Pioglitazona
Descripción general
Descripción
La pioglitazona es un compuesto farmacéutico perteneciente a la clase de las tiazolidindionas, utilizado principalmente como medicamento antidiabético para tratar la diabetes mellitus tipo 2. Funciona mejorando la sensibilidad de los tejidos a la insulina, lo que ayuda a controlar los niveles de azúcar en sangre. La this compound se utiliza a menudo en combinación con otros medicamentos antidiabéticos como metformina, sulfonilureas o insulina .
Mecanismo De Acción
La pioglitazona actúa como un agonista selectivo del receptor activado por proliferadores de peroxisomas gamma (PPARγ) en tejidos diana como tejido adiposo, músculo esquelético e hígado. La activación de PPARγ aumenta la transcripción de genes sensibles a la insulina implicados en el metabolismo de la glucosa y los lípidos. Esto lleva a una mejor sensibilidad a la insulina, una mayor captación de glucosa y un mejor control glucémico .
Aplicaciones Científicas De Investigación
La pioglitazona tiene una amplia gama de aplicaciones de investigación científica:
Química: Se utiliza como compuesto modelo para estudiar la reactividad de las tiazolidindionas.
Biología: Se investiga por sus efectos sobre el metabolismo celular y la expresión génica.
Medicina: Se ha estudiado ampliamente por su papel en el control de la diabetes tipo 2 y sus posibles beneficios cardiovasculares. .
Industria: Se utiliza en la formulación de varios productos farmacéuticos para el control de la diabetes.
Análisis Bioquímico
Biochemical Properties
Pioglitazone interacts with various enzymes, proteins, and other biomolecules. It primarily promotes insulin sensitivity and improves the uptake of blood glucose via agonism at the peroxisome proliferator-activated receptor-gamma (PPARγ) . PPARs are ligand-activated transcription factors that are involved in the expression of more than 100 genes and affect numerous metabolic processes, most notably lipid and glucose homeostasis .
Cellular Effects
Pioglitazone has been shown to have significant effects on various types of cells and cellular processes. It enhances cellular responsiveness to insulin, increases insulin-dependent glucose disposal, and improves impaired glucose homeostasis . In addition, pioglitazone has been found to reduce proliferative and invasive abilities in non-small cell lung cancer (NSCLC) cells .
Molecular Mechanism
Pioglitazone exerts its effects at the molecular level primarily by promoting insulin sensitivity and the improved uptake of blood glucose via agonism at the peroxisome proliferator-activated receptor-gamma (PPARγ) . It modulates the transcription of the genes involved in the control of glucose and lipid metabolism in the muscle, adipose tissue, and the liver .
Temporal Effects in Laboratory Settings
In laboratory settings, pioglitazone has been shown to have temporal effects. For instance, a study showed that pioglitazone treatment resulted in improved perfusion and modulation of capillary density in ischemic skeletal muscle of diabetic mice over time .
Dosage Effects in Animal Models
In animal models, the effects of pioglitazone vary with different dosages. For instance, a study showed that pioglitazone at a concentration of 45 mg kg –1 b.wt., for the duration of 28 days did not elicit any measurable biochemical toxicity on non-diabetic rat model .
Metabolic Pathways
Pioglitazone is involved in several metabolic pathways. It enhances insulin sensitivity, which is achieved by promoting glucose uptake and utilization in adipose tissue, skeletal muscle, and liver tissue . This activity contributes to better glycemic control, as more glucose is transported into cells for energy consumption .
Métodos De Preparación
Rutas sintéticas y condiciones de reacción
La síntesis de la pioglitazona implica varios pasos, comenzando con la preparación del anillo de tiazolidindiona. Un método común implica la reacción de 2,4-tiazolidindiona con cloruro de bencilo en presencia de una base para formar el compuesto intermedio. Este intermedio se hace reaccionar luego con 2-(5-etilpiridin-2-il)etanol en condiciones básicas para producir this compound .
Métodos de producción industrial
La producción industrial de this compound generalmente implica la hidrogenación de una sal de adición ácida de un compuesto bencilideno a baja presión de gas hidrógeno. Este proceso utiliza un agente reductor para lograr altos rendimientos del derivado de tiazolidindiona .
Análisis De Reacciones Químicas
Tipos de reacciones
La pioglitazona sufre varias reacciones químicas, que incluyen:
Oxidación: La this compound se puede oxidar para formar sus derivados de sulfóxido y sulfona correspondientes.
Reducción: El compuesto se puede reducir para formar sus derivados dihidro.
