granisetron   Click here for help

GtoPdb Ligand ID: 2300

Synonyms: BRL 43694 | BRL-43694 | Kytril® | LY-278584 | Sancuso® | Sustol®
Approved drug
granisetron is an approved drug (FDA (1993), EMA (2012))
Compound class: Synthetic organic
Comment: There is some ambiguity in that the FDA label specifies 1-methyl-N-[(1R,3r,5S)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide. The closest to this in PubChem is the 1S, 5R, as shown. However, the majority of the bioactivity data is linked to the enantiomer CID 3510.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 50.16
Molecular weight 312.2
XLogP 2.61
No. Lipinski's rules broken 0
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Canonical SMILES CN1C2CCCC1CC(C2)NC(=O)c1nn(c2c1cccc2)C
Isomeric SMILES CN1[C@@H]2CCC[C@H]1CC(C2)NC(=O)c1nn(c2c1cccc2)C
InChI InChI=1S/C18H24N4O/c1-21-13-6-5-7-14(21)11-12(10-13)19-18(23)17-15-8-3-4-9-16(15)22(2)20-17/h3-4,8-9,12-14H,5-7,10-11H2,1-2H3,(H,19,23)/t12?,13-,14+
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Summary of Clinical Use Click here for help
This antiemetic and antinauseant drug is used to prevent nausea and vomiting in cancer patients receiving chemotherapy. It may be administered orally (Kytril®) or via transdermal patch (Sancuso®). An extended-release injectable formulation (Sustol®) is also available.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Granisetron is a selective 5-HT3 serotonin receptor antagonist. Serotonin released as a result of chemotherapy, is thought to stimulate the vagal and splanchnic nerve receptors that project to the medullary vomiting center, and the 5-HT3 receptors in the area postrema, and that this initiates the vomiting reflex. Antagonising the serotonin effect on the 5-HT3 receptors therefore reduces nausea and vomiting.