Bevantolol - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (3)

Targets (3)Biointeractions (3)

Identification

Name

Bevantolol

Accession Number

DB01295

Type

Small Molecule

Groups

Approved

Description

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. Mechanism of Action Animal experiments confirm both agonist and antagonist effects on alpha-receptors, in addition to antagonist activity at beta-1 receptors.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

(+-)-Bevantolol

1-((2-(3,4-Dimethoxyphenyl)ethyl)amino)-3-(3-methylphenoxy)-2-propanol

1-(3,4-Dimethoxyphenethylamino)-3-(m-tolyloxy)-2-propanol

1-(3,4-Dimethoxyphenethylamino)-3-m-tolyloxy-propan-2-ol

1-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-3-m-tolyloxy-propan-2-ol

Bevantololum

External IDs

Not Available

Product Ingredients

Not Available

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Not Available

Brand mixtures

Not Available

Categories

UNII

34ZXW6ZV21

CAS number

59170-23-9

Weight

Average: 345.4327
Monoisotopic: 345.194008357

Chemical Formula

C₂₀H₂₇NO₄

InChI Key

HXLAFSUPPDYFEO-UHFFFAOYSA-N

InChI

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

IUPAC Name

1-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-3-(3-methylphenoxy)propan-2-ol

SMILES

COC1=C(OC)C=C(CCNCC(O)COC2=CC=CC(C)=C2)C=C1

Pharmacology

Indication

For the treatment of angina pectoris and hypertension.

Structured Indications

Not Available

Pharmacodynamics

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.

Mechanism of action

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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Beta-1 adrenergic receptor	Protein	yes	antagonist	Human	P08588	details
Beta-2 adrenergic receptor	Protein	unknown	antagonist	Human	P07550	details
Alpha-1A adrenergic receptor	Protein	unknown	antagonist	Human	P35348	details

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Pathway	Category	SMPDB ID
Bevantolol Action Pathway	Drug action	SMP00668