Sustitución: La this compound puede sufrir reacciones de sustitución nucleófila, particularmente en la posición bencílica.
Reactivos y condiciones comunes
Oxidación: Los agentes oxidantes comunes incluyen peróxido de hidrógeno y ácido m-cloroperbenzoico.
Reducción: Se utilizan agentes reductores como hidruro de aluminio y litio o borohidruro de sodio.
Sustitución: Se pueden utilizar nucleófilos como aminas o tioles en condiciones básicas.
Principales productos
Los principales productos formados a partir de estas reacciones incluyen los derivados de sulfóxido, sulfona y dihidro de la this compound .
Comparación Con Compuestos Similares
Compuestos similares
Rosiglitazona: Otra tiazolidindiona con efectos sensibilizadores a la insulina similares, pero asociada con mayores riesgos cardiovasculares.
Singularidad de la pioglitazona
La this compound es única en su capacidad para mejorar los perfiles lipídicos al aumentar el colesterol de lipoproteínas de alta densidad y reducir los triglicéridos. También tiene un efecto favorable sobre la relación albúmina/creatinina urinaria, lo que indica posibles beneficios renales . A pesar de sus beneficios, la this compound está asociada con riesgos como el aumento de peso y la insuficiencia cardíaca, que deben controlarse cuidadosamente .
Propiedades
IUPAC Name |
5-[[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
HYAFETHFCAUJAY-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C19H20N2O3S |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID3037129 |
Source
|
| Record name | Pioglitazone | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID3037129 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
356.4 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 | Pioglitazone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015264 | |
| 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. | |
Solubility |
Practically insoluble, 4.42e-03 g/L |
Source
|
| Record name | Pioglitazone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01132 | |
| 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 | Pioglitazone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015264 | |
| 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 |
Pioglitazone is a selective agonist at peroxisome proliferator-activated receptor-gamma (PPARγ) in target tissues for insulin action such as adipose tissue, skeletal muscle, and liver. Activation of PPARγ increases the transcription of insulin-responsive genes involved in the control of glucose and lipid production, transport, and utilization. Through this mechanism, pioglitazone both enhances tissue sensitivity to insulin and reduces the hepatic production of glucose (i.e. gluconeogenesis) - insulin resistance associated with type 2 diabetes mellitus is therefore improved without an increase in insulin secretion by pancreatic beta cells., Repeated administration of peroxisome proliferator-activated receptor gamma (PPARgamma) agonists reduces neuropathic pain-like behavior and associated changes in glial activation in the spinal cord dorsal horn. As PPARgamma is a nuclear receptor, sustained changes in gene expression are widely believed to be the mechanism of pain reduction. However, we recently reported that a single intrathecal (i.t.) injection of pioglitazone, a PPARgamma agonist, reduced hyperalgesia within 30 minutes, a time frame that is typically less than that required for genomic mechanisms. To determine the very rapid antihyperalgesic actions of PPARgamma activation, we administered pioglitazone to rats with spared nerve injury and evaluated hyperalgesia. Pioglitazone inhibited hyperalgesia within 5 minutes of injection, consistent with a nongenomic mechanism. Systemic or i.t. administration of GW9662, a PPARgamma antagonist, inhibited the antihyperalgesic actions of intraperitoneal or i.t. pioglitazone, suggesting a spinal PPAR?-dependent mechanism. To further address the contribution of nongenomic mechanisms, we blocked new protein synthesis in the spinal cord with anisomycin. When coadministered intrathecally, anisomycin did not change pioglitazone antihyperalgesia at an early 7.5-minute time point, further supporting a rapid nongenomic mechanism. At later time points, anisomycin reduced pioglitazone antihyperalgesia, suggesting delayed recruitment of genomic mechanisms. Pioglitazone reduction of spared nerve injury-induced increases in GFAP expression occurred more rapidly than expected, within 60 minutes. We are the first to show that activation of spinal PPARgamma rapidly reduces neuropathic pain independent of canonical genomic activity. We conclude that acute pioglitazone inhibits neuropathic pain in part by reducing astrocyte activation and through both genomic and nongenomic PPARgamma mechanisms., Pioglitazone hydrochloride is a thiazolidinedione that depends on the presence of insulin for its mechanism of action. Pioglitazone hydrochloride decreases insulin resistance in the periphery and in the liver resulting in increased insulin-dependent glucose disposal and decreased hepatic glucose output. Pioglitazone is not an insulin secretagogue. Pioglitazone is an agonist for peroxisome proliferator-activated receptor-gamma (PPARgamma). PPAR receptors are found in tissues important for insulin action such as adipose tissue, skeletal muscle, and liver. Activation of PPARgamma nuclear receptors modulates the transcription of a number of insulin responsive genes involved in the control of glucose and lipid metabolism., ... Thiazolidinediones reduce insulin