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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
Molecular Formula C23H28N2O3
Molecular Weight 380.48
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )
Molecular Formula C3H4O4
Molecular Weight 104.0615
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

CNS Activity

Originator

Sandoz
40
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 7.44 null [pKi]
Antagonist
2778
 7.33 null [pKi]
Interacts
323
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

PubMed

TitleDatePubMed
Beta-blockers and psychic stress: a double-blind, placebo-controlled study of bopindolol vs lorazepam and butalbital in surgical patients.
1985 Sep
Bopindolol. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy.
1991 Jan
[Multicenter study of isradipine in the treatment of hypertension].
1992 Apr
Hypotensive effect of bopindolol in pithed rats.
1993 Mar
Comparison of chlorthalidone, propranolol and bopindolol in six-month treatment of arterial hypertension.
1998
Bopindolol: pharmacological basis and clinical implications.
2001 Spring
Effect of vasodilatory beta-adrenoceptor blockers on cardiovascular haemodynamics in anaesthetized rats.
2002 Mar
Determination of bopindolol in pharmaceuticals by capillary isotachophoresis.
2002 May 15
Spin trapping study of reactive oxygen species formation during bopindolol peroxidation.
2002 Oct 15
Determination of bopindolol using the flow injection technique coupled with solid phase extraction.
2003 Dec 4
Determination of bopindolol by sequential injection technique with spectrophotometric detection.
2003 Oct
Role of chemical structure in stereoselective recognition of beta-blockers and H1-antihistamines by human serum transferrin in capillary zone electrophoresis.
2006 Apr
Transdermal delivery of beta-blockers.
2006 May
Role of chemical structure in stereoselective recognition of beta-blockers by cyclodextrins in capillary zone electrophoresis.
2008 Apr 24
Management of hyperuricemia in gout: focus on febuxostat.
2010 Feb 2
Chiral separations of some beta-adrenergic agonists and antagonists on AmyCoat column by HPLC.
2010 Jan
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

EP0155229A2
3
EP1553091A1
3

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:27:18 GMT 2023
Edited
by admin
on Fri Dec 15 17:27:18 GMT 2023
Record UNII
S3UWR70991
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
Structure of BOPINDOLOL
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of BOPINDOLOL
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