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
1,10-Phenanthroline	1,10-Phenanthroline may increase the bradycardic activities of Bevantolol.	Experimental
4-Methoxyamphetamine	4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Experimental, Illicit
Aceclofenac	Aceclofenac may decrease the antihypertensive activities of Bevantolol.	Approved
Acepromazine	Acepromazine may increase the hypotensive activities of Bevantolol.	Approved, Vet Approved
Aceprometazine	Aceprometazine may increase the hypotensive activities of Bevantolol.	Approved
Acetohexamide	Bevantolol may increase the hypoglycemic activities of Acetohexamide.	Withdrawn
Acetylcholine	The risk or severity of adverse effects can be increased when Bevantolol is combined with Acetylcholine.	Approved
Acetyldigitoxin	Bevantolol may increase the bradycardic activities of Acetyldigitoxin.	Approved
Acetylsalicylic acid	Acetylsalicylic acid may decrease the antihypertensive activities of Bevantolol.	Approved, Vet Approved
Adapalene	Adapalene may decrease the antihypertensive activities of Bevantolol.	Approved
Agmatine	Agmatine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Experimental, Investigational
Alfentanil	Alfentanil may increase the bradycardic activities of Bevantolol.	Approved, Illicit
Alfuzosin	Bevantolol may increase the orthostatic hypotensive activities of Alfuzosin.	Approved, Investigational
Alimemazine	Alimemazine may increase the hypotensive activities of Bevantolol.	Approved, Vet Approved
Ambenonium	Ambenonium may increase the bradycardic activities of Bevantolol.	Approved
Amiodarone	Amiodarone may increase the bradycardic activities of Bevantolol.	Approved, Investigational
Amobarbital	The serum concentration of Bevantolol can be decreased when it is combined with Amobarbital.	Approved, Illicit
Amodiaquine	The metabolism of Bevantolol can be decreased when combined with Amodiaquine.	Approved
Andrographolide	HMPL-004 may decrease the antihypertensive activities of Bevantolol.	Investigational
Anisodamine	Anisodamine may decrease the antihypertensive activities of Bevantolol.	Investigational
Antipyrine	Antipyrine may decrease the antihypertensive activities of Bevantolol.	Approved
Apocynin	Acetovanillone may decrease the antihypertensive activities of Bevantolol.	Investigational
Apomorphine	Apomorphine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Investigational
Apremilast	Apremilast may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Arecoline	The risk or severity of adverse effects can be increased when Bevantolol is combined with Arecoline.	Experimental
Azapropazone	Azapropazone may decrease the antihypertensive activities of Bevantolol.	Withdrawn
Azelastine	Azelastine may decrease the antihypertensive activities of Bevantolol.	Approved
Balsalazide	Balsalazide may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Barbexaclone	The serum concentration of Bevantolol can be decreased when it is combined with Barbexaclone.	Experimental
Barbital	The serum concentration of Bevantolol can be decreased when it is combined with Barbital.	Illicit
Benoxaprofen	Benoxaprofen may decrease the antihypertensive activities of Bevantolol.	Withdrawn
Benzphetamine	Benzphetamine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Illicit
Bethanechol	The risk or severity of adverse effects can be increased when Bevantolol is combined with Bethanechol.	Approved
Bethanidine	Bethanidine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Betulinic Acid	Betulinic Acid may decrease the antihypertensive activities of Bevantolol.	Investigational
BL-1020	BL-1020 may increase the hypotensive activities of Bevantolol.	Investigational
Brimonidine	Brimonidine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Bromfenac	Bromfenac may decrease the antihypertensive activities of Bevantolol.	Approved
Bromocriptine	Bromocriptine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Investigational
Bucillamine	Bucillamine may decrease the antihypertensive activities of Bevantolol.	Investigational
Bucindolol	Bevantolol may increase the orthostatic hypotensive activities of Bucindolol.	Investigational
Bupivacaine	The serum concentration of Bupivacaine can be increased when it is combined with Bevantolol.	Approved, Investigational
Cabergoline	Bevantolol may increase the vasoconstricting activities of Cabergoline.	Approved
Carbachol	The risk or severity of adverse effects can be increased when Bevantolol is combined with Carbachol.	Approved
Carprofen	Carprofen may decrease the antihypertensive activities of Bevantolol.	Approved, Vet Approved, Withdrawn
Carvedilol	Bevantolol may increase the orthostatic hypotensive activities of Carvedilol.	Approved, Investigational
Castanospermine	Castanospermine may decrease the antihypertensive activities of Bevantolol.	Experimental
Celecoxib	Celecoxib may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Cevimeline	The risk or severity of adverse effects can be increased when Bevantolol is combined with Cevimeline.	Approved
Chloroquine	The metabolism of Bevantolol can be decreased when combined with Chloroquine.	Approved, Vet Approved
Chlorpromazine	Chlorpromazine may increase the hypotensive activities of Bevantolol.	Approved, Vet Approved
Chlorpropamide	Bevantolol may increase the hypoglycemic activities of Chlorpropamide.	Approved
