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Revision as of 14:32, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,104 edits Saving copy of the {{drugbox}} taken from revid 456806923 of page Tropisetron for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').  Latest revision as of 08:16, 14 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Distinguish|Tropanserin}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 402706483 | verifiedrevid = 470618047
| IUPAC_name = (1''R'',5''S'')-8-methyl-8-azabicyclooctan-3-yl 1''methyl''-indole-3-carboxylate | IUPAC_name = (1''R'',5''S'')-8-methyl-8-azabicyclooctan-3-yl 1''methyl''-indole-3-carboxylate
| image = Tropisetron structural formulae v.1.png | image = Tropisetron2DACS.svg
| image_class = skin-invert-image
| width = 200px | width = 250
| image2 = Tropisetron_3D.png
| image2 = Tropisetron3Dan.gif
| width2 = 250


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Navoban
| Drugs.com = {{drugs.com|international|tropisetron}} | Drugs.com = {{drugs.com|international|tropisetron}}
| pregnancy_AU = X | pregnancy_AU = B3
| legal_AU = S4 | legal_AU = S4
| legal_US = Not available or approved
| legal_UK = POM | legal_UK = POM
| routes_of_administration = Oral, ] | routes_of_administration = Oral, ]
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<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 89565-68-4 --> | CAS_number = 89565-68-4
| ATC_prefix = A04 | ATC_prefix = A04
| ATC_suffix = AA03 | ATC_suffix = AA03
| DrugBank = DB11699
| PubChem = 72165 | PubChem = 72165
| IUPHAR_ligand = 260 | IUPHAR_ligand = 260
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736476 | ChemSpiderID = 16736476
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6I819NIK1W | UNII = 6I819NIK1W
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02130 | KEGG = D02130
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 32269
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 496980 --> | ChEMBL = 496980
| synonyms = ICS 205-930

<!--Chemical data-->
| C=17 | H=20 | N=2 | O=2 | C=17 | H=20 | N=2 | O=2
⚫ | smiles = CN41CC4C(C1)OC(=O)c3cc2ccccc23
| molecular_weight = 284.353 g/mol
⚫ | smiles = CN41CC4C(C1)OC(=O)c3cnc2ccccc23
| InChI = 1/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+
| InChIKey = ZNRGQMMCGHDTEI-ITGUQSILBO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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+ | StdInChI = 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+
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| StdInChIKey = ZNRGQMMCGHDTEI-ITGUQSILSA-N | StdInChIKey = ZNRGQMMCGHDTEI-ITGUQSILSA-N
}} }}

'''Tropisetron''' is a ] ] used mainly as an ] to treat ] and ] following ], although it has been used experimentally as an ] in cases of ].<ref name="pain">{{cite journal | vauthors = Müller W, Stratz T | title = Local treatment of tendinopathies and myofascial pain syndromes with the 5-HT3 receptor antagonist tropisetron | journal = Scandinavian Journal of Rheumatology. Supplement | volume = 119 | issue = 119 | pages = 44–48 | date = 2004 | pmid = 15515413 | doi = 10.1080/03009740410007032 | s2cid = 24916914 }}</ref>

<!-- Society and culture -->
It was patented in 1982 and approved for medical use in 1992.<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=448 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA448 |language=en}}</ref> It is on the ].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> It is marketed by ] in Europe, Australia, New Zealand, Japan, South Korea and the Philippines as '''Navoban''', but is not available in the U.S. It is also available from Novell Pharmaceutical Laboratories and marketed in several Asian countries as '''Setrovel'''.

== Pharmacology ==
Tropisetron acts as both a selective ] and ] ].<ref name="pmid11212100">{{cite journal | vauthors = Macor JE, Gurley D, Lanthorn T, Loch J, Mack RA, Mullen G, Tran O, Wright N, Gordon JC | title = The 5-HT3 antagonist tropisetron (ICS 205-930) is a potent and selective alpha7 nicotinic receptor partial agonist | journal = Bioorganic & Medicinal Chemistry Letters | volume = 11 | issue = 3 | pages = 319–321 | date = February 2001 | pmid = 11212100 | doi = 10.1016/S0960-894X(00)00670-3 }}</ref><ref name="pmid19374878">{{cite journal | vauthors = Cui R, Suemaru K, Li B, Kohnomi S, Araki H | title = Tropisetron attenuates naloxone-induced place aversion in single-dose morphine-treated rats: role of alpha7 nicotinic receptors | journal = European Journal of Pharmacology | volume = 609 | issue = 1–3 | pages = 74–77 | date = May 2009 | pmid = 19374878 | doi = 10.1016/j.ejphar.2008.12.051 }}</ref>

Tropisetron have been shown to sensitise human ] to low concentrations of acetylcholine, indicative of a possible co-agonist or other modulatory action of tropisetron at these receptors.<ref>{{cite journal | vauthors = Callahan PM, Bertrand D, Bertrand S, Plagenhoef MR, Terry AV | title = Tropisetron sensitizes α7 containing nicotinic receptors to low levels of acetylcholine in vitro and improves memory-related task performance in young and aged animals | journal = Neuropharmacology | volume = 117 | pages = 422–433 | date = May 2017 | pmid = 28259598 | doi = 10.1016/j.neuropharm.2017.02.025 | s2cid = 9400277 }}</ref>

== Adverse effects ==
Tropisetron is a well-tolerated drug with few side effects. ], ], and ] are the most commonly reported side effects associated with its use. ], transient liver enzyme elevation, immune hypersensitivity syndromes and extrapyramidal side effects have also been associated with its use on at least one occasion. There have been no significant drug interactions reported with this drug's use. It is broken down by the hepatic ] system and it has little effect on the metabolism of other drugs broken down by this system.


==Other uses==
As a biological stain and as ].{{cn|date=August 2018}}

== See also ==
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== References ==
{{Reflist|2}}

== External links ==
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{{Antiemetics}}
{{Analgesics}}
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{{Glycine receptor modulators}}
{{Nicotinic acetylcholine receptor modulators}}
{{Serotonin receptor modulators}}
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