Rosiglitazone
Title: Rosiglitazone
CAS Registry Number: 122320-73-4
CAS Name: 5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione
Additional Names: 5-[4-[2-[N-methyl-N-(2-pyridinyl)amino]ethoxy]benzyl]-2,4-thiazolidinedione
Manufacturers' Codes: BRL-49653
Molecular Formula: C18H19N3O3S
Molecular Weight: 357.43
Percent Composition: C 60.49%, H 5.36%, N 11.76%, O 13.43%, S 8.97%
Literature References: Insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR-g). 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).
Properties: Colorless crystals from methanol, mp 153-155°.
Melting point: mp 153-155°
 
Derivative Type: Maleate
CAS Registry Number: 155141-29-0
Manufacturers' Codes: BRL-49653c
Trademarks: Avandia (GSK)
Molecular Formula: C18H19N3O3S.C4H4O4
Molecular Weight: 473.50
Percent Composition: 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.
Melting point: mp 122-123°
pKa: pKa 6.1; 6.8
 
Therap-Cat: Antidiabetic.
Keywords: Insulin Sensitizer; Antidiabetic; Thiazolidinediones.

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