Page last updated: 2024-11-04

bevantolol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

bevantolol: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

bevantolol : A propanolamine that is 3-aminopropane-1,2-diol in which the hydrogen of the primary hydroxy group is substituted by 3-methylphenyl and one of the hydrogens attached to the nitrogen is substituted by 2-(3,4-dimethoxyphenyl)ethyl. A beta1 adrenoceptor antagonist, it has been shown to be as effective as other beta-blockers for the treatment of angina pectoris and hypertension. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID2372
CHEMBL ID314010
CHEBI ID238698
SCHEMBL ID49721
MeSH IDM0075645

Synonyms (45)

Synonym
CHEMBL314010
unii-34zxw6zv21
34zxw6zv21 ,
nsc 132348
59170-23-9
nsc132348
nsc-132348
2-propanol, 1-((2-(3,4-dimethoxyphenyl)ethyl)amino)-3-(3-methylphenoxy)-
bevantolol [inn:ban]
brn 2769444
bevantololum [inn-latin]
bevantolol
1-(3,4-dimethoxyphenethylamino)-3-(m-tolyloxy)-2-propanol
1-((2-(3,4-dimethoxyphenyl)ethyl)amino)-3-(3-methylphenoxy)-2-propanol
DB01295
(+/-)-bevantolol
1-(3,4-dimethoxyphenethylamino)-3-m-tolyloxy-propan-2-ol
1-[2-(3,4-dimethoxy-phenyl)-ethylamino]-3-m-tolyloxy-propan-2-ol
L013370
1-[2-(3,4-dimethoxyphenyl)ethylamino]-3-(3-methylphenoxy)propan-2-ol
(+-)-bevantolol
bevantololum
chebi:238698 ,
1-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-3-(3-methylphenoxy)propan-2-ol
AKOS016014301
smr002529477
MLS003876814
2-propanol, 1-((2-(3,4-dimethoxyphenyl)ethyl)amino)-3-(3-methylphenoxy)-, (+/-)-
bevantolol [inn]
bevantolol [who-dd]
bevantolol [mi]
(+/-)-1-((3,4-dimethoxyphenethyl)amino)-3-(m-tolyloxy)-2-propanol
SCHEMBL49721
HXLAFSUPPDYFEO-UHFFFAOYSA-N
1-[[2-(3,4-dimethoxyphenyl) ethyl]amino]-3-(3-methyl-phenoxy)-2-propanol
1-((3,4-dimethoxyphenethyl)amino)-3-(m-tolyloxy)propan-2-ol
HMS3604B08
A917858
DTXSID70860597
Q1956953
(+/-)-bevantolol; dl-bevantolol; nsc 132348
()-bevantolol; dl-bevantolol; nsc 132348
HY-A0249
EN300-741859
Z31382955

Research Excerpts

Overview

Bevantolol is a cardioselective, beta-adrenoreceptor antagonist, devoid of intrinsic beta sympathomimetic activity and with weak membrane-stabilizing and local anesthetic properties. Bevantolol appeared to be an effective, well-tolerated drug in the management of angina pectoris.

ExcerptReferenceRelevance
"Bevantolol appeared to be an effective, well-tolerated drug in the management of angina pectoris."( Effectiveness of bevantolol in the treatment of angina--a placebo-controlled study.
Farnham, DJ, 1986
)
1.33
"Bevantolol is a cardioselective, beta-adrenoreceptor antagonist, devoid of intrinsic beta sympathomimetic activity and with weak membrane-stabilizing and local anesthetic properties. "( Pharmacology of bevantolol hydrochloride.
Kaplan, HR, 1986
)
2.06
"Bevantolol is a beta-1 adrenoceptor antagonist that has been shown to be as effective as other beta blockers for the treatment of angina pectoris and hypertension. "( Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions.
Vaughan Williams, EM, 1987
)
3.16
"Bevantolol is a new, cardioselective beta-receptor antagonist that undergoes extensive hepatic biotransformation. "( Bevantolol disposition in patients with hepatic cirrhosis.
Lawand, S; Matthews, C; McCans, J; Nattel, S, 1987
)
3.16
"Bevantolol is a new beta-adrenoceptor antagonist which possesses a relatively high degree of selectivity for beta 1-adrenoceptors. "( Bevantolol. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in hypertension and angina pectoris.
Benfield, P; Frishman, WH; Goldberg, RJ, 1988
)
3.16
"Bevantolol is a novel beta 1-selective beta-adrenoceptor antagonist. "( Bevantolol vs propranolol: a double-blind controlled trial in essential hypertension.
Maclean, D, 1988
)
3.16

Effects

Bevantolol has remarkably few side effects, does not cause cold extremities, and does not significantly affect glomerular filtration rate in patients with renal impairment.

