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It:Rosiglitazone

From ChemWiki

Introduction

Structure of Rosiglitazone (note: the carbon in the 5-membered ring between the carbonyl carbon and the sulfur atom is a stereocentre

Rosiglitazone can be used to treat diabetes mellitus. Insulin is made naturally in the Islets of Langerhans in the pancreas. However, sometimes the pancreas does not make enough insulin to meet its needs which results in the condition known as diabetes mellitus. Rosiglitazone works by making the body more sensitive to insulin, so that insuline can be used more effectively. High blood sugar can lead to other complications such as kidney failure, heart disease and blindness.

Avandia

Rosiglitazone is sold commercially as AVANDIA, as Rosiglitazone maleate. AVANDIA is a registered trademark of GlaxoSmithKline. When taking the medicine, it is important to exercise and lose excess weight so that the drug can work efficiently. The usual safety precautions apply when taking AVANDIA i.e. do not take when pregnant or trying to become pregnant or have had heart problems. AVANDIA should not be taken if a patient has or has had previously Type I diabetes. The safety of AVANDIA is unknown for people under 18 years old.








3D structure of Rosiglitazone

(Obtained using a SMILES string created in Chemdraw and inserting into CORINA website)

Chemical Information

Chemical Formula C18H19N3O3S
IUPAC Name (5S)-5-[[4-[2-(methyl-pyridin-2-yl-amino)ethoxy]phenyl]methyl]thiazolidine- 2,4-dione
Other Names 2,4-Thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]- (9CI), 5-[4-[2-(N-Methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione; 5-[[4-[2-[N-Methyl-N-(2-pyridyl)amino]ethoxy]phenyl]methyl]thiazolidine-2,4-dione; BRL 49653; Rosiglitazone; Rosiglizole; TDZ 01
Molecular Weight 357.43
Elemental Analysis C, 60.49; H, 5.36; N, 11.76; O, 13.43; S, 8.97
pKa 6.48+/- 0.12
Melting Point 122.0-123.0oC
Boiling Point 585.0-590.0oC
Density 1.315+/- 0.06 gcm-3
Enthalpy of Vaporisation 87.40+/- 3.0 kJmol-1
Flash Point 307.6+/- 25.9 oC
SMILES O=C(NC3=O)SC3CC(C=C2)=CC=C2OCCN(C)C1=CC=CC=N1
MSDS MSDS


References