| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
The primary target of 2,4-thiazolidinedione is the peroxisome proliferator-activated receptor gamma (PPARγ), a nuclear receptor involved in glucose and lipid metabolism. As a PPARγ agonist and insulin sensitizer, it exerts its effects by acting as a ligand for the PPARγ nuclear receptor. Derivatives of 2,4-thiazolidinedione enhance insulin sensitivity in adipose tissue, muscle, and liver. The compound has also been studied for its effects on the aging process using kidneys from Fischer 344 rats. The scaffold is also used to design inhibitors of pancreatic cholesterol esterase.
|
|---|---|
| ln Vitro |
PPARγ agonists. sensitizer to insulin.
In vitro, 2,4-thiazolidinedione acts as a PPARγ agonist and insulin sensitizer. New derivatives of 2,4-thiazolidinedione have shown promising in vitro antibacterial and antifungal activities, suggesting potential applications in the treatment of microbial infections. The compound is used in the synthesis of drugs with antihyperglycemic activity. A library of conjugates of 2,4-thiazolidinedione has been synthesized by Knoevenagel condensation followed by reduction. The compound also serves as a starting material for the synthesis of various bioactive molecules. Cellular assays typically evaluate its effects on PPARγ activation and insulin sensitivity. |
| ln Vivo |
In vivo, 2,4-thiazolidinedione has been studied for its effects on the aging process using kidneys from Fischer 344 rats. PPARγ agonists, including thiazolidinediones, are known to exert anti-fibrotic effects in the kidney. The compound's derivatives have been investigated for antihyperglycemic activity in animal models of diabetes. As a PPARγ activator, the compound influences glucose and lipid metabolism in vivo. The compound is classified for research use only and is not intended for human or veterinary applications. In vivo studies typically evaluate metabolic parameters, insulin sensitivity, and organ-specific effects.
|
| Enzyme Assay |
In vitro enzyme/receptor binding assays for 2,4-thiazolidinedione typically evaluate its activity as a PPARγ agonist. A standard assay protocol involves incubating the compound with PPARγ ligand-binding domain in a suitable buffer system. Binding affinity is assessed using techniques such as fluorescence polarization, scintillation proximity assay, or surface plasmon resonance. Transactivation assays using PPARγ-responsive reporter gene constructs in cell lines are also commonly employed. The compound's ability to activate PPARγ is measured by quantifying reporter gene expression (e.g., luciferase activity). EC₅₀ values are calculated from dose-response curves.
|
| Cell Assay |
Cellular assays for 2,4-thiazolidinedione typically evaluate its effects on PPARγ activation and insulin sensitivity. A standard protocol involves culturing appropriate cell lines (e.g., 3T3-L1 adipocytes, HepG2 hepatocytes) in growth medium at 37°C with 5% CO₂. Cells are treated with varying concentrations of the compound (typically 0.1-100 μM) for 24-72 hours. PPARγ activation is assessed using reporter gene assays or by measuring the expression of PPARγ target genes (e.g., adiponectin, GLUT4) by qRT-PCR or Western blot. Insulin sensitivity is evaluated by glucose uptake assays or by measuring adipocyte differentiation.
|
| Animal Protocol |
In vivo animal studies for 2,4-thiazolidinedione derivatives typically use rodent models of diabetes and metabolic syndrome. A common protocol involves administering the compound to diabetic or high-fat diet-fed mice or rats. Animals are treated with the compound via oral gavage at doses ranging from 1-100 mg/kg, daily for 2-8 weeks. Blood glucose, insulin levels, and lipid profiles are monitored regularly. Tissue samples (liver, adipose, kidney) are collected for histopathological and molecular analysis. The compound's effects on insulin sensitivity, glucose tolerance, and organ-specific outcomes are evaluated.
|
| ADME/Pharmacokinetics |
Pharmacokinetic data for 2,4-thiazolidinedione is limited, as it is primarily a scaffold compound rather than a therapeutic agent. The compound has a molecular weight of 117.13 g/mol and is a solid at room temperature with a melting point of 125-127°C. It is soluble in organic solvents and has moderate lipophilicity. As a PPARγ agonist scaffold, its derivatives typically exhibit good oral bioavailability. The compound is stored at room temperature in sealed containers. Specific ADME data for the parent compound is not well-characterized in the public literature.
