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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
Inhibition of ganglionic long-term potentiation decreases blood pressure in spontaneously hypertensive rats.
2001 Dec
Association between increased 5-HIAA plasma concentrations and postoperative nausea and vomiting in patients undergoing general anaesthesia for surgery.
2001 Dec
Relaxation induced by serotonin and sumatriptan in isolated guinea pig gallbladder strips.
2001 Mar
Infusional 5-fluorouracil, cisplatin and mitomycin C in advanced gastric cancer: a low cost effective regimen.
2002 Jan 21
Small-dose dexamethasone reduces nausea and vomiting after laparoscopic cholecystectomy: a comparison of tropisetron with saline.
2002 Jul
[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
The prophylactic effect of tropisetron on epidural morphine-related nausea and vomiting: a comparison of dexamethasone with saline.
2002 Mar
[Pilot study with 5-HT3 antagonists. Good outcome in fibromyalgia pain].
2002 Mar 14
Simultaneous determination of ondansetron and tropisetron in human plasma using HPLC with UV detection.
2002 May
Low-dose dexamethasone reduces nausea and vomiting after tympanomastoid surgery: a comparison of tropisetron with saline.
2002 Sep-Oct
[What's new in the therapy of fibromyalgia?].
2003 Dec
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
Effect of the CYP2D6 genotype on the pharmacokinetics of tropisetron in healthy Korean subjects.
2003 Jun
The assessment of vegetative and functional symptoms in fibromyalgia patients: the tropisetron experience.
2004
Intravenous treatment of fibromyalgia with the 5-HT3 receptor antagonist tropisetron in a rheumatological practice.
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
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
Tropisetron improves deficits in auditory P50 suppression in schizophrenia.
2005 Jul 1
New treatment options using 5-HT3 receptor antagonists in rheumatic diseases.
2006
A randomized, placebo-controlled trial of a single dose of tropisetron for the prevention of vomiting after strabismus surgery in children.
2006 Dec
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
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
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