Choline magnesium trisalicylate	Trisalicylate-choline may decrease the antihypertensive activities of Bevantolol.	Approved
Clonidine	Clonidine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Clonixin	Clonixin may decrease the antihypertensive activities of Bevantolol.	Approved
Curcumin	Curcumin may decrease the antihypertensive activities of Bevantolol.	Investigational
Dapoxetine	The serum concentration of Bevantolol can be increased when it is combined with Dapoxetine.	Investigational
Decamethonium	Decamethonium may increase the bradycardic activities of Bevantolol.	Approved
Demecarium	Demecarium may increase the bradycardic activities of Bevantolol.	Approved
Deslanoside	Bevantolol may increase the bradycardic activities of Deslanoside.	Approved
Desvenlafaxine	The serum concentration of Bevantolol can be increased when it is combined with Desvenlafaxine.	Approved
Dexmedetomidine	Dexmedetomidine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Vet Approved
Diclofenac	Diclofenac may decrease the antihypertensive activities of Bevantolol.	Approved, Vet Approved
Diflunisal	Diflunisal may decrease the antihypertensive activities of Bevantolol.	Approved
Digitoxin	Bevantolol may increase the bradycardic activities of Digitoxin.	Approved
Digoxin	Bevantolol may increase the bradycardic activities of Digoxin.	Approved
Dihydroergotamine	Dihydroergotamine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Diltiazem	Diltiazem may increase the hypotensive activities of Bevantolol.	Approved
Dipivefrin	Dipivefrin may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Dipyridamole	Dipyridamole may increase the bradycardic activities of Bevantolol.	Approved
Disopyramide	Disopyramide may increase the bradycardic activities of Bevantolol.	Approved
Donepezil	Donepezil may increase the bradycardic activities of Bevantolol.	Approved
Doxazosin	Bevantolol may increase the orthostatic hypotensive activities of Doxazosin.	Approved
Dronedarone	Dronedarone may increase the bradycardic activities of Bevantolol.	Approved
Droxicam	Droxicam may decrease the antihypertensive activities of Bevantolol.	Approved
Droxidopa	Droxidopa may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Investigational
Duloxetine	The serum concentration of Bevantolol can be increased when it is combined with Duloxetine.	Approved
Duvelisib	Duvelisib may decrease the antihypertensive activities of Bevantolol.	Investigational
E-6201	E6201 may decrease the antihypertensive activities of Bevantolol.	Investigational
Ebselen	Ebselen may decrease the antihypertensive activities of Bevantolol.	Investigational
Echothiophate	Echothiophate may increase the bradycardic activities of Bevantolol.	Approved
Edrophonium	Edrophonium may increase the bradycardic activities of Bevantolol.	Approved
Ephedra	Ephedra may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Nutraceutical, Withdrawn
Epibatidine	The risk or severity of adverse effects can be increased when Bevantolol is combined with EPIBATIDINE.	Experimental
Epinephrine	Epinephrine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Vet Approved
Epirizole	Epirizole may decrease the antihypertensive activities of Bevantolol.	Approved
Ergoloid mesylate	Bevantolol may increase the vasoconstricting activities of Ergoloid mesylate.	Approved
Ergonovine	Bevantolol may increase the vasoconstricting activities of Ergonovine.	Approved
Ergotamine	Ergotamine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Etanercept	Etanercept may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Etodolac	Etodolac may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational, Vet Approved
Etofenamate	Etofenamate may decrease the antihypertensive activities of Bevantolol.	Approved
Etomidate	Etomidate may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Etoperidone	The serum concentration of Bevantolol can be increased when it is combined with Etoperidone.	Approved
Etoricoxib	Etoricoxib may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Fenbufen	Fenbufen may decrease the antihypertensive activities of Bevantolol.	Approved
Fenoprofen	Fenoprofen may decrease the antihypertensive activities of Bevantolol.	Approved
Fentanyl	Fentanyl may increase the bradycardic activities of Bevantolol.	Approved, Illicit, Investigational, Vet Approved
Fingolimod	Bevantolol may increase the bradycardic activities of Fingolimod.	Approved, Investigational
Floctafenine	The risk or severity of adverse effects can be increased when Floctafenine is combined with Bevantolol.	Approved, Withdrawn
Fluoxetine	The serum concentration of Bevantolol can be increased when it is combined with Fluoxetine.	Approved, Vet Approved
Fluphenazine	Fluphenazine may increase the hypotensive activities of Bevantolol.	Approved
Flurbiprofen	Flurbiprofen may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Galantamine	Galantamine may increase the bradycardic activities of Bevantolol.	Approved
Gallamine Triethiodide	Gallamine Triethiodide may increase the bradycardic activities of Bevantolol.	Approved
Ginkgo biloba	Ginkgo biloba may increase the bradycardic activities of Bevantolol.	Approved, Nutraceutical
Glibornuride	Bevantolol may increase the hypoglycemic activities of Glibornuride.	Withdrawn