ExcerptReferenceRelevance
"Thus bevantolol has relative beta 1-adrenoceptor antagonist selectivity."( Selectivity of bevantolol hydrochloride, a beta 1-adrenoceptor antagonist, in asthmatic patients.
Löfdahl, CG; Svedmyr, K; Svedmyr, N,
)
0.94
"bevantolol has remarkably few side effects, does not cause cold extremities, and does not significantly affect glomerular filtration rate in patients with renal impairment. "( Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions.
Vaughan Williams, EM, 1987
)
3.16

Treatment

ExcerptReferenceRelevance
"Bevantolol treatment (250 mg kg-1) increased the Bmax to 137% and completely inhibited the downregulation of beta-adrenoceptors by stress."( Effects of bevantolol HCl on immobilization stress-induced hypertension and central beta-adrenoceptors in rats.
Kigoshi, S; Muramatsu, I; Takita, M, 1993
)
1.4

Toxicity

ExcerptReferenceRelevance
" The drug was associated with a low incidence of adverse experiences similar to that observed with placebo."( Safety profile of bevantolol.
Bray, JS, 1986
)
0.6

Pharmacokinetics

Bevantolol (the hydrochloride salt) has pharmacokinetic properties that are clinically advantageous. It had a short serum half-life and high systemic availability after oral administration.

ExcerptReferenceRelevance
"The pharmacokinetic handling of the beta 1 selective adrenoceptor blocking drug, bevantolol, was studied in 12 healthy volunteers."( Pharmacokinetics and concentration--effect relationships of bevantolol (CI-775) in normal volunteers.
Anderson, AI; Drummer, OH; Louis, WJ; McNeil, JJ,
)
0.6
"Bevantolol (the hydrochloride salt) has pharmacokinetic properties that are clinically advantageous."( Clinical pharmacokinetics and metabolism of bevantolol.
Latts, JR, 1986
)
1.97
" Bevantolol had a short serum half-life (86 +/- 33 min) and high systemic availability after oral administration."( Pharmacokinetic parameters of bevantolol in volunteers.
van Brummelen, P; Vermeij, P, 1986
)
1.47
" However, disproportionate increases in Cmax, and in AUC, but not in tmax values were observed between Days 1 and 14."( Comparative single dose and steady-state pharmacokinetics of bevantolol in young and elderly subjects.
Darke, AC; Greene, DS; Kinkel, AW; Selen, A; Welling, PG, 1986
)
0.51
" The kinetics of the drug (including plasma drug levels, plasma half-life and plasma clearance) and its effects on renal function were observed for 24 hours."( Renal hemodynamics and pharmacokinetics of bevantolol in patients with impaired renal function.
Campese, VM; Massry, SG; Solimon, M, 1986
)
0.53
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Bioavailability

The bioavailability of bevantolol was compared in 12 healthy volunteers given single doses of the drug as the HCl salt after an overnight fast, or 15 minutes before or after a standardized breakfast in a nonblind, randomized crossover design.

ExcerptReferenceRelevance
" After oral administration of the same dose, the bioavailability averaged 57% (range 26-98%) and peak plasma levels varied over a threefold range."( Pharmacokinetics and concentration--effect relationships of bevantolol (CI-775) in normal volunteers.
Anderson, AI; Drummer, OH; Louis, WJ; McNeil, JJ,
)
0.37
" Bevantolol is well absorbed orally (greater than 70%); and the systemic bioavailability is 60%."( Clinical pharmacokinetics and metabolism of bevantolol.
Latts, JR, 1986
)
1.44
"The bioavailability of bevantolol was compared in 12 healthy volunteers given single doses of the drug as the HCl salt after an overnight fast, or 15 minutes before or after a standardized breakfast in a nonblind, randomized crossover design."( The influence of food on the oral absorption of bevantolol.
Goulet, JR; Kinkel, AW; Nelson, C; Randinitis, EJ; Toothaker, RD, 1987
)
0.84
"The quantitative structure-bioavailability relationship of 232 structurally diverse drugs was studied to evaluate the feasibility of constructing a predictive model for the human oral bioavailability of prospective new medicinal agents."( QSAR model for drug human oral bioavailability.
Topliss, JG; Yoshida, F, 2000
)
0.31

Dosage Studied

Bevantolol may be useful as first-line therapy in a once-daily dosage for the treatment of essential hypertension.