resistance not only in type 2 diabetes but also in non-diabetic conditions associated with insulin resistance such as obesity. The mechanism of action involves binding to the peroxisome proliferator-activated receptor (PPAR)gamma, a transcription factor that regulates the expression of specific genes especially in fat cells but also in other tissues. It is likely that thiazolidinediones primarily act in adipose tissue where PPARgamma is predominantly expressed. Thiazolidinediones have been shown to interfere with expression and release of mediators of insulin resistance originating in adipose tissue (e.g. free fatty acids, adipocytokines such as tumor necrosis factor alpha, resistin, adiponectin) in a way that results in net improvement of insulin sensitivity (i.e. in muscle and liver). Nevertheless, a direct molecular effect in skeletal muscle cannot be excluded. ..., Pioglitazone, a full peroxisome proliferator-activated receptor (PPAR)-gamma agonist, improves insulin sensitivity by increasing circulating adiponectin levels. However, the molecular mechanisms by which pioglitazone induces insulin sensitization are not fully understood. In this study, we investigated whether pioglitazone improves insulin resistance via upregulation of either 2 distinct receptors for adiponectin (AdipoR1 or AdipoR2) expression in 3T3-L1 adipocytes. Glucose uptake was evaluated by 2-[(3)H] deoxy-glucose uptake assay in 3T3-L1 adipocytes with pioglitazone treatment. AdipoR1 and AdipoR2 mRNA expressions were analyzed by qRT-PCR. /The investigators/ first confirmed that pioglitazone significantly increased insulin-induced 2-deoxyglucose (2-DOG) uptake in 3T3-L1 adipocytes. Next, we investigated the mRNA expression and regulation of AdipoR1 and AdipoR2 after treatment with pioglitazone. Interestingly, pioglitazone significantly induced AdipoR2 expression but it did not affect AdipoR1 expression. In addition, adenovirus-mediated PPARgamma expression significantly enhanced the effects of pioglitazone on insulin-stimulated 2-DOG uptake and AdipoR2 expression in 3T3-L1 adipocytes. These data suggest that pioglitazone enhances adiponectin's autocrine and paracrine actions in 3T3-L1 adipocytes via upregulation of PPARgamma-mediated AdipoR2 expression. Furthermore, we found that pioglitazone significantly increased AMP-activated protein kinase (AMPK) phosphorylation in insulin-stimulated 3T3-L1 adipocytes, but it did not lead to the phosphorylation of IRS-1, Akt, or protein kinase ... Pioglitazone increases insulin sensitivity, at least partly, by PPARgamma-AdipoR2-mediated AMPK phosphorylation in 3T3-L1 adipocytes. In conclusion, the upregulation of AdipoR2 expression may be one of the mechanisms by which pioglitazone improves insulin resistance in 3T3-L1 adipocytes., For more Mechanism of Action (Complete) data for Pioglitazone (6 total), please visit the HSDB record page. |
Source
|
| Record name | Pioglitazone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01132 | |
| 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 | Pioglitazone | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7322 | |
| 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. | |
Color/Form |
Colorless needles from dimethylformamide and water | |
CAS No. |
111025-46-8, 112529-15-4 |
Source
|
| Record name | Pioglitazone | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=111025-46-8 | |
| 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. | |
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| Record name | Pioglitazone [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0111025468 | |
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| Record name | Pioglitazone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01132 | |
| 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 | pioglitazone hydrochloride | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=758876 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
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| Record name | Pioglitazone | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID3037129 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | 5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.114.441 | |
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| Record name | PIOGLITAZONE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/X4OV71U42S | |
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| Record name | Pioglitazone | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7322 | |
| 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 | Pioglitazone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015264 | |
| 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 |
193-194C, 183-184 °C, Colorless prisms from ethanol, MP: 193-194 °C. Soluble in dimethyl formamide; slightly soluble in ethanol; very slightly soluble in acetone, acetonitrile. Practically insoluble in water; insoluble in ether. /Pioglitazone hydrochloride/, 183 - 184 °C |
Source
|
| Record name | Pioglitazone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01132 | |
| 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 | Pioglitazone | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7322 | |
| 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 | Pioglitazone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015264 | |
| 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 I
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Retrosynthesis Analysis
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