Gliclazide	Bevantolol may increase the hypoglycemic activities of Gliclazide.	Approved
Glimepiride	Bevantolol may increase the hypoglycemic activities of Glimepiride.	Approved
Glipizide	Bevantolol may increase the hypoglycemic activities of Glipizide.	Approved
Gliquidone	Bevantolol may increase the hypoglycemic activities of Gliquidone.	Approved
Glisoxepide	Bevantolol may increase the hypoglycemic activities of Glisoxepide.	Approved
Glyburide	Bevantolol may increase the hypoglycemic activities of Glyburide.	Approved
GTS-21	The risk or severity of adverse effects can be increased when Bevantolol is combined with GTS-21.	Investigational
Guanabenz	Guanabenz may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Guanfacine	Guanfacine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Investigational
Hexobarbital	The serum concentration of Bevantolol can be decreased when it is combined with Hexobarbital.	Approved
Higenamine	Higenamine may decrease the antihypertensive activities of Bevantolol.	Investigational
Huperzine A	Huperzine A may increase the bradycardic activities of Bevantolol.	Investigational
Hydroxychloroquine	The metabolism of Bevantolol can be decreased when combined with Hydroxychloroquine.	Approved
Ibuprofen	Ibuprofen may decrease the antihypertensive activities of Bevantolol.	Approved
Ibuproxam	Ibuproxam may decrease the antihypertensive activities of Bevantolol.	Withdrawn
Icatibant	Icatibant may decrease the antihypertensive activities of Bevantolol.	Approved
Indalpine	The serum concentration of Bevantolol can be increased when it is combined with Indalpine.	Investigational, Withdrawn
Indomethacin	Indomethacin may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Indoprofen	Indoprofen may decrease the antihypertensive activities of Bevantolol.	Withdrawn
Indoramin	Bevantolol may increase the orthostatic hypotensive activities of Indoramin.	Withdrawn
Insulin Pork	Bevantolol may increase the hypoglycemic activities of Insulin Pork.	Approved
Isoflurophate	Isoflurophate may increase the bradycardic activities of Bevantolol.	Approved, Withdrawn
Isoxicam	Isoxicam may decrease the antihypertensive activities of Bevantolol.	Withdrawn
Kebuzone	Kebuzone may decrease the antihypertensive activities of Bevantolol.	Experimental
Ketoprofen	Ketoprofen may decrease the antihypertensive activities of Bevantolol.	Approved, Vet Approved
Ketorolac	Ketorolac may decrease the antihypertensive activities of Bevantolol.	Approved
Labetalol	Bevantolol may increase the orthostatic hypotensive activities of Labetalol.	Approved
Leflunomide	Leflunomide may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Levomilnacipran	The serum concentration of Bevantolol can be increased when it is combined with Levomilnacipran.	Approved
Lidocaine	The serum concentration of Lidocaine can be increased when it is combined with Bevantolol.	Approved, Vet Approved
Lisofylline	Lisofylline may decrease the antihypertensive activities of Bevantolol.	Investigational
Lobeline	The risk or severity of adverse effects can be increased when Bevantolol is combined with Lobeline.	Investigational
Lofexidine	Lofexidine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Investigational
Lornoxicam	Lornoxicam may decrease the antihypertensive activities of Bevantolol.	Approved
Loxoprofen	Loxoprofen may decrease the antihypertensive activities of Bevantolol.	Approved
Lumiracoxib	Lumiracoxib may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Magnesium salicylate	Magnesium salicylate may decrease the antihypertensive activities of Bevantolol.	Approved
Malathion	Malathion may increase the bradycardic activities of Bevantolol.	Approved, Investigational
Masoprocol	Masoprocol may decrease the antihypertensive activities of Bevantolol.	Approved
Meclofenamic acid	Meclofenamic acid may decrease the antihypertensive activities of Bevantolol.	Approved, Vet Approved
Mefenamic acid	Mefenamic acid may decrease the antihypertensive activities of Bevantolol.	Approved
Mefloquine	Mefloquine may increase the bradycardic activities of Bevantolol.	Approved
Meloxicam	Meloxicam may decrease the antihypertensive activities of Bevantolol.	Approved, Vet Approved
Memantine	Memantine may increase the bradycardic activities of Bevantolol.	Approved, Investigational
Mepivacaine	The serum concentration of Mepivacaine can be increased when it is combined with Bevantolol.	Approved, Vet Approved
Mesalazine	Mesalazine may decrease the antihypertensive activities of Bevantolol.	Approved
Mesoridazine	Mesoridazine may increase the hypotensive activities of Bevantolol.	Approved
Metamizole	Metamizole may decrease the antihypertensive activities of Bevantolol.	Withdrawn
Methacholine	The risk or severity of adverse effects can be increased when Bevantolol is combined with Methacholine.	Approved
Methamphetamine	Methamphetamine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Illicit
Methanesulfonyl Fluoride	Methanesulfonyl Fluoride may increase the bradycardic activities of Bevantolol.	Investigational
Methohexital	The serum concentration of Bevantolol can be decreased when it is combined with Methohexital.	Approved
Methotrimeprazine	Methotrimeprazine may increase the hypotensive activities of Bevantolol.	Approved
Methylene blue	Methylene blue may increase the hypotensive activities of Bevantolol.	Investigational
