Pioglitazone
Vue d'ensemble
Description
Pioglitazone is a pharmaceutical compound belonging to the thiazolidinedione class, primarily used as an anti-diabetic medication to treat type 2 diabetes mellitus. It works by improving the sensitivity of tissues to insulin, thereby helping to control blood sugar levels. This compound is often used in combination with other anti-diabetic medications such as metformin, sulfonylureas, or insulin .
Mécanisme D'action
Target of Action
Pioglitazone primarily targets the Peroxisome Proliferator-Activated Receptor-gamma (PPARγ) . PPARγ is a ligand-activated transcription factor involved in the expression of more than 100 genes affecting numerous metabolic processes, most notably lipid and glucose homeostasis .
Mode of Action
This compound acts as a selective agonist at 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 . This leads to enhanced cellular responsiveness to insulin, increased insulin-dependent glucose disposal, and improved impaired glucose homeostasis .
Biochemical Pathways
This compound’s action affects several biochemical pathways. It promotes insulin sensitivity and the improved uptake of blood glucose via agonism at PPARγ . It also down-regulates the MAPK, Myc, and Ras genes, affecting the MAPK cascade . Furthermore, it influences the TGFβ pathway, which is important in the epithelial-to-mesenchymal transition (EMT) process, by down-regulating TGFβR1 and SMAD3 mRNA expression .
Pharmacokinetics
This compound’s ADME (Absorption, Distribution, Metabolism, and Excretion) properties impact its bioavailability. It is administered as a racemic mixture, with no pharmacologic difference between the enantiomers, and they appear to interconvert in vivo with little consequence . The metabolism of this compound is primarily via CYP2C8 .
Result of Action
The molecular and cellular effects of this compound’s action result in lower plasma glucose concentrations, lower plasma insulin concentrations, and lower HbA1c values in patients with type 2 diabetes mellitus . It also reduces proliferative and invasive abilities in non-small cell lung cancer (NSCLC) cells and induces apoptosis . Moreover, it modulates cell bioenergetics .
Action Environment
Environmental factors can influence the action, efficacy, and stability of this compound. Genetic variation in this compound pathway genes contributes meaningfully to the clinically observed variability in drug response . For instance, the magnitude of drug-drug interaction is greater in individuals having the genotype associated with higher activity or clearance .
Applications De Recherche Scientifique
Pioglitazone has a wide range of scientific research applications:
Chemistry: Used as a model compound to study the reactivity of thiazolidinediones.
Biology: Investigated for its effects on cellular metabolism and gene expression.
Medicine: Extensively studied for its role in managing type 2 diabetes and its potential cardiovascular benefits. .
Industry: Used in the formulation of various pharmaceutical products for diabetes management.
Analyse Biochimique
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
This compound 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, this compound has been found to reduce proliferative and invasive abilities in non-small cell lung cancer (NSCLC) cells .
Molecular Mechanism
This compound 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, this compound has been shown to have temporal effects. For instance, a study showed that this compound 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 this compound vary with different dosages. For instance, a study showed that this compound 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
This compound 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 .
Méthodes De Préparation
Synthetic Routes and Reaction Conditions
The synthesis of pioglitazone involves several steps, starting with the preparation of the thiazolidinedione ring. One common method involves the reaction of 2,4-thiazolidinedione with benzyl chloride in the presence of a base to form the intermediate compound. This intermediate is then reacted with 2-(5-ethylpyridin-2-yl)ethanol under basic conditions to yield this compound .
Industrial Production Methods
Industrial production of this compound typically involves the hydrogenation of an acid addition salt of a benzylidene compound under low hydrogen gas pressure. This process uses a reducing agent to achieve high yields of the thiazolidinedione derivative .
Analyse Des Réactions Chimiques
Types of Reactions
Pioglitazone undergoes various chemical reactions, including:
Oxidation: this compound can be oxidized to form its corresponding sulfoxide and sulfone derivatives.
Reduction: The compound can be reduced to form its dihydro derivatives.
Substitution: This compound can undergo nucleophilic substitution reactions, particularly at the benzyl position.
Common Reagents and Conditions
Oxidation: Common oxidizing agents include hydrogen peroxide and m-chloroperbenzoic acid.
Reduction: Reducing agents such as lithium aluminum hydride or sodium borohydride are used.
Substitution: Nucleophiles like amines or thiols can be used under basic conditions.
Major Products
The major products formed from these reactions include sulfoxide, sulfone, and dihydro derivatives of this compound .
Comparaison Avec Des Composés Similaires
Similar Compounds
Rosiglitazone: Another thiazolidinedione with similar insulin-sensitizing effects but associated with higher cardiovascular risks.
Metformin: A non-thiazolidinedione anti-diabetic medication that improves insulin sensitivity but through a different mechanism.
Semaglutide: A glucagon-like peptide-1 receptor agonist that lowers blood sugar levels by stimulating insulin secretion.
Uniqueness of Pioglitazone
This compound is unique in its ability to improve lipid profiles by increasing high-density lipoprotein cholesterol and reducing triglycerides. It also has a favorable effect on urinary albumin/creatinine ratio, indicating potential renal benefits . Despite its benefits, this compound is associated with risks such as weight gain and heart failure, which need to be carefully managed .
Propriétés
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 | |
| 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 | 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 | |
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| 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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Synthesis routes and methods II
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Retrosynthesis Analysis
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