An internal standard for the quantification of rosiglitazone
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Rosiglitazone-d3

Item No. 22562

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[[4-[2-(methyl-d3-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione
CAS Number
1132641-22-5
Molecular Formula
C18H16D3N3O3S
Formula Weight
360.4
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
O=C(C(S1)CC(C=C2)=CC=C2OCCN(C([2H])([2H])[2H])C3=NC=CC=C3)NC1=O
InChi Code
InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)/i1D3
InChi Key
YASAKCUCGLMORW-FIBGUPNXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $215

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    5 mg

    $858

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    Product Description

    Rosiglitazone-d3 is intended for use as an internal standard for the quantification of rosiglitazone (Item Nos. 71740 | 11884 | 71742) by GC- or LC-MS. Rosiglitazone is an agonist of peroxisome proliferator-activated receptor γ (PPARγ).1 It activates PPARγ1 and PPARγ2 in reporter assays (EC50s = 30 and 100 nM, respectively). Rosiglitazone selectively activates chimeras containing the ligand-binding domains (LBDs) of PPARγ over PPARα and PPARδ in a cell-based reporter assay at 10 mM. It induces differentiation of C3H10T1/2 stem cells into adipocytes when used at a concentration of 1 µM. Rosiglitazone is also an inhibitor of long-chain acyl-CoA synthetase 4 (ACSL4; IC50 = 0.5 µM), inhibits RSL3-induced ferroptosis in Pfa1 cells and Pparg knockout (KO) cells, and increases survival in a Gpx4 KO mouse model of ferroptosis when used at a concentration of 0.0125 mg/ml in the drinking water.2,3 It decreases hemoglobin A1c (HbA1c) and fasting blood glucose levels in a rat model of type 2 diabetes induced by streptozotocin (STZ; Item No. 13104) and a high-carbohydrate and high-fat diet when administered at a dose of 4 mg/kg.4 Formulations containing rosiglitazone have been used to improve glycemic control in the treatment of type 2 diabetes.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lehmann, J.M., Moore, L.B., Smith-Oliver, T.A., et al. An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor γ (PPARγ). The Journal of Biological Chemisty 270(22), 12953-12956 (1995).

    2. Kim, J.-H., Lewin, T.M., and Coleman, R.A. Expression and characterization of recombinant rat Acyl-CoA synthetases 1, 4, and 5. Selective inhibition by triacsin C and thiazolidinediones. The Journal of Biological Chemisty 276(27), 24667-24673 (2001).

    3. Doll, S., Proneth, B., Tyurina, Y.Y., et al. ACSL4 dictates ferroptosis sensitivity by shaping cellular lipid composition. Nat. Chem. Biol. 13(1), 91-98 (2017).

    4. Zhou, J.Y., Zhou, S.W., Zhang, K.B., et al. Chronic effects of berberine on blood, liver glucolipid metabolism and liver PPARs expression in diabetic hyperlipidemic rats. Biol. Pharm. Bull. 31(6), 1169-1176 (2008).