BENZONITRILE HYDROCHLORIDE
Systematic Name English
1-TERT-BUTYLAMINO-3-(2-CYANOPHENOXY)-2-PROPANOL HYDROCHLORIDE
Systematic Name English
2-(3-TERT-BUTYLAMINO-2-HYDROXYPROPOXY)BENZONITRILE HYDROCHLORIDE
Systematic Name English
BUNITROLOL HYDROCHLORIDE [MART.]
Common Name English
BUNITROLOL HYDROCHLORIDE [MI]
Common Name English
BENZONITRILE, 2-(3-((1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXY)-, MONOHYDROCHLORIDE, (±)-
Systematic Name English
KO-1366 HYDROCHLORIDE
Code English
BUNITROLOL HCL
Common Name English
BUNITROLOL HYDROCHLORIDE [JAN]
Common Name English
STRESSON
Brand Name English
BETRIOL
Brand Name English
BENZONITRILE, 2-(3-((1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXY)-, MONOHYDROCHLORIDE
Systematic Name English
Bunitrolol hydrochloride [WHO-DD]
Common Name English
2-(3-((1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXY)BENZONITRILE, HYDROCHLORIDE
Systematic Name English
BENZONITRILE, O-(3-(TERT-BUTYLAMINO)-2-HYDROXYPROPOXY)-, MONOHYDROCHLORIDE, (±)-
Systematic Name English
2-(2-HYDROXY-3-(T-BUTYLAMINO)PROPOXY)BENZONITRILE HYDROCHLORIDE
Systematic Name English
1-(2-CYANOPHENOXY)-2-HYDROXY-3-TERT-BUTYLAMINOPROPANE HYDROCHLORIDE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID80945768
Created by admin on Fri Dec 15 17:10:54 GMT 2023 , Edited by admin on Fri Dec 15 17:10:54 GMT 2023
PRIMARY
MERCK INDEX
m2763
Created by admin on Fri Dec 15 17:10:54 GMT 2023 , Edited by admin on Fri Dec 15 17:10:54 GMT 2023
PRIMARY
CAS
29876-08-2
Created by admin on Fri Dec 15 17:10:54 GMT 2023 , Edited by admin on Fri Dec 15 17:10:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL418134
Created by admin on Fri Dec 15 17:10:54 GMT 2023 , Edited by admin on Fri Dec 15 17:10:54 GMT 2023
PRIMARY
PUBCHEM
31641
Created by admin on Fri Dec 15 17:10:54 GMT 2023 , Edited by admin on Fri Dec 15 17:10:54 GMT 2023
PRIMARY
ECHA (EC/EINECS)
245-427-5
Created by admin on Fri Dec 15 17:10:54 GMT 2023 , Edited by admin on Fri Dec 15 17:10:54 GMT 2023
PRIMARY
CAS
23093-74-5
Created by admin on Fri Dec 15 17:10:54 GMT 2023 , Edited by admin on Fri Dec 15 17:10:54 GMT 2023
SUPERSEDED
SMS_ID
100000084854
Created by admin on Fri Dec 15 17:10:54 GMT 2023 , Edited by admin on Fri Dec 15 17:10:54 GMT 2023
PRIMARY
EVMPD
SUB00900MIG
Created by admin on Fri Dec 15 17:10:54 GMT 2023 , Edited by admin on Fri Dec 15 17:10:54 GMT 2023
PRIMARY
FDA UNII
A42VUS2X73
Created by admin on Fri Dec 15 17:10:54 GMT 2023 , Edited by admin on Fri Dec 15 17:10:54 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of BUNITROLOL
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966