Ziprasidone

Title: Ziprasidone
CAS Registry Number: 146939-27-7
CAS Name: 5-[2-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one
Additional Names: 5-(2-(4-(1,2-benzisothiazol-3-yl)piperazinyl)ethyl)-6-chlorooxindole
Manufacturers' Codes: CP-88059
Molecular Formula: C21H21ClN4OS
Molecular Weight: 412.94
Percent Composition: C 61.08%, H 5.13%, Cl 8.59%, N 13.57%, O 3.87%, S 7.77%
Literature 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).
Derivative Type: Hydrochloride monohydrate
CAS Registry Number: 138982-67-9; 122883-93-6 (anhydrous)
Manufacturers' Codes: CP-88059-1
Trademarks: Geodon (Pfizer); Zeldox (Pfizer)
Molecular Formula: C21H21ClN4OS.HCl.H2O
Molecular Weight: 467.41
Percent Composition: C 53.96%, H 5.18%, Cl 15.17%, N 11.99%, O 6.85%, S 6.86%
Literature 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°.
Melting point: mp >300°
Therap-Cat: Antipsychotic.
Keywords: Antipsychotic; Serotonin-Dopamine Antagonist.
Zirconium Chloride Zirconium Fluoride Zirconium Hydride Zirconium Hydroxide Zirconium Iodide

Ziprasidone
Ziprasidone2D.svg
Ziprasidone3Dan.gif
Systematic (IUPAC) name
5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one
Clinical data
Trade names Geodon, Zeldox
AHFS/Drugs.com monograph
MedlinePlus a699062
Licence data US FDA:link
Pregnancy cat. B3 (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (US)
Routes Oral, IM
Pharmacokinetic data
Bioavailability 60% (oral)
100% (IM)
Metabolism hepatic (aldehyde reductase)
Half-life 7 hours
Excretion Urine and feces
Identifiers
CAS number 146939-27-7 YesY
ATC code N05AE04
PubChem CID 60854
IUPHAR ligand 59
DrugBank DB00246
ChemSpider 54841 YesY
UNII 6UKA5VEJ6X YesY
KEGG D08687 YesY
ChEBI CHEBI:10119 YesY
ChEMBL CHEMBL708 YesY
Chemical data
Formula C21H21ClN4OS 
Mol. mass 412.936 g/mol
 YesY (what is this?)  (verify)

Ziprasidone (marketed as Geodon, Zeldox by Pfizer) was the fifth atypical antipsychotic to gain approval (February 2001) in the United States. It is approved by the U.S. Food and Drug Administration (FDA) for the treatment of schizophrenia, and acute mania and mixed states associated with bipolar disorder. Its intramuscular injection form is approved for acute agitation in schizophrenic patients for whom treatment with just ziprasidone is appropriate. Ziprasidone is also used off-label for depression, bipolar maintenance, mood disorders, anxiety, aggression, dementia, attention deficit hyperactivity disorder, obsessive compulsive disorder, autism, and post-traumatic stress disorder.

The oral form of ziprasidone is the hydrochloride salt, ziprasidone hydrochloride. The intramuscular form, on the other hand, is the mesylate salt, ziprasidone mesylate trihydrate, and is provided as a lyophilized powder.