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Chemistry

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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
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 Weight 489.4 g/mol
Molecular Formula C18H19F8N5O2
XLogP30.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count13
Rotatable Bond Count4
Exact Mass489.14110016 g/mol
Monoisotopic Mass489.14110016 g/mol
Topological Polar Surface Area92.4 Ų
Heavy Atom Count33
Formal Charge0
Complexity746
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 ATC Code

A - Alimentary tract and metabolism

A10 - Drugs used in diabetes

A10B - Blood glucose lowering drugs, excl. insulins

A10BH - Dipeptidyl peptidase 4 (dpp-4) inhibitors

A10BH06 - Gemigliptin


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