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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-
Avoid life-threatening adverse drug eventsImprove clinical decision support with information oncontraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support. - 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肾上腺素能受体 antagonistHumans UBeta-2 adrenergic receptor antagonistHumans UAlpha-1A adrenergic receptor antagonistHumans - Absorption
-
Not Available
- Volume of distribution
-
Not Available
- 蛋白质n 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.Improve decision support & research outcomes with our structured adverse effects data. - Toxicity
-
Not Available
- Pathways
-
Pathway Category Bevantolol Action Pathway Drug action - Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug InteractionsLearn More" title="" 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. Aceclofenac Aceclofenac may decrease the antihypertensive activities of Bevantolol. Acemetacin Acemetacin may decrease the antihypertensive activities of Bevantolol. Acetaminophen The metabolism of Bevantolol can be decreased when combined with Acetaminophen. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Bevantolol. Acetophenazine The serum concentration of Bevantolol can be increased when it is combined with Acetophenazine. 
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- 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
- 丙醇
- Chemical TaxonomyProvided byClassyfire
-
- 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
-
- 沃恩威廉姆斯EM:贝凡洛尔: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 TrialsLearn More" title="" 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 光谱类型 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
Targets
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- Kind
- 蛋白质n
- 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肾上腺素能受体
- 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: b的选择性evantolol hydrochloride, a beta 1-adrenoceptor antagonist, in asthmatic patients. Pharmacotherapy. 1984 Jul-Aug;4(4):205-10. [Article]
- 沃恩威廉姆斯EM:贝凡洛尔: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
- 蛋白质n
- Organism
- Humans
- Pharmacological action
-
Unknown
- Actions
-
Antagonist
- General Function
- 蛋白质n 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
- 蛋白质n
- Organism
- Humans
- Pharmacological action
-
Unknown
- Actions
-
Antagonist
- General Function
- 蛋白质n 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
- 蛋白质n
- 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