molecular formula C18H31NO4 B1195378 ビスプロロール CAS No. 66722-44-9

ビスプロロール

カタログ番号: B1195378
CAS番号: 66722-44-9
分子量: 325.4 g/mol
InChIキー: VHYCDWMUTMEGQY-UHFFFAOYSA-N
注意: 研究専用です。人間または獣医用ではありません。
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説明

ビスプロロールは、β遮断薬として一般的に知られている、心臓選択性β1アドレナリン受容体遮断薬です。主に高血圧、狭心症、心不全などの心臓血管疾患の管理に使用されます。 ビスプロロールは、心拍数と収縮力を低下させることで血圧を下げ、心臓の酸素需要を減少させます .

科学的研究の応用

Bisoprolol has a wide range of scientific research applications:

作用機序

ビスプロロールは、心臓のβ1アドレナリン受容体を選択的に遮断することにより、その効果を発揮します。この作用は、心拍数と収縮力を低下させ、心臓の出力と血圧の低下につながります。 関与する分子標的は、交感神経系の一部であるβ1アドレナリン受容体です .

生化学分析

Biochemical Properties

Bisoprolol plays a significant role in biochemical reactions by selectively inhibiting beta-1 adrenergic receptors. These receptors are primarily found in the heart muscle cells and heart conduction tissue . By blocking these receptors, bisoprolol reduces the effects of catecholamines (adrenaline and noradrenaline), which are responsible for increasing heart rate and contractility . This inhibition leads to a decrease in heart rate and myocardial oxygen demand, making bisoprolol effective in managing cardiovascular conditions .

Cellular Effects

Bisoprolol exerts various effects on different types of cells and cellular processes. In myocardial cells, bisoprolol reduces oxygen consumption by decreasing heart rate and contractility . This reduction in workload helps alleviate symptoms of angina and heart failure. Additionally, bisoprolol influences cell signaling pathways by blocking the beta-1 adrenergic receptors, which are involved in the sympathetic nervous system’s response to stress . This blockade results in decreased cyclic AMP (cAMP) levels and reduced activation of protein kinase A (PKA), ultimately leading to decreased phosphorylation of target proteins involved in cardiac contraction .

Molecular Mechanism

The molecular mechanism of bisoprolol involves its selective and competitive binding to beta-1 adrenergic receptors . By blocking these receptors, bisoprolol prevents the binding of catecholamines, thereby inhibiting the downstream signaling cascade that leads to increased heart rate and contractility . This competitive inhibition results in decreased activation of adenylate cyclase, reduced cAMP production, and subsequent inhibition of PKA activity . The overall effect is a reduction in myocardial oxygen demand and improved cardiac function .

Temporal Effects in Laboratory Settings

In laboratory settings, the effects of bisoprolol have been observed to change over time. Bisoprolol exhibits a long plasma-elimination half-life of approximately 10-12 hours, allowing for once-daily dosing . Studies have shown that bisoprolol maintains its efficacy over extended periods, with stable blood pressure control and heart rate reduction . Additionally, bisoprolol is metabolized in the liver and excreted by the kidneys, with no significant accumulation of metabolites . Long-term studies have demonstrated that bisoprolol remains effective and well-tolerated in managing cardiovascular conditions .

Dosage Effects in Animal Models

In animal models, the effects of bisoprolol vary with different dosages. Studies have shown that low to moderate doses of bisoprolol effectively reduce heart rate and blood pressure without causing significant adverse effects . At higher doses, bisoprolol may lead to bradycardia, hypotension, and other cardiovascular complications . Toxicity studies in animals have indicated that bisoprolol has a wide therapeutic window, with a low risk of severe toxicity at therapeutic doses .

Metabolic Pathways

Bisoprolol is metabolized through oxidative pathways in the liver, primarily by the cytochrome P450 enzymes CYP3A4 and CYP2D6 . Approximately 50% of the administered dose is metabolized to inactive metabolites, which are then excreted by the kidneys . The remaining 50% is excreted unchanged in the urine . Bisoprolol’s metabolism is not significantly affected by genetic polymorphisms, making it a reliable medication for a wide range of patients .

Transport and Distribution

Bisoprolol is rapidly absorbed after oral administration, with a bioavailability of over 90% . It is widely distributed throughout the body, with the highest concentrations found in the heart, liver, lungs, and saliva . Bisoprolol crosses the blood-brain barrier, although its central nervous system effects are minimal due to its high selectivity for beta-1 adrenergic receptors . The drug is approximately 30% bound to plasma proteins, which contributes to its distribution and elimination .

Subcellular Localization

At the subcellular level, bisoprolol primarily localizes to the plasma membrane, where it interacts with beta-1 adrenergic receptors . These receptors are part of the G protein-coupled receptor family and are involved in the regulation of cardiac function . Bisoprolol’s selective binding to these receptors inhibits the activation of downstream signaling pathways, leading to decreased cardiac contractility and heart rate . The drug’s localization to the plasma membrane ensures its targeted action on cardiac cells, minimizing off-target effects .

