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Also known as: 146062-44-4, Leriglitazone, Hydroxy pioglitazone (m-iv), Min-102, Chebi:82937, Leriglitazone [usan]

Molecular Formula

C₁₉H₂₀N₂O₄S

Molecular Weight

372.4 g/mol

InChI Key

OXVFDZYQLGRLCD-UHFFFAOYSA-N

FDA UNII

K824X25AYA

Leriglitazone is under investigation in clinical trial NCT03917225 (A Clinical Study to Evaluate the Effect of MIN-102 on the Progression of Friedreich's Ataxia in Male and Female Patients).

1 2D Structure

Leriglitazone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C19H20N2O4S/c1-12(22)14-4-5-15(20-11-14)8-9-25-16-6-2-13(3-7-16)10-17-18(23)21-19(24)26-17/h2-7,11-12,17,22H,8-10H2,1H3,(H,21,23,24)

2.1.3 InChI Key

OXVFDZYQLGRLCD-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3)O

2.2 Other Identifiers

2.2.1 UNII

K824X25AYA

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Leriglitazone

2.3.2 Depositor-Supplied Synonyms

1. 146062-44-4

2. Leriglitazone

3. Hydroxy Pioglitazone (m-iv)

4. Min-102

5. Chebi:82937

6. Leriglitazone [usan]

7. 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

8. K824x25aya

9. 2,4-thiazolidinedione, 5-[[4-[2-[5-(1-hydroxyethyl)-2-pyridinyl]ethoxy]phenyl]methyl]-

10. 2,4-thiazolidinedione, 5-((4-(2-(5-(1-hydroxyethyl)-2-pyridinyl)ethoxy)phenyl)methyl)-

11. Hydroxy Pioglitazone-d4 (m-iv) (deuterated)

12. Hydroxy Pioglitazone

13. 1-hydroxypioglitazone

14. Pioglitazone, Hydroxy

15. Leriglitazone [inn]

16. Leriglitazone (usan/inn)

17. Chembl1267

18. Unii-k824x25aya

19. Schembl4098326

20. Dtxsid30399914

21. Bdbm50530214

22. Who 10868

23. Zinc01482947

24. Akos015856344

25. Db15021

26. 5-[[4-[2-[5-(1-hydroxyethyl)-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione

27. Hydroxy Pioglitazone (m-iv Metabolite)

28. Db-042820

29. Hy-117727

30. Cs-0067030

31. Ft-0643388

32. D11603

33. 062h444

34. U-91322

35. A1-01710

36. J-008187

37. Q27156475

38. 5-(4-(2-(5-(1-hydroxyethyl)pyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione

39. 5-(4-{2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione

40. 5-[4-[2-[5-(1-hydroxyethyl)-2-pyridyl]ethoxy]benzyl]-2,4-thiazolidinedione

41. All-ambo-5-((4-(2-(5-(1-hydroxyethyl)pyridin-2-yl)ethoxy)phenyl)methyl)-1,3-thiazole-2,4(3h,5h)-dione

2.4 Create Date

2005-09-13

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₀N₂O₄S
Molecular Weight	372.4 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Exact Mass	372.11437830 g/mol
Monoisotopic Mass	372.11437830 g/mol
Topological Polar Surface Area	114 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	496
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Treatment of adrenoleukodystrophy

5 Pharmacology and Biochemistry

5.1 Metabolism/Metabolites

5-[(4-{2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione is a known human metabolite of Pioglitazone.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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