ExcerptRelevanceReference
" Plasma levels after oral dosing with food showed an average 75-min delay in achievement of peak plasma levels and an average 14% increase in the extent of bioavailability of the drug."( Pharmacokinetics and concentration--effect relationships of bevantolol (CI-775) in normal volunteers.
Anderson, AI; Drummer, OH; Louis, WJ; McNeil, JJ,
)
0.37
"In a placebo controlled double-blind cross-over study following a dose titration phase, we compared the efficacy of benantolol, a new beta 1 adrenoceptor antagonist with alpha-adrenoceptor partial antagonist activity at 12 and 24 hours after dosing in patients with angina of effort."( Comparison of once and twice daily oral dosing schedules of bevantolol, a new beta-adrenoceptor antagonist with alpha-adrenoceptor partial antagonist activity in patients with angina of effort.
Bray, CL; Hillier, V; Molajo, AO, 1989
)
0.52
" Bevantolol itself induced bradycardia, so that it was not possible to estimate the pA2 from nonparallel dose-response curves relating isoprenaline concentration to tachycardia."( Cardiovascular effects of bevantolol, a selective beta 1-adrenoceptor antagonist with a novel pharmacological profile.
Dukes, ID; Vaughan Williams, EM, 1985
)
1.48
" Twice a day dosing is indicated since efficacy was evident 12 hours post-dosing."( Dose response studies of bevantolol in hypertensive patients.
Okawa, KK, 1986
)
0.57
" These results suggest that bevantolol may be useful as first-line therapy in a once-daily dosage for the treatment of essential hypertension."( Once- and twice-daily bevantolol for systemic hypertension using 24-hour ambulatory intraarterial blood pressure recording.
Al-Khawaja, IM; Caruana, MP; Prince, H; Raftery, EB; Whittington, J, 1986
)
0.88
" Renal impairment did not change the percentages of the bevantolol dosage excreted unchanged or as conjugated drug in the urine, and no toxic or active drug metabolites accumulated in the blood."( Renal hemodynamics and pharmacokinetics of bevantolol in patients with impaired renal function.
Campese, VM; Massry, SG; Solimon, M, 1986
)
0.78
" Recordings were obtained 2 and 24 h following a single dose and 24 h after continuous dosage for 7 days."( Peripheral vascular effects of beta-adrenoceptor blockade: comparison of two agents.
Bowcock, SA; Camm, AJ; Cooke, ED; Maltz, MB; Smith, RE; Watkins, CJ, 1987
)
0.27
" Dosing was stopped if symptoms warranted or if there was a fall of greater than or equal to 20% in the forced expiratory volume in 1 second."( Respiratory and cardiac effects of metoprolol and bevantolol in patients with asthma.
Ahmad, D; Carruthers, SG; Darke, AC; Parsons, J; Wilcox, PG, 1986
)
0.52
" A dose-response curve was then plotted after inhalation of the beta 2-adrenoceptor agonist terbutaline."( Ventilatory effects of atenolol and bevantolol in asthma.
Folgering, HT; Lammers, JW; van Herwaarden, CL, 1985
)
0.54
" Dose-response curves to a beta agonist, albuterol, were obtained in six normal subjects by measuring specific airway conductance (sGaw) after increasing doses of inhaled albuterol."( Assessment of bronchial beta blockade after oral bevantolol.
Baldwin, CJ; Gribbin, HR; Mackay, AD; Tattersfield, AE, 1981
)
0.52
" Following a single oral dose of placebo, bevantolol 75 or 150 mg or propranolol hydrochloride 40 mg, forced expiratory volume in 1 second (FEV1), heart rate, blood pressure and skeletal muscle tremor were measured before and after 4 increasing intravenous doses of terbutaline sulfate to establish terbutaline dose-response curves."( Selectivity of bevantolol hydrochloride, a beta 1-adrenoceptor antagonist, in asthmatic patients.
Löfdahl, CG; Svedmyr, K; Svedmyr, N,
)
0.75
" The method has been applied to the determination of (-)-(S)- and (+)-(R)-bevantolol in plasma from healthy volunteers dosed with racemic bevantolol hydrochloride."( Determination of bevantolol enantiomers in human plasma by coupled achiral-chiral high performance-liquid chromatography.
Kang, JS; Kim, KH; Oh, JW; Sin, KS; Trung, TQ, 2007
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
beta-adrenergic antagonistAn agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
calcium channel blockerOne of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools.
antihypertensive agentAny drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
anti-arrhythmia drugA drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
propanolamine
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
Bevantolol Action Pathway478

Bioassays (12)

Assay IDTitleYearJournalArticle
AID425652Total body clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID27167Delta logD (logD6.5 - logD7.4)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID226029Tested for the multidrug resistance reversal activity against P388 murine leukemia cell line, activity is expressed as RF(ED50 with no adriamycin (ADR)/ED50 with 200 nM ADR)2000Journal of medicinal chemistry, Nov-16, Volume: 43, Issue:23
Classification of multidrug-resistance reversal agents using structure-based descriptors and linear discriminant analysis.
AID29359Ionization constant (pKa)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID425653Renal clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID540211Fraction unbound in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID29813Oral bioavailability in human2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID28681Partition coefficient (logD6.5)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (68)

TimeframeStudies, This Drug (%)All Drugs %
pre-199043 (63.24)18.7374
1990's10 (14.71)18.2507
2000's13 (19.12)29.6817
2010's1 (1.47)24.3611
2020's1 (1.47)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.50

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index29.50 (24.57)
Research Supply Index4.62 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.50)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials27 (36.49%)5.53%
Reviews2 (2.70%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other45 (60.81%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Phase IIb, Randomized, Double-blind, Placebo-controlled Study in Parallel Groups Assessing the Efficacy and Safety of Two Doses of SOM3355 in Patients Suffering From Huntington's Disease With Choreic Movements [NCT05475483]Phase 2129 participants (Anticipated)Interventional2022-08-02Recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]