Tegaserod maleate | HTF 919 | CAS#145158-71-0 | CAS#189188-57-6 | 5-HT4 agonist

MedKoo Cat#: 326864 | Name: Tegaserod maleate

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Description:

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

Tegaserod, also known as SDZ-HTF-919; HTF 919 is a 5-HT4 agonist for the management of irritable bowel syndrome and constipation. Approved by the FDA in 2002, it was subsequently removed from the market in 2007 due to FDA concerns about possible adverse cardiovascular effects. Before then, it was the only drug approved by the United States Food and Drug Administration to help relieve the abdominal discomfort, bloating, and constipation associated with irritable bowel syndrome. Its use was also approved to treat chronic idiopathic constipation.

Chemical Structure

Tegaserod maleate

CAS#189188-57-6 (maleate)

Theoretical Analysis

MedKoo Cat#: 326864

Name: Tegaserod maleate

CAS#: 189188-57-6 (maleate)

Chemical Formula: C20H27N5O5

Exact Mass:

Molecular Weight: 417.47

Elemental Analysis: C, 57.54; H, 6.52; N, 16.78; O, 19.16

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 400.00
25mg	USD 550.00
50mg	USD 850.00

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Related CAS #

145158-71-0 (free base) 189188-57-6 (maleate)

Synonym

SDZ-HTF-919; SDZ-HTF919; SDZ-HTF 919; SDZ HTF-919; SDZHTF-919; HTF919; HTF-919; HTF 919; Tegaserod. Tegaserod maleate. Brand name: Zelnorm and Zelmac

IUPAC/Chemical Name

(E)-2-((5-methoxy-1H-indol-3-yl)methylene)-N-pentylhydrazine-1-carboximidamide maleate

InChi Key

CPDDZSSEAVLMRY-FEQFWAPWSA-N

InChi Code

InChI=1S/C16H23N5O.C4H4O4/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15-7-6-13(22-2)9-14(12)15;5-3(6)1-2-4(7)8/h6-7,9-11,19H,3-5,8H2,1-2H3,(H3,17,18,21);1-2H,(H,5,6)(H,7,8)/b20-11+;2-1-

SMILES Code

COC1=CC2=C(NC=C2/C=N/NC(NCCCCC)=N)C=C1.O=C(O)/C=C\C(O)=O

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

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

Related CAS# 145158-71-0 (Tegaserod ) 189188-57-6 (Tegaserod Maleate)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 417.47 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

