Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H20N2O2 |
| Molecular Weight | 284.3529 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C3=CNC4=C3C=CC=C4
InChI
InChIKey=ZNRGQMMCGHDTEI-ITGUQSILSA-N
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+
| Molecular Formula | C17H20N2O2 |
| Molecular Weight | 284.3529 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7507039
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7507039
Tropisetron (Tropisetron-AFT) is a potent and selective serotonin 3 (5-hydroxytryptamine3; 5-HT3) receptor antagonist with antiemetic properties, probably mediated via antagonism of receptors both at peripheral sites and in the central nervous system. Surgery and treatment with certain substances, including some chemotherapeutic agents, may trigger the release of serotonin from enterochromaffin-like cells in the visceral mucosa and initiate the emesis reflex and its accompanying feeling of nausea. Tropisetron (Tropisetron-AFT) selectively blocks the excitation of the presynaptic 5-HT3 receptors of the peripheral neurons in this reflex, and may exert additional direct actions within the CNS on 5-HT3 receptors mediating the actions of vagal input to the area postrema.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1899 |
8.48 null [pKi] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Tropisetron-AFT Approved UseFor the prevention of nausea and vomiting induced by cytotoxic therapy (5 mg/5 mL ampoule only).
For the treatment and prevention of post-operative nausea and vomiting in adults (2 mg/2 mL ampoule only). Launch Date2012 |
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| Preventing | Tropisetron-AFT Approved UseFor the prevention of nausea and vomiting induced by cytotoxic therapy (5 mg/5 mL ampoule only).
For the treatment and prevention of post-operative nausea and vomiting in adults (2 mg/2 mL ampoule only). Launch Date2012 |
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| Preventing | Tropisetron-AFT Approved UseFor the prevention of nausea and vomiting induced by cytotoxic therapy (5 mg/5 mL ampoule only).
For the treatment and prevention of post-operative nausea and vomiting in adults (2 mg/2 mL ampoule only). Launch Date2012 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [3H]5-hydroxytryptamine labels the agonist high affinity state of the cloned rat 5-HT4 receptor. | 1996 May 23 |
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| Fibromyalgia treatment with intravenous tropisetron administration. | 2001 |
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| Oral ondansetron, tropisetron or metoclopramide to prevent postoperative nausea and vomiting: a comparison in high-risk patients undergoing thyroid or parathyroid surgery. | 2002 May |
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| [5-HT3-receptor-antagonists in therapy of rheumatic diseases]. | 2003 Feb |
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| Plasma serotonin and histamine levels in hemodialysis-related pruritus are not significantly influenced by 5-HT3 receptor blocker and antihistaminic therapy. | 2003 Feb |
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| The efficacy and cost-effectiveness of prophylactic 5-hydroxytryptamine3 receptor antagonists: tropisetron, ondansetron and dolasetron. | 2003 Feb |
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| Benzodiazepines block alpha2-containing inhibitory glycine receptors in embryonic mouse hippocampal neurons. | 2003 Jul |
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| [Tolerance induction in anaphylaxis to carboplatin]. | 2003 Jul 25 |
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| Participation of the serotonin system in rofecoxib-induced antinociception. | 2004 |
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| Tamoxifen treatment reverses the adverse effects of chemotherapy-induced ovarian failure on serum lipids. | 2004 Aug 2 |
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| Association of the ABCB1 3435C>T polymorphism with antiemetic efficacy of 5-hydroxytryptamine type 3 antagonists. | 2005 Dec |
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| Tooth-pulp-evoked rostral spinal trigeminal nucleus neuron activity is inhibited by conditioning sciatic nerve stimulation in the rat: possible role of 5-HT3 receptor mediated GABAergic inhibition. | 2005 Feb 15 |
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| Biology and therapy of fibromyalgia. New therapies in fibromyalgia. | 2006 |
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| A randomized, placebo-controlled trial of a single dose of tropisetron for the prevention of vomiting after strabismus surgery in children. | 2006 Dec |
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| Phencyclidine-induced cognitive deficits in mice are improved by subsequent subchronic administration of tropisetron: role of alpha7 nicotinic receptors. | 2006 Dec 28 |
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| [A pilot study: gastric motility and nausea/vomiting in two leukemia children receiving chemotherapy]. | 2006 Feb |
