BEVANTOLOL

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H27NO4
Molecular Weight	345.4327
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(CCNCC(O)COC2=CC(C)=CC=C2)C=C1OC

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

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Description
Sources: https://www.drugbank.ca/drugs/DB01295
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 Bevantolol was discovered and developed by Warner-Lambert but in January 1989 the company announced that it had withdrawn the New Drug Application.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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor beta 87 Target ID: CHEMBL2094118 Sources: http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3466.1985.tb00473.x/full	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7620695	Primary		Withdrawn	Unknown Approved Use Unknown
Angina of effort 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2572566	Primary		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

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.

Name

Type

Language

BEVANTOLOL

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 [INN]

Common Name

English

Bevantolol [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C07AB06