Piboserod

Piboserod is a selective 5-HT4 receptor antagonist which was marketed and manufactured by GlaxoSmithKline (GSK) under the trade name Serlipet for the management of atrial fibrillation and irritable bowel syndrome. In 2007 the Norwegian company Bio-Medisinsk Innovasjon AS (BMI)[1] completed a clinical phase II study to investigate the effect of piboserod in patients with chronic heart failure.

Piboserod
Clinical data
Trade namesSerlipet
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Clinical phase II
Identifiers
IUPAC name
  • N-((1-Butyl-4-piperidyl)-methyl)-3,4-dihydro-2H-(1,3)oxazino(3,2-a)indole-10-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H31N3O2
Molar mass369.509 g·mol−1
3D model (JSmol)
SMILES
  • CCCCN1CCC(CNC(=O)c2c3n(c4ccccc24)CCCO3)CC1
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) N
  • Key:KVCSJPATKXABRQ-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Mechanism of action

In 2002 a research group at the University of Oslo discovered that muscles from the ventricle of failing hearts have increased responsiveness to serotonin.[2] They later demonstrated that the effect was due to an expression of functional 5-HT4 receptors in the failing muscle. On the basis of these findings, and in analogy with the success of betablockers in heart failure, the group made the hypothesis that 5-HT4 receptor antagonists could be useful to treat heart failure. Their hypothesis was tested in animal models of heart failure with positive results.[3]

References
  1. Company web-page
  2. Brattelid T, Qvigstad E, Lynham JA, Molenaar P, Aass H, Geiran O, et al. (September 2004). "Functional serotonin 5-HT4 receptors in porcine and human ventricular myocardium with increased 5-HT4 mRNA in heart failure". Naunyn-Schmiedeberg's Archives of Pharmacology. 370 (3): 157–66. doi:10.1007/s00210-004-0963-0. PMID 15365689. S2CID 12306762.
  3. Birkeland JA, Sjaastad I, Brattelid T, Qvigstad E, Moberg ER, Krobert KA, et al. (January 2007). "Effects of treatment with a 5-HT4 receptor antagonist in heart failure". British Journal of Pharmacology. 150 (2): 143–52. doi:10.1038/sj.bjp.0706966. PMC 2042907. PMID 17160012.
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