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Piboserod

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Synopsis

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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

Piboserod

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 Formula	C₂₂H₃₁N₃O₂
Molecular Weight	369.5 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	369.24162724 g/mol
Monoisotopic Mass	369.24162724 g/mol
Topological Polar Surface Area	46.5 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	492
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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