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    Gemigliptin

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    2D Structure
    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

    2D Structure

    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