tropisetron   Click here for help

GtoPdb Ligand ID: 260

Synonyms: ICF 205-930 | ICS 205930 | Navoban® | tropisteron
Approved drug PDB Ligand
tropisetron is an approved drug
Compound class: Synthetic organic
Comment: There is some ambiguity in the literature as to the exact stereochemistry of tropisetron. The structure shown here matches the INN-assigned structure and is the same as the the ChEBI and ChEMBL entries linked to above. There is no exact match in PubChem for the structure shown here.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 45.33
Molecular weight 284.15
XLogP 3.43
No. Lipinski's rules broken 0
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Canonical SMILES CN1C2CCC1CC(C2)OC(=O)c1c[nH]c2c1cccc2
Isomeric SMILES CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(=O)c1c[nH]c2c1cccc2
InChI InChI=1S/C17H20N2O2/c1-19-11-6-7-12(19)9-13(8-11)21-17(20)15-10-18-16-5-3-2-4-14(15)16/h2-5,10-13,18H,6-9H2,1H3/t11-,12+,13+
1. Adham N, Gerald C, Schechter L, Vaysse P, Weinshank R, Branchek T. (1996)
[3H]5-hydroxytryptamine labels the agonist high affinity state of the cloned rat 5-HT4 receptor.
Eur J Pharmacol, 304 (1-3): 231-5. [PMID:8813606]
2. Bach T, Syversveen T, Kvingedal AM, Krobert KA, Brattelid T, Kaumann AJ, Levy FO. (2001)
5HT4(a) and 5-HT4(b) receptors have nearly identical pharmacology and are both expressed in human atrium and ventricle.
Naunyn Schmiedebergs Arch Pharmacol, 363 (2): 146-60. [PMID:11218067]
3. Claeysen S, Sebben M, Journot L, Bockaert J, Dumuis A. (1996)
Cloning, expression and pharmacology of the mouse 5-HT(4L) receptor.
FEBS Lett, 398 (1): 19-25. [PMID:8946946]
4. Lankiewicz S, Lobitz N, Wetzel CH, Rupprecht R, Gisselmann G, Hatt H. (1998)
Molecular cloning, functional expression, and pharmacological characterization of 5-hydroxytryptamine3 receptor cDNA and its splice variants from guinea pig.
Mol Pharmacol, 53 (2): 202-12. [PMID:9463477]
5. Maksay G, Laube B, Betz H. (1999)
Selective blocking effects of tropisetron and atropine on recombinant glycine receptors.
J Neurochem, 73 (2): 802-6. [PMID:10428078]
6. Miyake A, Mochizuki S, Takemoto Y, Akuzawa S. (1995)
Molecular cloning of human 5-hydroxytryptamine3 receptor: heterogeneity in distribution and function among species.
Mol Pharmacol, 48 (3): 407-16. [PMID:7565620]
7. Supplisson S, Chesnoy-Marchais D. (2000)
Glycine receptor beta subunits play a critical role in potentiation of glycine responses by ICS-205,930.
Mol Pharmacol, 58 (4): 763-70. [PMID:10999946]
8. Van den Wyngaert I, Gommeren W, Verhasselt P, Jurzak M, Leysen J, Luyten W, Bender E. (1997)
Cloning and expression of a human serotonin 5-HT4 receptor cDNA.
J Neurochem, 69 (5): 1810-9. [PMID:9349523]
9. Yang Z, Ney A, Cromer BA, Ng HL, Parker MW, Lynch JW. (2007)
Tropisetron modulation of the glycine receptor: femtomolar potentiation and a molecular determinant of inhibition.
J Neurochem, 100 (3): 758-69. [PMID:17181559]