molecular formula C18H31NO4 B011590 r-(+)-bisoprolol CAS No. 111051-40-2

r-(+)-bisoprolol

Cat. No.: B011590
CAS No.: 111051-40-2
M. Wt: 325.4 g/mol
InChI Key: VHYCDWMUTMEGQY-QGZVFWFLSA-N
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Description

®-Bisoprolol is a selective beta-1 adrenergic receptor blocker used primarily in the treatment of cardiovascular diseases such as hypertension and heart failure. It is the enantiomer of bisoprolol, meaning it has a specific three-dimensional arrangement that allows it to interact more effectively with biological targets.

Scientific Research Applications

®-Bisoprolol has a wide range of applications in scientific research:

    Chemistry: It is used as a model compound in studies of beta-blocker synthesis and reactivity.

    Biology: Researchers study its effects on beta-1 adrenergic receptors in various biological systems.

    Medicine: It is extensively researched for its therapeutic effects in treating cardiovascular diseases.

    Industry: The compound is used in the development of new pharmaceuticals and in the study of drug-receptor interactions.

Preparation Methods

Synthetic Routes and Reaction Conditions

The synthesis of ®-Bisoprolol typically involves the following steps:

    Starting Material: The synthesis begins with the preparation of a chiral intermediate, often derived from natural sources or through asymmetric synthesis.

    Key Reactions: The intermediate undergoes several chemical transformations, including alkylation, reduction, and cyclization, to form the desired ®-Bisoprolol.

    Reaction Conditions: These reactions are carried out under controlled conditions, such as specific temperatures, pressures, and pH levels, to ensure high yield and purity.

Industrial Production Methods

In industrial settings, the production of ®-Bisoprolol involves large-scale chemical reactors and continuous flow processes. The use of catalysts and optimized reaction conditions helps in achieving efficient production with minimal by-products.

Chemical Reactions Analysis

Types of Reactions

®-Bisoprolol undergoes various chemical reactions, including:

    Oxidation: The compound can be oxidized to form corresponding oxides.

    Reduction: Reduction reactions can convert ®-Bisoprolol into its reduced forms.

    Substitution: It can undergo substitution reactions where functional groups are replaced by other groups.

Common Reagents and Conditions

    Oxidation: Common oxidizing agents include potassium permanganate and hydrogen peroxide.

    Reduction: Reducing agents like lithium aluminum hydride are used.

    Substitution: Conditions vary depending on the substituent, but typically involve nucleophiles or electrophiles.

Major Products Formed

The major products formed from these reactions depend on the specific reagents and conditions used. For example, oxidation may yield bisoprolol oxides, while reduction may produce bisoprolol alcohols.

Mechanism of Action

®-Bisoprolol exerts its effects by selectively blocking beta-1 adrenergic receptors, which are primarily found in the heart. This action reduces heart rate and contractility, leading to decreased blood pressure and reduced workload on the heart. The molecular targets include the beta-1 adrenergic receptors, and the pathways involved are related to the sympathetic nervous system.

Comparison with Similar Compounds

Similar Compounds

    Metoprolol: Another selective beta-1 blocker used for similar indications.

    Atenolol: Also a selective beta-1 blocker with similar therapeutic uses.

    Propranolol: A non-selective beta-blocker that affects both beta-1 and beta-2 receptors.

Uniqueness

®-Bisoprolol is unique due to its high selectivity for beta-1 adrenergic receptors, which results in fewer side effects related to beta-2 receptor blockade, such as bronchoconstriction. This makes it particularly suitable for patients with respiratory conditions who require beta-blocker therapy.

Properties

IUPAC Name

(2R)-1-(propan-2-ylamino)-3-[4-(2-propan-2-yloxyethoxymethyl)phenoxy]propan-2-ol
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI

InChI=1S/C18H31NO4/c1-14(2)19-11-17(20)13-23-18-7-5-16(6-8-18)12-21-9-10-22-15(3)4/h5-8,14-15,17,19-20H,9-13H2,1-4H3/t17-/m1/s1
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI Key

VHYCDWMUTMEGQY-QGZVFWFLSA-N
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Canonical SMILES

CC(C)NCC(COC1=CC=C(C=C1)COCCOC(C)C)O
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Isomeric SMILES

CC(C)NC[C@H](COC1=CC=C(C=C1)COCCOC(C)C)O
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Molecular Formula

C18H31NO4
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Molecular Weight

325.4 g/mol
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

CAS No.

111051-40-2
Record name Bisoprolol, (R)-
Source ChemIDplus
URL https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0111051402
Description ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system.
Record name BISOPROLOL, (R)-
Source FDA Global Substance Registration System (GSRS)
URL https://gsrs.ncats.nih.gov/ginas/app/beta/substances/L68D148Q8N
Description The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions.
Explanation Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.

Synthesis routes and methods

Procedure details

A solution of bisoprolol was prepared as follows. To 529.2 g of purified water were added 180 g of bisoprolol fumarate 2:1. The mixture was stirred for 10 minutes to dissolve the drug. 10.8 g of talc USP (Whitaker, Clark and Daniels Inc., South Plainfield, N.J., USA) were added to the solution and the mixture was stirred for 20 minutes.
[Compound]
Name
talc
Quantity
10.8 g
Type
reactant
Reaction Step One
Quantity
180 g
Type
reactant
Reaction Step Two
Name
Quantity
529.2 g
Type
solvent
Reaction Step Two

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.

Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring Relevance Heuristic
Min. plausibility 0.01
Model Template_relevance
Template Set Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph 6

Feasible Synthetic Routes

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