Piboserod
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MedKoo CAT#: 317120

CAS#: 152811-62-6 (free base)

Description: Piboserod, also known as SB-207266, 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) completed a clinical phase II study to investigate the effect of piboserod in patients with chronic heart failure.


Chemical Structure

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Piboserod
CAS# 152811-62-6 (free base)

Theoretical Analysis

MedKoo Cat#: 317120
Name: Piboserod
CAS#: 152811-62-6 (free base)
Chemical Formula: C22H31N3O2
Exact Mass: 369.24163
Molecular Weight: 369.51
Elemental Analysis: C, 71.51; H, 8.46; N, 11.37; O, 8.66

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 2 Weeks
25.0mg USD 250.0 2 Weeks
50.0mg USD 450.0 2 Weeks
100.0mg USD 650.0 2 Weeks
200.0mg USD 950.0 2 Weeks
500.0mg USD 1450.0 2 Weeks
1.0g USD 2450.0 2 Weeks
2.0g USD 3650.0 2 Weeks
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Related CAS #: 152811-62-6 (free base)   178273-87-5 (HCl)    

Synonym: SB-207266; SB 207266; SB207266; Piboserod, brand name: Serlipet.

IUPAC/Chemical Name: N-((1-Butyl-4-piperidyl)-methyl)-3,4-dihydro-2H-(1,3)oxazino(3,2-a)indole-10-carboxamide

InChi Key: KVCSJPATKXABRQ-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(C1=C(OCCC2)N2C3=C1C=CC=C3)NCC4CCN(CCCC)CC4

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 369.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Ruan M, Yu B, Xu L, Zhang L, Long J, Shen X. Attenuation of stress-induced gastrointestinal motility disorder by gentiopicroside, from Gentiana macrophylla Pall. Fitoterapia. 2015 Jun;103:265-76. doi: 10.1016/j.fitote.2015.04.015. Epub 2015 May 1. PubMed PMID: 25936770.

2: Brudeli B, Andressen KW, Moltzau LR, Nilsen NO, Levy FO, Klaveness J. Acidic biphenyl derivatives: synthesis and biological activity of a new series of potent 5-HT(4) receptor antagonists. Bioorg Med Chem. 2013 Nov 15;21(22):7134-45. doi: 10.1016/j.bmc.2013.09.004. Epub 2013 Sep 11. PubMed PMID: 24113240.

3: Nirogi R, Kandikere V, Bhyrapuneni G, Saralaya R, Ajjala DR, Aleti RR, Rasheed MA. In-vivo rat striatal 5-HT4 receptor occupancy using non-radiolabelled SB207145. J Pharm Pharmacol. 2013 May;65(5):704-12. doi: 10.1111/jphp.12030. Epub 2013 Jan 25. PubMed PMID: 23600388.

4: Kjekshus JK, Torp-Pedersen C, Gullestad L, Køber L, Edvardsen T, Olsen IC, Sjaastad I, Qvigstad E, Skomedal T, Osnes JB, Levy FO. Effect of piboserod, a 5-HT4 serotonin receptor antagonist, on left ventricular function in patients with symptomatic heart failure. Eur J Heart Fail. 2009 Aug;11(8):771-8. doi: 10.1093/eurjhf/hfp087. Epub 2009 Jun 30. PubMed PMID: 19567409.

5: Marner L, Gillings N, Comley RA, Baaré WF, Rabiner EA, Wilson AA, Houle S, Hasselbalch SG, Svarer C, Gunn RN, Laruelle M, Knudsen GM. Kinetic modeling of 11C-SB207145 binding to 5-HT4 receptors in the human brain in vivo. J Nucl Med. 2009 Jun;50(6):900-8. doi: 10.2967/jnumed.108.058552. PubMed PMID: 19470850.

6: Levy FO, Qvigstad E, Krobert KA, Skomedal T, Osnes JB. Effects of serotonin in failing cardiac ventricle: signalling mechanisms and potential therapeutic implications. Neuropharmacology. 2008 Nov;55(6):1066-71. doi: 10.1016/j.neuropharm.2008.07.010. Epub 2008 Jul 16. Review. PubMed PMID: 18675829.

7: McCullough JL, Armstrong SR, Hegde SS, Beattie DT. The 5-HT2B antagonist and 5-HT4 agonist activities of tegaserod in the anaesthetized rat. Pharmacol Res. 2006 Apr;53(4):353-8. Epub 2006 Feb 21. PubMed PMID: 16495076.

8: Armstrong SR, McCullough JL, Beattie DT. Measurement of 5-HT4 receptor-mediated esophageal responses by digital sonomicrometry in the anesthetized rat. J Pharmacol Toxicol Methods. 2006 May-Jun;53(3):198-205. Epub 2005 Sep 15. PubMed PMID: 16168678.

9: Darblade B, Behr-Roussel D, Gorny D, Lebret T, Benoit G, Hieble JP, Brooks D, Alexandre L, Giuliano F. Piboserod (SB 207266), a selective 5-HT4 receptor antagonist, reduces serotonin potentiation of neurally-mediated contractile responses of human detrusor muscle. World J Urol. 2005 Jun;23(2):147-51. Epub 2005 May 18. PubMed PMID: 15902472.

10: Camilleri M, Talley NJ. Pathophysiology as a basis for understanding symptom complexes and therapeutic targets. Neurogastroenterol Motil. 2004 Apr;16(2):135-42. Review. PubMed PMID: 15086867.

11: Singh S. Trials of new antiarrhythmic drugs for maintenance of sinus rhythm in patients with atrial fibrillation. J Interv Card Electrophysiol. 2004;10 Suppl 1:71-6. Review. PubMed PMID: 14739742.

12: Axelsson LG, Wallin B, Gillberg PG, Sjöberg B, Söderberg C, Hellström PM. Regulatory role of 5-HT and muscarinic receptor antagonists on the migrating myoelectric complex in rats. Eur J Pharmacol. 2003 Apr 25;467(1-3):211-8. PubMed PMID: 12706477.

13: De Ponti F, Tonini M. Irritable bowel syndrome: new agents targeting serotonin receptor subtypes. Drugs. 2001;61(3):317-32. Review. PubMed PMID: 11293643.