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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 451220265
| verifiedrevid = 451220265
| IUPAC_name = endo-N-(8-methyl-8-azabicyclo[3.2.1]oct-3yl)-2,3-dihydro-3,3-dimethyl-indole-1-carboxamide
| IUPAC_name = ''endo''-''N''-(8-Methyl-8-azabicyclo[3.2.1]oct-3yl)-2,3-dihydro-3,3-dimethyl-indole-1-carboxamide
| image = Ricasetron.png
| image = Ricasetron.svg
| width = 220
| width = 200

<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
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| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =

<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
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| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| IUPHAR_ligand = 2302
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 117086-68-7
| CAS_number = 117086-68-7
| ATC_prefix = none
| ATC_prefix = none
| ATC_suffix =
| ATC_suffix =
| PubChem = 71785
| PubChem = 14850173
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL 285999
| ChEMBL = 2105377
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = R92JB88O88
| UNII = R92JB88O88
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 16736765


<!--Chemical data-->
<!--Chemical data-->
| C=19 | H=27 | N=3 | O=1
| 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
| molecular_weight = 313.436 g/mol
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| smiles = C4C2CCC(N2C)CC4NC(=O)N(CC1(C)C)c3c1cccc3
| 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 (pharmacology)|antagonist]] at the [[serotonin]] [[5-HT3 receptor|5-HT<sub>3</sub>]] [[Receptor (biochemistry)|receptor]].<ref name="pmid8413836">{{cite journal |author=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 |year=1993 |month=August |pmid=8413836 |doi= 10.1016/0028-3908(93)90180-B|url=}}</ref> It has [[antiemetic]] effects as with other 5-HT<sub>3</sub> antagonists,<ref name="pmid7932054">{{cite journal |author=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 |year=1994 |month=June |pmid=7932054 |doi= |url=}}</ref> and also has [[anxiolytic]] effects significantly stronger than other related drugs,<ref name="pmid7831418">{{cite journal |author=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|url=}}</ref> and with less side effects than [[benzodiazepine]] anxiolytics.<ref name="pmid8485019">{{cite journal |author=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 |year=1993 |month=April |pmid=8485019 |pmc=1381550 |doi= |url=}}</ref><ref name="pmid8155281">{{cite journal |author=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 |year=1993 |month=December |pmid=8155281 |doi= 10.1016/0166-4328(93)90160-R|url=}}</ref> However it has never been developed for medical use.
'''Ricasetron''' ('''BRL-46470''') is a drug which acts as a selective [[Antagonist (pharmacology)|antagonist]] at the [[serotonin]] [[5-HT3 receptor|5-HT<sub>3</sub>]] [[Receptor (biochemistry)|receptor]].<ref name="pmid8413836">{{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 }}</ref> It has [[antiemetic]] effects as with other 5-HT<sub>3</sub> antagonists,<ref name="pmid7932054">{{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 }}</ref> and also has [[anxiolytic]] effects significantly stronger than other related drugs,<ref name="pmid7831418">{{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 }}</ref> and with less side effects than [[benzodiazepine]] anxiolytics.<ref name="pmid8485019">{{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}}</ref><ref name="pmid8155281">{{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 }}</ref> However, it has never been developed for medical use.

== See also ==
*[[Zatosetron]]
*[[Bemesetron]]
*[[Tropanserin]]
*[[Tropisetron]]
*[[Granisetron]]


== References ==
== References ==

Latest revision as of 18:42, 25 August 2022

Ricasetron
Clinical data
ATC code
  • none
Identifiers
  • endo-N-(8-Methyl-8-azabicyclo[3.2.1]oct-3yl)-2,3-dihydro-3,3-dimethyl-indole-1-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC19H27N3O
Molar mass313.445 g·mol−1
3D model (JSmol)
  • CC1(CN(c2c1cccc2)C(=O)N[C@H]3C[C@H]4CC[C@@H](C3)N4C)C
  • InChI=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- ☒N
  • Key:ILXWRFDRNAKTDD-QDMKHBRRSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Ricasetron (BRL-46470) is a drug which acts as a selective antagonist at the serotonin 5-HT3 receptor.[1] It has antiemetic effects as with other 5-HT3 antagonists,[2] and also has anxiolytic effects significantly stronger than other related drugs,[3] and with less side effects than benzodiazepine anxiolytics.[4][5] However, it has never been developed for medical use.

See also

[edit]

References

[edit]
  1. ^ Newberry NR, Watkins CJ, Sprosen TS, Blackburn TP, Grahame-Smith DG, Leslie RA (August 1993). "BRL 46470 potently antagonizes neural responses activated by 5-HT3 receptors". Neuropharmacology. 32 (8): 729–35. doi:10.1016/0028-3908(93)90180-B. PMID 8413836. S2CID 19469831.
  2. ^ Bermudez J, Sanger GJ (June 1994). "Prolonged anti-emetic activity and 5-HT3-receptor antagonism by BRL 46470 in conscious ferrets". The Journal of Pharmacy and Pharmacology. 46 (6): 520–1. doi:10.1111/j.2042-7158.1994.tb03843.x. PMID 7932054. S2CID 11799269.
  3. ^ Blackburn TP, Baxter GS, Kennett GA, King FD, Piper DC, Sanger GJ, Thomas DR, Upton N, Wood MD (1993). "BRL 46470A: a highly potent, selective and long acting 5-HT3 receptor antagonist with anxiolytic-like properties". Psychopharmacology. 110 (3): 257–64. doi:10.1007/BF02251279. PMID 7831418. S2CID 9595942.
  4. ^ Link CG, Leigh TJ, Dennison JK (April 1993). "The effects of BRL 46470A, a novel 5-HT3 receptor antagonist, and lorazepam on psychometric performance and the EEG". British Journal of Clinical Pharmacology. 35 (4): 395–9. doi:10.1111/j.1365-2125.1993.tb04156.x. PMC 1381550. PMID 8485019.
  5. ^ de Souza Silva M, Guimarães FS, Graeff FG, Tomaz C (December 1993). "Absence of amnestic effect of an anxiolytic 5-HT3 antagonist (BRL 46470A) injected into basolateral amygdala, as opposed to diazepam". Behavioural Brain Research. 59 (1–2): 141–5. doi:10.1016/0166-4328(93)90160-R. PMID 8155281. S2CID 3999586.


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