Bisoprolol
Vue d'ensemble
Description
Le bisoprolol est un agent bêta-bloqueur bêta-1 adrénergique sélectif, communément appelé bêta-bloqueur. Il est principalement utilisé pour gérer les maladies cardiovasculaires telles que l’hypertension artérielle, l’angine de poitrine et l’insuffisance cardiaque. Le this compound agit en réduisant la fréquence cardiaque et la force de contraction, ce qui abaisse la pression artérielle et réduit les besoins en oxygène du cœur .
Applications De Recherche Scientifique
Bisoprolol has a wide range of scientific research applications:
Chemistry: Used as a model compound in studies involving beta-blockers and their interactions with various receptors.
Biology: Studied for its effects on cellular processes and its interactions with beta-adrenergic receptors.
Medicine: Extensively used in clinical trials to evaluate its efficacy in treating cardiovascular diseases.
Industry: Employed in the development of new pharmaceutical formulations and drug delivery systems
Mécanisme D'action
Le bisoprolol exerce ses effets en bloquant sélectivement les récepteurs bêta-1 adrénergiques du cœur. Cette action réduit la fréquence cardiaque et la force de contraction, ce qui entraîne une diminution du débit cardiaque et de la pression artérielle. Les cibles moléculaires impliquées comprennent les récepteurs bêta-1 adrénergiques, qui font partie du système nerveux sympathique .
Analyse Biochimique
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, this compound 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 this compound effective in managing cardiovascular conditions .
Cellular Effects
This compound exerts various effects on different types of cells and cellular processes. In myocardial cells, this compound reduces oxygen consumption by decreasing heart rate and contractility . This reduction in workload helps alleviate symptoms of angina and heart failure. Additionally, this compound 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 this compound involves its selective and competitive binding to beta-1 adrenergic receptors . By blocking these receptors, this compound 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 this compound have been observed to change over time. This compound exhibits a long plasma-elimination half-life of approximately 10-12 hours, allowing for once-daily dosing . Studies have shown that this compound maintains its efficacy over extended periods, with stable blood pressure control and heart rate reduction . Additionally, this compound is metabolized in the liver and excreted by the kidneys, with no significant accumulation of metabolites . Long-term studies have demonstrated that this compound remains effective and well-tolerated in managing cardiovascular conditions .
Dosage Effects in Animal Models
In animal models, the effects of this compound vary with different dosages. Studies have shown that low to moderate doses of this compound effectively reduce heart rate and blood pressure without causing significant adverse effects . At higher doses, this compound may lead to bradycardia, hypotension, and other cardiovascular complications . Toxicity studies in animals have indicated that this compound has a wide therapeutic window, with a low risk of severe toxicity at therapeutic doses .
Metabolic Pathways
This compound 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 . This compound’s metabolism is not significantly affected by genetic polymorphisms, making it a reliable medication for a wide range of patients .
Transport and Distribution
This compound 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 . This compound 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, this compound 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 . This compound’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 .
Méthodes De Préparation
Le bisoprolol peut être synthétisé par plusieurs méthodes. Une voie de synthèse courante implique la réaction du 4-isopropoxyéthoxy méthyl phénol avec l’épichlorhydrine pour former du 2-[4-(2-isopropoxyéthoxy)méthyl]phénoxy méthyl oxirane. Cet intermédiaire est ensuite mis en réaction avec de l’isopropylamine pour donner du this compound . Les méthodes de production industrielle impliquent souvent des étapes similaires, mais sont optimisées pour la production à grande échelle, assurant un rendement élevé et une pureté élevée .
Analyse Des Réactions Chimiques
Le bisoprolol subit diverses réactions chimiques, notamment :
Oxydation : Le this compound peut être oxydé pour former divers métabolites.
Réduction : Les réactions de réduction sont moins fréquentes, mais peuvent se produire dans des conditions spécifiques.
Substitution : Le this compound peut subir des réactions de substitution, en particulier impliquant ses groupes phénolique et amine.
Les réactifs courants utilisés dans ces réactions comprennent les oxydants comme le peroxyde d’hydrogène et les réducteurs comme le borohydrure de sodium. Les principaux produits formés à partir de ces réactions sont généralement des métabolites qui sont soit excrétés, soit métabolisés davantage dans l’organisme .
Applications de la recherche scientifique
Le this compound a un large éventail d’applications de recherche scientifique :
Chimie : Utilisé comme composé modèle dans des études impliquant des bêta-bloqueurs et leurs interactions avec divers récepteurs.
