Identification
- Generic Name
- Bevantolol
- DrugBank Accession Number
- DB01295
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Bevantolol (DB01295)
- Weight
- Average: 345.4327
Monoisotopic: 345.194008357 - Chemical Formula
- C20H27NO4
- 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
Pharmacology
- Indication
For the treatment of angina pectoris and hypertension.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Bevantolol Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Integrate drug-drug
interactions in your softwareAbaloparatide Abaloparatide may increase the hypotensive activities of Bevantolol. Abatacept The metabolism of Bevantolol can be increased when combined with Abatacept. Abiraterone The metabolism of Bevantolol can be decreased when combined with Abiraterone. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Bevantolol. Acebutolol Acebutolol may increase the orthostatic hypotensive activities of Bevantolol. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Bevantolol hydrochloride 4VB9HU07BC 42864-78-8 FJTKCFSPYUMXJB-UHFFFAOYSA-N
Categories
- ATC Codes
- C07AB06 — Bevantolol
- C07AB — Beta blocking agents, selective
- C07A — BETA BLOCKING AGENTS
- C07 — BETA BLOCKING AGENTS
- C — CARDIOVASCULAR SYSTEM
- Drug 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
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic homomonocyclic compound / Dimethoxybenzene / Ether / Hydrocarbon derivative show 13 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- propanolamine (CHEBI:238698)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 34ZXW6ZV21
- CAS number
- 59170-23-9
- 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
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. [Article]
- 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
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Recruiting Treatment Huntington's Disease (HD) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet - 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 splash10-05fu-0910000000-8aa5d780fe28a27f2446 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00ds-0195000000-fa02652f1229f0f96c13 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0090000000-9d9185ae1779135df115 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0933000000-acaefdff582cb85b3e18 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-2920000000-acef2ebbc6057fb3e2ac Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014l-3911000000-fea81954462671eeb5bd Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0931000000-fe56c8b4971d0ea636c4 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 193.0658379 predictedDarkChem Lite v0.1.0 [M-H]- 182.41696 predictedDeepCCS 1.0 (2019) [M+H]+ 193.4071379 predictedDarkChem Lite v0.1.0 [M+H]+ 184.77498 predictedDeepCCS 1.0 (2019) [M+Na]+ 192.8280379 predictedDarkChem Lite v0.1.0 [M+Na]+ 191.13829 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- 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. [Article]
- 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. [Article]
- 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. [Article]
- Vaughan Williams EM: Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions. J Clin Pharmacol. 1987 Jul;27(7):450-60. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
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 . [Article]
- Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
- 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. [Article]
Drug created at June 30, 2007 14:18 / Updated at June 12, 2020 16:51