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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Bevantolol
- Accession Number
- DB01295
- Type
- Small Molecule
- Groups
- Experimental
- 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
Structure for Bevantolol (DB01295)
- 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
- Bevantolol
- Bévantolol
- Bevantololum
- Product Ingredients
Ingredient UNII CAS InChI Key Bevantolol hydrochloride 4VB9HU07BC 42864-78-8 FJTKCFSPYUMXJB-UHFFFAOYSA-N - Categories
- Adrenergic Agents
- Adrenergic alpha-1 Receptor Antagonists
- Adrenergic alpha-Antagonists
- Adrenergic Antagonists
- Adrenergic beta-1 Receptor Antagonists
- Adrenergic beta-Antagonists
- Agents causing hyperkalemia
- Alcohols
- Amines
- Amino Alcohols
- Antihypertensive Agents
- Beta Blocking Agents and Thiazides
- Beta Blocking Agents, Selective
- Beta Blocking Agents, Selective, and Thiazides
- Bradycardia-Causing Agents
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Neurotransmitter Agents
- Propanols
- 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.
- 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 Actions Organism ABeta-1 adrenergic receptor antagonistHumans UBeta-2 adrenergic receptor antagonistHumans UAlpha-1A adrenergic receptor antagonistHumans - 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 Bevantolol Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional Data1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine The metabolism of Bevantolol can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine. 1-benzylimidazole 1-benzylimidazole may decrease the antihypertensive activities of Bevantolol. 1,10-Phenanthroline 1,10-Phenanthroline may increase the bradycardic activities of Bevantolol. 2,4-thiazolidinedione The therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Bevantolol. 2,5-Dimethoxy-4-ethylamphetamine The therapeutic efficacy of Bevantolol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine. 2,5-Dimethoxy-4-ethylthioamphetamine The therapeutic efficacy of Bevantolol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine. 25-desacetylrifapentine The metabolism of Bevantolol can be increased when combined with 25-desacetylrifapentine. 3-isobutyl-1-methyl-7H-xanthine The risk or severity of adverse effects can be increased when Bevantolol is combined with 3-isobutyl-1-methyl-7H-xanthine. 4-Bromo-2,5-dimethoxyamphetamine The therapeutic efficacy of Bevantolol can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine. 4-Bromo-2,5-dimethoxyphenethylamine The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Bevantolol. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- 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
- Human Metabolome Database
- HMDB0015409
- PubChem Compound
- 2372
- PubChem Substance
- 46506014
- ChemSpider
- 2282
- ChEBI
- 238698
- ChEMBL
- CHEMBL314010
- Therapeutic Targets Database
- DAP000897
- PharmGKB
- PA164743236
- Wikipedia
- Bevantolol
- ATC Codes
- C07AB06 — Bevantolol
- C07AB — Beta blocking agents, selective
- C07A — BETA BLOCKING AGENTS
- C07 — BETA BLOCKING AGENTS
- C — CARDIOVASCULAR SYSTEM
Clinical Trials
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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Methoxybenzenes
- Direct Parent
- Dimethoxybenzenes
- Alternative Parents
- Phenethylamines / Phenoxy compounds / Anisoles / Toluenes / Aralkylamines / Alkyl aryl ethers / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds show 1 more
- Substituents
- Dimethoxybenzene / O-dimethoxybenzene / Phenethylamine / Anisole / Phenol ether / Phenoxy compound / Alkyl aryl ether / Aralkylamine / Toluene / 1,2-aminoalcohol show 13 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- propanolamine (CHEBI:238698)
Targets
- Kind
- Protein
- Organism
- Humans
- 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 e...
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- 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]
- Kind
- Protein
- Organism
- Humans
- 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 ...
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- 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]
- Kind
- Protein
- Organism
- Humans
- 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) prot...
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- 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]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [PubMed:17125412]
- Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [PubMed:14732961]
- Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [PubMed:27836712]
Drug created on June 30, 2007 08:18 / Updated on June 12, 2020 10:51
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