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| Palliative chemotherapy beyond three courses conveys no survival or consistent quality-of-life benefits in advanced non-small-cell lung cancer. | 2006 Oct 23 |
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| 5-HT(3) receptors in the central amygdala mediate the modulation of thymus function in rats. | 2007 Feb 25 |
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| 5-HT acts on nociceptive primary afferents through an indirect mechanism to induce hyperalgesia in the subcutaneous tissue. | 2007 Mar 16 |
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| Postoperative colonic motility after tropisetron and a standardized meal in patients undergoing conventional colorectal surgery. | 2007 May |
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| Acute selective serotonin reuptake inhibitors increase conditioned fear expression: blockade with a 5-HT(2C) receptor antagonist. | 2007 Nov 15 |
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| Chemotherapy-and cancer-related nausea and vomiting. | 2008 Jan |
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| Cutaneous adverse drug reactions during chemotherapy: consider non-antineoplastic drugs. | 2008 Jun |
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| [Palonosetron in the prevention of chemotherapy-induced nausea and vomiting (CINV) in Italy: pharmacologic, clinical and economic aspects]. | 2008 Mar-Apr |
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| [11C]CHIBA-1001 as a novel PET ligand for alpha7 nicotinic receptors in the brain: a PET study in conscious monkeys. | 2008 Sep 18 |
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| Prevention of acute chemotherapy-induced nausea and vomiting: the role of palonosetron. | 2009 Aug 10 |
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| Receptor occupancy theory-based analysis of interindividual differences in antiemetic effects of 5-HT3 receptor antagonists. | 2009 Dec |
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| Impact of the 5-HT3 receptor channel system for insulin secretion and interaction of ginger extracts. | 2009 Dec 10 |
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| Use of granisetron transdermal system in the prevention of chemotherapy-induced nausea and vomiting: a review. | 2009 Dec 16 |
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| Optimizing emetic control in children receiving antineoplastic therapy: beyond the guidelines. | 2010 |
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| Anti-emetic doses of dexamethasone suppress cortisol response in laparoscopic cholecystectomy. | 2010 Jul |
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| HPLC, TLC, and first-derivative spectrophotometry stability-indicating methods for the determination of tropisetron in the presence of its acid degradates. | 2010 Jul-Aug |
Sample Use Guides
Prevention of nausea and vomiting induced by cytotoxic therapy:
Tropisetron-AFT is recommended as six-day courses of 5 mg per day, given intravenously on day 1 immediately before cancer chemotherapy followed by oral administration on days 2 to 6.
Treatment and prevention of post-operative nausea and vomiting:
Tropisetron-AFT is recommended as a 2 mg dose given intravenously. For the prevention of post- operative nausea and vomiting, tropisetron should be administered shortly before the induction of anaesthesia.
Route of Administration:
Intravenous
The effects of tropisetron on 5-HT3 receptors were examined in N1E-115 mouse neuroblastoma x rat glioma hybrid cells. The 5HT3 receptor ligand [3H] quipazine was displaced by tropisetron with Ki value of 2.25 nM. IC50 value for inhibition of 5HT-induced inward current by tropisetron was 0.22 nM at a holding potential of -65 mV.
| Substance Class |
Chemical
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| Record UNII |
6I819NIK1W
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Validated (UNII)
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C267
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A04AA03
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C94726
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Tropisetron
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET -> AGONIST |
TROPISETRON ACTS AS BOTH A SELECTIVE 5-HT3 RECEPTOR ANTAGONIST AND .ALPHA.7-NICOTINIC RECEPTOR AGONIST.
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SALT/SOLVATE -> PARENT |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Tmax | PHARMACOKINETIC |
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SINGLE DOSE |
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| Biological Half-life | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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| Tmax | PHARMACOKINETIC |
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SINGLE DOSE |
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| Biological Half-life | PHARMACOKINETIC |
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SINGLE DOSE |
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