準備方法

ビスプロロールは、いくつかの方法で合成できます。一般的な合成経路の1つは、4-イソプロポキシエトキシメチルフェノールをエピクロロヒドリンと反応させて2-[4-(2-イソプロポキシエトキシ)メチル]フェノキシメチルオキシランを生成することです。 この中間体を次にイソプロピルアミンと反応させてビスプロロールを得ます . 工業生産方法は、多くの場合、類似の工程を伴いますが、大規模生産向けに最適化されており、高収率と純度が保証されています .

化学反応解析

ビスプロロールは、以下を含むさまざまな化学反応を起こします。

    酸化: ビスプロロールは、酸化されてさまざまな代謝物を生成する可能性があります。

    還元: 還元反応はあまり一般的ではありませんが、特定の条件下で発生する可能性があります。

    置換: ビスプロロールは、特にフェノール基とアミン基に関与する置換反応を起こす可能性があります。

これらの反応に使用される一般的な試薬には、過酸化水素などの酸化剤と、水素化ホウ素ナトリウムなどの還元剤が含まれます。 これらの反応から生成される主要な生成物は、一般的に体内で排泄されるか、さらに代謝される代謝物です .

科学研究の応用

ビスプロロールは、さまざまな科学研究の応用があります。

    化学: β遮断薬とそのさまざまな受容体との相互作用に関する研究でモデル化合物として使用されます。

    生物学: 細胞プロセスに対する効果と、βアドレナリン受容体との相互作用について研究されています。

    医学: 心臓血管疾患の治療における有効性を評価するために、臨床試験で広く使用されています。

    産業: 新しい医薬製剤と薬物送達システムの開発に採用されています

化学反応の分析

Bisoprolol undergoes various chemical reactions, including:

    Oxidation: Bisoprolol can be oxidized to form various metabolites.

    Reduction: Reduction reactions are less common but can occur under specific conditions.

    Substitution: Bisoprolol can undergo substitution reactions, particularly involving its phenolic and amine groups.

Common reagents used in these reactions include oxidizing agents like hydrogen peroxide and reducing agents like sodium borohydride. The major products formed from these reactions are typically metabolites that are either excreted or further metabolized in the body .

類似化合物との比較

特性

IUPAC Name

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

InChI Key

VHYCDWMUTMEGQY-UHFFFAOYSA-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

Molecular Formula

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

DSSTOX Substance ID

DTXSID6022682
Record name Bisoprolol
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Molecular Weight

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

Physical Description

Solid
Record name Bisoprolol
Source Human Metabolome Database (HMDB)
URL http://www.hmdb.ca/metabolites/HMDB0014750
Description The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
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Boiling Point

445.0±45.0
Record name Bisoprolol
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Solubility

7.07e-02 g/L
Record name Bisoprolol
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Mechanism of Action

Though the mechanism of action of bisoprolol has not been fully elucidated in hypertension, it is thought that therapeutic effects are achieved through the antagonism of β-1adrenoceptors to result in lower cardiac output. Bisoprolol is a competitive, cardioselective β1-adrenergic antagonist. When β1-receptors (located mainly in the heart) are activated by adrenergic neurotransmitters such as epinephrine, both the blood pressure and heart rate increase, leading to greater cardiovascular work, increasing the demand for oxygen. Bisoprolol reduces cardiac workload by decreasing contractility and the need for oxygen through competitive inhibition of β1-adrenergic receptors. Bisoprolol is also thought to reduce the output of renin in the kidneys, which normally increases blood pressure. Additionally, some central nervous system effects of bisoprolol may include diminishing sympathetic nervous system output from the brain, decreasing blood pressure and heart rate.
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CAS No.

66722-44-9
Record name Bisoprolol
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Record name 2-Propanol, 1-[4-[[2-(1-methylethoxy)ethoxy]methyl]phenoxy]-3-[(1-methylethyl)amino]
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Record name BISOPROLOL
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Record name Bisoprolol
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Record name Bisoprolol
Source Human Metabolome Database (HMDB)
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Explanation HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Melting Point

100-103, 100 °C
Record name Bisoprolol
Source DrugBank
URL https://www.drugbank.ca/drugs/DB00612
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Record name Bisoprolol
Source Human Metabolome Database (HMDB)
URL http://www.hmdb.ca/metabolites/HMDB0014750
Description The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

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

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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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Customer
Q & A

Q1: How does bisoprolol exert its effects on the cardiovascular system?

A1: Bisoprolol is a highly selective β1-adrenergic receptor antagonist []. This means it primarily blocks the action of adrenaline and noradrenaline at the β1-adrenergic receptors found mainly in the heart. [, , ] By blocking these receptors, bisoprolol reduces heart rate, myocardial contractility, and ultimately lowers blood pressure. [, , ]

Q2: Does bisoprolol affect β2-adrenergic receptors?