Methylphenobarbital	The serum concentration of Bevantolol can be decreased when it is combined with Methylphenobarbital.	Approved
Midodrine	Bevantolol may increase the bradycardic activities of Midodrine.	Approved
Milnacipran	The serum concentration of Bevantolol can be increased when it is combined with Milnacipran.	Approved
Minaprine	Minaprine may increase the bradycardic activities of Bevantolol.	Approved
Mizoribine	Mizoribine may decrease the antihypertensive activities of Bevantolol.	Investigational
Moricizine	Moricizine may increase the hypotensive activities of Bevantolol.	Approved, Withdrawn
Mycophenolate mofetil	Mycophenolate mofetil may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Mycophenolic acid	Mycophenolic acid may decrease the antihypertensive activities of Bevantolol.	Approved
Nabumetone	Nabumetone may decrease the antihypertensive activities of Bevantolol.	Approved
Nafamostat	Nafamostat may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Naftifine	Naftifine may decrease the antihypertensive activities of Bevantolol.	Approved
Naphazoline	Naphazoline may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Naproxen	Naproxen may decrease the antihypertensive activities of Bevantolol.	Approved, Vet Approved
NCX 4016	NCX 4016 may decrease the antihypertensive activities of Bevantolol.	Investigational
Nefazodone	The serum concentration of Bevantolol can be increased when it is combined with Nefazodone.	Approved, Withdrawn
Neostigmine	Neostigmine may increase the bradycardic activities of Bevantolol.	Approved, Vet Approved
Nepafenac	Nepafenac may decrease the antihypertensive activities of Bevantolol.	Approved
Nicotine	The risk or severity of adverse effects can be increased when Bevantolol is combined with Nicotine.	Approved
Nifedipine	Nifedipine may increase the hypotensive activities of Bevantolol.	Approved
Niflumic Acid	Niflumic Acid may decrease the antihypertensive activities of Bevantolol.	Approved
Nimesulide	Nimesulide may decrease the antihypertensive activities of Bevantolol.	Approved, Withdrawn
Nitroaspirin	Nitroaspirin may decrease the antihypertensive activities of Bevantolol.	Investigational
Norepinephrine	Norepinephrine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Oleandrin	Bevantolol may increase the bradycardic activities of Anvirzel.	Experimental
Olopatadine	Olopatadine may decrease the antihypertensive activities of Bevantolol.	Approved
Olsalazine	Olsalazine may decrease the antihypertensive activities of Bevantolol.	Approved
Ouabain	Bevantolol may increase the bradycardic activities of Ouabain.	Approved
Oxaprozin	Oxaprozin may decrease the antihypertensive activities of Bevantolol.	Approved
Oxymetazoline	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Oxyphenbutazone	Oxyphenbutazone may decrease the antihypertensive activities of Bevantolol.	Withdrawn
Paliperidone	Paliperidone may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Parecoxib	Parecoxib may decrease the antihypertensive activities of Bevantolol.	Approved
Paroxetine	The serum concentration of Bevantolol can be increased when it is combined with Paroxetine.	Approved, Investigational
Pentobarbital	The serum concentration of Bevantolol can be decreased when it is combined with Pentobarbital.	Approved, Vet Approved
Perazine	Perazine may increase the hypotensive activities of Bevantolol.	Investigational
Pergolide	Pergolide may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Vet Approved, Withdrawn
Perphenazine	Perphenazine may increase the hypotensive activities of Bevantolol.	Approved
Phenobarbital	The serum concentration of Bevantolol can be decreased when it is combined with Phenobarbital.	Approved
Phenylbutazone	Phenylbutazone may decrease the antihypertensive activities of Bevantolol.	Approved, Vet Approved
Phenylpropanolamine	Phenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Vet Approved, Withdrawn
Physostigmine	Physostigmine may increase the bradycardic activities of Bevantolol.	Approved
Pilocarpine	The risk or severity of adverse effects can be increased when Bevantolol is combined with Pilocarpine.	Approved
Pimecrolimus	Pimecrolimus may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Pirfenidone	Pirfenidone may decrease the antihypertensive activities of Bevantolol.	Investigational
Piroxicam	Piroxicam may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Prazosin	Bevantolol may increase the orthostatic hypotensive activities of Prazosin.	Approved
Primaquine	The metabolism of Bevantolol can be decreased when combined with Primaquine.	Approved
Primidone	The serum concentration of Bevantolol can be decreased when it is combined with Primidone.	Approved, Vet Approved
Prochlorperazine	Prochlorperazine may increase the hypotensive activities of Bevantolol.	Approved, Vet Approved
Promazine	Promazine may increase the hypotensive activities of Bevantolol.	Approved, Vet Approved
Promethazine	Promethazine may increase the hypotensive activities of Bevantolol.	Approved
Propacetamol	Propacetamol may decrease the antihypertensive activities of Bevantolol.	Approved
Propafenone	The serum concentration of Bevantolol can be increased when it is combined with Propafenone.	Approved
Pseudoephedrine	Pseudoephedrine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
