Chemistry:Zatosetron

Zatosetron
Clinical data
ATC code	none;
Identifiers
	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;
CAS Number	123482-22-4 ;
PubChem CID	60763;
ChemSpider	16736584;
UNII	901MC95XSB;
Chemical and physical data
Formula	C19H25ClN2O2
Molar mass	348.87 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1(Cc2cc(cc(c2O1)C(=O)N[C@H]3C[C@H]4CC[C@@H](C3)N4C)Cl)C;
	InChI InChI=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-; Key:SPKBYQZELVEOLL-QDMKHBRRSA-N;
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Short description: Chemical compound

Zatosetron (LY-277,359) is a drug which acts as an antagonist at the 5HT₃ receptor^[1] It is orally active and has a long duration of action, producing antinauseant effects but without stimulating the rate of gastrointestinal transport.^[2]^[3] It is also an effective anxiolytic in both animal studies and human trials,^[4] although with some side effects at higher doses.^[5]^[6]

References

↑ "LY277359 maleate: a potent and selective 5-HT3 receptor antagonist without gastroprokinetic activity". The Journal of Pharmacology and Experimental Therapeutics 254 (1): 350–5. July 1990. PMID 2366187.
↑ "Zatosetron, a potent, selective, and long-acting 5HT3 receptor antagonist: synthesis and structure-activity relationships". Journal of Medicinal Chemistry 35 (2): 310–9. January 1992. doi:10.1021/jm00080a016. PMID 1732548.
↑ "Effect of zatosetron on ipecac-induced emesis in dogs and healthy men". Journal of Clinical Pharmacology 34 (3): 250–4. March 1994. doi:10.1002/j.1552-4604.1994.tb03994.x. PMID 7517409.
↑ "Pilot study of zatosetron (LY277359) maleate, a 5-hydroxytryptamine-3 antagonist, in the treatment of anxiety". Journal of Clinical Psychopharmacology 19 (2): 125–31. April 1999. doi:10.1097/00004714-199904000-00006. PMID 10211913.
↑ "General pharmacology of a new potent 5-hydroxytryptamine antagonist". Arzneimittel-Forschung 41 (3): 189–95. March 1991. PMID 1867653.
↑ "Chronic toxicity of zatosetron, a 5-HT3 receptor antagonist, in rhesus monkeys". Drug and Chemical Toxicology 18 (1): 61–82. February 1995. doi:10.3109/01480549509017858. PMID 7768200.

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[1] "LY277359 maleate: a potent and selective 5-HT3 receptor antagonist without gastroprokinetic activity". The Journal of Pharmacology and Experimental Therapeutics 254 (1): 350–5. July 1990. PMID 2366187.

[2] "Zatosetron, a potent, selective, and long-acting 5HT3 receptor antagonist: synthesis and structure-activity relationships". Journal of Medicinal Chemistry 35 (2): 310–9. January 1992. doi:10.1021/jm00080a016. PMID 1732548.

[3] "Effect of zatosetron on ipecac-induced emesis in dogs and healthy men". Journal of Clinical Pharmacology 34 (3): 250–4. March 1994. doi:10.1002/j.1552-4604.1994.tb03994.x. PMID 7517409.

[4] "Pilot study of zatosetron (LY277359) maleate, a 5-hydroxytryptamine-3 antagonist, in the treatment of anxiety". Journal of Clinical Psychopharmacology 19 (2): 125–31. April 1999. doi:10.1097/00004714-199904000-00006. PMID 10211913.

[5] "General pharmacology of a new potent 5-hydroxytryptamine antagonist". Arzneimittel-Forschung 41 (3): 189–95. March 1991. PMID 1867653.

[6] "Chronic toxicity of zatosetron, a 5-HT3 receptor antagonist, in rhesus monkeys". Drug and Chemical Toxicology 18 (1): 61–82. February 1995. doi:10.3109/01480549509017858. PMID 7768200.

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v t e Anxiolytics (N05B)
5-HT_1AR agonists	Buspirone Gepirone^† Tandospirone
GABA_AR PAMs	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Chlormezanone^‡ Ethanol (alcohol) Etifoxine Imepitoin; Herbs: Kava Skullcap Valerian
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIs (e.g., escitalopram) SNRIs (e.g., duloxetine) SARIs (e.g., trazodone) TCAs (e.g., clomipramine^#) TeCAs (e.g., mirtazapine) MAOIs (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

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

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Clinical data

ATC code	none
Identifiers
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
CAS Number	123482-22-4^Y
PubChem CID	60763
ChemSpider	16736584
UNII	901MC95XSB
Chemical and physical data
Formula	C₁₉H₂₅ClN₂O₂
Molar mass	348.87 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1(Cc2cc(cc(c2O1)C(=O)N[C@H]3C[C@H]4CC[C@@H](C3)N4C)Cl)C
InChI InChI=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- Key:SPKBYQZELVEOLL-QDMKHBRRSA-N
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