BUNITROLOL

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H20N2O2
Molecular Weight	248.3208
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)NCC(O)COC1=CC=CC=C1C#N

InChI

InChIKey=VCVQSRCYSKKPBA-UHFFFAOYSA-N

InChI=1S/C14H20N2O2/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

HIDE SMILES / InChI

Molecular Formula	C14H20N2O2
Molecular Weight	248.3208
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22426 | https://www.ncbi.nlm.nih.gov/pubmed/18374 | https://www.ncbi.nlm.nih.gov/pubmed/6117988 | https://www.ncbi.nlm.nih.gov/pubmed/2893855

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

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-1 adrenergic receptor 163 Target ID: P08588 Gene ID: 153.0 Gene Symbol: ADRB1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2570175	Antagonist 2849		42.0 nM [Ki]
Beta-2 adrenergic receptor 209 Target ID: P07550\|\|\|Q53GA6\|\|\|Q9UCZ3 Gene ID: 154.0 Gene Symbol: ADRB2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2570175	Antagonist 2849		3.55 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Coronary heart disease 43 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18374 https://www.ncbi.nlm.nih.gov/pubmed/6117988	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Extrapolating in vitro metabolic interactions to isolated perfused liver: predictions of metabolic interactions between R-bufuralol, bunitrolol, and debrisoquine.	2010-10	20310018
CYP2D-related metabolism in animals of the Canoidea superfamily - species differences.	2006-07	16755362
Roles of phenylalanine at position 120 and glutamic acid at position 222 in the oxidation of chiral substrates by cytochrome P450 2D6.	2006-02	16432914
MetaSite: understanding metabolism in human cytochromes from the perspective of the chemist.	2005-11-03	16250655
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].	2004-02-20	14971294
Functional evaluation of cytochrome P450 2D6 with Gly42Arg substitution expressed in Saccharomyces cerevisiae.	2001-11	11692080
Inactivation of rat cytochrome P450 2D enzyme by a further metabolite of 4-hydroxypropranolol, the major and active metabolite of propranolol.	2001-09	11558582
Plasma catecholamines, plasma renin activity and haemodynamics during sodium nitroprusside-induced hypotension and additional beta-blockage with bunitrolol.	1981	6113146
Haemodynamic observations with KO. 1366 (bunitrolol), a new beta-adrenergic blocking agent.	1977	22426

Patents

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:55:32 GMT 2025` Edited by `admin` on `Wed Apr 02 07:55:32 GMT 2025`
Record UNII	F2613LO055
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BUNITROLOL

Official Name

English

KO 1366

Preferred Name

English

Bunitrolol [WHO-DD]

Common Name

English

bunitrolol [INN]

Common Name

English

BUNITROLOL [MI]

Common Name

English

KO-1366

Code

English

(±)-1-(2-CYANOPHENOXY)-2-HYDROXY-3-TERT-BUTYLAMINOPROPANE

Systematic Name

English

1-(2-CYANOPHENOXY)-2-HYDROXY-3-TERT-BUTYLAMINOPROPANE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29576