BUNITROLOL

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=C(C=CC=C1)C#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 158 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 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) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2570175	Antagonist 2778		3.55 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Coronary heart disease 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18374 https://www.ncbi.nlm.nih.gov/pubmed/6117988	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Haemodynamic observations with KO. 1366 (bunitrolol), a new beta-adrenergic blocking agent.	1977	22426
Plasma catecholamines, plasma renin activity and haemodynamics during sodium nitroprusside-induced hypotension and additional beta-blockage with bunitrolol.	1981	6113146
Roles of phenylalanine at position 120 and glutamic acid at position 222 in the oxidation of chiral substrates by cytochrome P450 2D6.	2006 Feb	16432914
Extrapolating in vitro metabolic interactions to isolated perfused liver: predictions of metabolic interactions between R-bufuralol, bunitrolol, and debrisoquine.	2010 Oct	20310018

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 `Sat Dec 16 16:31:41 GMT 2023` Edited by `admin` on `Sat Dec 16 16:31:41 GMT 2023`
Record UNII	F2613LO055
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUNITROLOL

Official Name

English

Bunitrolol [WHO-DD]

Common Name

English

bunitrolol [INN]

Common Name

English

KO 1366

Code

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