Biologie : Étudié pour ses effets sur les processus cellulaires et ses interactions avec les récepteurs bêta-adrénergiques.
Médecine : Largement utilisé dans les essais cliniques pour évaluer son efficacité dans le traitement des maladies cardiovasculaires.
Industrie : Employé dans le développement de nouvelles formulations pharmaceutiques et de systèmes d’administration de médicaments
Comparaison Avec Des Composés Similaires
Le bisoprolol est souvent comparé à d’autres bêta-bloqueurs tels que l’aténolol, le métoprolol et le propranolol. Bien que tous ces composés partagent un mécanisme d’action similaire, le this compound est unique par sa haute sélectivité pour les récepteurs bêta-1 adrénergiques, ce qui réduit le risque d’effets secondaires liés au blocage des récepteurs bêta-2, comme la bronchoconstriction .
Composés similaires
- Aténolol
- Métoprolol
- Propranolol
- Carvedilol
- Labétalol
La sélectivité du this compound pour les récepteurs bêta-1 le rend particulièrement adapté aux patients atteints de maladies respiratoires comme l’asthme, car elle minimise le risque de bronchospasme .
Propriétés
IUPAC Name |
1-(propan-2-ylamino)-3-[4-(2-propan-2-yloxyethoxymethyl)phenoxy]propan-2-ol |
Source
|
|---|---|---|
| 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
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
VHYCDWMUTMEGQY-UHFFFAOYSA-N |
Source
|
| 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
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C18H31NO4 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID6022682 |
Source
|
| Record name | Bisoprolol | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID6022682 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
325.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| 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. | |
Boiling Point |
445.0±45.0 |
Source
|
| Record name | Bisoprolol | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00612 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
Solubility |
7.07e-02 g/L |
Source
|
| 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. | |
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. |
Source
|
| Record name | Bisoprolol | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00612 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
CAS No. |
66722-44-9 |
Source
|
| Record name | Bisoprolol | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=66722-44-9 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Bisoprolol [USAN:INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0066722449 | |
| 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 | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00612 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Bisoprolol | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID6022682 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | 2-Propanol, 1-[4-[[2-(1-methylethoxy)ethoxy]methyl]phenoxy]-3-[(1-methylethyl)amino] | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.108.941 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | BISOPROLOL | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/Y41JS2NL6U | |
| 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. | |
| Record name | Bisoprolol | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/8316 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| 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. | |
Melting Point |
100-103, 100 °C |
Source
|
| Record name | Bisoprolol | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00612 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| 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
Retrosynthesis Analysis
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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
Q1: How does bisoprolol exert its effects on the cardiovascular system?
A1: this compound 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, this compound reduces heart rate, myocardial contractility, and ultimately lowers blood pressure. [, , ]
Q2: Does this compound affect β2-adrenergic receptors?
A2: this compound 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 this compound beyond its immediate hemodynamic effects?
A3: Research suggests that this compound might provide additional benefits by reducing oxidative stress and inflammation, particularly in the context of heart failure. [, ] Studies in animal models have shown that this compound 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 this compound?
A4: this compound 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 this compound for various applications.
Q5: What spectroscopic techniques are commonly used to characterize this compound?
A5: Spectroscopic techniques like UV-Vis spectrophotometry are frequently employed for the analysis of this compound. This compound 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 this compound?
A6: this compound 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. [, ] this compound is primarily metabolized in the liver and excreted in the urine. []
Q7: How do the pharmacokinetic properties of this compound compare to other beta-blockers?
A7: this compound'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 this compound?
A8: this compound 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 this compound compare to other beta-blockers in treating heart failure?
A10: Clinical trials like the Cardiac Insufficiency this compound Study (CIBIS) have shown that this compound 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 this compound with other drugs in specific patient populations?
A11: Studies suggest that combining this compound with other antihypertensive agents like amlodipine can significantly improve blood pressure control in patients who haven't responded well to monotherapy. [] Additionally, adding this compound 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 this compound?
A12: Although generally well-tolerated, this compound 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 this compound use should be approached with caution?
A13: this compound 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 this compound 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 this compound in biological samples like plasma or cell lysates. [, , ] These methods offer high sensitivity and selectivity for accurate determination of this compound concentrations.
Q14: Are there any specialized formulations of this compound available?
A15: Aside from oral tablets, this compound 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 this compound?
A16: Further research is needed to optimize the use of this compound 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 this compound in delaying the progression of heart failure and reducing cardiovascular events warrants further investigation.
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