Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H20N2O2 |
| Molecular Weight | 284.3535 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@@]2([H])CC[C@]1([H])C[C@@]([H])(C2)OC(=O)c3c[nH]c4ccccc34
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 | 284.3535 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| 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 Date1.35293764E12 |
|||
| 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 Date1.35293764E12 |
|||
| 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 Date1.35293764E12 |
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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| [5-HT3 receptor antagonists as a new therapeutic principle in rheumatology?]. | 2001 Feb |
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| Relaxation induced by serotonin and sumatriptan in isolated guinea pig gallbladder strips. | 2001 Mar |
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| Neuroepithelial bodies in mammalian lung express functional serotonin type 3 receptor. | 2001 Oct |
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| Local treatment of tendinopathies: a comparison between tropisetron and depot corticosteroids combined with local anesthetics. | 2002 |
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| [Pain modification by the 5-HT3 receptor antagonist tropisetron in secondary fibromyalgias]. | 2002 |
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| Inhibitory interactions between 5-HT3 and P2X channels in submucosal neurons. | 2002 Dec |
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| Infusional 5-fluorouracil, cisplatin and mitomycin C in advanced gastric cancer: a low cost effective regimen. | 2002 Jan 21 |
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| [Pharmacoeconomical model for cost calculation using a study on prophylaxis of nausea and vomiting in the postoperative phase as an example. Cost effectiveness analysis of a tropisetron supplemented desflurane anaesthesia in comparison to a propofol total intravenous anaesthesia (TIVA)]. | 2002 Jun |
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| 5-HT(4) receptor antagonists: structure-affinity relationships and ligand-receptor interactions. | 2002 Jun |
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| Simultaneous determination of ondansetron and tropisetron in human plasma using HPLC with UV detection. | 2002 May |
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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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| Low-dose dexamethasone reduces nausea and vomiting after tympanomastoid surgery: a comparison of tropisetron with saline. | 2002 Sep-Oct |
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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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| Effects of serotonin-3 receptor antagonists on the intracranial self-administration of ethanol within the ventral tegmental area of Wistar rats. | 2003 Jan |
|
| Further evidence that the discriminative stimulus properties of indorenate are mediated by 5-HT 1A/1B/2C receptors. | 2003 Jan |
|
| Benzodiazepines block alpha2-containing inhibitory glycine receptors in embryonic mouse hippocampal neurons. | 2003 Jul |
|
| [Tolerance induction in anaphylaxis to carboplatin]. | 2003 Jul 25 |
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| The assessment of vegetative and functional symptoms in fibromyalgia patients: the tropisetron experience. | 2004 |
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| The influence of the 5-HT3 receptor antagonist tropisetron on pain in fibromyalgia: a functional magnetic resonance imaging pilot study. | 2004 |
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| Participation of the serotonin system in rofecoxib-induced antinociception. | 2004 |
|
| Tamoxifen treatment reverses the adverse effects of chemotherapy-induced ovarian failure on serum lipids. | 2004 Aug 2 |
|
| Cloning, pharmacological characterisation and tissue distribution of a novel 5-HT4 receptor splice variant, 5-HT4(i). | 2004 Jun |
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| 5HT3-receptor antagonists as antiemetics in cancer. | 2005 Aug |
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| Regional heterogeneity for the intracranial self-administration of ethanol and acetaldehyde within the ventral tegmental area of alcohol-preferring (P) rats: involvement of dopamine and serotonin. | 2005 Feb |
|
| 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 |
|
| Granisetron versus tropisetron for prophylaxis of acute chemotherapy-induced emesis: a pooled analysis. | 2005 Jan |
|
| Contribution of the peripheral 5-HT 2A receptor to mechanical hyperalgesia in a rat model of neuropathic pain. | 2005 Nov |
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| New treatment options using 5-HT3 receptor antagonists in rheumatic diseases. | 2006 |
|
| Phencyclidine-induced cognitive deficits in mice are improved by subsequent subchronic administration of tropisetron: role of alpha7 nicotinic receptors. | 2006 Dec 28 |
|
| [A pilot study: gastric motility and nausea/vomiting in two leukemia children receiving chemotherapy]. | 2006 Feb |
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| Ondansetron and tropisetron do not prevent intraspinal morphine- and fentanyl-induced pruritus in elective cesarean delivery. | 2006 Feb |
|
| Supraventricular tachycardia and ST segment depression after intravenous administration of tropisetron. | 2006 Jan |
|
| Fibromyalgia--new concepts of pathogenesis and treatment. | 2006 Jan-Mar |
|
| Palliative chemotherapy beyond three courses conveys no survival or consistent quality-of-life benefits in advanced non-small-cell lung cancer. | 2006 Oct 23 |
|
| Randomized, double-blind trial comparing the antiemetic effect of tropisetron plus metopimazine with tropisetron plus placebo in patients receiving multiple cycles of multiple-day cisplatin-based chemotherapy. | 2007 Apr |
|
| 5-HT(3) receptors in the central amygdala mediate the modulation of thymus function in rats. | 2007 Feb 25 |
|
| 5-HT acts on nociceptive primary afferents through an indirect mechanism to induce hyperalgesia in the subcutaneous tissue. | 2007 Mar 16 |
|
| Postoperative colonic motility after tropisetron and a standardized meal in patients undergoing conventional colorectal surgery. | 2007 May |
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| Biology and therapy of fibromyalgia. Evidence-based biomarkers for fibromyalgia syndrome. | 2008 |
|
| Myocardial ischemia-mediated excitatory reflexes: a new function for thromboxane A2? | 2008 Dec |
|
| Chemotherapy-and cancer-related nausea and vomiting. | 2008 Jan |
|
| Prophylactic antiemetic therapy for acute abdominal surgery. A comparative study of droperidol, metoclopramide, tropisetron, granisetron and dexamethasone. | 2008 Jan-Feb |
|
| Prevention of acute chemotherapy-induced nausea and vomiting: the role of palonosetron. | 2009 Aug 10 |
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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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| Management of postoperative nausea and vomiting: focus on palonosetron. | 2009 Feb |
|
| A comparative study of prophylactic antiemetic treatment in cancer patients receiving radiotherapy. | 2010 Jan-Mar |
|
| Anti-emetic doses of dexamethasone suppress cortisol response in laparoscopic cholecystectomy. | 2010 Jul |
|
| 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
Created
by
admin
on
Edited
Fri Jun 25 22:40:59 UTC 2021
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| Record UNII |
6I819NIK1W
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| Record Status |
Validated (UNII)
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| Record Version |
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QA04AA03
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NCI_THESAURUS |
C267
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WHO-ATC |
A04AA03
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NCI_THESAURUS |
C94726
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6I819NIK1W
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DB11699
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89565-68-4
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C1131
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SUB11345MIG
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CHEMBL56564
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M11232
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Tropisetron
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27392
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89565-68-4
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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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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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