900. Azasetron
Nomenclature
CAS number: 123040-69-7
N-1-Azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide; (±)-6-chloro-3,4-dihydro-4-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide; nazasetron. C17H20ClN3O3; mol wt 349.81.
C 58.37%, H 5.76%, Cl 10.13%, N 12.01%, O 13.72%.
Description and references
Serotonin 5-HT3 receptor antagonist. Prepn: T. Tahara et al., EP 313393; eidem, US 4892872 (1989, 1990 both to Yoshitomi); T. Kawakita et al., Chem. Pharm. Bull. 40, 624 (1992). Receptor binding study: N. Sato et al., Jpn. J. Pharmacol. 59, 443 (1992). Pharmacology: K. Haga et al., ibid. 63, 377 (1993). Toxicity study: S. Takagi et al., Oyo Yakuri 42, 255 (1991), C.A. 117, 40208q (1991).
Derivative
Hydrochloride.Nomenclature
CAS number: 123040-16-4
Y-25130; Serotone (Yoshitomi; Japan Tobacco). C17H20ClN3O3.HCl; mol wt 386.27.
C 52.86%, H 5.48%, Cl 18.36%, N 10.88%, O 12.43%.
Properties
Crystals from ethanolic HCl, mp 281° (dec). Also reported as crystals from ethanol, mp 305° (dec) (Kawakita). LD50 in male, female rats (mg/kg): 135, 132 i.v. (Takagi).Therapeutic Category
Antiemetic.
Keywords
Antiemetic; Serotonin Receptor Antagonist