palonosetron   Click here for help

GtoPdb Ligand ID: 7486

Synonyms: Aloxi® | aurothioglucose | RS-25259-197
Approved drug PDB Ligand
palonosetron is an approved drug (FDA (2003), EMA (2009))
Compound class: Synthetic organic
Comment: Palonosetron is a 'serton' family drug, that is a serotonin 5-HT3 antagonist. Most setrons are antiemetics, apart from alosetron and cilansetron, which are irritable bowel syndrome therapeutics. Setrons are the most widely prescribed antiemetic drugs used in the management of chemotherapy-induced nausea and vomiting (CINV).
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View more information in the IUPHAR Pharmacology Education Project: palonosetron

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 23.55
Molecular weight 296.19
XLogP 2.69
No. Lipinski's rules broken 0
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Canonical SMILES O=C1N(CC2c3c1cccc3CCC2)C1CN2CCC1CC2
Isomeric SMILES O=C1N(C[C@@H]2c3c1cccc3CCC2)[C@@H]1CN2CCC1CC2
InChI InChI=1S/C19H24N2O/c22-19-16-6-2-4-14-3-1-5-15(18(14)16)11-21(19)17-12-20-9-7-13(17)8-10-20/h2,4,6,13,15,17H,1,3,5,7-12H2/t15-,17-/m1/s1
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Summary of Clinical Use Click here for help
Used to prevent nausea and vomiting caused by highly emetogenic cancer chemotherapy.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Palonosetron is an antagonist of the serotonin 5-HT3 receptor. Many chemotherapies cause the release of serotonin from the enterochromaffin cells of the small intestine. This neurotransmitter is then able to activate 5-HT3 receptors in the gut and on vagal afferents which activates the vomiting reflex. By inhibiting the activity of endogenous serotonin at these receptors, the drug reduces chemotherapy related nausea and vomiting [1].
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