A2: Bisoprolol exhibits high selectivity for β1-adrenergic receptors, demonstrating minimal effects on bronchial β2-adrenergic receptors at therapeutic doses. [, ] This selectivity makes it a preferred choice for treating hypertension in patients with asthma compared to less selective beta-blockers like atenolol. []

Q3: Are there any potential long-term benefits of bisoprolol beyond its immediate hemodynamic effects?

A3: Research suggests that bisoprolol might provide additional benefits by reducing oxidative stress and inflammation, particularly in the context of heart failure. [, ] Studies in animal models have shown that bisoprolol can improve cardiac function, reduce myocardial damage, and delay the progression of heart failure, potentially by attenuating oxidative stress and reducing the levels of inflammatory markers. []

Q4: What is the molecular formula and weight of bisoprolol?

A4: Bisoprolol has a molecular formula of C18H31NO4 and a molecular weight of 325.44 g/mol. This information is essential for researchers working on synthesizing, characterizing, and formulating bisoprolol for various applications.

Q5: What spectroscopic techniques are commonly used to characterize bisoprolol?

A5: Spectroscopic techniques like UV-Vis spectrophotometry are frequently employed for the analysis of bisoprolol. Bisoprolol exhibits maximum UV absorbance (λmax) at 208 nm. [] This property enables its detection and quantification using high-performance liquid chromatography (HPLC) coupled with UV detectors. [, ]

Q6: What is the pharmacokinetic profile of bisoprolol?

A6: Bisoprolol is well-absorbed after oral administration, reaching peak plasma concentrations within 2-4 hours. [, , ] It has a relatively long half-life of 10-12 hours, allowing for once-daily dosing. [, ] Bisoprolol is primarily metabolized in the liver and excreted in the urine. []

Q7: How do the pharmacokinetic properties of bisoprolol compare to other beta-blockers?

A7: Bisoprolol's longer half-life allows for once-daily dosing compared to other beta-blockers like atenolol, which requires twice-daily administration. [, , ] This difference in dosing frequency can influence patient adherence and potentially impact therapeutic outcomes.

Q8: What are the main clinical indications for bisoprolol?

A8: Bisoprolol is primarily used to treat hypertension, angina pectoris, and chronic heart failure. [, , , ] Its beneficial effects on heart rate, blood pressure, and myocardial oxygen consumption contribute to its efficacy in these conditions. [, , ]

Q9: How does bisoprolol compare to other beta-blockers in treating heart failure?

A10: Clinical trials like the Cardiac Insufficiency Bisoprolol Study (CIBIS) have shown that bisoprolol significantly improves symptoms and reduces mortality in patients with chronic heart failure. [, , ] While other beta-blockers like carvedilol and metoprolol are also effective, studies comparing their efficacy have yielded varying results. [, ]

Q10: What are the potential benefits of combining bisoprolol with other drugs in specific patient populations?

A11: Studies suggest that combining bisoprolol with other antihypertensive agents like amlodipine can significantly improve blood pressure control in patients who haven't responded well to monotherapy. [] Additionally, adding bisoprolol to standard treatment in heart failure patients with preserved ejection fraction has shown potential benefits in specific subgroups. []

Q11: What are some common side effects of bisoprolol?

A12: Although generally well-tolerated, bisoprolol can cause side effects like bradycardia (slow heart rate), fatigue, dizziness, and cold extremities. [, , ] These side effects are often dose-dependent and can be minimized by starting with a low dose and titrating it gradually based on patient response and tolerance. [, ]

Q12: Are there specific patient populations where bisoprolol use should be approached with caution?

A13: Bisoprolol should be used cautiously in patients with pre-existing bradycardia, heart block, or severe heart failure. [] Careful dose adjustments and close monitoring are crucial in these patients to minimize the risk of adverse events.

Q13: What analytical methods are commonly used to quantify bisoprolol in biological samples?

A14: High-performance liquid chromatography (HPLC) coupled with various detection methods, such as UV detection or mass spectrometry (MS), is widely employed to quantify bisoprolol in biological samples like plasma or cell lysates. [, , ] These methods offer high sensitivity and selectivity for accurate determination of bisoprolol concentrations.

Q14: Are there any specialized formulations of bisoprolol available?

A15: Aside from oral tablets, bisoprolol is also available as a transdermal patch. [] This formulation can provide more stable drug levels and potentially reduce certain side effects compared to oral administration. []

Q15: What are some areas for future research on bisoprolol?

A16: Further research is needed to optimize the use of bisoprolol in specific patient populations, such as those with chronic obstructive pulmonary disease (COPD) or elderly patients with hypertension and diabetes. [, ] Additionally, exploring the potential benefits of bisoprolol in delaying the progression of heart failure and reducing cardiovascular events warrants further investigation.

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