PTC299	PTC299 may decrease the antihypertensive activities of Bevantolol.	Investigational
Pyridostigmine	Pyridostigmine may increase the bradycardic activities of Bevantolol.	Approved
Regorafenib	Regorafenib may increase the bradycardic activities of Bevantolol.	Approved
Remifentanil	Remifentanil may increase the bradycardic activities of Bevantolol.	Approved
Reserpine	Reserpine may increase the hypotensive activities of Bevantolol.	Approved
Resveratrol	Resveratrol may decrease the antihypertensive activities of Bevantolol.	Experimental, Investigational
Rifampicin	The serum concentration of Bevantolol can be decreased when it is combined with Rifampicin.	Approved
Rifapentine	The serum concentration of Bevantolol can be decreased when it is combined with Rifapentine.	Approved
Risperidone	Risperidone may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Investigational
Rivastigmine	Rivastigmine may increase the bradycardic activities of Bevantolol.	Approved, Investigational
Rofecoxib	Rofecoxib may decrease the antihypertensive activities of Bevantolol.	Investigational, Withdrawn
Ropinirole	Ropinirole may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved, Investigational
Salicylamide	Salicylamide may decrease the antihypertensive activities of Bevantolol.	Approved
Salicylic acid	Salicylic acid may decrease the antihypertensive activities of Bevantolol.	Approved, Vet Approved
Salsalate	Salsalate may decrease the antihypertensive activities of Bevantolol.	Approved
Secobarbital	The serum concentration of Bevantolol can be decreased when it is combined with Secobarbital.	Approved, Vet Approved
Sertraline	The serum concentration of Bevantolol can be increased when it is combined with Sertraline.	Approved
Silodosin	Bevantolol may increase the orthostatic hypotensive activities of Silodosin.	Approved
SRT501	SRT501 may decrease the antihypertensive activities of Bevantolol.	Investigational
Sufentanil	Sufentanil may increase the bradycardic activities of Bevantolol.	Approved, Investigational
Sulfasalazine	Sulfasalazine may decrease the antihypertensive activities of Bevantolol.	Approved
Sulindac	Sulindac may decrease the antihypertensive activities of Bevantolol.	Approved
Suprofen	Suprofen may decrease the antihypertensive activities of Bevantolol.	Approved, Withdrawn
Tacrine	Tacrine may increase the bradycardic activities of Bevantolol.	Withdrawn
Tamsulosin	Bevantolol may increase the orthostatic hypotensive activities of Tamsulosin.	Approved, Investigational
Tenoxicam	Tenoxicam may decrease the antihypertensive activities of Bevantolol.	Approved
Terazosin	Bevantolol may increase the orthostatic hypotensive activities of Terazosin.	Approved
Teriflunomide	Teriflunomide may decrease the antihypertensive activities of Bevantolol.	Approved
Thiamylal	The serum concentration of Bevantolol can be decreased when it is combined with Thiamylal.	Approved, Vet Approved
Thiethylperazine	Thiethylperazine may increase the hypotensive activities of Bevantolol.	Withdrawn
Thiopental	The serum concentration of Bevantolol can be decreased when it is combined with Thiopental.	Approved, Vet Approved
Thioridazine	Thioridazine may increase the hypotensive activities of Bevantolol.	Withdrawn
Tiaprofenic acid	Tiaprofenic acid may decrease the antihypertensive activities of Bevantolol.	Approved
Tinoridine	Tinoridine may decrease the antihypertensive activities of Bevantolol.	Investigational
Tizanidine	Tizanidine may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Tolazamide	Bevantolol may increase the hypoglycemic activities of Tolazamide.	Approved
Tolbutamide	Bevantolol may increase the hypoglycemic activities of Tolbutamide.	Approved
Tolfenamic Acid	Tolfenamic Acid may decrease the antihypertensive activities of Bevantolol.	Approved
Tolmetin	Tolmetin may decrease the antihypertensive activities of Bevantolol.	Approved
Tranilast	Tranilast may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational
Trifluoperazine	Trifluoperazine may increase the hypotensive activities of Bevantolol.	Approved
Triflupromazine	Triflupromazine may increase the hypotensive activities of Bevantolol.	Approved, Vet Approved
Trimazosin	Bevantolol may increase the orthostatic hypotensive activities of Trimazosin.	Experimental
Tubocurarine	Tubocurarine may increase the bradycardic activities of Bevantolol.	Approved
Valdecoxib	Valdecoxib may decrease the antihypertensive activities of Bevantolol.	Investigational, Withdrawn
Varenicline	The risk or severity of adverse effects can be increased when Bevantolol is combined with Varenicline.	Approved, Investigational
Venlafaxine	The serum concentration of Bevantolol can be increased when it is combined with Venlafaxine.	Approved
Verapamil	Verapamil may increase the hypotensive activities of Bevantolol.	Approved
Xylometazoline	Xylometazoline may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Zaltoprofen	Zaltoprofen may decrease the antihypertensive activities of Bevantolol.	Approved
Zileuton	Zileuton may decrease the antihypertensive activities of Bevantolol.	Approved, Investigational, Withdrawn
Zimelidine	The serum concentration of Bevantolol can be increased when it is combined with Zimelidine.	Withdrawn
Zomepirac	Zomepirac may decrease the antihypertensive activities of Bevantolol.	Withdrawn

