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MedKoo Cat#: 317120 | Name: Piboserod
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Piboserod
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: 369.2416

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
25mg USD 250.00 2 Weeks
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,250.00 2 Weeks
500mg USD 2,450.00 2 Weeks
1g USD 3,850.00 2 Weeks
2g USD 6,250.00 2 Weeks
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Related CAS #
152811-62-6 (free base) 178273-87-5 (HCl)
Synonym
SB-207266; SB 207266; SB207266; Piboserod.
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Piboserod (SB 207266) is a selective 5-HT(4) receptor antagonist.
In vitro activity:
The aim of this study is to evaluate the potency of piboserod (SB 207266), a selective 5-HT(4) receptor antagonist, at inhibiting the 5-HT(4)-mediated potentiating effect of serotonin (5-HT) on the neurally-mediated contractile responses of human detrusor strips to electrical field stimulations (EFS). In presence of 1 and 100 nM of piboserod, the maximal 5-HT-induced potentiations were reduced to 45.0+/-7.9 and 38.7+/-8.7%, respectively. Reference: World J Urol. 2005 Jun;23(2):147-51. https://pubmed.ncbi.nlm.nih.gov/15902472/
In vivo activity:
Rats were given either the 5-HT(4) antagonist SB207266 (0.5 mg kg(-1) 24h(-1); MI(int)) or placebo (MI(pl)) through mini-osmotic pumps for 6 weeks subsequent to induction of post-infarction CHF. LV diastolic function improved, with 4.6% lower LV diastolic diameter and 24.2% lower mitral flow deceleration in MI(int) compared to MI(pl). SB207266 reduced LV systolic diameter by 6.1%, heart weight by 10.2% and lung weight by 13.1%. Reference: Br J Pharmacol. 2007 Jan;150(2):143-52. https://pubmed.ncbi.nlm.nih.gov/17160012/
Solvent mg/mL mM comments
Solubility
DMF 30.0 81.19
DMSO 22.5 60.89
Ethanol 30.0 81.19
Ethanol:PBS (pH 7.2) (1:20) 0.1 0.14
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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
Formulation protocol:
1. Goto K, Kawahara I, Inada H, Misawa H, Kuniyasu H, Nabekura J, Takaki M. Activation of 5-HT4 receptors facilitates neurogenesis from transplanted neural stem cells in the anastomotic ileum. J Physiol Sci. 2016 Jan;66(1):67-76. doi: 10.1007/s12576-015-0396-1. Epub 2015 Sep 3. PMID: 26335766; PMCID: PMC4676964. 2. 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. doi: 10.1007/s00345-005-0499-z. Epub 2005 May 18. PMID: 15902472. 3. Birkeland JA, Sjaastad I, Brattelid T, Qvigstad E, Moberg ER, Krobert KA, Bjørnerheim R, Skomedal T, Sejersted OM, Osnes JB, Levy FO. Effects of treatment with a 5-HT4 receptor antagonist in heart failure. Br J Pharmacol. 2007 Jan;150(2):143-52. doi: 10.1038/sj.bjp.0706966. Epub 2006 Dec 11. PMID: 17160012; PMCID: PMC2042907. 4. Sanger GJ, Yoshida M, Yahyah M, Kitazumi K. Increased defecation during stress or after 5-hydroxytryptophan: selective inhibition by the 5-HT(4) receptor antagonist, SB-207266. Br J Pharmacol. 2000 Jun;130(3):706-12. doi: 10.1038/sj.bjp.0703367. PMID: 10821802; PMCID: PMC1572116.
In vitro protocol:
1. Goto K, Kawahara I, Inada H, Misawa H, Kuniyasu H, Nabekura J, Takaki M. Activation of 5-HT4 receptors facilitates neurogenesis from transplanted neural stem cells in the anastomotic ileum. J Physiol Sci. 2016 Jan;66(1):67-76. doi: 10.1007/s12576-015-0396-1. Epub 2015 Sep 3. PMID: 26335766; PMCID: PMC4676964. 2. 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. doi: 10.1007/s00345-005-0499-z. Epub 2005 May 18. PMID: 15902472.
In vivo protocol:
1. Birkeland JA, Sjaastad I, Brattelid T, Qvigstad E, Moberg ER, Krobert KA, Bjørnerheim R, Skomedal T, Sejersted OM, Osnes JB, Levy FO. Effects of treatment with a 5-HT4 receptor antagonist in heart failure. Br J Pharmacol. 2007 Jan;150(2):143-52. doi: 10.1038/sj.bjp.0706966. Epub 2006 Dec 11. PMID: 17160012; PMCID: PMC2042907. 2. Sanger GJ, Yoshida M, Yahyah M, Kitazumi K. Increased defecation during stress or after 5-hydroxytryptophan: selective inhibition by the 5-HT(4) receptor antagonist, SB-207266. Br J Pharmacol. 2000 Jun;130(3):706-12. doi: 10.1038/sj.bjp.0703367. PMID: 10821802; PMCID: PMC1572116.
1: Kim H, Park KT, Jo H, Shin Y, Chung G, Ko SG, Jin YH, Kim W. The effect of ginger extract on cisplatin-induced acute anorexia in rats. Front Pharmacol. 2023 Nov 9;14:1267254. doi: 10.3389/fphar.2023.1267254. PMID: 38026983; PMCID: PMC10665510. 2: Jiang SS, Gong MN, Rao W, Chai W, Chen WZ, Zhang X, Nie HB, Xu RS. 5-Hydroxytryptamine: a potential therapeutic target in amyotrophic lateral sclerosis. Neural Regen Res. 2023 Sep;18(9):2047-2055. doi: 10.4103/1673-5374.367929. PMID: 36926731; PMCID: PMC10233787. 3: 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. PMID: 25936770. 4: 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. PMID: 24113240. 5: 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. PMID: 23600388. 6: 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. PMID: 19567409. 7: 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. PMID: 19470850. 8: 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. PMID: 18675829. 9: 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. doi: 10.1016/j.phrs.2006.01.003. Epub 2006 Feb 21. PMID: 16495076. 10: 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. doi: 10.1016/j.vascn.2005.08.004. Epub 2005 Sep 15. PMID: 16168678. 11: 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. doi: 10.1007/s00345-005-0499-z. Epub 2005 May 18. PMID: 15902472. 12: Camilleri M, Talley NJ. Pathophysiology as a basis for understanding symptom complexes and therapeutic targets. Neurogastroenterol Motil. 2004 Apr;16(2):135-42. doi: 10.1111/j.1365-2982.2004.00516.x. PMID: 15086867. 13: 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. doi: 10.1023/B:JICE.0000011348.05608.e5. PMID: 14739742. 14: 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. doi: 10.1016/s0014-2999(03)01637-6. PMID: 12706477. 15: De Ponti F, Tonini M. Irritable bowel syndrome: new agents targeting serotonin receptor subtypes. Drugs. 2001;61(3):317-32. doi: 10.2165/00003495-200161030-00001. PMID: 11293643.