Piboserod | SB207266 | CAS#152811-62-6 | 5-HT4 receptor antagonist

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

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

Piboserod

CAS# 152811-62-6 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317120
Name: Piboserod
CAS#: 152811-62-6 (free base)
Chemical Formula: C22H31N3O2
Exact Mass: 369.24
Molecular Weight: 369.509
Elemental Analysis: C, 71.51; H, 8.46; N, 11.37; O, 8.66

Price and Availability

Size	Price	Availability
25mg	USD 250
50mg	USD 450
100mg	USD 750	2 Weeks
200mg	USD 1250	2 Weeks
500mg	USD 2450	2 Weeks
1g	USD 3850	2 Weeks
2g	USD 6250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
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

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.

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.

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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.

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