U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C20H27NO4.ClH
Molecular Weight 381.8943
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEVANTOLOL HYDROCHLORIDE

SMILES

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

InChI

InChIKey=FJTKCFSPYUMXJB-UHFFFAOYSA-N
InChI=1S/C20H27NO4.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 Bevantolol was discovered and developed by Warner-Lambert but in January 1989 the company announced that it had withdrawn the New Drug Application.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
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 Sat Jun 26 13:29:48 UTC 2021
Edited
by admin
on Sat Jun 26 13:29:48 UTC 2021
Record UNII
4VB9HU07BC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BEVANTOLOL HYDROCHLORIDE
JAN   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
SOM3355
Code English
CL-775
Code English
BEVANTOLOL HCL
Common Name English
CALVAN
Brand Name English
SOM-3355
Code English
BEVANTOLOL HYDROCHLORIDE [MI]
Common Name English
2-PROPANOL, 1-((2-(3,4-DIMETHOXYPHENYL)ETHYL)AMINO)-3-(3-METHYLPHENOXY)-, HYDROCHLORIDE, (+/-)-
Systematic Name English
CL 775
Code English
BEVANTOLOL HYDROCHLORIDE [JAN]
Common Name English
BEVANTOLOL HYDROCHLORIDE [WHO-DD]
Common Name English
(+/-)-1-((3,4-DIMETHOXYPHENETHYL)AMINO)-3-(M-TOLYLOXY)-2-PROPANOL HYDROCHLORIDE
Systematic Name English
BEVANTOLOL HYDROCHLORIDE [USAN]
Common Name English
VANTOL
Brand Name English
BEVANTOLOL HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Sat Jun 26 13:29:48 UTC 2021 , Edited by admin on Sat Jun 26 13:29:48 UTC 2021
Code System Code Type Description
DRUG BANK
DBSALT002868
Created by admin on Sat Jun 26 13:29:48 UTC 2021 , Edited by admin on Sat Jun 26 13:29:48 UTC 2021
PRIMARY
ChEMBL
CHEMBL314010
Created by admin on Sat Jun 26 13:29:48 UTC 2021 , Edited by admin on Sat Jun 26 13:29:48 UTC 2021
PRIMARY
NCI_THESAURUS
C142952
Created by admin on Sat Jun 26 13:29:48 UTC 2021 , Edited by admin on Sat Jun 26 13:29:48 UTC 2021
PRIMARY
CAS
42864-78-8
Created by admin on Sat Jun 26 13:29:48 UTC 2021 , Edited by admin on Sat Jun 26 13:29:48 UTC 2021
PRIMARY
EVMPD
SUB00793MIG
Created by admin on Sat Jun 26 13:29:48 UTC 2021 , Edited by admin on Sat Jun 26 13:29:48 UTC 2021
PRIMARY
MESH
C021148
Created by admin on Sat Jun 26 13:29:48 UTC 2021 , Edited by admin on Sat Jun 26 13:29:48 UTC 2021
PRIMARY
PUBCHEM
39324
Created by admin on Sat Jun 26 13:29:48 UTC 2021 , Edited by admin on Sat Jun 26 13:29:48 UTC 2021
PRIMARY
EPA CompTox
42864-78-8
Created by admin on Sat Jun 26 13:29:48 UTC 2021 , Edited by admin on Sat Jun 26 13:29:48 UTC 2021
PRIMARY
FDA UNII
4VB9HU07BC
Created by admin on Sat Jun 26 13:29:48 UTC 2021 , Edited by admin on Sat Jun 26 13:29:48 UTC 2021
PRIMARY
MERCK INDEX
M2465
Created by admin on Sat Jun 26 13:29:48 UTC 2021 , Edited by admin on Sat Jun 26 13:29:48 UTC 2021
PRIMARY Merck Index
Related Record Type Details
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY