Tropisetron

Last updated

Tropisetron
Tropisetron2DACS.svg
Tropisetron3Dan.gif
Clinical data
Trade names Navoban
Other namesICS 205-930
AHFS/Drugs.com International 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 binding 71%
Metabolism Liver (CYP3A4, CYP1A2, CYP2D6)
Elimination half-life 6–8 hours
Excretion Kidney, 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
Formula C17H20N2O2
Molar mass 284.359 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+ Yes check.svgY
  • Key:ZNRGQMMCGHDTEI-ITGUQSILSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

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

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

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

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

References

  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. 1 2 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. 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.