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Bevantolol

July 24, 2017
Common Name

Bevantolol 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+-)-BevantololChEBI 1-((2-(3,4-Dimethoxyphenyl)ethyl)amino)-3-(3-methylphenoxy)-2-propanolChEBI 1-(3,4-dimethoxyphenethylamino)-3-(m-Tolyloxy)-2-propanolChEBI 1-(3,4-dimethoxyphenethylamino)-3-m-Tolyloxy-propan-2-olChEBI 1-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-3-m-tolyloxy-propan-2-olChEBI BevantololumChEBI Bevantolol hydrochlorideMeSH

Chemical Formlia

C20H27NO4 Average Molecliar Weight

345.4327 Monoisotopic Molecliar Weight

345.194008357 IUPAC Name

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

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

59170-23-9 SMILES

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

InChI Identifier

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

InChI Key

HXLAFSUPPDYFEO-UHFFFAOYSA-N Chemical 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
  • Hydrocarbon derivatives

    • Substituents

  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Phenethylamine
  • Anisole
  • Phenol ether
  • Phenoxy compound
  • Alkyl aryl ether
  • Aralkylamine
  • Toluene
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Ether
  • Secondary aliphatic amine
  • Secondary amine
  • Alcohol
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • propanolamine (CHEBI:238698 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adrenergic beta-Antagonists
  • Antihypertensive Agents
  • Calcium Channel Blockers

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point137 – 138 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.37e-02 g/LNot Available LogP3.00HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source Water Solubility0.014 mg/mLALOGPS 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 Area59.95 Å2ChemAxon Rotatable Bond Count10ChemAxon Refractivity98.54 m3·mol-1ChemAxon Polarizability39.75 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Bevantolol Action PathwaySMP00668Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01295

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01295

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01295 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    2282 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB15409 Metagene Link

    HMDB15409 METLIN ID

    Not Available PubChem Compound

    2372 PDB ID

    Not Available ChEBI ID

    238698

    Product: Balsalazide

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Vaughan Williams EM: Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions. J Clin Pharmacol. 1987 Jul;27(7):450-60. [PubMed:2888789 ]

    Enzymes

    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    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
    Gene Name:
    ADRB1
    Uniprot ID:
    P08588
    Molecular weight:
    51322.1
    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:2568629 ]
    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:2858236 ]
    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:6148733 ]
    4. Vaughan Williams EM: Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions. J Clin Pharmacol. 1987 Jul;27(7):450-60. [PubMed:2888789 ]
    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:17628611 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    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:
    46458.3
    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:17628611 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    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
    Gene Name:
    ADRA1A
    Uniprot ID:
    P35348
    Molecular weight:
    51486.0
    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:1358746 ]

    PMID: 16354677

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