CAS Number111025-46-8
Synonyms5-[[4-[2-[(5-ethyl-2-pyridyl)]ethoxy]phenyl]methyl]thiazolidine- 2,4-dione; 5-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione; Actos; Pioglitazone; 5-{4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione; Pioglitazone [Ban:Inn]; 5-((4-(2-(5-Ethyl-2-pyridinyl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione; 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-Thiazolidinedione
Molecular FormulaC19H20O3N2S1
Molecular Weight356.45
Purity98%
Density1.3±0.1 g/cm3
Boiling Point575.4±45.0 °C at 760 mmHg
Melting Point183-184ºC
Appearancewhite powder
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 111025-46-8 |
| Catalog No. | 2A-9012027 |
| Chinese Name | 匹格列酮 |
| Synonyms | 5-[[4-[2-[(5-ethyl-2-pyridyl)]ethoxy]phenyl]methyl]thiazolidine- 2,4-dione; 5-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione; Actos; Pioglitazone; 5-{4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione; Pioglitazone [Ban:Inn]; 5-((4-(2-(5-Ethyl-2-pyridinyl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione; 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-Thiazolidinedione |
| Molecular Formula | C19H20O3N2S1 |
| Molecular Weight | 356.45 |
| Purity | 98 |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 575.4±45.0 °C at 760 mmHg |
| Melting Point | 183-184ºC |
| Appearance | white powder |
| Storage Condition | Sealed in a cool, dry environment |
| Application | Pioglitazone is a potent and selective PPARγ agonist that binds with high affinity to the PPARγ ligand binding domain. For human and mouse PPARγ, EC50 is 0.93 and 0.99 μM respectively. |
| MDL Number | MFCD00865504 |
| SMILES | CCc1ccc(CCOc2ccc(CC3SC(=O)NC3=O)cc2)nc1 |
| 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) |
| InChI Key | HYAFETHFCAUJAY-UHFFFAOYSA-N |
| MSDS | msds/12027_1_111025_46_8.pdf |
| Bioactivity | Pioglitazone is a potent and selective PPARγ agonist with high affinity binding to the PPARγ ligand-binding domain with EC50 of 0.93 and 0.99 μM for human and mouse PPARγ, respectively. Related Catalog Natural Products >> Alkaloid Research Areas >> Metabolic Disease Target PPARδ:0.01 μM (EC50, Human PPARδ) PPARα:0.93 μM (EC50, Human PPARα) PPARγ:43 μM (EC50, Human PPARγ) In Vitro AGEs-induced beta cell necrosis is completely abrogated by adding Pioglitazone to the AGEs culture medium. Furthermore Pioglitazone completely prevented any AGEs-induced increment in caspase-3 activation, thereby restoring caspase-3 activity to the same levels as the control cells. As expected AG is able to counteract AGEs-induced impaired viability[2]. In Vivo The serum-free fatty acid and triglyceride levels as well as adipocyte sizes in ob/ob and adipo-/- ob/ob mice are unchanged after 10 mg/kg Pioglitazone but are significantly reduced to a similar degree after 30 mg/kg Pioglitazone. Moreover, the expressions of TNFα and resistin in adipose tissues of ob/ob and adipo-/- ob/ob mice are unchanged after 10 mg/kg Pioglitazone but are decreased after 30 mg/kg Pioglitazone. Thus, Pioglitazone-induced amelioration of insulin resistance and diabetes may occur adiponectin dependently in the liver and adiponectin independently in skeletal muscle[3]. Pioglitazone (10 mg/kg per d) treatment significantly attenuates the loss of body weight (BW) and cardiac hypertrophy. Pioglitazone treatment significantly reduces the elevated serum glucose levels and markedly improved the associated dyslipidemia. Furthermore, there is a slight but significant increase in serum creatinine level in D rats over their N controls (P <0.05). However, a marked renal dysfunction is observed in diabetic nephropathic (DN) group (P<0.05). Moreover, DN rats exhibits the highest serum activity of CK-MB, relative to both N and D rats (P<0.05). Pioglitazone is able to decrease the elevated serum levels of both creatinine and creatine kinase-MB (CK-MB)[4]. Cell Assay In order to evaluate cell proliferation, HIT-T15 cells are seeded on 96-well plates (3×104 cells/well) and cultured for 5 days as described. Viable cells are determined using the Cell Titer 96 Aqueous One Solution Cell Proliferation Assay. To evaluate cell apoptosis and cell necrosis, HIT-T15 cells are plated on 6-well dishes (7×105 cells/well) for 5 days in standard conditions (CTR) or in the presence of AGEs (AGEs) with or without Pioglitazone (0.5 or 1 μM) or AG (1 mM). They are then processed to measure both the activity of caspase-3 and the activity of lactate dehydrogenase (LDH) (a stable cytosolic enzyme that is a marker of cell membrane damage and cell death due to necrosis) using Cytotox 96 Non Radioactive Cytotoxicity Assay[2]. Animal Admin Mice[3] 10 mg/kg Pioglitazone HCl or vehicle (0.25% carboxymethylcellulose) is adnimistered to ob/ob and adipo-/- ob/ob mice by oral gavage once daily for 14 consecutive days. 30 mg/kg Pioglitazone or vehicle is also adnimistered to ob/ob and adipo-/- ob/ob mice by oral gavage once daily for 14 consecutive days. Rats[4] Male Wistar albino rats (weighing 250±20 g) are ued.Rats that achieved serum glucose level ≥250 mg/dL and serum creatinine level ≥1.5 mg/dL are divided into 2 groups (n=10 per each group): diabetic nephropathic (DN) group in which rats received an equal amount of vehicle (0.5% carboxy methyl cellulose) and Pioglitazone-treated (DN+Pio) group in which rats treated with Pioglitazone. Pioglitazone (10 mg/kg BW) is given orally by gastric gavage, once daily, for 4 weeks. References [1]. Kuwabara K, et al. A novel selective peroxisome proliferator-activated receptor alpha agonist, 2-methyl-c-5-[4-[5-methyl-2-(4-methylphenyl)-4-oxazolyl]butyl]-1,3-dioxane-r-2-carboxylic acid (NS-220), potently decreases plasma triglyceride and glucose leve [2]. Puddu A, et al. Pioglitazone attenuates the detrimental effects of advanced glycation end-products in the pancreatic beta cell line HIT-T15. Regul Pept. 2012 Aug 20;177(1-3):79-84. [3]. Kubota N, et al. Pioglitazone ameliorates insulin resistance and diabetes by both adiponectin-dependent and -independent pathways. J Biol Chem. 2006 Mar 31;281(13):8748-55. [4]. Elrashidy RA, et al. Pioglitazone attenuates cardiac fibrosis and hypertrophy in a rat model of diabetic nephropathy. J Cardiovasc Pharmacol Ther. 2012 Sep;17(3):324-33. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 575.4±45.0 °C at 760 mmHg Melting Point 183-184ºC Molecular Formula C19H20N2O3S Molecular Weight 356.44 Flash Point 301.8±28.7 °C PSA 93.59000 LogP 2.94 Vapour Pressure 0.0±1.6 mmHg at 25°C Index of Refraction 1.611 InChIKey HYAFETHFCAUJAY-UHFFFAOYSA-N SMILES CCc1ccc(CCOc2ccc(CC3SC(=O)NC3=O)cc2)nc1 |
| Use of | Pioglitazone is a potent and selective PPARγ agonist with high affinity binding to the PPARγ ligand-binding domain with EC50 of 0.93 and 0.99 μM for human and mouse PPARγ, respectively. Properties Name pioglitazone Synonym More Synonyms Pioglitazone Biological Activity Description Pioglitazone is a potent and selective PPARγ agonist with high affinity binding to the PPARγ ligand-binding domain with EC50 of 0.93 and 0.99 μM for human and mouse PPARγ, respectively. Related Catalog Natural Products >> Alkaloid Research Areas >> Metabolic Disease PPARδ:0.01 μM (EC50, Human PPARδ) PPARα:0.93 μM (EC50, Human PPARα) PPARγ:43 μM (EC50, Human PPARγ) In Vitro AGEs-induced beta cell necrosis is completely abrogated by adding Pioglitazone to the AGEs culture medium. Furthermore Pioglitazone completely prevented any AGEs-induced increment in caspase-3 activation, thereby restoring caspase-3 activity to the same levels as the control cells. As expected AG is able to counteract AGEs-induced impaired viability[2]. References [1]. Kuwabara K, et al. A novel selective peroxisome proliferator-activated receptor alpha agonist, 2-methyl-c-5-[4-[5-methyl-2-(4-methylphenyl)-4-oxazolyl]butyl]-1,3-dioxane-r-2-carboxylic acid (NS-220), potently decreases plasma triglyceride and glucose leve [2]. Puddu A, et al. Pioglitazone attenuates the detrimental effects of advanced glycation end-products in the pancreatic beta cell line HIT-T15. Regul Pept. 2012 Aug 20;177(1-3):79-84. [3]. Kubota N, et al. Pioglitazone ameliorates insulin resistance and diabetes by both adiponectin-dependent and -independent pathways. J Biol Chem. 2006 Mar 31;281(13):8748-55. [4]. Elrashidy RA, et al. Pioglitazone attenuates cardiac fibrosis and hypertrophy in a rat model of diabetic nephropathy. J Cardiovasc Pharmacol Ther. 2012 Sep;17(3):324-33. Chemical & Physical Properties Molecular Formula C19H20N2O3S PSA 93.59000 Index of Refraction 1.611 InChIKey HYAFETHFCAUJAY-UHFFFAOYSA-N |
| Transport Info | Product name: Pioglitazone |
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