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CHEMISTRY
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ACTIVE PHARMA INGREDIENTS

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1 USDMF

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Chemistry

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Also known as: (r)-rosiglitazone, 163860-16-0, Rosiglitazone, (r)-, Rosiglitazone, (+)-, Sb 210232, 3u8pbh2bon

Molecular Formula

C₁₈H₁₉N₃O₃S

Molecular Weight

357.4 g/mol

InChI Key

YASAKCUCGLMORW-OAHLLOKOSA-N

FDA UNII

3U8PBH2BON

1 2D Structure

Sb 210232

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5R)-5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

2.1.2 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)/t15-/m1/s1

2.1.3 InChI Key

YASAKCUCGLMORW-OAHLLOKOSA-N

2.1.4 Canonical SMILES

CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3

2.1.5 Isomeric SMILES

CN(CCOC1=CC=C(C=C1)C[C@@H]2C(=O)NC(=O)S2)C3=CC=CC=N3

2.2 Other Identifiers

2.2.1 UNII

3U8PBH2BON

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. (r)-rosiglitazone

2. 163860-16-0

3. Rosiglitazone, (r)-

4. Rosiglitazone, (+)-

5. Sb 210232

6. 3u8pbh2bon

7. Chebi:50123

8. Sb-210232

9. (5r)-5-(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione

10. (5r)-5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione

11. (5r)-5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

12. 2,4-thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-, (5r)-

13. 2,4-thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-, (r)-

14. Unii-3u8pbh2bon

15. Chembl333304

16. Schembl11957687

17. Zinc968330

18. (r)-brl-49653

19. Q27121917

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₉N₃O₃S
Molecular Weight	357.4 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Exact Mass	357.11471265 g/mol
Monoisotopic Mass	357.11471265 g/mol
Topological Polar Surface Area	96.8 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	469
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1