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Also known as: 911637-19-9, Gemigliptin [inn], Lc15-0444, 5dhu18m5d6, (s)-1-(2-amino-4-(2,4-bis(trifluoromethyl)-5,8-dihydropyrido[3,4-d]pyrimidin-7(6h)-yl)-4-oxobutyl)-5,5-difluoropiperidin-2-one, Lc-15-0444

Molecular Formula

C₁₈H₁₉F₈N₅O₂

Molecular Weight

489.4 g/mol

InChI Key

ZWPRRQZNBDYKLH-VIFPVBQESA-N

FDA UNII

5DHU18M5D6

Gemigliptin is an orally bioavailable inhibitor of the serine protease dipeptidyl peptidase 4 (DPP-4), with hypoglycemic and potential renoprotective activities. Upon administration, gemigliptin binds to DPP-4 and inhibits the breakdown of the incretin hormones, glucagon-like peptide-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP). This prolongs incretin activity, increases postprandial insulin secretion from pancreatic beta cells, decreases glucagon secretion, delays gastric emptying and lowers blood glucose levels. In addition, gemigliptin exerts a renoprotective effect, probably through enhanced GLP-1 signaling, may prevent apoptosis and acute kidney injury induced by nephrotoxic agents, and may protect against diabetic nephropathy.

1 2D Structure

Gemigliptin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(2S)-2-amino-4-[2,4-bis(trifluoromethyl)-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5,5-difluoropiperidin-2-one

2.1.2 InChI

InChI=1S/C18H19F8N5O2/c19-16(20)3-1-12(32)31(8-16)6-9(27)5-13(33)30-4-2-10-11(7-30)28-15(18(24,25)26)29-14(10)17(21,22)23/h9H,1-8,27H2/t9-/m0/s1

2.1.3 InChI Key

ZWPRRQZNBDYKLH-VIFPVBQESA-N

2.1.4 Canonical SMILES

C1CC(CN(C1=O)CC(CC(=O)N2CCC3=C(C2)N=C(N=C3C(F)(F)F)C(F)(F)F)N)(F)F

2.1.5 Isomeric SMILES

C1CC(CN(C1=O)C[C@H](CC(=O)N2CCC3=C(C2)N=C(N=C3C(F)(F)F)C(F)(F)F)N)(F)F

2.2 Other Identifiers

2.2.1 UNII

5DHU18M5D6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Lc15-0444

2.3.2 Depositor-Supplied Synonyms

1. 911637-19-9

2. Gemigliptin [inn]

3. Lc15-0444

4. 5dhu18m5d6

5. (s)-1-(2-amino-4-(2,4-bis(trifluoromethyl)-5,8-dihydropyrido[3,4-d]pyrimidin-7(6h)-yl)-4-oxobutyl)-5,5-difluoropiperidin-2-one

6. Lc-15-0444

7. 911637-19-9 (free Base)

8. Lc-150444

9. (s)-1-(2-amino-4-(2,4-bis(trifluoromethyl)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8h)-yl)-4-oxobutyl)-5,5-difluoropiperidin-2-one

10. 2-piperidinone, 1-((2s)-2-amino-4-(5,8-dihydro-2,4-bis(trifluoromethyl)pyrido(3,4-d)pyrimidin-7(6h)-yl)-4-oxobutyl)-5,5-difluoro-

11. Pyrido(3,4-d)pyrimidine, 7-((3s)-3-amino-4-(5,5-difluoro-2-oxo-1-piperidinyl)-1-oxobutyl)-5,6,7,8-tetrahydro-2,4-bis(trifluoromethyl)-

12. Unii-5dhu18m5d6

13. 1-[(2s)-2-amino-4-[2,4-bis(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5,5-difluoropiperidin-2-one

14. Gemigliptin Hydrochloride

15. Gemigliptin (prop.inn)

16. Gemigliptin [who-dd]

17. Schembl1262740

18. Chembl3707235

19. Chebi:134731

20. Dtxsid501030150

21. Zinc68245464

22. Akos025290873

23. Db12412

24. As-75936

25. Hy-14892

26. Cs-0003618

27. D10502

28. A854536

29. Q5530612

30. 1-((2s)-2-amino-4-(2,4-bis(trifluoromethyl)-5,8-dihydropyrido(3,4-d)pyrimidin-7(6h)-yl)-4-oxobutyl)-5,5-difluoropiperidin-2-one

31. 1-((2s)-2-amino-4-(2,4-bis(trifluoromethyl)-5,8-dihydropyrido(3,4-d)pyrimidin-7(6h)-yl)-4-oxobutyl-5,5-difluoropiperidin-2-one

2.4 Create Date

2006-11-20

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₉F₈N₅O₂
Molecular Weight	489.4 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	4
Exact Mass	489.14110016 g/mol
Monoisotopic Mass	489.14110016 g/mol
Topological Polar Surface Area	92.4 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	746
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