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    Velusetrag

    PharmaCompass
    Xls

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    2D Structure
    Also known as: Td-5108, 866933-46-2, J4vnv64arb, 1,2-dihydro-n-[(3-endo)-8-[(2r)-2-hydroxy-3-[methyl(methylsulfonyl)amino]propyl]-8-azabicyclo[3.2.1]oct-3-yl]-1-(1-methylethyl)-2-oxo-3-quinolinecarboxamide, 3-quinolinecarboxamide, 1,2-dihydro-n-((3-endo)-8-((2r)-2-hydroxy-3-(methyl(methylsulfonyl)amino)propyl)-8-azabicyclo(3.2.1)oct-3-yl)-1-(1-methylethyl)-2-oxo-, Td 5108
    Molecular Formula
    C25H36N4O5S
    Molecular Weight
    504.6  g/mol
    InChI Key
    HXLOHDZQBKCUCR-VTHDOGFWSA-N
    FDA UNII
    J4VNV64ARB
    Velusetrag has been used in trials studying the treatment of Gastroparesis and Alzheimer's Disease. It is a highly selective serotonin receptor agonist effective in patients with chronic constipation. It is being developed by Theravance. Velusetrag was discovered by Theravance through the application of its multivalent drug design in a research program dedicated to finding new treatments for GI motility disorders.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[(1S,5R)-8-[(2R)-2-hydroxy-3-[methyl(methylsulfonyl)amino]propyl]-8-azabicyclo[3.2.1]octan-3-yl]-2-oxo-1-propan-2-ylquinoline-3-carboxamide
    2.1.2 InChI
    InChI=1S/C25H36N4O5S/c1-16(2)29-23-8-6-5-7-17(23)11-22(25(29)32)24(31)26-18-12-19-9-10-20(13-18)28(19)15-21(30)14-27(3)35(4,33)34/h5-8,11,16,18-21,30H,9-10,12-15H2,1-4H3,(H,26,31)/t18?,19-,20+,21-/m0/s1
    2.1.3 InChI Key
    HXLOHDZQBKCUCR-VTHDOGFWSA-N
    2.1.4 Canonical SMILES
    CC(C)N1C2=CC=CC=C2C=C(C1=O)C(=O)NC3CC4CCC(C3)N4CC(CN(C)S(=O)(=O)C)O
    2.1.5 Isomeric SMILES
    CC(C)N1C2=CC=CC=C2C=C(C1=O)C(=O)NC3C[C@H]4CC[C@@H](C3)N4C[C@H](CN(C)S(=O)(=O)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    J4VNV64ARB
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid ((1s,3r,5r)-8-((r)-2-hydroxy-3-(methanesulfonyl-methyl-amino)propyl)-8-aza-bicyclo(3.2.1)oct-3-yl)amide

    2. Td-5108

    3. Td5108

    2.3.2 Depositor-Supplied Synonyms

    1. Td-5108

    2. 866933-46-2

    3. J4vnv64arb

    4. 1,2-dihydro-n-[(3-endo)-8-[(2r)-2-hydroxy-3-[methyl(methylsulfonyl)amino]propyl]-8-azabicyclo[3.2.1]oct-3-yl]-1-(1-methylethyl)-2-oxo-3-quinolinecarboxamide

    5. 3-quinolinecarboxamide, 1,2-dihydro-n-((3-endo)-8-((2r)-2-hydroxy-3-(methyl(methylsulfonyl)amino)propyl)-8-azabicyclo(3.2.1)oct-3-yl)-1-(1-methylethyl)-2-oxo-

    6. Td 5108

    7. Velusetrag [usan]

    8. Velusetrag [inn]

    9. Unii-j4vnv64arb

    10. Velusetrag [usan:inn]

    11. Velusetrag [who-dd]

    12. Gtpl8425

    13. Schembl2917361

    14. Chembl2087337

    15. Dtxsid001029768

    16. Serotonin 5-ht4 Receptor Agonists

    17. Bdbm50391069

    18. Zinc15821733

    19. Compound 15 [pmid 22959244]

    20. Db12702

    21. Hy-10457

    22. Cs-0002610

    23. E98885

    24. N-((1r,3r,5s)-8-((2r)-2-hydroxy-3-(methyl(methylsulfonyl)amino)propyl)-8- Azabicyclo(3.2.1)oct-3-yl)-1-(1-methylethyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide

    25. N-((1r,3r,5s)-8-((2r)-2-hydroxy-3-(methyl(methylsulfonyl)amino)propyl)-8-azabicyclo(3.2.1)oct-3-yl)-1-(1-methylethyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide

    26. N-[(1r,5s)-8-[(2r)-2-hydroxy-3-(methyl-methylsulfonylamino)propyl]-8-azabicyclo[3.2.1]octan-3-yl]-2-oxo-1-propan-2-ylquinoline-3-carboxamide

    27. N-[(1s,5r)-8-[(2r)-2-hydroxy-3-[methyl(methylsulfonyl)amino]propyl]-8-azabicyclo[3.2.1]octan-3-yl]-2-oxo-1-propan-2-ylquinoline-3-carboxamide

    2.4 Create Date
    2006-11-06
    3 Chemical and Physical Properties
    Molecular Weight 504.6 g/mol
    Molecular Formula C25H36N4O5S
    XLogP31.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count8
    Exact Mass504.24064144 g/mol
    Monoisotopic Mass504.24064144 g/mol
    Topological Polar Surface Area119 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity932
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Pharmacology

    Studies demonstrating the in vivo preclinical profile of Velusetrag showed that the compound has potent 5-HT4 receptor agonist activity by several routes of administration, including oral, providing robust prokinetic activity in the digestive tract of three different animal species, consistent with its highly potent and selective 5-HT4 receptor agonist in vitro profile.

    4.2 Mechanism of Action

    Velusetrag is a potent, highly selective agonist with high intrinsic activity at the 5-HT4 receptor. Relative to other 5-HT receptor types, Velusetrag is > 500-fold selective for binding to the human 5-HT4 receptor. Theravance anticipates that the high degree of selectivity of Velusetrag provides the potential for it to be a better and safer medicine for the treatment of patients with severe constipation and possibly constipation predominant irritable bowel syndrome.