1: Pan HC, Shen YQ, Loers G, Jakovcevski I, Schachner M. Tegaserod, a small compound mimetic of polysialic acid, promotes functional recovery after spinal cord injury in mice. Neuroscience. 2014 Sep 26;277:356-66. doi: 10.1016/j.neuroscience.2014.06.069. Epub 2014 Jul 9. PubMed PMID: 25014876. 2: Bushman J, Mishra B, Ezra M, Gul S, Schulze C, Chaudhury S, Ripoll D, Wallqvist A, Kohn J, Schachner M, Loers G. Tegaserod mimics the neurostimulatory glycan polysialic acid and promotes nervous system repair. Neuropharmacology. 2014 Apr;79:456-66. doi: 10.1016/j.neuropharm.2013.09.014. Epub 2013 Sep 22. PubMed PMID: 24067923; PubMed Central PMCID: PMC4618794. 3: Seeger JD, Quinn S, Earnest DL, Lembo A, Kuo B, Rivero E, Walker AM. The Zelnorm epidemiologic study (ZEST): a cohort study evaluating incidence of abdominal and pelvic surgery related to tegaserod treatment. BMC Gastroenterol. 2012 Nov 30;12:171. doi: 10.1186/1471-230X-12-171. PubMed PMID: 23198861; PubMed Central PMCID: PMC3536557. 4: Wood P. Tegaserod in the treatment of constipation-predominant irritable bowel syndrome. Do the risks outweigh the benefits? Naunyn Schmiedebergs Arch Pharmacol. 2012 Jan;385(1):1-3. doi: 10.1007/s00210-011-0694-y. Epub 2011 Oct 4. PubMed PMID: 21969099. 5: Higgins DL, Ero MP, Loeb M, Kersey K, Hopkins A, Beattie DT. The inability of tegaserod to affect platelet aggregation and coronary artery tone at supratherapeutic concentrations. Naunyn Schmiedebergs Arch Pharmacol. 2012 Jan;385(1):103-9. doi: 10.1007/s00210-011-0687-x. Epub 2011 Sep 8. PubMed PMID: 21901313. 6: Haenisch B, Bönisch H. Pharmacological characterization of tegaserod at the wild type and 124Cys variant of the human 5-HT1B receptor. Pharmacogenet Genomics. 2011 Jul;21(7):432-5. doi: 10.1097/FPC.0b013e3283469f1d. PubMed PMID: 21478802. 7: Tack J, Janssen P, Bisschops R, Vos R, Phillips T, Tougas G. Influence of tegaserod on proximal gastric tone and on the perception of gastric distention in functional dyspepsia. Neurogastroenterol Motil. 2011 Feb;23(2):e32-9. doi: 10.1111/j.1365-2982.2010.01613.x. Epub 2010 Oct 27. PubMed PMID: 20979591. 8: Pimentel M, Morales W, Lezcano S, Sun-Chuan D, Low K, Yang J. Low-dose nocturnal tegaserod or erythromycin delays symptom recurrence after treatment of irritable bowel syndrome based on presumed bacterial overgrowth. Gastroenterol Hepatol (N Y). 2009 Jun;5(6):435-42. PubMed PMID: 20574504; PubMed Central PMCID: PMC2886395. 9: Jung HK. Comments on tegaserod trial on irritable bowel syndrome. J Neurogastroenterol Motil. 2010 Apr;16(2):222. doi: 10.5056/jnm.2010.16.2.222. Epub 2010 Apr 27. PubMed PMID: 20535361; PubMed Central PMCID: PMC2879858. 10: Kim YS, Choi SC, Park JM, Choi CH, Lee DH, Son HJ, Sung IK, Jeong JJ, Lee JS, Shim KN, Lee KJ, Hong SJ, Choi MG; IBS Club of the Korean Society of Neurogastroenterology and Motility. The effect of tegaserod on symptoms and quality of life in korean women with irritable bowel syndrome with constipation. J Neurogastroenterol Motil. 2010 Jan;16(1):61-70. doi: 10.5056/jnm.2010.16.1.61. Epub 2010 Jan 31. PubMed PMID: 20535328; PubMed Central PMCID: PMC2879829. 11: Al-Judaibi B, Chande N, Gregor J. Safety and efficacy of tegaserod therapy in patients with irritable bowel syndrome or chronic constipation. Can J Clin Pharmacol. 2010 Winter;17(1):e194-200. Epub 2010 Apr 20. PubMed PMID: 20410554. 12: Ramirez R, Zuckerman MJ, Hejazi RA, Chokhavatia S. Treatment of acute colonic pseudo-obstruction with tegaserod. Am J Med Sci. 2010 Jun;339(6):575-6. doi: 10.1097/MAJ.0b013e3181db6b95. PubMed PMID: 20400888. 13: Loughlin J, Quinn S, Rivero E, Wong J, Huang J, Kralstein J, Earnest DL, Seeger JD. Tegaserod and the risk of cardiovascular ischemic events: an observational cohort study. J Cardiovasc Pharmacol Ther. 2010 Jun;15(2):151-7. doi: 10.1177/1074248409360357. Epub 2010 Mar 3. PubMed PMID: 20200325. 14: Rajput SJ, Raj HA. Estimation of tegaserod maleate by differential pulse polarography. Indian J Pharm Sci. 2009 Jan;71(1):50-2. doi: 10.4103/0250-474X.51956. PubMed PMID: 20177456; PubMed Central PMCID: PMC2810048. 15: Suffredini S, Cerbai E, Giunti G, El Mouelhi M, Pfannkuche HJ, Mugelli A. Electrophysiological characterization of isolated human atrial myocytes exposed to tegaserod. Basic Clin Pharmacol Toxicol. 2010 May;106(5):416-21. doi: 10.1111/j.1742-7843.2009.00507.x. Epub 2009 Dec 30. PubMed PMID: 20050846. 16: Chey WD, Howden CW, Tack J, Ligozio G, Earnest DL. Long-term tegaserod treatment for dysmotility-like functional dyspepsia: results of two identical 1-year cohort studies. Dig Dis Sci. 2010 Mar;55(3):684-97. doi: 10.1007/s10620-009-1049-0. Epub 2009 Dec 3. PubMed PMID: 19957035. 17: Nasr I, Rao SS, Attaluri A, Hashmi SM, Summers R. Effects of tegaserod and erythromycin in upper gut dysmotility: a comparative study. Indian J Gastroenterol. 2009 Jul-Aug;28(4):136-42. doi: 10.1007/s12664-009-0048-6. Epub 2009 Nov 24. PubMed PMID: 19937173; PubMed Central PMCID: PMC3883142. 18: Serebruany VL, El Mouelhi M, Pfannkuche HJ, Rose K, Marro M, Angiolillo DJ. Investigations on 5-HT₄ receptor expression and effects of tegaserod on human platelet aggregation in vitro. Am J Ther. 2010 Nov-Dec;17(6):543-52. doi: 10.1097/MJT.0b013e3181b63f21. PubMed PMID: 19797939. 19: Painsipp E, Shahbazian A, Holzer P. Alosetron, cilansetron and tegaserod modify mesenteric but not colonic blood flow in rats. Br J Pharmacol. 2009 Nov;158(5):1210-26. doi: 10.1111/j.1476-5381.2009.00392.x. Epub 2009 Sep 25. PubMed PMID: 19785647; PubMed Central PMCID: PMC2782331. 20: Vakil N, Kianifard F, Bottoli I. Exploratory Study of Tegaserod for Dyspepsia in Women Receiving PPIs for Heartburn. Arch Drug Inf. 2008 Dec;1(3):79-88. PubMed PMID: 19639028; PubMed Central PMCID: PMC2710991.