5243. Itasetron

Nomenclature

CAS number: 123258-84-4
2,3-Dihydro-N-[(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]-2-oxo-1H-benzimidazole-1-carboxamide; 2-oxo-N-1αH,5αH-tropan-3α-yl-1-benzimidazoline-1-carboxamide.
C16H20N4O2; mol wt 300.36.
C 63.98%, H 6.71%, N 18.65%, O 10.65%.

Description and references

Serotonin (5-HT3) receptor antagonist. Prepn: M. Turconi et al., EP 309423 (1989 to Istituto De Angeli); eidem, US 5223511 (1993 to Boehringer, Ing.); M. Turconi et al., J. Med. Chem. 33, 2101 (1990). Pharmacology: idem et al., Eur. J. Pharmacol. 203, 203 (1991). Mode of action: M. B. Passani et al., Br. J. Pharmacol. 112, 695 (1994). Clinical efficacy and tolerability: H. Goldschmidt et al., Anti-Cancer Drugs 8, 436 (1997). Review of therapeutic potential: M. B. Passani, R. Corradetti, CNS Drug Rev. 2, 195-213 (1996).

Chemical structure

Properties

Crystals from acetonitrile, mp 205-207°. LD50 in mice, rats (mg/kg): 56, 62 i.v. (Passani).

Derivative

Hydrochloride.

Nomenclature

CAS number: 127618-28-4
DAU 6215.
C16H20N4O2.HCl; mol wt 336.82.
C 57.05%, H 6.28%, N 16.63%, O 9.50%, Cl 10.53%.

Properties

Colorless crystals, mp 270°.

Therapeutic Category

Antiemetic.

Keywords

Antiemetic; Serotonin Receptor Antagonist