|
| Toxicity/Toxicokinetics |
Toxicological data for 2,4-thiazolidinedione is limited, as it is primarily a research scaffold. The compound is classified for research use only and is not intended for human or veterinary applications. Standard safety precautions include handling with appropriate personal protective equipment (gloves, lab coat, safety goggles) in a well-ventilated area. The compound is classified as a combustible solid (Storage Class 11) and has a WGK of 3. Acute toxicity data is not readily available in the public literature. As with all research chemicals, appropriate laboratory safety practices should be followed.
|
| Additional Infomation |
1,3-Thiazolidin-2,4-dione is a thiazolidinedione with oxygen substituents at the 2 and 4 positions. It is derived from the hydride of 1,3-thiazolidinediones. Thiazolidinediones have been investigated for the treatment of type 2 diabetes, diabetes mellitus, and type 2 diabetes.
2,4-Thiazolidinedione (CAS 2295-31-0) is a well-known PPARγ activator and a key scaffold in medicinal chemistry. The compound has a molecular formula of C₃H₃NO₂S and a molecular weight of 117.13 g/mol. It is used as a starting material for the synthesis of drugs with antihyperglycemic activity. The compound is classified as a research-use-only compound not intended for diagnostic or therapeutic purposes. It is available from multiple commercial suppliers in various pack sizes. No clinical trials or approved drug status exist for the parent compound, though its derivatives (e.g., rosiglitazone, pioglitazone) are FDA-approved for type 2 diabetes. |
| Molecular Formula |
C3H3NO2S
|
|---|---|
| Molecular Weight |
117.13
|
| Exact Mass |
116.988
|
| CAS # |
2295-31-0
|
| Related CAS # |
39131-10-7 (potassium)
|
| PubChem CID |
5437
|
| Appearance |
White to off-white solid powder
|
| Density |
1.5±0.1 g/cm3
|
| Boiling Point |
178-179 ºC (19 mmHg)
|
| Melting Point |
123-126 ºC
|
| Flash Point |
138.7±19.3 °C
|
| Vapour Pressure |
0.0±0.6 mmHg at 25°C
|
| Index of Refraction |
1.577
|
| LogP |
-0.54
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
7
|
| Complexity |
122
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
S1C(N([H])C(C1([H])[H])=O)=O
|
| InChi Key |
ZOBPZXTWZATXDG-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C3H3NO2S/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6)
|
| Chemical Name |
1,3-thiazolidine-2,4-dione
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: ~200 mg/mL (~1707.5 mM; with ultrasonication)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (42.69 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (50.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 5 mg/mL (42.69 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), Clear solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (50.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 5 mg/mL (42.69 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (50.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 8.5375 mL | 42.6876 mL | 85.3752 mL | |
| 5 mM | 1.7075 mL | 8.5375 mL | 17.0750 mL | |
| 10 mM | 0.8538 mL | 4.2688 mL | 8.5375 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Link: https://clinicaltrials.gov/ct2/show/NCT06838286
Conditions:Diabetes Mellitus, Type 2Link: https://clinicaltrials.gov/ct2/show/NCT00285844
Conditions:Insulin Resistance|Obesity|Metabolic SyndromeLink: https://clinicaltrials.gov/ct2/show/NCT03249506
Conditions:Diabetes Mellitus, Type 2
Title:A Study to Determine the Long Term Safety and Efficacy of Albiglutide in Combination With Oral Monotherapy Antihyperglycemic Medications in Japanese Patients With Type 2 Diabetes Mellitus
Status:Completed
updateDate:2017-05-03
Ctid:NCT01777282
Link: https://clinicaltrials.gov/ct2/show/NCT01777282
Conditions:Diabetes MellitusLink: https://clinicaltrials.gov/ct2/show/NCT00214253
Conditions:Type 1 DiabetesLink: https://clinicaltrials.gov/ct2/show/NCT00683878
Conditions:Type 2 DiabetesLink: https://clinicaltrials.gov/ct2/show/NCT00396227
Conditions:Diabetes Mellitus, Type 2Link: https://clinicaltrials.gov/ct2/show/NCT00975286
Conditions:Type 2 Diabetes MellitusLink: https://clinicaltrials.gov/ct2/show/NCT01468181
Conditions:Type 2 Diabetes MellitusLink: https://clinicaltrials.gov/ct2/show/NCT00046462
Conditions:Diabetes MellitusProducts are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