Food Interactions

Not Available

References

Synthesis Reference

Yutaka Nomura, "Process for preparation of bevantolol hydrochloride." U.S. Patent US5382689, issued December, 1974.

US5382689

General References

Vaughan Williams EM: Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions. J Clin Pharmacol. 1987 Jul;27(7):450-60. [PubMed:2888789 ]

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB15409
PubChem Compound	2372
PubChem Substance	46506014
ChemSpider	2282
ChEBI	238698
ChEMBL	CHEMBL314010
Therapeutic Targets Database	DAP000897
PharmGKB	PA164743236

ATC Codes

C07AB06 — Bevantolol

C07BB06 — Bevantolol and thiazides

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Clinical Trials

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	137-138 °C	PhysProp
logP	3.00	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	0.0137 mg/mL	ALOGPS
logP	2.83	ALOGPS
logP	3.03	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	59.95 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	98.54 m³·mol^-1	ChemAxon
Polarizability	39.75 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.8271
Blood Brain Barrier	-	0.9297
Caco-2 permeable	-	0.6012
P-glycoprotein substrate	Substrate	0.8119
P-glycoprotein inhibitor I	Inhibitor	0.625
P-glycoprotein inhibitor II	Inhibitor	0.8061
Renal organic cation transporter	Non-inhibitor	0.6935
CYP450 2C9 substrate	Non-substrate	0.7741
CYP450 2D6 substrate	Substrate	0.5792
CYP450 3A4 substrate	Substrate	0.5727
CYP450 1A2 substrate	Non-inhibitor	0.6261
CYP450 2C9 inhibitor	Non-inhibitor	0.9068
CYP450 2D6 inhibitor	Non-inhibitor	0.7311
CYP450 2C19 inhibitor	Non-inhibitor	0.9218
CYP450 3A4 inhibitor	Non-inhibitor	0.6133
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9339
Ames test	Non AMES toxic	0.9124
Carcinogenicity	Non-carcinogens	0.926
Biodegradation	Not ready biodegradable	0.8696
Rat acute toxicity	2.0966 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.6187
hERG inhibition (predictor II)	Inhibitor	0.8681

