Rosiglitazone

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Description: Potent and selective PPARγ agonist; antidiabetic agent
Alternative Names: BRL 49653
Chemical Name: 5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione
Purity: ≥98% (HPLC)
Datasheet
Citations (15)
Reviews (1)

Biological Activity for Rosiglitazone

Rosiglitazone is a potent and selective PPARγ agonist (EC50 = 60 nM); exhibits no activity at PPARα and PPARβ. Promotes differentiation of pluripotent C3H10T1/2 stem cells into adipocytes. Also promotes differentiation of urothelial organoids in combination with Erlotinib (Cat. No. 7194). Exhibits antihyperglycemic activity in diabetic ob/ob mouse model. Antidiabetic agent.

Compound Libraries for Rosiglitazone

Rosiglitazone is also offered as part of the Tocriscreen 2.0 Max, Tocriscreen FDA-Approved Drugs and Tocriscreen Stem Cell Library. Find out more about compound libraries available from Tocris.

Technical Data for Rosiglitazone

M. Wt 357.43
Formula C18H19N3O3S
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 122320-73-4
PubChem ID 77999
InChI Key YASAKCUCGLMORW-UHFFFAOYSA-N
Smiles CN(CCOC1=CC=C(CC2SC(NC2=O)=O)C=C1)C3=CC=CC=N3

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for Rosiglitazone

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 35.74 100

Preparing Stock Solutions for Rosiglitazone

The following data is based on the product molecular weight 357.43. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.8 mL 13.99 mL 27.98 mL
5 mM 0.56 mL 2.8 mL 5.6 mL
10 mM 0.28 mL 1.4 mL 2.8 mL
50 mM 0.06 mL 0.28 mL 0.56 mL

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Product Datasheets for Rosiglitazone

Certificate of Analysis / Product Datasheet
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References for Rosiglitazone

References are publications that support the biological activity of the product.

Lehmann et al (1995) An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor gamma (PPAR gamma). J.Biol.Chem. 270 12953 PMID: 7768881

Willson et al (1996) The structure-activity relationship between peroxisome proliferator-activated receptor gamma agonism and the antihyperglycemic activity of thiazolidinediones. J.Med.Chem. 39 665 PMID: 8576907

Santos et al (2019) Urothelial organoids originating from Cd49fhigh mouse stem cells display Notch-dependent differentiation capacity. Nat.Commun. 10 4407 PMID: 31562298


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Keywords: Rosiglitazone, Rosiglitazone supplier, BRL49653, High, affinity, selective, PPAR, agonist, thiazolidinedione, TZD, derivative, antidiabetic, agent, organoids, differentiation, BRL, 49653, PPARgamma, Receptors, Other, Differentiation, Products, Organoids, 5325, Tocris Bioscience

15 Citations for Rosiglitazone

Citations are publications that use Tocris products. Selected citations for Rosiglitazone include:

Vincenzo et al (2021) Beneficial Effects of Akkermansia muciniphila Are Not Associated with Major Changes in the Circulating Endocannabinoidome but Linked to Higher Mono-Palmitoyl-Glycerol Levels as New PPARα Agonists. Cells 10 PMID: 33477821

Vincenzo et al (2021) Three of a Kind: Control of the Expression of Liver-Expressed Antimicrobial Peptide 2 (LEAP2) by the Endocannabinoidome and the Gut Microbiome. Molecules 27 PMID: 35011234

Chang et al (2021) Ketogenic diet prevents paclitaxel-induced neuropathic nociception through activation of PPARγ signalling pathway and inhibition of neuroinflammation in rat dorsal root ganglion. Eur J Neurosci 54 5341-5356 PMID: 34318540

Mark et al (2017) High Concentrations of Rosiglitazone Reduce mRNA and Protein Levels of LRP1 in HepG2 Cells. Front Pharmacol 8 772 PMID: 29201005

Matsa et al (2016) Transcriptome Profiling of Patient-Specific Human iPSC-Cardiomyocytes Predicts Individual Drug Safety and Efficacy Responses In Vitro. Cell Stem Cell. 19 311 PMID: 27545504

Warrick et al (2016) FOXA1, GATA3 and PPARγ Cooperate to Drive Luminal Subtype in Bladder Cancer: A Molecular Analysis of Established Human Cell Lines. Sci Rep 6 38531 PMID: 27924948

Ahlem et al (2011) Studies of the pharmacology of 17α-ethynyl-androst-5-ene-3β,7β,17β-triol, a synthetic anti-inflammatory androstene. Int J Clin Exp Med 4 119 PMID: 21686136

Luciano et al (2020) Identification and Characterization of Cannabimovone, a Cannabinoid from Cannabis sativa, as a Novel PPARγ Agonist via a Combined Computational and Functional Study. Molecules 25 PMID: 32138197

Liang et al (2020) Generation of Functional Brown Adipocytes from Human Pluripotent Stem Cells via Progression through a Paraxial Mesoderm State. Cell Stem Cell 27 784-797.e11 PMID: 32783886

Elisabetta et al (2023) Targeting gut dysbiosis against inflammation and impaired autophagy in Duchenne muscular dystrophy. EMBO Mol Med 15 e16225 PMID: 36594243

Fellous et al (2020) Phytocannabinoids promote viability and functional adipogenesis of bone marrow-derived mesenchymal stem cells through different molecular targets Biochemical Pharmacology 175 PMID: 32061773

Vitale et al (2018) Fishing for Targets of Alien Metabolites: A Novel Peroxisome Proliferator-Activated Receptor (PPAR) Agonist from a Marine Pest. Mar Drugs 16 PMID: 30400299

Brust et al (2018) A structural mechanism for directing corepressor-selective inverse agonism of PPARγ. Nat Commun 9 4687 PMID: 30409975

Smith et al (2019) Identification and characterization of a novel anti-inflammatory lipid isolated from Mycobacterium vaccae, a soil-derived bacterium with immunoregulatory and stress resilience properties. Psychopharmacology (Berl) PMID: 31119329

Yun-Hee et al (2009) Inhibition of thymic adipogenesis by caloric restriction is coupled with reduction in age-related thymic involution. J Immunol 183 3040-52 PMID: 19648267


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Reviews for Rosiglitazone

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Agonist dose-response analyses of the Human PPAR gamma Assay..
By GAJANAN KATKAR on 12/07/2019
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: PPARg reporter cells

PPAR gamma Assay was performed using manual dispensing and following the protocol described in this Technical Manual, using the Rosiglitazone. PPAR gamma reporter cells treated with 2,500 nM Rosiglitazone yielded an average RLU value with CV=7%, S/B = 162 and a corresponding Z’= 0.78.