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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
Structure of TROPISETRON

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+

HIDE SMILES / InChI

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

Description
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.

Originator

Curator's Comment:: # Novartis International AG

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.48 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Tropisetron-AFT

Approved Use

For 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 Date

1.35293764E12
Preventing
Tropisetron-AFT

Approved Use

For 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 Date

1.35293764E12
Preventing
Tropisetron-AFT

Approved Use

For 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 Date

1.35293764E12
PubMed

PubMed

TitleDatePubMed
[3H]5-hydroxytryptamine labels the agonist high affinity state of the cloned rat 5-HT4 receptor.
1996 May 23
[5-HT3 receptor antagonists as a new therapeutic principle in rheumatology?].
2001 Feb
Relaxation induced by serotonin and sumatriptan in isolated guinea pig gallbladder strips.
2001 Mar
Neuroepithelial bodies in mammalian lung express functional serotonin type 3 receptor.
2001 Oct
Local treatment of tendinopathies: a comparison between tropisetron and depot corticosteroids combined with local anesthetics.
2002
[Pain modification by the 5-HT3 receptor antagonist tropisetron in secondary fibromyalgias].
2002
Inhibitory interactions between 5-HT3 and P2X channels in submucosal neurons.
2002 Dec
Infusional 5-fluorouracil, cisplatin and mitomycin C in advanced gastric cancer: a low cost effective regimen.
2002 Jan 21
[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
5-HT(4) receptor antagonists: structure-affinity relationships and ligand-receptor interactions.
2002 Jun
Simultaneous determination of ondansetron and tropisetron in human plasma using HPLC with UV detection.
2002 May
Oral ondansetron, tropisetron or metoclopramide to prevent postoperative nausea and vomiting: a comparison in high-risk patients undergoing thyroid or parathyroid surgery.
2002 May
Low-dose dexamethasone reduces nausea and vomiting after tympanomastoid surgery: a comparison of tropisetron with saline.
2002 Sep-Oct
Plasma serotonin and histamine levels in hemodialysis-related pruritus are not significantly influenced by 5-HT3 receptor blocker and antihistaminic therapy.
2003 Feb
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
The assessment of vegetative and functional symptoms in fibromyalgia patients: the tropisetron experience.
2004
The influence of the 5-HT3 receptor antagonist tropisetron on pain in fibromyalgia: a functional magnetic resonance imaging pilot study.
2004
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
5HT3-receptor antagonists as antiemetics in cancer.
2005 Aug
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
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
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
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
Impact of the 5-HT3 receptor channel system for insulin secretion and interaction of ginger extracts.
2009 Dec 10
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
Patents

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
In Vitro Use Guide
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 Fri Jun 25 22:40:59 UTC 2021
Edited
by admin
on Fri Jun 25 22:40:59 UTC 2021
Record UNII
6I819NIK1W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TROPISETRON
INN   MART.   MI   WHO-DD  
INN  
Official Name English
1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-YL INDOLE-3-CARBOXYLATE
Common Name English
TROPISETRON [INN]
Common Name English
TROPISETRON [MART.]
Common Name English
TROPISETRON [WHO-DD]
Common Name English
TROPISETRON [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QA04AA03
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
NCI_THESAURUS C267
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
WHO-ATC A04AA03
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
NCI_THESAURUS C94726
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
Code System Code Type Description
FDA UNII
6I819NIK1W
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY
DRUG BANK
DB11699
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY
EPA CompTox
89565-68-4
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY
NCI_THESAURUS
C1131
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY
EVMPD
SUB11345MIG
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL56564
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY
INN
6535
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY
DRUG CENTRAL
2775
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY
IUPHAR
260
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY
MERCK INDEX
M11232
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
Tropisetron
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY
RXCUI
27392
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY RxNorm
CAS
89565-68-4
Created by admin on Fri Jun 25 22:40:59 UTC 2021 , Edited by admin on Fri Jun 25 22:40:59 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
TARGET -> AGONIST
TROPISETRON ACTS AS BOTH A SELECTIVE 5-HT3 RECEPTOR ANTAGONIST AND .ALPHA.7-NICOTINIC RECEPTOR AGONIST.
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
PARENT -> SALT/SOLVATE
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE

Tmax PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION