ricasetron

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 451220265

| IUPAC_name = endo-N-(8-Methyl-8-azabicyclo[3.2.1]oct-3yl)-2,3-dihydro-3,3-dimethyl-indole-1-carboxamide

| image = Ricasetron.svg

| width = 200

| tradename =

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| bioavailability =

| protein_bound =

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| IUPHAR_ligand = 2302

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 117086-68-7

| ATC_prefix = none

| ATC_suffix =

| PubChem = 14850173

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2105377

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = R92JB88O88

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 16736765

| C=19 | H=27 | N=3 | O=1

| smiles = CC1(CN(c2c1cccc2)C(=O)N[C@H]3C[C@H]4CC[C@@H](C3)N4C)C

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C19H27N3O/c1-19(2)12-22(17-7-5-4-6-16(17)19)18(23)20-13-10-14-8-9-15(11-13)21(14)3/h4-7,13-15H,8-12H2,1-3H3,(H,20,23)/t13-,14+,15-

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ILXWRFDRNAKTDD-QDMKHBRRSA-N

}}

Ricasetron (BRL-46470) is a drug which acts as a selective antagonist at the serotonin 5-HT₃ receptor.{{cite journal |vauthors=Newberry NR, Watkins CJ, Sprosen TS, Blackburn TP, Grahame-Smith DG, Leslie RA |title=BRL 46470 potently antagonizes neural responses activated by 5-HT3 receptors |journal=Neuropharmacology |volume=32 |issue=8 |pages=729–35 |date=August 1993 |pmid=8413836 |doi= 10.1016/0028-3908(93)90180-B|s2cid=19469831 }} It has antiemetic effects as with other 5-HT₃ antagonists,{{cite journal |vauthors=Bermudez J, Sanger GJ |title=Prolonged anti-emetic activity and 5-HT3-receptor antagonism by BRL 46470 in conscious ferrets |journal=The Journal of Pharmacy and Pharmacology |volume=46 |issue=6 |pages=520–1 |date=June 1994 |pmid=7932054 |doi= 10.1111/j.2042-7158.1994.tb03843.x|s2cid=11799269 }} and also has anxiolytic effects significantly stronger than other related drugs,{{cite journal |vauthors=Blackburn TP, Baxter GS, Kennett GA, King FD, Piper DC, Sanger GJ, Thomas DR, Upton N, Wood MD |title=BRL 46470A: a highly potent, selective and long acting 5-HT3 receptor antagonist with anxiolytic-like properties |journal=Psychopharmacology |volume=110 |issue=3 |pages=257–64 |year=1993 |pmid=7831418 |doi= 10.1007/BF02251279|s2cid=9595942 }} and with less side effects than benzodiazepine anxiolytics.{{cite journal |vauthors=Link CG, Leigh TJ, Dennison JK |title=The effects of BRL 46470A, a novel 5-HT3 receptor antagonist, and lorazepam on psychometric performance and the EEG |journal=British Journal of Clinical Pharmacology |volume=35 |issue=4 |pages=395–9 |date=April 1993 |pmid=8485019 |pmc=1381550 |doi= 10.1111/j.1365-2125.1993.tb04156.x}}{{cite journal |vauthors=de Souza Silva M, Guimarães FS, Graeff FG, Tomaz C |title=Absence of amnestic effect of an anxiolytic 5-HT3 antagonist (BRL 46470A) injected into basolateral amygdala, as opposed to diazepam |journal=Behavioural Brain Research |volume=59 |issue=1–2 |pages=141–5 |date=December 1993 |pmid=8155281 |doi= 10.1016/0166-4328(93)90160-R|s2cid=3999586 }} However, it has never been developed for medical use.