Zatosetron

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 448140429

| IUPAC_name = 5-chloro-2,2-dimethyl-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-2,3-dihydro-1-benzofuran-7-carboxamide

| image = Zatosetron.svg

| width = 230

| tradename =

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| routes_of_administration =

| bioavailability =

| protein_bound =

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

| CAS_number = 123482-22-4

| ATC_prefix = none

| ATC_suffix =

| PubChem = 60763

| ChemSpiderID = 16736584

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

| DrugBank =

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

| UNII = 901MC95XSB

| C=19 | H=25 | Cl=1 | N=2 | O=2

| smiles = CC1(Cc2cc(cc(c2O1)C(=O)N[C@H]3C[C@H]4CC[C@@H](C3)N4C)Cl)C

| StdInChI = 1S/C19H25ClN2O2/c1-19(2)10-11-6-12(20)7-16(17(11)24-19)18(23)21-13-8-14-4-5-15(9-13)22(14)3/h6-7,13-15H,4-5,8-10H2,1-3H3,(H,21,23)/t13-,14+,15-

| StdInChIKey = SPKBYQZELVEOLL-QDMKHBRRSA-N

}}

Zatosetron (LY-277,359) is a drug which acts as an antagonist at the 5HT₃ receptor{{cite journal | vauthors = Cohen ML, Bloomquist W, Gidda JS, Lacefield W | title = LY277359 maleate: a potent and selective 5-HT3 receptor antagonist without gastroprokinetic activity | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 254 | issue = 1 | pages = 350–5 | date = July 1990 | pmid = 2366187 }} It is orally active and has a long duration of action, producing antinauseant effects but without stimulating the rate of gastrointestinal transport.{{cite journal | vauthors = Robertson DW, Lacefield WB, Bloomquist W, Pfeifer W, Simon RL, Cohen ML | title = Zatosetron, a potent, selective, and long-acting 5HT3 receptor antagonist: synthesis and structure-activity relationships | journal = Journal of Medicinal Chemistry | volume = 35 | issue = 2 | pages = 310–9 | date = January 1992 | pmid = 1732548 | doi = 10.1021/jm00080a016 }}{{cite journal | vauthors = Schwartz SM, Goldberg MJ, Gidda JS, Cerimele BJ | title = Effect of zatosetron on ipecac-induced emesis in dogs and healthy men | journal = Journal of Clinical Pharmacology | volume = 34 | issue = 3 | pages = 250–4 | date = March 1994 | pmid = 7517409 | doi = 10.1002/j.1552-4604.1994.tb03994.x | s2cid = 23486859 }} It is also an effective anxiolytic in both animal studies and human trials,{{cite journal | vauthors = Smith WT, Londborg PD, Blomgren SL, Tollefson GD, Sayler ME | title = Pilot study of zatosetron (LY277359) maleate, a 5-hydroxytryptamine-3 antagonist, in the treatment of anxiety | journal = Journal of Clinical Psychopharmacology | volume = 19 | issue = 2 | pages = 125–31 | date = April 1999 | pmid = 10211913 | doi = 10.1097/00004714-199904000-00006 }} although with some side effects at higher doses.{{cite journal | vauthors = Williams PD, Calligaro DO, Colbert WE, Helton DR, Shetler T, Turk JA, Jordan WH | title = General pharmacology of a new potent 5-hydroxytryptamine antagonist | journal = Arzneimittel-Forschung | volume = 41 | issue = 3 | pages = 189–95 | date = March 1991 | pmid = 1867653 }}{{cite journal | vauthors = Bendele A, Means J, Shoufler J, Schmalz C, Hanasono G, Symanowski J, Adams E | title = Chronic toxicity of zatosetron, a 5-HT3 receptor antagonist, in rhesus monkeys | journal = Drug and Chemical Toxicology | volume = 18 | issue = 1 | pages = 61–82 | date = February 1995 | pmid = 7768200 | doi = 10.3109/01480549509017858 }}