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Chemistry

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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
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 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.


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