Rosiglitazone

Rosiglitazone

Cayman Chemical Item Number 71740

BRL 49653 (CAS 122320-73-4)

Rosiglitazone (CAS 122320-73-4)

Description

Thiazolidinediones (TZDs) are a group of structurally related peroxisome proliferator-activated receptor γ (PPARγ) agonists with antidiabetic actions in vivo.^1,2 Rosiglitazone (BRL 49653) is a prototypical TZD 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 luciferase-based expression constructs PPARγ1 and PPARγ2 with EC₅₀ values of approximately 30 nM and 100 nM, respectively.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.

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).

Synonyms

BRL 49653

Formal Name

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

CAS Number

122320-73-4

Molecular Formula

C₁₈H₁₉N₃O₃S

Formula Weight

357.4

Formulation

A crystalline solid

Purity

≥98%

λ_max

248, 311 nm

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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O=C1NC(=O)C(S1)Cc1ccc(OCCN(C)c2ccccn2)cc1

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).

Size

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