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Details

Stereochemistry RACEMIC
Molecular Formula C20H27NO4
Molecular Weight 345.4334
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEVANTOLOL

SMILES

Cc1cccc(c1)OCC(CNCCc2ccc(c(c2)OC)OC)O

InChI

InChIKey=HXLAFSUPPDYFEO-UHFFFAOYSA-N
InChI=1S/C20H27NO4/c1-15-5-4-6-18(11-15)25-14-17(22)13-21-10-9-16-7-8-19(23-2)20(12-16)24-3/h4-8,11-12,17,21-22H,9-10,13-14H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C20H27NO4
Molecular Weight 345.4334
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26961574 | https://www.ncbi.nlm.nih.gov/pubmed/18426954 | https://www.ncbi.nlm.nih.gov/pubmed/7620695 | https://www.ncbi.nlm.nih.gov/pubmed/2572566

Bevantolol (INN) was a drug candidate for angina and hypertension that acted as both a beta blocker and a calcium channel blocker. Animal experiments confirm both agonist and antagonist effects on alpha-receptors, in addition to antagonist activity at beta-1 receptors. By binding and antagonizing beta-1 receptors Bevantolol inhibits the normal normal epinephrine-mediated sympathetic actions such as increased heart rate. This has the effect of decreasing preload and blood pressure. Bevantolol was discovered and developed by Warner-Lambert but in January 1989 the company announced that it had withdrawn the New Drug Application. As of 2016 it wasn't marketed in the US, UK, or Europe.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pharmacology of bevantolol hydrochloride.
1986 Nov 26
Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions.
1987 Jul
Different changes of plasma membrane beta-adrenoceptors in rat heart after chronic administration of propranolol, atenolol and bevantolol.
2007 Jul 12
Patents

Patents

Sample Use Guides

The patients were given bevantolol 100 mg twice daily for four weeks. Exercise tolerance testing was performed at the end of this period; ten to twelve hours after the last dose. If the patient’s symptoms were controlled during this period, as shown by at least 30% increased exercise time, the double-blind phase was conducted on the same daily dose. Patients who were not controlled received bevantolol 400 mg daily either once in the morning or 200 mg twice daily during the double-blind randomised cross-over phase.
Route of Administration: Oral
In Vitro Use Guide
Effects of Bevantolol on salbutamol (3 × 10^-7 M)-induded increases in impulse-evoked 3H efflux from spirally cut pulmonary arteries of guinea-pigs was evaluated. Strips were incubated for 60 min in 10^-7 M [3H]norepinephrine, rinsed, set up then superfused with Krebs solution. Transmural field stimulation (5 Hz, 2 msec, 10V, 20 sec) was applied twice, 90 min and 120 min after the start of superfusion, Bevantolol were superfused simultaneously with salbutamol between 2 periods of stimulation. In the abscissa, the total 3H efflux caused by the 2rid stimulation is expressed as a percentage of that caused by the 1st stimulation.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:07:22 UTC 2021
Edited
by admin
on Fri Jun 25 22:07:22 UTC 2021
Record UNII
34ZXW6ZV21
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BEVANTOLOL
INN   MI   WHO-DD  
INN  
Official Name English
NSC-132348
Code English
2-PROPANOL, 1-((2-(3,4-DIMETHOXYPHENYL)ETHYL)AMINO)-3-(3-METHYLPHENOXY)-, (+/-)-
Systematic Name English
BEVANTOLOL [MI]
Common Name English
(+/-)-1-((3,4-DIMETHOXYPHENETHYL)AMINO)-3-(M-TOLYLOXY)-2-PROPANOL
Systematic Name English
BEVANTOLOL [WHO-DD]
Common Name English
BEVANTOLOL [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC C07AB06
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
NCI_THESAURUS C29576
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
WHO-VATC QC07BB06
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
WHO-ATC C07BB06
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
WHO-VATC QC07AB06
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL314010
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY
PUBCHEM
2372
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY
DRUG BANK
DB01295
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY
MESH
C021148
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY
EVMPD
SUB05808MIG
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY
NCI_THESAURUS
C79556
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY
CAS
59170-23-9
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY
DRUG CENTRAL
360
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY
WIKIPEDIA
BEVANTOLOL
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY
INN
4115
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY
FDA UNII
34ZXW6ZV21
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY
MERCK INDEX
M2465
Created by admin on Fri Jun 25 22:07:22 UTC 2021 , Edited by admin on Fri Jun 25 22:07:22 UTC 2021
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY