1.0 2011-09-21 00:32:12 UTC 2015-07-21 06:57:47 UTC FDB023598 Rosiglitazone Rosiglitazone is an anti-diabetic drug from the thiazolidinedione class. Like other thiazolidinediones, its mechanism of action is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPAR-gamma. Rosiglitazone is a pure ligand of PPAR-gamma, and has no PPAR-alpha-binding action. Apart from its effect on insulin resistance, it appears to have an anti-inflammatory effect: nuclear factor kappa-B (NFκB) levels fall and inhibitor (IκB) levels increase in patients on rosiglitazone (Mohanty et al). It increases glyceroneogenesis and reduces the release of free fatty acids from adipocytes; Rosiglitazone is an anti-diabetic drug from the thiazolidinedione class. It is being marketed as Avandia by the pharmaceutical company GlaxoSmithKline, both as a standalone preparation and in combination with metformin (Avandamet). Another combination drug approved by the FDA is Avandaryl (with glimepiride); Like other thiazolidinediones, its mechanism of action is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPAR-gamma. Rosiglitazone is a pure ligand of PPAR-gamma, and has no PPAR-alpha binding action. Apart from its effect on insulin resistance, it appears to have an anti-inflammatory effect: nuclear factor kappa-B (NFkB) levels fall and inhibitor (IkB) levels increase in patients on rosiglitazone (Mohanty et al). It increases glyceroneogenesis and reduces the release of free fatty acids from adipocytes . [HMDB] 5-((4-(2-(Methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione Avandia BRL-49653 Rosiglitazona Rosiglitazone maleate Rosiglitazonum Rosiglizole C18H19N3O3S 357.427 357.114712179 5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione rosiglitazone 122320-73-4 CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1 InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23) YASAKCUCGLMORW-UHFFFAOYSA-N belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Phenol ethers Organic compounds Benzenoids Phenol ethers Aromatic heteromonocyclic compounds Alkyl aryl ethers Aminopyridines and derivatives Azacyclic compounds Carbonyl compounds Dialkylarylamines Heteroaromatic compounds Hydrocarbon derivatives Imidolactams Organic carbonic acids and derivatives Organic oxides Organopnictogen compounds Phenoxy compounds Propargyl-type 1,3-dipolar organic compounds Thiazolines Alkyl aryl ether Aminopyridine Aromatic heteromonocyclic compound Azacycle Carbonic acid derivative Carbonyl group Dialkylarylamine Ether Heteroaromatic compound Hydrocarbon derivative Imidolactam Meta-thiazoline Monocyclic benzene moiety Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol ether Phenoxy compound Propargyl-type 1,3-dipolar organic compound Pyridine aminopyridine thiazolidenediones Solid logp 2.95 ALOGPS logs -3.97 ALOGPS solubility 3.80e-02 g/l ALOGPS logp 2.45 ChemAxon pka_strongest_acidic 6.84 ChemAxon pka_strongest_basic 6.23 ChemAxon iupac 5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione ChemAxon average_mass 357.427 ChemAxon mono_mass 357.114712179 ChemAxon smiles CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1 ChemAxon formula C18H19N3O3S ChemAxon inchi InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23) ChemAxon inchikey YASAKCUCGLMORW-UHFFFAOYSA-N ChemAxon polar_surface_area 71.53 ChemAxon refractivity 97.79 ChemAxon polarizability 37.8 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 5 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 23539 Specdb::CMs 159044 Specdb::MsMs 69159 Specdb::MsMs 69160 Specdb::MsMs 69161 Specdb::MsMs 127374 Specdb::MsMs 127375 Specdb::MsMs 127376 Specdb::MsMs 374337 Specdb::MsMs 450863 Specdb::MsMs 450952 Specdb::MsMs 450997 Specdb::MsMs 2229651 Specdb::MsMs 2229818 Specdb::MsMs 3042832 Specdb::MsMs 3042833 Specdb::MsMs 3042834 Specdb::MsMs 3097366 Specdb::MsMs 3097367 Specdb::MsMs 3097368 HMDB05031 Peroxisome proliferator-activated receptor gamma P37231 PPARG