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Structural formula
Non-proprietary name Ziprasidone
other names
  • 5- {2- [4- (1,2-Benzisothiazol-3-yl) -piperazin-1-yl] ethyl} -6-chloroindolin-2-one ( IUPAC )
  • Ziprasidonum ( Latin )
Molecular formula C 21 H 21 ClN 4 OS
External identifiers / databases
CAS number
  • 146939-27-7 (ziprasidon)
  • 122883-93-6 (ziprasidone hydrochloride )
  • 185021-64-1 (ziprasidon mesilate )
  • 138982-67-9 (ziprasidone hydrochloride 1 water )
EC number 928-541-6
ECHA InfoCard 100.106.954
PubChem 60854
ChemSpider 54841
DrugBank DB00246
Wikidata Q205517
Drug information
ATC code

N05 AE04

Drug class

Atypical neuroleptics

Molar mass 412.94 g · mol -1
Melting point

> 300 ° C

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances


07 - Warning 08 - Dangerous to health


H and P phrases H: 317-373
P: 280-333 + 313
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The drug ziprasidone is used in psychiatry as an antipsychotic for schizophrenia and bipolar disorder to treat manic and mixed episodes. The substance is one of the atypical neuroleptics , i.e. one of the antipsychotics, which have fewer extrapyramidal motor side effects than the older phenothiazines or butyrophenones if the desired effect is satisfactory .

There is a distant structural relationship to risperidone .



Ziprasidone binds in vitro with high affinity to dopamine D 2 and D 3 -, serotonin -5HT 2A , 5HT 2C -, 5HT 1A - and 5-HT 1D receptors as well as α 1 - adrenoceptors . There is moderate affinity for the histamine H 1 receptor. Ziprasidone acts as an antagonist on D 2 , 5HT 2A and 5HT 1D and as an agonist on 5HT 1A .

Ziprasidone inhibits the reuptake of serotonin and norepinephrine from the synaptic cleft .


Ziprasidone acts in an unchanged form; its metabolites are largely inactive. The substance is mainly metabolized in the liver ; the mean plasma half-life is 7 hours.

The bioavailability after oral ingestion is about 60% when it is coupled with food consumption at the same time. When taken on an empty stomach , it is only about half.


The antipsychotic effect of ziprasidone allows it to be classified as a moderately potent neuroleptic . A special effect on negative symptoms has been claimed for ziprasidone as for the other atypical neuroleptics, but has not yet been reliably proven.

unwanted effects

A lower possible weight gain during therapy with ziprasidone than with other atypicals such as B. olanzapine , clozapine or risperidone has been claimed, but has not yet been reliably proven.

Ziprasidone causes a slight to moderate increase in the QT interval in the ECG , depending on the dose . In patients with a low heart rate, irregular heart rate and certain heart diseases, an ECG check is indicated; if the QT prolongation is severe, discontinuation of treatment may be considered.

Common side effects reported are drowsiness, nausea, constipation, and indigestion. Sexual function disorders (→ erectile dysfunction , increased erections) rarely occur.

Also tardive dyskinesia are possible.


Ziprasidone is approved for the treatment of schizophrenia as well as manic and mixed episodes in bipolar disorder ( oral galenics, capsules, juice) and for the rapid control of acute psychotic states of excitement in schizophrenia ( parenteral galenics, intramuscular injections). It may also be useful for treating post-traumatic stress disorder .


Ziprasidone must not be used if QT prolongation is known in the ECG. Before and during an application, ECG recordings must be performed regularly; if the QT interval increases to over 500 ms, the drug must be discontinued.

Simultaneous administration of drugs that can prolong the QT interval, such as class IA and III antiarrhythmics , thioridazine , gatifloxacin , moxifloxacin , mefloquine and halofantrine, is also prohibited .

Acute myocardial infarction , heart failure and cardiac arrhythmias are also contraindications .

Use in elderly patients in the context of dementia treatment is not permitted, as ziprasidone here also leads to increased mortality.


Several multi-step syntheses for ziprasidone are described in the literature.

Commercial preparations

Ziprasidon is commercially available in Germany and many other European countries under the name Zeldox . In the USA the drug is marketed by Pfizer under the name Geodon . There are preparations for oral and parenteral use. At the beginning of 2013, the patent for ziprasidone expired in Germany. Since then, several cheaper generic drugs have become available, e.g. B. Ziprasidon Actavis or Ziprasidon beta.

See also


  • Möller, Müller, Bandelow: Neuroleptics, Pharmacological Basics, Clinical Knowledge and Therapeutic Approach . Knowledge Publishing company, Stuttgart 2001, ISBN 978-3-8047-1773-2

Individual evidence

  1. Entry on ziprasidone in the DrugBank of the University of Alberta .
  2. a b Data sheet Ziprasidone hydrochloride monohydrate, ≥98% (HPLC), solid from Sigma-Aldrich , accessed on October 31, 2016 ( PDF ).
  3. Article about ziprasidone from the Pharmazeutische Zeitung from 2002.
  4. RoteListe Online®, as of December 2008.
  5. William Annitto: Ziprasidone treatment for post-traumatic stress disorder: 128 cases. In: Psychiatry. Volume 2, number 9, September 2005, p. 19, PMID 21120101 , PMC 2993529 (free full text).
  6. ^ Axel Kleemann, Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.