Rosiglitazone
PubChem CID: 77999
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| Compound Synonyms | rosiglitazone, 122320-73-4, Avandia, Rosiglizole, 5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione, Brl-49653, Brl 49653, Rezult, rosiglitazona, Gaudil, Rosvel, BRL49653, TDZ 01, rosiglitazonum, Avandamet, Avandaryl, rosiglitazone (Avandia), DTXSID7037131, C18H19N3O3S, CHEBI:50122, Rosiglitazone base, UNII-05V02F2KDG, MFCD00871760, NSC-758698, 05V02F2KDG, TDZ-01, HSDB 7555, 2,4-Thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-, 2,4-thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione, Rosigilitazone, 5-((4-(2-Methyl-2-(pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione-2-butenedioate, DTXCID5017131, 5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione, Rosiglitazone (INN), NSC 758698, NCGC00095124-01, BRL 49653C, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione, 5-(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione, ROSIGLITAZONE [INN], 5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione, ROSIGLITAZONE (IARC), ROSIGLITAZONE [IARC], ROSIGLITAZONE (MART.), ROSIGLITAZONE [MART.], Rosiglitazone [INN:BAN], 5-[4-[2-(N-Methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, 5-(4-(2-(N-METHYL-N-(2-PYRIDINYL)AMINO)ETHOXY)BENZYL)-2,4-THIAZOLIDINEDIONE, CAS-122320-73-4, SR-01000763023, Rosiglitazon, Rosigltazone, Rosi, 5-(4-(2-(methyl(pyridin-2-yl)amino)ethoxy)benzyl)-1,3-thiazolidine-2,4-dione, 5-[4-[2-[N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, RGZ, Gaudil (TN), Spectrum_001703, Rosiglitazone (Standard), 1217260-35-9, Spectrum2_001241, Spectrum3_000997, Spectrum4_001125, Spectrum5_001464, ROSIGLITAZONE [MI], SCHEMBL5169, ROSIGLITAZONE [HSDB], BSPBio_002693, KBioGR_001609, KBioSS_002183, ROSIGLITAZONE [VANDF], SPECTRUM1504263, SPBio_001142, ROSIGLITAZONE [WHO-DD], GTPL1056, ROSIGLITAZONE [EMA EPAR], SCHEMBL14383595, KBio2_002183, KBio2_004751, KBio2_007319, KBio3_001913, A10BG02, Rosiglitazone - Bio-X trade mark, Rosiglitazone, >=98% (HPLC), HMS1922J11, HMS2094O13, HMS3649G08, HMS3656K16, HMS3744M11, HMS3871L03, HMS3884N08, Pharmakon1600-01504263, BCP03047, Tox21_111434, BDBM50030474, CCG-39102, HB2556, HY-17386R, NSC758698, STL350047, AKOS015894872, O-De-Me, 2-O-B-D-galactopyranoside, Tox21_111434_1, AC-3459, BCP9000017, CS-1088, DB00412, FR39350, SB17326, NCGC00095124-02, NCGC00095124-03, NCGC00095124-04, NCGC00095124-05, NCGC00095124-06, NCGC00095124-08, BR164372, HY-17386, SY031184, BCP0726000232, NS00008920, R0106, S2556, SW197573-6, 6P-065, D08491, S00306, AB00698473-15, AB00698473-17, AB00698473-18, AB00698473-19, AB00698473_20, AB00698473_21, AB00698473_22, AB00698473_23, Q424771, SR-01000763023-5, SR-01000763023-6, BRD-A97437073-001-02-3, BRD-A97437073-001-03-1, BRD-A97437073-001-04-9, BRD-A97437073-001-08-0, BRD-A97437073-003-14-4, BRD-A97437073-050-13-7, BRD-A97437073-050-14-5, SR-01000763023-12, (+-)-5-(p-(2-(methyl-2-pyridylamino)ethoxy)benzyl)-2,4-thiazolidinedione, (RS)-5-{4-[2-(Methyl-2-pyridylamino)ethoxy]benzyl}-2,4-thiazolidinedion, 5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)-benzyl)thiazolidine-2,4-dione, 5-[4-[2-(N-Methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4dione, 5-[4-[2-[Methyl(2-pyridyl)amino]ethoxy]benzyl]thiazolidine-2,4-dione, IDMB (1uM BRL49653, 1uM Dexamethasone, 0.5uM IBMX, 10ug/mL Insulin), (+/-)-5-[p-[2-(methyl-2-pyridylamino)ethoxy]benzyl]-2,4-thiazolidinedione, 2,4-Thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]- (9CI), 5-[[4-[2-(methyl-(2-pyridyl)amino)ethoxy]phenyl]methyl] thiazolidine-2,4-dione, 5-[[4-[2-(methyl-2-pyridinylamino) ethoxy]phenyl]methyl]-2,4-thiazolidinedione, 5-[[4-[2-(Methyl-2-pyridinylamino)e thoxy]phenyl]methyl]-2,4-thiazolidinedione, 5-[[4-[2-(methyl-pyridin-2-ylamino)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione, 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 |
|---|---|
| Topological Polar Surface Area | 96.8 |
| Hydrogen Bond Donor Count | 1.0 |
| Heavy Atom Count | 25.0 |
| Description | 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 (NFκ, B) levels fall and inhibitor (Iκ, B) 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] |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 468.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Enzyme Uniprot Id | P37231 |
| Iupac Name | 5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione |
| Prediction Hob | 1.0 |
| Class | Benzene and substituted derivatives |
| Target Id | NPT99, NPT866, NPT106, NPT178, NPT582, NPT261, NPT869, NPT713, NPT1028, NPT98, NPT748 |
| Xlogp | 3.1 |
| Superclass | Benzenoids |
| Subclass | Phenol ethers |
| Molecular Formula | C18H19N3O3S |
| Prediction Swissadme | 1.0 |
| Inchi Key | YASAKCUCGLMORW-UHFFFAOYSA-N |
| Fcsp3 | 0.2777777777777778 |
| Logs | -4.167 |
| Rotatable Bond Count | 7.0 |
| State | Solid |
| Logd | 3.024 |
| Synonyms | 5-((4-(2-(Methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione, Avandia, BRL-49653, Rosiglitazona, Rosiglitazone maleate, Rosiglitazonum, Rosiglizole |
| Substituent Name | Dialkylarylamine, Phenol ether, Aralkylamine, Thiazolidinedione, Aminopyridine, Alkyl aryl ether, Imidolactam, Pyridine, Heteroaromatic compound, Thiazolidine, Tertiary amine, Carboxamide group, Azacycle, Organoheterocyclic compound, Thioether, Ether, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Organonitrogen compound, Carbonyl group, Amine, Aromatic heteromonocyclic compound |
| Compound Name | Rosiglitazone |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 1.0 |
| Exact Mass | 357.115 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 357.115 |
| Hydrogen Bond Acceptor Count | 6.0 |
| Molecular Weight | 357.4 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 1.0 |
| Total Bond Stereocenter Count | 0.0 |
| Esol | -4.116496999999999 |
| 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) |
| Smiles | CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3 |
| Nring | 3.0 |
| Defined Bond Stereocenter Count | 0.0 |
- 1. Outgoing r'ship
FOUND_INto/from Liriope Spicata (Plant) Rel Props:Source_db:cmaup_ingredients - 2. Outgoing r'ship
FOUND_INto/from Murraya Koenigii (Plant) Rel Props:Source_db:cmaup_ingredients - 3. Outgoing r'ship
FOUND_INto/from Tadehagi Triquetrum (Plant) Rel Props:Source_db:cmaup_ingredients