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 |
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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 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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| Inhibition of ganglionic long-term potentiation decreases blood pressure in spontaneously hypertensive rats. | 2001 Dec |
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| Association between increased 5-HIAA plasma concentrations and postoperative nausea and vomiting in patients undergoing general anaesthesia for surgery. | 2001 Dec |
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| Relaxation induced by serotonin and sumatriptan in isolated guinea pig gallbladder strips. | 2001 Mar |
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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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| Small-dose dexamethasone reduces nausea and vomiting after laparoscopic cholecystectomy: a comparison of tropisetron with saline. | 2002 Jul |
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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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| The prophylactic effect of tropisetron on epidural morphine-related nausea and vomiting: a comparison of dexamethasone with saline. | 2002 Mar |
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| [Pilot study with 5-HT3 antagonists. Good outcome in fibromyalgia pain]. | 2002 Mar 14 |
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| Simultaneous determination of ondansetron and tropisetron in human plasma using HPLC with UV detection. | 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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| [What's new in the therapy of fibromyalgia?]. | 2003 Dec |
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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 |
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| Further evidence that the discriminative stimulus properties of indorenate are mediated by 5-HT 1A/1B/2C receptors. | 2003 Jan |
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| Effect of the CYP2D6 genotype on the pharmacokinetics of tropisetron in healthy Korean subjects. | 2003 Jun |
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| The assessment of vegetative and functional symptoms in fibromyalgia patients: the tropisetron experience. | 2004 |
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| Intravenous treatment of fibromyalgia with the 5-HT3 receptor antagonist tropisetron in a rheumatological practice. | 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 |
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| Cloning, pharmacological characterisation and tissue distribution of a novel 5-HT4 receptor splice variant, 5-HT4(i). | 2004 Jun |
|
| Stimulation of the lateral hypothalamus produces antinociception mediated by 5-HT1A, 5-HT1B and 5-HT3 receptors in the rat spinal cord dorsal horn. | 2005 |
|
| Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same? | 2005 |
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| Tropisetron improves deficits in auditory P50 suppression in schizophrenia. | 2005 Jul 1 |
|
| New treatment options using 5-HT3 receptor antagonists in rheumatic diseases. | 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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| Luminal hypotonicity increases duodenal mucosal permeability by a mechanism involving 5-hydroxytryptamine. | 2006 Jan |
|
| [5-HT3 receptor antagonist als analgetics in rheumatic diseases]. | 2006 Oct |
|
| Increased 5-HT(3)-mediated signalling in pelvic afferent neurons from mice deficient in P2X(2) and/or P2X (3) receptor subunits. | 2006 Sep |
|
| 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 |
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| Translating pharmacogenomics: challenges on the road to the clinic. | 2007 Aug |
|
| Systemic anticancer therapy in gynecological cancer patients with renal dysfunction. | 2007 Jul-Aug |
|
| 5-HT acts on nociceptive primary afferents through an indirect mechanism to induce hyperalgesia in the subcutaneous tissue. | 2007 Mar 16 |
|
| Serotonin mediates PGE2 overexpression through 5-HT2A and 5-HT3 receptor subtypes in serum-free tissue culture of macrophage-like synovial cells. | 2008 Aug |
|
| New treatment options in the management of fibromyalgia: role of pregabalin. | 2008 Dec |
|
| Myocardial ischemia-mediated excitatory reflexes: a new function for thromboxane A2? | 2008 Dec |
|
| Chemotherapy-and cancer-related nausea and vomiting. | 2008 Jan |
|
| Fibromyalgia: diagnosis and treatment options. | 2009 |
|
| Prevention of acute chemotherapy-induced nausea and vomiting: the role of palonosetron. | 2009 Aug 10 |
|
| Palonosetron for the prevention of chemotherapy-induced nausea and vomiting: approval and efficacy. | 2009 Dec 10 |
|
| [Nicotinic acetylcholine receptors are possible therapeutic targets for schizophrenia]. | 2009 Feb |
|
| The antiemetic interaction of Delta9-tetrahydrocannabinol when combined with tropisetron or dexamethasone in the least shrew. | 2009 Jan |
|
| [Therapeutic effect of acupuncture on cisplatin-induced nausea and vomiting]. | 2009 Jan |
|
| Retraction Notice: Current Management of Vomiting after Tonsillectomy in Children | 2009 Jan |
|
| Liquid chromatography/tandem mass spectrometry method for the quantification of deserpidine in human plasma: Application to a pharmacokinetic study. | 2009 Oct 1 |
|
| Optimizing emetic control in children receiving antineoplastic therapy: beyond the guidelines. | 2010 |
|
| [Impact of intrathecal morphine on the tolerance of early feeding after cesarean section]. | 2010 Feb |
|
| A comparative study of prophylactic antiemetic treatment in cancer patients receiving radiotherapy. | 2010 Jan-Mar |
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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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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