Tropisetron

Tropisetron
Clinical data
Trade names	Navoban
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: B3; ;
Routes of; administration	Oral, IV
ATC code	A04AA03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only);
Pharmacokinetic data
Bioavailability	~60–80%
Protein binding	71%
Metabolism	Hepatic (CYP3A4, CYP1A2, CYP2D6)
Biological half-life	6–8 hours
Excretion	Renal, Fecal
Identifiers
	IUPAC name (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 1methyl-indole-3-carboxylate;
Synonyms	ICS 205-930
CAS Number	89565-68-4
PubChem (CID)	72165
IUPHAR/BPS	260
ChemSpider	16736476
UNII	6I819NIK1W
KEGG	D02130
ChEBI	CHEBI:32269
ChEMBL	CHEMBL496980
Chemical and physical data
Formula	C17H20N2O2
Molar mass	284.353 g/mol
3D model (Jmol)	Interactive image
	SMILES CN4[C@@H]1CC[C@H]4C[C@H](C1)OC(=O)c3cnc2ccccc23 ;
	InChI 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+ ; Key:ZNRGQMMCGHDTEI-ITGUQSILSA-N ;
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Tropisetron (INN) 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] The drug is available in a 5 mg oral preparation or in 2 mg intravenous form. It is marketed by Novartis 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[edit]

Tropisetron acts as both a selective 5-HT₃ receptor antagonist and α₇-nicotinic receptor agonist.^[2]^[3]

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. Hypotension, 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 cytochrome P450 system and it has little effect on the metabolism of other drugs broken down by this system.

Other uses[edit]

As a biological stain and as trypanocide.

References[edit]

^ Müller, W.; Stratz, T. (2004). "Local treatment of tendinopathies and myofascial pain syndromes with the 5-HT3 receptor antagonist tropisetron". Scand J Rheumatic Suppl. 119 (119): 44–48. PMID 15515413. Retrieved 2007-05-17.
^ Macor, J.E.; Gurley, D.; Lanthorn, T.; Loch, J.; Mack, R.A.; Mullen, G.; Tran, O.; Wright, N.; Gordon, J.C. (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): 319–21. doi:10.1016/S0960-894X(00)00670-3. PMID 11212100.
^ 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): 74–7. doi:10.1016/j.ejphar.2008.12.051. PMID 19374878.

External links[edit]

[pain-1] Müller, W.; Stratz, T. (2004). "Local treatment of tendinopathies and myofascial pain syndromes with the 5-HT3 receptor antagonist tropisetron". Scand J Rheumatic Suppl. 119 (119): 44–48. PMID 15515413. Retrieved 2007-05-17.

[pmid11212100-2] Macor, J.E.; Gurley, D.; Lanthorn, T.; Loch, J.; Mack, R.A.; Mullen, G.; Tran, O.; Wright, N.; Gordon, J.C. (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): 319–21. doi:10.1016/S0960-894X(00)00670-3. PMID 11212100.

[pmid19374878-3] 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): 74–7. doi:10.1016/j.ejphar.2008.12.051. PMID 19374878.

[1]

[2]

[3]

v t e Antiemetics (A04)

5-HT₃ serotonin ion channel antagonists	Alosetron Azasetron Bemesetron Cilansetron Clozapine Dazopride Dolasetron Granisetron Lerisetron Metoclopramide Mianserin Mirtazapine Olanzapine Ondansetron Palonosetron (+netupitant) Quetiapine Ramosetron Ricasetron Tropisetron Zatosetron

5-HT serotonin G-protein receptor antagonists	Clozapine Cyproheptadine Hydroxyzine Olanzapine Risperidone Ziprasidone

CB₁ agonists (cannabinoids)	Dronabinol Nabilone Tetrahydrocannabinol (cannabis)

D₂/D₃ antagonists	Alizapride Bromopride Chlorpromazine Clebopride Domperidone Haloperidol Hydroxyzine Itopride Metoclopramide Metopimazine Prochlorperazine Thiethylperazine Trimethobenzamide

H₁ antagonists (antihistamines)	Cyclizine Dimenhydrinate Diphenhydramine Hydroxyzine Meclizine Promethazine

mACh antagonists (anticholinergics)	Atropine Diphenhydramine Hydroxyzine (very mild) Hyoscyamine Scopolamine

NK₁ antagonists	Aprepitant Casopitant Ezlopitant Fosaprepitant Maropitant Netupitant Rolapitant Vestipitant

Others	Cerium oxalate Dexamethasone Lorazepam Midazolam Propofol

Tropisetron

Contents

Pharmacology[edit]

Adverse effects[edit]

Other uses[edit]

See also[edit]

References[edit]

External links[edit]

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