Bevantolol

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
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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Contraindications & Blackbox Warnings
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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
antagonist
Humans
UBeta-2 adrenergic receptor
antagonist
Humans
UAlpha-1A adrenergic receptor
antagonist
Humans
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
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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
Abaloparatide 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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Food Interactions
Not Available

Products

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Product Ingredients
Ingredient UNII CAS InChI Key
Bevantolol hydrochloride 4VB9HU07BC 42864-78-8 FJTKCFSPYUMXJB-UHFFFAOYSA-N

Categories

ATC Codes
C07AB06 — Bevantolol C07BB06 — Bevantolol and thiazides
Drug Categories
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
  1. 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]
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
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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
  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. [Article]
  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. [Article]
  3. 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]
  4. 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]
  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. [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
  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. [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
  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. [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
  1. 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]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
  3. 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