(+)-Rosiglitazone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (+)-Rosiglitazone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (+)-Rosiglitazone?

The molecule (+)-Rosiglitazone presents a molecular formula of C18H19N3O3S and its IUPAC name is (5R)-5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione.

Rosiglitazone, marketed under the brand name Avandia, is a medication used to treat diabetes mellitus type 2. Rosiglitazone is an insulin sensitizer, working to increase the sensitivity of cells to insulin. Rosiglitazone is used together with diet and exercise to improve blood sugar control in adults with type 2 diabetes mellitus. Rosiglitazone is not for treating type 1 diabetes..

Common side effects of rosiglitazone include headache, muscle pain, bloating, and nausea. Rosiglitazone can also cause fluid retention, which can lead to or worsen heart failure. Serious side effects may include liver problems, low blood sugar, or an increased risk of heart attack or stroke. Use of rosiglitazone is generally not recommended in people with severe heart failure..

Rosiglitazone was approved for medical use in the United States in 1999. In 2010, the U.S. Food and Drug Administration (FDA) issued a safety warning that rosiglitazone may be associated with an increased risk of heart attack. As a result, the FDA restricted the use of rosiglitazone to patients who could not control their diabetes with other medications and who did not have heart failure. In 2016, the FDA removed the restrictions on rosiglitazone..

Rosiglitazone is a white to off-white powder. It is insoluble in water and slightly soluble in methanol..

3D structure

Cartesian coordinates

Geometry of (+)-Rosiglitazone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(+)-Rosiglitazone YASAKCUCGLMORW-OAHLLOKOSA-N chemical compound 2D structure molecule svg
(+)-Rosiglitazone

 

Molecule descriptors

 
IUPAC name(5R)-5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
InChI codeInChI=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)/t15-/m1/s1
InChI KeyYASAKCUCGLMORW-OAHLLOKOSA-N
SMILESCN(CCOc1ccc(C[C@H]2SC(=O)NC2=O)cc1)c1ccccn1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-Rosiglitazone
  • (+)-rosiglitazone
  • (5R)-5-((4-(2-(Methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione
  • (R)-BRL-49653
  • (R)-Rosiglitazone
  • 163860-16-0
  • 2,4-Thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-, (5R)-
  • 2,4-Thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-, (R)-
  • 3U8PBH2BON
  • Q27121917
  • Rosiglitazone, (+)-
  • Rosiglitazone, (R)-
  • SB-210232
  • sb 210232

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC968330
  • UNII-3U8PBH2BON
  • CHEMBL333304
  • CHEBI:50123
  • SCHEMBL11957687

Physico-Chemical properties

IUPAC name(5R)-5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
Molecular formulaC18H19N3O3S
Molecular weight357.427
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity101.63
LogP2.8
Topological polar surface area96.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.