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Benzenoids

Sub Class

Benzene and substituted derivatives

Direct Parent

Dimethoxybenzenes

Alternative Parents

Phenethylamines / Phenoxy compounds / Anisoles / Toluenes / Aralkylamines / Alkyl aryl ethers / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds

Substituents

Dimethoxybenzene / O-dimethoxybenzene / Phenethylamine / Anisole / Phenol ether / Phenoxy compound / Alkyl aryl ether / Aralkylamine / Toluene / 1,2-aminoalcohol

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

propanolamine (CHEBI:238698 )

Targets

Details

1. Beta-1 adrenergic receptor

Kind: Protein
Organism: Human
Pharmacological action: yes
Actions: antagonist

General Function:: Receptor signaling protein activity
Specific Function:: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:: ADRB1
Uniprot ID:: P08588
Molecular Weight:: 51322.1 Da

References

Hino T, Sakai K, Ichihara K, Abiko Y: Attenuation of ischaemia-induced regional myocardial acidosis by bevantolol, a beta 1-adrenoceptor antagonist, in dogs. Pharmacol Toxicol. 1989 Apr;64(4):324-8. [PubMed:2568629 ]
Dukes ID, Vaughan Williams EM: Cardiovascular effects of bevantolol, a selective beta 1-adrenoceptor antagonist with a novel pharmacological profile. Br J Pharmacol. 1985 Feb;84(2):365-80. [PubMed:2858236 ]
Lofdahl CG, Svedmyr K, Svedmyr N: Selectivity of bevantolol hydrochloride, a beta 1-adrenoceptor antagonist, in asthmatic patients. Pharmacotherapy. 1984 Jul-Aug;4(4):205-10. [PubMed:6148733 ]
Vaughan Williams EM: Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions. J Clin Pharmacol. 1987 Jul;27(7):450-60. [PubMed:2888789 ]
Horinouchi T, Morishima S, Tanaka T, Suzuki F, Tanaka Y, Koike K, Miwa S, Muramatsu I: Different changes of plasma membrane beta-adrenoceptors in rat heart after chronic administration of propranolol, atenolol and bevantolol. Life Sci. 2007 Jul 12;81(5):399-404. Epub 2007 Jun 16. [PubMed:17628611 ]

Details

2. Beta-2 adrenergic receptor

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: antagonist

General Function:: Protein homodimerization activity
Specific Function:: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:: ADRB2
Uniprot ID:: P07550
Molecular Weight:: 46458.32 Da

References

Horinouchi T, Morishima S, Tanaka T, Suzuki F, Tanaka Y, Koike K, Miwa S, Muramatsu I: Different changes of plasma membrane beta-adrenoceptors in rat heart after chronic administration of propranolol, atenolol and bevantolol. Life Sci. 2007 Jul 12;81(5):399-404. Epub 2007 Jun 16. [PubMed:17628611 ]

Details

3. Alpha-1A adrenergic receptor

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: antagonist

General Function:: Protein heterodimerization activity
Specific Function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular Weight:: 51486.005 Da

References

Shiraishi K, Moriya M, Miyake N, Takayanagi I: Alpha 1-adrenoceptor blocking activities of bevantolol hydrochloride(NC-1400) and labetalol in rat isolated thoracic aorta--do they distinguish between subtypes? Gen Pharmacol. 1992 Sep;23(5):843-5. [PubMed:1358746 ]

Drug created on June 30, 2007 08:18 / Updated on July 18, 2017 16:58

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Structure for DB01295 (Bevantolol)

Targets

References

References

References