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Tropisetron

Names

[ CAS No. ]:
89565-68-4

[ Name ]:
Tropisetron

[Synonym ]:
1aH,5aH-Tropan-3a-yl indole-3-carboxylate
TROPICACID
ICF 205-930
1H-Indole-3-carboxylic acid, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
SS-TROPISETRON
3-Tropanylindole-3-carboxylate
3a-Tropanyl-1H-indole-3-carboxylic acid ester
UNII-6I819NIK1W
Indole-3-carbonyl chloride
MFCD00864399
Tropisetron
endo-1H-Indole-3-carboxylic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
icf205-930
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate
ICS 205-930
TROPISHTRON HYDROCHLORIDE

Biological Activity

[Description]:

Tropisetron(SDZ-ICS 930) is a selective 5-HT3 receptor antagonist and α7-nicotinic receptor agonist with an IC50 of 70.1 ± 0.9 nM for 5-HT3 receptor. IC50 value: 70.1 ± 0.9 nM [1]Target: 5-HT3 receptorin vitro: Tropisetron specifically inhibited both IL-2 gene transcription and IL-2 synthesis in stimulated T cells. tropisetron inhibited both the binding to DNA and the transcriptional activity of NFAT and AP-1. We also observed that tropisetron is a potent inhibitor of PMA plus ionomycin-induced NF-(kappa)B activation but in contrast TNF(alpha)-mediated NF-(kappa)B activation was not affected by this antagonist [2]. Tropisetron prevents the phosphorylation and thus activation of the p38 MAPK, which is involved in post-transcriptional regulation of various cytokines [3].in vivo: Two different doses of tropisetron (5 and 10 mg/kg) or vehicle were administered intraperitoneally 30 min before pMCAO. Neurological deficit scores, mortality rate and infarct volume were determined 24 h after permanent focal cerebral ischemia [4].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor
Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor
Natural Products >> Alkaloid
Research Areas >> Neurological Disease

[References]

[1]. Macor JE, et al. The 5-HT3 antagonist tropisetron (ICS 205-930) is a potent and selective alpha7 nicotinic receptor partial agonist. Bioorg Med Chem Lett. 2001 Feb 12;11(3):319-21.

[2]. Vega Lde L, et al. The 5-HT3 receptor antagonist tropisetron inhibits T cell activation by targeting the calcineurin pathway. Biochem Pharmacol. 2005 Aug 1;70(3):369-80.

[3]. Stratz C, et al. The anti-inflammatory effects of the 5-HT? receptor antagonist tropisetron are mediated by the inhibition of p38 MAPK activation in primary human monocytes. Int Immunopharmacol. 2012 Aug;13(4):398-402.

[4]. Candelario-Jalil E, et al. Detrimental effects of tropisetron on permanent ischemic stroke in the rat. BMC Neurosci. 2008 Feb 6;9:19.


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Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
448.5±35.0 °C at 760 mmHg

[ Melting Point ]:
201-202 °C

[ Molecular Formula ]:
C17H20N2O2

[ Molecular Weight ]:
284.35

[ Flash Point ]:
225.0±25.9 °C

[ PSA ]:
83.80000

[ LogP ]:
3.55

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.644

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
H2O: soluble

Safety Information

[ Hazard Codes ]:
Xi

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds