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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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
1-(3,4-Dimethoxyphenethylamino)-3-(m-tolyloxy)-2-propanol
Bevantololum [inn-latin]
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Antihypertensive Agents
  • Adrenergic beta-Antagonists
  • Calcium Channel Blockers
CAS number 59170-23-9
Weight Average: 345.4327
Monoisotopic: 345.194008357
Chemical Formula C20H27NO4
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Catecholamines and Derivatives
Substructures
  • Hydroxy Compounds
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Amino Alcohols
  • Catechols
  • Phenethylamines
  • Aromatic compounds
  • Anisoles
  • Alcohols and Polyols
  • Phenyl Esters
  • Catecholamines and Derivatives
Pharmacology
Indication For the treatment of angina pectoris and hypertension.
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.
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 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 137-138 °C PhysProp
logP 3.00 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 1.37e-02 g/l 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 ChemAxon
rotatable bond count 10 ChemAxon
refractivity 98.54 ChemAxon
polarizability 39.75 ChemAxon
References
Synthesis Reference Not Available
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
Resource Link
PubChem Compound 2372 Link_out
PubChem Substance 46506014 Link_out
ChemSpider 2282 Link_out
ChEBI 238698 Link_out
ChEMBL 238698 Link_out
Therapeutic Targets Database DAP000897 Link_out
PharmGKB PA164743236 Link_out
ATC Codes
  • C07AB06
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Chlorpropamide The beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
Clonidine Increased hypertension when clonidine stopped
Dihydroergotamine Ischemia with risk of gangrene
Disopyramide The beta-blocker, bevantolol, may increase the toxicity of disopyramide.
Epinephrine Hypertension, then bradycardia
Ergotamine Ischemia with risk of gangrene
Fenoterol Antagonism
Formoterol Antagonism
Gliclazide The beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
Glyburide The beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
Ibuprofen Risk of inhibition of renal prostaglandins
Indomethacin Risk of inhibition of renal prostaglandins
Insulin Glargine The beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
Methysergide Ischemia with risk of gangrene
Orciprenaline Antagonism
Pipobroman Antagonism
Piroxicam Risk of inhibition of renal prostaglandins
Prazosin Risk of hypotension at the beginning of therapy
Repaglinide The beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
Terbutaline Antagonism
Food Interactions Not Available
Targets

1. Beta-1 adrenergic receptor

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: antagonist

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

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: antagonist

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

Organism class: human
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 30, 2007 08:18 / Updated on February 08, 2013 16:20