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    Piboserod

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 152811-62-6, Sb-207266, N-((1-butylpiperidin-4-yl)methyl)-3,4-dihydro-2h-[1,3]oxazino[3,2-a]indole-10-carboxamide, N-[(1-butylpiperidin-4-yl)methyl]-3,4-dihydro-2h-[1,3]oxazino[3,2-a]indole-10-carboxamide, Sb207256, 4uq3s81b25
    Molecular Formula
    C22H31N3O2
    Molecular Weight
    369.5  g/mol
    InChI Key
    KVCSJPATKXABRQ-UHFFFAOYSA-N
    FDA UNII
    4UQ3S81B25
    Piboserod (SB 207266) is a selective 5-HT(4) receptor antagonist.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[(1-butylpiperidin-4-yl)methyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide
    2.1.2 InChI
    InChI=1S/C22H31N3O2/c1-2-3-11-24-13-9-17(10-14-24)16-23-21(26)20-18-7-4-5-8-19(18)25-12-6-15-27-22(20)25/h4-5,7-8,17H,2-3,6,9-16H2,1H3,(H,23,26)
    2.1.3 InChI Key
    KVCSJPATKXABRQ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCN1CCC(CC1)CNC(=O)C2=C3N(CCCO3)C4=CC=CC=C42
    2.2 Other Identifiers
    2.2.1 UNII
    4UQ3S81B25
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 152811-62-6

    2. Sb-207266

    3. N-((1-butylpiperidin-4-yl)methyl)-3,4-dihydro-2h-[1,3]oxazino[3,2-a]indole-10-carboxamide

    4. N-[(1-butylpiperidin-4-yl)methyl]-3,4-dihydro-2h-[1,3]oxazino[3,2-a]indole-10-carboxamide

    5. Sb207256

    6. 4uq3s81b25

    7. Sb 207266

    8. Piboserod,2h-(1,3)oxazino(3,2-a)indole-10-carboxamide, N-((1-butyl-4-piperidinyl)methyl)-3,4-dihydro-

    9. N-[(1-butyl-4-piperidinyl)methyl]-3,4-dihydro-2h-[1,3]-oxazino[3,2-a]indole-10-carboxamide

    10. Piboserod [inn]

    11. Piboserod [inn:ban]

    12. Serotonin 5-ht4 Receptor Antagonists

    13. Unii-4uq3s81b25

    14. Piboserod [mi]

    15. Sb207266(piboserod)

    16. Piboserod [who-dd]

    17. Gtpl225

    18. Schembl467339

    19. Chembl356359

    20. Bdbm85026

    21. Dtxsid60165129

    22. Bcp15982

    23. Ex-a1189

    24. Zinc1537633

    25. Mfcd00923681

    26. Pdsp1_001702

    27. Pdsp2_001685

    28. Akos015909931

    29. Db04873

    30. Fd10684

    31. Sb 207266-a

    32. Ncgc00250378-01

    33. Ac-36094

    34. As-82492

    35. Bp166459

    36. Hy-15574

    37. Sb 207256

    38. Ft-0722955

    39. Q75884

    40. Sb-207266, >=98% (hplc)

    41. L000973

    42. N-(1-butylpiperidine-4-ylmethyl)-1,2-(trimethyleneoxy)-1h-indole-3-carboxamide

    43. 2h-(1,3)oxazino(3,2-a)indole-10-carboxamide, N-((1-butyl-4-piperidinyl)methyl)-3,4-dihydro-

    44. N-((1-butyl-4-piperidyl)-methyl)-3,4-dihydro-2h-(1,3)oxazino(3,2-a)indole-10-carboxamide

    45. N-((1-butyl-4-piperidyl)methyl)-3,4-dihydro-2h-(1,3)oxazino(3,2-a)indole-10-carboxamide

    46. N-[(1-butyl-4-piperidinyl)methyl]-3,4-dihydro-2h-[1,3]-oxazino[3,2-alpha]indole-10-carboxamide

    47. N-[(1-butyl4-piperidinyl)methyl]-3,4-dihydro-2h-[1,3]-oxazino[3,2-a]indole-10-carboxamide

    48. N-[(1-butylpiperidin-4-yl)methyl]-2h,3h,4h-[1,3]oxazino[3,2-a]indole-10-carboxamide

    2.4 Create Date
    2005-08-09
    3 Chemical and Physical Properties
    Molecular Weight 369.5 g/mol
    Molecular Formula C22H31N3O2
    XLogP33.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count6
    Exact Mass369.24162724 g/mol
    Monoisotopic Mass369.24162724 g/mol
    Topological Polar Surface Area46.5 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity492
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of atrial fibrillation and irritable bowel syndrome (IBS).

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    GlaxoSmithKline was investigating piboserod, a 5HT4 antagonist, for the treatment of atrial fibrillation. Phase II trials were ongoing in March 2004, but by December of that year, development had been discontinued. Piboserod had previously being investigated for the treatment of irritable bowel syndrome (IBS), but development for this indication was terminated in 1999.

    5.2 Mechanism of Action

    Piboserod appears to act as a specific antagonist of one of the receptors for 5-hydroxytryptamine, the 5-HT4 receptor. The 5-HT4 receptor antagonists are thought to antagonize both the ability of serotonin to sensitize the peristaltic reflex and 5-HT-induced defecation, at least in animal studies. As 5-HT4 receptors are present in human atrial cells and when stimulated may cause atrial arrhythmias, piboserod was under investigation in clinical trials for atrial fibrillation.