Ziprasidone

Ziprasidone

Clinical data
Trade names	Geodon, Zeldox, Zipwell
AHFS/Drugs.com	Monograph
MedlinePlus	a699062
License data	US FDA: Ziprasidone
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	Oral (capsules), IM
ATC code	N05AE04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	60% (oral) 100% (IM)
Metabolism	Hepatic (aldehyde reductase)
Biological half-life	7 to 10 hours
Excretion	Urine and feces
Identifiers
IUPAC name 5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one
CAS Number	146939-27-7 Y
PubChem CID	60854
IUPHAR/BPS	59
DrugBank	DB00246 Y
ChemSpider	54841 Y
UNII	6UKA5VEJ6X
KEGG	D08687 Y
ChEBI	CHEBI:10119 Y
ChEMBL	CHEMBL708 Y
ECHA InfoCard	100.106.954
Chemical and physical data
Formula	C21H21ClN4OS
Molar mass	412.936 g/mol
3D model (Jmol)	Interactive image
SMILES O=C1Cc2c(N1)cc(Cl)c(c2)CCN3CCN(CC3)c4nsc5ccccc45
InChI InChI=1S/C21H21ClN4OS/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)28-24-21/h1-4,11,13H,5-10,12H2,(H,23,27) Y Key:MVWVFYHBGMAFLY-UHFFFAOYSA-N Y

60% (oral)

Ziprasidone (marketed as Geodon among others) is a medication of the atypical antipsychotic type. It is used for the treatment of schizophrenia as well as acute mania and mixed states associated with bipolar disorder. Its intramuscular injection form is approved for acute agitation in people with schizophrenia. Ziprasidone is also used off-label for depression, bipolar maintenance, and posttraumatic stress disorder (PTSD).

The by mouth 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. Ziprasidone gained approval in the United States in 2001.

Ziprazidone is approved by the U.S. Food and Drug Administration (FDA) for the treatment of schizophrenia as well as 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 effective in the treatment of schizophrenia, though evidence from the CATIE trials suggests it is less effective than olanzapine, and equally as effective compared to quetiapine. There are higher discontinuation rates for lower doses of Ziprasidone, which are also less effective than higher doses.

The British National Formulary recommends a gradual withdrawal when discontinuing antipsychotic treatment to avoid acute withdrawal syndrome or rapid relapse.