Tropisetron

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Not to be confused with Tropanserin.

Tropisetron
Clinical data
Trade namesNavoban
Other namesICS 205-930
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • AU: B3
Routes of
administration		Oral, intravenous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability~60–80%
Protein binding71%
MetabolismLiver (CYP3A4, CYP1A2, CYP2D6)
Elimination half-life6–8 hours
ExcretionKidney, Feces
Identifiers
  • (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 1methyl-indole-3-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H20N2O2
Molar mass284.359 g·mol−1
3D model (JSmol)
  • CN4[C@@H]1CC[C@H]4C[C@H](C1)OC(=O)c3c[nH]c2ccccc23
  • 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+ checkY
  • Key:ZNRGQMMCGHDTEI-ITGUQSILSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tropisetron is a serotonin 5-HT3 receptor antagonist used mainly as an antiemetic to treat nausea and vomiting following chemotherapy, although it has been used experimentally as an analgesic in cases of fibromyalgia.[1]

It was patented in 1982 and approved for medical use in 1992.[2] Tropisetron is a therapeutic alternative on the World Health Organization's List of Essential Medicines.[3] It is sold by Novartis in Europe, Australia, New Zealand, Japan, South Korea and the Philippines as Navoban, but is not available in the US. It is also available from Novell Pharmaceutical Laboratories and sold in several Asian countries as Setrovel.

Pharmacology

[edit]

Tropisetron acts as both a selective 5-HT3 receptor antagonist and α7-nicotinic receptor partial agonist.[4][5]

Tropisetron have been shown to sensitise human α7-nicotinic receptors to low concentrations of acetylcholine, indicative of a possible co-agonist or other modulatory action of tropisetron at these receptors.[6]

Adverse effects

[edit]

Tropisetron is a well-tolerated drug with few side effects. Headache, constipation, and dizziness are the most commonly reported side effects associated with its use.[7][8][9] Hypotension, transient liver enzyme elevation, immune hypersensitivity syndromes and extrapyramidal side effects have also been associated with its use on at least one occasion.[7] There have been no significant drug interactions reported with this drug's use. It is broken down by the hepatic cytochrome P450 system and it has little effect on the metabolism of other drugs broken down by this system.[10]

Other uses

[edit]

As a biological stain and as trypanocide.[11][12]

References

[edit]
  1. ^ Müller W, Stratz T (2004). "Local treatment of tendinopathies and myofascial pain syndromes with the 5-HT3 receptor antagonist tropisetron". Scandinavian Journal of Rheumatology. Supplement. 119 (119): 44–48. doi:10.1080/03009740410007032. PMID 15515413. S2CID 24916914.
  2. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 448. ISBN 978-3-527-60749-5.
  3. ^ World Health Organization (2025). The selection and use of essential medicines, 2025: WHO Model List of Essential Medicines, 24th list. Geneva: World Health Organization. hdl:10665/382243.
  4. ^ Macor JE, Gurley D, Lanthorn T, Loch J, Mack RA, Mullen G, et al. (February 2001). "The 5-HT3 antagonist tropisetron (ICS 205-930) is a potent and selective alpha7 nicotinic receptor partial agonist". Bioorganic & Medicinal Chemistry Letters. 11 (3): 319–321. doi:10.1016/S0960-894X(00)00670-3. PMID 11212100.
  5. ^ Cui R, Suemaru K, Li B, Kohnomi S, Araki H (May 2009). "Tropisetron attenuates naloxone-induced place aversion in single-dose morphine-treated rats: role of alpha7 nicotinic receptors". European Journal of Pharmacology. 609 (1–3): 74–77. doi:10.1016/j.ejphar.2008.12.051. PMID 19374878.
  6. ^ Callahan PM, Bertrand D, Bertrand S, Plagenhoef MR, Terry AV (May 2017). "Tropisetron sensitizes α7 containing nicotinic receptors to low levels of acetylcholine in vitro and improves memory-related task performance in young and aged animals". Neuropharmacology. 117: 422–433. doi:10.1016/j.neuropharm.2017.02.025. PMID 28259598. S2CID 9400277.
  7. ^ a b Goodin S, Cunningham R (2002). "5-HT(3)-receptor antagonists for the treatment of nausea and vomiting: a reappraisal of their side-effect profile". The Oncologist. 7 (5): 424–436. doi:10.1634/theoncologist.7-5-424. ISSN 1083-7159. PMID 12401905.
  8. ^ Abali H, Celik I (2007). "Tropisetron, ondansetron, and granisetron for control of chemotherapy-induced emesis in Turkish cancer patients: a comparison of efficacy, side-effect profile, and cost". Cancer Investigation. 25 (3): 135–139. doi:10.1080/07357900701208709. ISSN 0735-7907. PMID 17530482.
  9. ^ Kovac AL (December 2016). "Comparative Pharmacology and Guide to the Use of the Serotonin 5-HT3 Receptor Antagonists for Postoperative Nausea and Vomiting". Drugs. 76 (18): 1719–1735. doi:10.1007/s40265-016-0663-3. ISSN 1179-1950. PMID 27988869.
  10. ^ Kaiser R, Sezer O, Papies A, Bauer S, Schelenz C, Tremblay PB, et al. (2002-06-15). "Patient-tailored antiemetic treatment with 5-hydroxytryptamine type 3 receptor antagonists according to cytochrome P-450 2D6 genotypes". Journal of Clinical Oncology: Official Journal of the American Society of Clinical Oncology. 20 (12): 2805–2811. doi:10.1200/JCO.2002.09.064. ISSN 0732-183X. PMID 12065557.
  11. ^ Shiee MR, Kia EB, Zahabiun F, Naderi M, Motevaseli E, Nekoeian S, et al. (2021-04-12). "In vitro effects of tropisetron and granisetron against Echinococcus granulosus (s.s.) protoscoleces by involvement of calcineurin and calmodulin". Parasites & Vectors. 14 (1) 197. doi:10.1186/s13071-021-04691-9. ISSN 1756-3305. PMC 8042905. PMID 33845889.
  12. ^ Pourheydar B, Samadi M, Habibi P, Nikibakhsh AA, Naderi R (2021-02-01). "Renoprotective effects of tropisetron through regulation of the TGF-β1, p53 and matrix metalloproteinases in streptozotocin-induced diabetic rats". Chemico-Biological Interactions. 335 109332. Bibcode:2021CBI...33509332P. doi:10.1016/j.cbi.2020.109332. ISSN 0009-2797. PMID 33387473.