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Details

Stereochemistry RACEMIC
Molecular Formula C23H28N2O3.C3H4O4
Molecular Weight 484.5415
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BOPINDOLOL MALONATE

SMILES

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

InChI

InChIKey=LDOONRJGLKHGJI-UHFFFAOYSA-N
InChI=1S/C23H28N2O3.C3H4O4/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;4-2(5)1-3(6)7/h5-13,18,24-25H,14-15H2,1-4H3;1H2,(H,4,5)(H,6,7)

HIDE SMILES / InChI

Description
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.

Originator

Curator's Comment: Berthold R, Waite R, Weber H (1981) Pharmacological studies with Bopindolol: a new long acting beta-adrenoceptor antagonist (Abstract). Br J Pharmacol 74:829 DOI: 10.1111/j.1476-5381.1981.tb10708.x

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BOPINDOLOL

Approved Use

Bopindolol is a nonselective beta-adrenoceptor antagonist with partial agonist activity which is used in the treatment of hypertension.
PubMed

PubMed

TitleDatePubMed
[Multicenter study of isradipine in the treatment of hypertension].
1992 Apr
Bopindolol: pharmacological basis and clinical implications.
2001 Spring
Chiral separations of some beta-adrenergic agonists and antagonists on AmyCoat column by HPLC.
2010 Jan
Patents

Sample Use Guides

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 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 MALONATE
JAN   MART.   MI   WHO-DD  
Common Name English
Bopindolol malonate [WHO-DD]
Common Name English
BOPINDOLOL MALONATE [MI]
Common Name English
WANDONORM
Brand Name English
PROPANEDIOIC ACID, COMPD. WITH 2-((1,1-DIMETHYLETHYL)AMINO)-1-(((2-METHYL-1H-INDOL-4-YL)OXY)METHYL)ETHYL BENZOATE (1:1)
Common Name English
LT-31-200
Code English
2-PROPANOL, 1-((1,1-DIMETHYLETHYL)AMINO)-3-((2-METHYL-1H-INDOL-4-YL)OXY)-, BENZOATE (ESTER), (±)-, PROPANEDIOATE (1:1) (SALT)
Common Name English
BOPINDOLOL HYDROGEN MALONATE
Common Name English
SANDONORM
Brand Name English
PROPANEDIOIC ACID, COMPD. WITH (±)-2-((1,1-DIMETHYLETHYL)AMINO)-1-(((2-METHYL-1H-INDOL-4-YL)OXY)METHYL)ETHYL BENZOATE (1:1)
Common Name English
BOPINDOLOL MALONATE [MART.]
Common Name English
2-PROPANOL, 1-((1,1-DIMETHYLETHYL)AMINO)-3-((2-METHYL-1H-INDOL-4-YL)OXY)-, BENZOATE (ESTER), PROPANEDIOATE (1:1) (SALT)
Common Name English
BOPINDOLOL MALONATE [JAN]
Common Name English
Code System Code Type Description
CHEBI
76749
Created by admin on Fri Dec 15 17:27:18 GMT 2023 , Edited by admin on Fri Dec 15 17:27:18 GMT 2023
PRIMARY
EVMPD
SUB00852MIG
Created by admin on Fri Dec 15 17:27:18 GMT 2023 , Edited by admin on Fri Dec 15 17:27:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID501002965
Created by admin on Fri Dec 15 17:27:18 GMT 2023 , Edited by admin on Fri Dec 15 17:27:18 GMT 2023
PRIMARY
ChEMBL
CHEMBL357995
Created by admin on Fri Dec 15 17:27:18 GMT 2023 , Edited by admin on Fri Dec 15 17:27:18 GMT 2023
PRIMARY
RXCUI
236903
Created by admin on Fri Dec 15 17:27:18 GMT 2023 , Edited by admin on Fri Dec 15 17:27:18 GMT 2023
PRIMARY RxNorm
SMS_ID
100000091995
Created by admin on Fri Dec 15 17:27:18 GMT 2023 , Edited by admin on Fri Dec 15 17:27:18 GMT 2023
PRIMARY
PUBCHEM
636368
Created by admin on Fri Dec 15 17:27:18 GMT 2023 , Edited by admin on Fri Dec 15 17:27:18 GMT 2023
PRIMARY
MERCK INDEX
m2605
Created by admin on Fri Dec 15 17:27:18 GMT 2023 , Edited by admin on Fri Dec 15 17:27:18 GMT 2023
PRIMARY Merck Index
FDA UNII
S3UWR70991
Created by admin on Fri Dec 15 17:27:18 GMT 2023 , Edited by admin on Fri Dec 15 17:27:18 GMT 2023
PRIMARY
CAS
82857-38-3
Created by admin on Fri Dec 15 17:27:18 GMT 2023 , Edited by admin on Fri Dec 15 17:27:18 GMT 2023
PRIMARY