CAS 155141-29-0|Rosiglitazone maleate
Introduction：Basic information about CAS 155141-29-0|Rosiglitazone maleate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Rosiglitazone maleate | ||
|---|---|---|---|
| CAS Number | 155141-29-0 | Molecular Weight | 473.50 |
| Density | 1.4±0.1 g/cm3 | Boiling Point | 585ºC at 760 mmHg |
| Molecular Formula | C22H23N3O7S | Melting Point | 235-240°C |
| MSDS | / | Flash Point | 307.6ºC |
Names
| Name | rosiglitazone maleate |
|---|---|
| Synonym | More Synonyms |
Rosiglitazone maleate BiologicalActivity
| Description | Rosiglitazone maleate is a potent and selective activator of PPARγ, with EC50s of 30 nM, 100 nM and 60 nM for PPARγ1, PPARγ2, and PPARγ, respectively, and a Kd of appr 40 nM for PPARγ; Rosiglitazone maleate is also an modulator of TRP channels, inhibits TRP melastatin 2 (TRPM2), TRPM3 and activates TRP canonical 5 (TRPC5). |
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| Related Catalog | Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Membrane Transporter/Ion Channel >>TRP ChannelResearch Areas >>Inflammation/ImmunologyResearch Areas >>Metabolic Disease |
| Target | PPARγ1:30 nM (EC50) PPARγ2:100 nM (EC50) |
| In Vitro | Rosiglitazone maleate is a potent and selective activator of PPARγ, with EC50s of 30 nM and 100 nM for PPARγ1 and PPARγ2, respectively, and a Kd of appr 40 nM for PPARγ. Rosiglitazone (BRL49653, 0.1, 1,10 μM) promotes differentiation of C3H10T1/2 stem cells to adipocytes[1]. Rosiglitazone (Compound 6) activates PPARγ, with an EC50 of 60 nM[2]. Rosiglitazone (1 μM) activates PPARγ, which binds to NF-α1 promoter to activate gene transcription in neurons. Rosiglitazone (1 μM) also protects Neuro2A cells and hippocampal neurons against oxidative stress, and up-regulates BCL-2 expression in an NF-α1-dependent manner[3]. Rosiglitazone completely inhibits TRPM3 with IC50 values of 9.5 and 4.6 μM against nifedipine- and PregS-evoked activity, but such effects are not via PPARγ. Rosiglitazone inhibits TRPM2 at higher concentration, with an IC50 of appr 22.5 μM. Rosiglitazone is a strong stimulator of TRPC5 channels, with an EC50 of ∼30 μM[4]. |
| In Vivo | Rosiglitazone (5 mg/kg, p.o.) decreases the serum glucose in diabetic rats. Rosiglitazone also decreases IL-6, TNF-α, and VCAM-1 levels in diabetic group. Rosiglitazone in combination with losartan increases glucose compared to diabetic and Los-treated groups. Rosiglitazone significantly ameliorates endothelial dysfunction indicated by a significantly lower contractile response to PE and Ang II and enhancement of ACh-provoked relaxation in aortas isolated from diabetic rats[5]. |
| Kinase Assay | cDNA encoding amino acids 174-475 of PPARγ1 is amplified via polymerase chain reaction and inserted into bacterial expression vector pGEX-2T. GST-PPARγ LBD is expressed in BL21(DE3)plysS cells and extracts. For saturation binding analysis, bacterial extracts (100 μg of protein) are incubated at 4°C for 3 h in buffer containing 10 mM Tris (pH 8.0), 50 mM KCl, 10 mM dithiothreitol with [3H]-BRL49653 (specific activity, 40 Ci/mmol) in the presence or absence of unlabeled Rosiglitazone. Bound is separated from free radioactivity by elution through 1-mL Sephadex G-25 desalting columns. Bound radioactivity eluted in the column void volume and is quantitated by liquid scintillation counting[1]. |
| Cell Assay | C3H10T1/2 cells are grown in a 24-well plate in DME medium supplemented with 10% fetal calf serum. Medium and compound (Rosiglitazone) are exchanged every 3 days. Cells are stained at day 7 with Oil Red O and photographed[1]. |
| Animal Admin | Rats are intravenously injected with 38 mg/kg streptozotocin and after 48 h, diabetes is identified by urinary glucosuria and then random blood sugar is measured and this day is regarded as day 0. Animals with a serum glucose level of 220-300 mg/dL are selected to be used in this study. Rats are randomly separated into five groups for daily drug administration for 8 weeks: group 1: control nondiabetic rats given a vehicle only (0.5 mL/kg of 0.5% carboxy methyl celleluse orally), group 2: control diabetic rats given a vehicle, group 3: diabetic rats receiving Rosiglitazone (5 mg/kg orally), group 4: diabetic rats receiving losartan (2 mg/kg, orally), and group 5: diabetic rats receiving both Rosiglitazone and losartan[2]. |
| References | [1]. Lehmann JM, et al. An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor gamma (PPAR gamma). J Biol Chem. 1995 Jun 2;270(22):12953-6. [2]. Willson TM, et al. The structure-activity relationship between peroxisome proliferator-activated receptor gamma agonism and the antihyperglycemic activity of thiazolidinediones. J Med Chem. 1996 Feb 2;39(3):665-8. [3]. Thouennon E, et al. Rosiglitazone-activated PPARγ induces neurotrophic factor-α1 transcription contributing to neuroprotection. J Neurochem. 2015 Aug;134(3):463-70. [4]. Majeed Y, et al. Rapid and contrasting effects of rosiglitazone on transient receptor potential TRPM3 and TRPC5 channels. Mol Pharmacol. 2011 Jun;79(6):1023-30. [5]. Ateyya H, et al. Beneficial effects of rosiglitazone and losartan combination in diabetic rats. Can J Physiol Pharmacol. 2018 Mar;96(3):215-220. |
Chemical & Physical Properties
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Boiling Point | 585ºC at 760 mmHg |
| Melting Point | 235-240°C |
| Molecular Formula | C22H23N3O7S |
| Molecular Weight | 473.50 |
| Flash Point | 307.6ºC |
| PSA | 96.83000 |
| LogP | 2.38 |
| Index of Refraction | 1.688 |
| InChIKey | SUFUKZSWUHZXAV-BTJKTKAUSA-N |
| SMILES | CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c1ccccn1.O=C(O)C=CC(=O)O |
| Storage condition | -20°C Freezer |
Safety Information
| Hazard Codes | Xi |
|---|---|
| Risk Phrases | R20/21/22 |
| Safety Phrases | S24/25 |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Synonyms
| (5-(4-(2-(N-Methyl-N-(2-pyridinyl)amino)ethoxy)benzylidene)-2,4-thiazolidinedione |
| (5E)-5-(4-{2-[Methyl(pyridin-2-yl)amino]ethoxy}benzylidene)-1,3-thiazolidine-2,4-dione |
| 5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione maleate salt |
| 2,4-Thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methylene]-, (5E)- |
| MFCD03427306 |
| (5E)-5-(4-{2-[Methyl(2-pyridinyl)amino]ethoxy}benzylidene)-1,3-thiazolidine-2,4-dione |
| Rosiglitazone maleate |
| Rosiglitazone (maleate) |
