tegaserod   Click here for help

GtoPdb Ligand ID: 226

Synonyms: HTF 919 | SDZ HTF 919 | Zelnorm®
Approved drug
tegaserod is an approved drug (FDA (2002))
Compound class: Synthetic organic
Comment: There is some ambiguity as to the exact structure of tegaserod. The structure shown here is PubChem match using the CAS number submitted to the WHO for the INN. Alternative structure renderings for tegaserod are numerous: PubChem CID 5362436 has the highest submitter consensus in PubChem but may not match renderings in references for the biological activity; CID 5487301, and CHEMBL76370 are further alternatives.
Marketed formulations include tegaserod maleate (PubChem CID 6918369)- again with the caveat of alternative representations.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 87.79
Molecular weight 301.19
XLogP 4.2
No. Lipinski's rules broken 0
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Canonical SMILES CCCCCN=C(N/N=C/c1c[nH]c2c1cc(OC)cc2)N
Isomeric SMILES CCCCCN=C(N/N=C/c1c[nH]c2c1cc(OC)cc2)N
InChI InChI=1S/C16H23N5O/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15-7-6-13(22-2)9-14(12)15/h6-7,9-11,19H,3-5,8H2,1-2H3,(H3,17,18,21)/b20-11+
No information available.
Summary of Clinical Use Click here for help
Tegaserod was approved by the FDA in 2002 for the management of irritable bowel syndrome with constipation (IBS-C) in women, but was withdrawn in 2007 due to safety concerns surrounding cardiovascular effects. It was however still available in the US (via a FDA approved expanded access program) and continued to be used in other countries, principally as it offers a treament option for a condition for which other new medications had been insufficient for meeting patients' needs. In April 2019, and following an extensive safety review, the FDA granted authorisation for the full reintroduction of Zelnorm® (tegaserod), as a twice-daily oral treatment for IBS-C in women under 65.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Tegaserod is the first-in-class selective 5-HT4 receptor agonist for the treatment of IBS-C. By targeting the 5-HT4 receptor at multiple neurons (sensory, motor, secretory motor) and in smooth muscle cells in the gastrointestinal tract tegaserod induces contraction and relaxation of the gut (i.e. improves peristalsis and gut motility), and decreases pain signalling.