A major metabolite of rosiglitazone
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N-desmethyl Rosiglitazone

Item No. 22103

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[[4-[2-(2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione
CAS Number
257892-31-2
Synonyms
  • SB-237216
Molecular Formula
C17H17N3O3S
Formula Weight
343.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 34 mg/mlDMSO:PBS(pH 7.2) (1:3): 0.5 mg/mlEthanol: 1 mg/ml
λmax
242, 309 nm
SMILES
O=C(C(S1)CC(C=C2)=CC=C2OCCNC3=NC=CC=C3)NC1=O
InChi Code
InChI=1S/C17H17N3O3S/c21-16-14(24-17(22)20-16)11-12-4-6-13(7-5-12)23-10-9-19-15-3-1-2-8-18-15/h1-8,14H,9-11H2,(H,18,19)(H,20,21,22)
InChi Key
ZJQTVMXUIGXRMR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    N-desmethyl Rosiglitazone is a major metabolite of rosiglitazone (Item Nos. 71740 | 71742 | 11884), a potent and selective PPARγ ligand present in formulations that have been used to treat type 2 diabetes.1,2 Rosiglitazone is metabolized by the cytochrome P450 (CYP) isoform CYP2C8 to form N-desmethyl rosiglitazone.

    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, K.-B., Lee, D.J., Yeo, C.-W., et al. Simultaneous quantification of rosiglitazone and its two major metabolites, N-desmethyl and p-hydroxy rosiglitazone in human plasma by liquid chromatography/tandem mass spectrometry: Application to a pharmacokinetic study. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 877(20-21), 1951-1956 (2009).