Rosiglitazone (potassium salt) (CAS 316371-84-3) || Cayman Chemical

Rosiglitazone (potassium salt)

Cayman Chemical Item Number 71742

(CAS 316371-84-3)

Rosiglitazone (potassium salt) (CAS 316371-84-3)

Description

Thiazolidinediones are a group of structurally related peroxisome proliferator-activated receptor γ (PPARγ) agonists with antidiabetic actions in vivo.^1,2 Rosiglitazone is a prototypical thiazolidinedione and has served as a reference compound for this class.³ Rosiglitazone is a potent and selective PPARγ ligand. It binds to the PPARγ ligand-binding domain with a K_d of 43 nM.³ It activates a luciferase-based PPARγ expression construct with an EC₅₀ of about 1.0 µM.³ Rosiglitazone is active in vivo as a antidiabetic agent in the ob/ob mouse model, and has been used as an oral hypoglycemic agent in the treatment of Type II diabetes in humans for many years. The potassium salt of rosiglitazone is a formulation designed to provide better aqueous solubility than the parent compound.

1 Willson, T.M., Cobb, J.E., Cowan, D.J., et al. The structure-activity relationship between peroxisome proliferator-activated receptor γ agonism and the antihyperglycemic activity of thiazolidinediones. J Med Chem 39 665-668 (1996).

2 Cantello, B.C.C., Cawthorne, M.A., Cottam, G.P., et al. [[ω-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents. J Med Chem 37 3977-3985 (1994).

3 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). J Biol Chem 270 12953-12956 (1995).

Formal Name

5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione, monopotassium salt

CAS Number

316371-84-3

Molecular Formula

C₁₈H₁₈N₃O₃S · K

Formula Weight

395.5

Formulation

A crystalline solid

Purity

>98%

λ_max

247 nm

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

Copy SMILES to clipboard

CN(CCOC1=CC=C(CC2SC([N-]C2=O)=O)C=C1)C3=NC=CC=C3.[K+]

Background Reading

Willson, T.M., Cobb, J.E., Cowan, D.J., et al. The structure-activity relationship between peroxisome proliferator-activated receptor γ agonism and the antihyperglycemic activity of thiazolidinediones. J Med Chem 39 665-668 (1996).

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). J Biol Chem 270 12953-12956 (1995).

Cantello, B.C.C., Cawthorne, M.A., Cottam, G.P., et al. [[ω-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents. J Med Chem 37 3977-3985 (1994).

Rosiglitazone (potassium salt) is available in the following screening library:

Bio-active Lipid I Screening Library (96-Well)

Size

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