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
SMILES / InChI / InChIKey
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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+
InChI Key IKBKZGMPCYNSLU-RGVLZGJSSA-N
References
1. Beattie DT, Smith JA, Marquess D, Vickery RG, Armstrong SR, Pulido-Rios T, McCullough JL, Sandlund C, Richardson C, Mai N et al.. (2004)
The 5-HT4 receptor agonist, tegaserod, is a potent 5-HT2B receptor antagonist in vitro and in vivo.
Br J Pharmacol, 143 (5): 549-60. [PMID:15466450]
2. Bender E, Pindon A, van Oers I, Zhang YB, Gommeren W, Verhasselt P, Jurzak M, Leysen J, Luyten W. (2000)
Structure of the human serotonin 5-HT4 receptor gene and cloning of a novel 5-HT4 splice variant.
J Neurochem, 74 (2): 478-89. [PMID:10646498]