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Identification
NameBevantolol
Accession NumberDB01295
Typesmall molecule
Groupsapproved
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
Thumb
Synonyms
SynonymLanguageCode
1-(3,4-Dimethoxyphenethylamino)-3-(m-tolyloxy)-2-propanolNot AvailableNot Available
BevantololumLatinINN
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number59170-23-9
WeightAverage: 345.4327
Monoisotopic: 345.194008357
Chemical FormulaC20H27NO4
InChI KeyHXLAFSUPPDYFEO-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
[2-(3,4-dimethoxyphenyl)ethyl][2-hydroxy-3-(3-methylphenoxy)propyl]amine
SMILES
COC1=C(OC)C=C(CCNCC(O)COC2=CC=CC(C)=C2)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenethylamines
Direct parentPhenethylamines
Alternative parentsAnisoles; Toluenes; Alkyl Aryl Ethers; Secondary Alcohols; 1,2-Aminoalcohols; Polyamines; Dialkylamines
Substituentsphenol ether; anisole; alkyl aryl ether; toluene; 1,2-aminoalcohol; secondary alcohol; secondary aliphatic amine; secondary amine; ether; polyamine; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the phenethylamines. These are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
Pharmacology
IndicationFor the treatment of angina pectoris and hypertension.
PharmacodynamicsBevantolol 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 actionAnimal 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Bevantolol Action PathwayDrug actionSMP00668
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9068
CYP450 2D6 substrate Non-inhibitor 0.7311
CYP450 2C19 substrate Non-inhibitor 0.9218
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point137-138 °CPhysProp
logP3.00HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility1.37e-02 g/lALOGPS
logP2.83ALOGPS
logP3.03ChemAxon
logS-4.4ALOGPS
pKa (strongest acidic)14.09ChemAxon
pKa (strongest basic)9.31ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count2ChemAxon
polar surface area59.95ChemAxon
rotatable bond count10ChemAxon
refractivity98.54ChemAxon
polarizability39.75ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

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

US5382689
General Reference
  1. Vaughan Williams EM: Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions. J Clin Pharmacol. 1987 Jul;27(7):450-60. Pubmed
External Links
ResourceLink
PubChem Compound2372
PubChem Substance46506014
ChemSpider2282
ChEBI238698
ChEMBLCHEMBL314010
Therapeutic Targets DatabaseDAP000897
PharmGKBPA164743236
ATC CodesC07AB06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
ChlorpropamideThe beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
ClonidineIncreased hypertension when clonidine stopped
DihydroergotamineIschemia with risk of gangrene
DisopyramideThe beta-blocker, bevantolol, may increase the toxicity of disopyramide.
EpinephrineHypertension, then bradycardia
ErgotamineIschemia with risk of gangrene
FenoterolAntagonism
FormoterolAntagonism
GliclazideThe beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
GlyburideThe beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
IbuprofenRisk of inhibition of renal prostaglandins
IndomethacinRisk of inhibition of renal prostaglandins
Insulin GlargineThe beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
MethysergideIschemia with risk of gangrene
OrciprenalineAntagonism
PipobromanAntagonism
PiroxicamRisk of inhibition of renal prostaglandins
PrazosinRisk of hypotension at the beginning of therapy
RepaglinideThe beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
TerbutalineAntagonism
Food InteractionsNot Available

Targets

1. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

References:

  1. 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
  2. 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
  3. 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
  4. Vaughan Williams EM: Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions. J Clin Pharmacol. 1987 Jul;27(7):450-60. Pubmed
  5. 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

2. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

References:

  1. 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

3. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

References:

  1. 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

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Drug created on June 30, 2007 08:18 / Updated on September 16, 2013 17:14