BOPINDOLOL

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H28N2O3
Molecular Weight	380.48
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3

InChI

InChIKey=UUOJIACWOAYWEZ-UHFFFAOYSA-N

InChI=1S/C23H28N2O3/c1-16-13-19-20(25-16)11-8-12-21(19)27-15-18(14-24-23(2,3)4)28-22(26)17-9-6-5-7-10-17/h5-13,18,24-25H,14-15H2,1-4H3

HIDE SMILES / InChI

Description
Sources: http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.1981.tb10708.x/epdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11314603 | https://www.ncbi.nlm.nih.gov/pubmed/1706984

Bopindolol (4-[benzoyloxy-3-tertbutylaminopropoxy]-2-methylindole hydrogen malonate) is an indole beta-adrenoceptor antagonist bearing a benzoyl ester residue on the beta-carbon atom of the propanolamine side chain. Bopindolol is metabolized by esterase to benzoic acid and an active metabolite, 18-502 [4-(3-t-butylamino-2-hydroxypropoxy)-2-methyl indole], which is further metabolized to 20-785 [4-(3-t-butylaminopropoxy)-2-carboxyl indole]. Bopindolol produces sustained blockade of beta 1- and beta 2-adrenoceptors, has intrinsic sympathomimetic as well as membrane stabilizing actions, inhibits renin secretion, and interacts with 5-HT receptors. Bopindolol is used in the treatment of hypertension. In limited trials bopindolol has also successfully reduced symptoms in patients with angina pectoris, anxiety and essential tremor.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Beta-1 adrenergic receptor 158 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11314603	Antagonist 2778	7.44 null [pKi]
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11314603	Antagonist 2778	7.33 null [pKi]
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11314603	Interacts 323

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1706984 https://www.ncbi.nlm.nih.gov/pubmed/2889554	Primary		Approved 8429	BOPINDOLOL Approved Use Bopindolol is a nonselective beta-adrenoceptor antagonist with partial agonist activity which is used in the treatment of hypertension.

PubMed

Title	Date	PubMed
Bopindolol: pharmacological basis and clinical implications.	2001 Spring	11314603
Determination of bopindolol in pharmaceuticals by capillary isotachophoresis.	2002 May 15	12008130
Determination of bopindolol using the flow injection technique coupled with solid phase extraction.	2003 Dec 4	14656606
Role of chemical structure in stereoselective recognition of beta-blockers and H1-antihistamines by human serum transferrin in capillary zone electrophoresis.	2006 Apr	16609932
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

antihypertensive effects of bopindolol 0.5 to 4 mg are sustained for more than 24 hours after once daily dosing

Route of Administration: Oral

In Vitro Use Guide

In guinea-pig isolated atria bopindolol at concentrations between 3.2 nM and 2 uM produced an inhibition of the positive chronotropic and inotropic effects of adrenaline

Name

Type

Language

BOPINDOLOL

Official Name

English

(±)-1-(TERT-BUTYLAMINO)-3-((2-METHYLINDOL-4-YL)OXY)-2-PROPANOL BENZOATE (ESTER)

Common Name

English

bopindolol [INN]

Common Name

English

BOPINDOLOL [MI]

Common Name

English

Bopindolol [WHO-DD]

Common Name

English

1-((1,1-DIMETHYLETHYL)AMINO)-3-((2-METHYL-1H-INDOL-4-YL)OXY)-2-PROPANOL BENZOATE ESTER

Common Name

English

Classification Tree Code System Code

WHO-ATC

C07AA17