10171. Ziprasidone

Nomenclature

CAS number: 146939-27-7
5-[2-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one; 5-(2-(4-(1,2-benzisothiazol-3-yl)piperazinyl)ethyl)-6-chlorooxindole; CP-88059.
C21H21ClN4OS; mol wt 412.94.
C 61.08%, H 5.13%, Cl 8.59%, N 13.57%, O 3.87%, S 7.77%.

Description and references

Combined serotonin (5HT2) and dopamine (D2) receptor antagonist. Prepn: J. A. Lowe III, A. A. Nagel, EP 281309; eidem, US 4831031 (1988, 1989 both to Pfizer). Clinical pharmacology: C. J. Bench et al., Psychopharmacology 112, 308 (1993). HPLC determn in serum: J. S. Janiszewski et al., J. Chromatogr. B 668, 133 (1995). Receptor binding profile: A. W. Schmidt et al., Eur. J. Pharmacol. 425, 197 (2001). Review of pharmacology and clinical experience: G. L. Stimmel et al., Clin. Ther. 24, 21-37 (2002); P. D. Harvey, C. R. Bowie, Expert Opin. Pharmacother. 6, 337-346 (2005).

Chemical structure

Derivative

Hydrochloride monohydrate.

Nomenclature

CAS number: 138982-67-9; 122883-93-6 (anhydrous)
CP-88059-1; Geodon (Pfizer); Zeldox (Pfizer).
C21H21ClN4OS.HCl.H2O; mol wt 467.41.
C 53.96%, H 5.18%, Cl 15.17%, N 11.99%, O 6.85%, S 6.86%.

Description and references

Prepn: D. J. M. Allen et al., EP 586191; eidem, US 5312925 (1993, 1994 both to Pfizer).

Properties

White to slightly pink powder. Also prepd as the hemihydrate, mp >300°.

Therapeutic Category

Antipsychotic.

Keywords

Antipsychotic; Serotonin-Dopamine Antagonist