8265. Rosiglitazone

Nomenclature

CAS number: 122320-73-4
5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione; 5-[4-[2-[N-methyl-N-(2-pyridinyl)amino]ethoxy]benzyl]-2,4-thiazolidinedione; BRL-49653.
C18H19N3O3S; mol wt 357.43.
C 60.49%, H 5.36%, N 11.76%, O 13.43%, S 8.97%.

Description and references

Insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR-γ). Prepn: R. M. Hindley, EP 306228; idem, US 5002953 (1989, 1991 both to Beecham); B. C. C. Cantello et al., J. Med. Chem. 37, 3977 (1994). Pharmacology: N. D. Oakes et al., Diabetes 43, 1203 (1994). Binding study: D. E. Mais et al., Med. Chem. Res. 7, 325 (1997). Clinical pharmacokinetics and bioavailability: M. I. Freed et al., Eur. J. Clin. Pharmacol. 55, 53 (1999). Review of pharmacology and clinical experience: J. A. Barman Balfour, G. L. Plosker, Drugs 57, 921-930 (1999).

Chemical structure

Properties

Colorless crystals from methanol, mp 153-155°.

Derivative

Maleate.

Nomenclature

CAS number: 155141-29-0
BRL-49653c; Avandia (GSK).
C18H19N3O3S.C4H4O4; mol wt 473.50.
C 55.80%, H 4.90%, N 8.87%, O 23.65%, S 6.77%.

Properties

White to off-white solid, mp 122-123°. pKa 6.1; 6.8. Readily sol in ethanol and in buffered aq soln with pH of 2.3; soly decreases with increasing pH in the physiological range.

Therapeutic Category

Antidiabetic.

Keywords

Insulin Sensitizer; Antidiabetic; Thiazolidinediones