Ziprasidone

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File:Ziprasidone3Dan.gif

3D-animation of a ziprasidone molecule.

File:GEODON60MG.png

Ziprasidon Krka brand medicine.

Ziprasidone, sold under the brand name Geodon among others, is an atypical antipsychotic used to treat schizophrenia and bipolar disorder.<ref name=AHFS2019/> It may be used by mouth and by injection into a muscle (IM).<ref name=AHFS2019/> The intramuscular form may be used for acute agitation in people with schizophrenia.<ref name=AHFS2019/>

Common side effects include tremors, tics, dizziness, dry mouth, restlessness, nausea, and mild sedation.<ref name=TGA-Zeldox-IM/><ref name=TGA-Zeldox/> Although it can also cause weight gain, the risk is much lower than for other atypical antipsychotics.<ref name=PsychDrugsComm/> How it works is not entirely clear but is believed to involve effects on serotonin and dopamine in the brain.<ref name=AHFS2019>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Ziprasidone was approved for medical use in the United States in 2001.<ref name=AHFS2019/> The pills are made up of the hydrochloride salt, ziprasidone hydrochloride. The intramuscular form is the mesylate, ziprasidone mesylate trihydrate, and is provided as a lyophilized powder. In 2020, it was the 282nd most commonly prescribed medication in the United States, with more than 1Template:Nbspmillion prescriptions.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Template:TOC limit

Medical uses

Ziprasidone is approved by the US 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.<ref name = "Off-label">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

In a 2013 study in a comparison of 15 antipsychotic drugs in effectiveness in treating schizophrenic symptoms, ziprasidone demonstrated mild-standard effectiveness. Ziprasidone was 15% more effective than lurasidone and iloperidone, approximately as effective as chlorpromazine and asenapine, and 9–13% less effective than haloperidol, quetiapine, and aripiprazole.<ref>Template:Cite journal</ref> 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.<ref>Template:Cite journal</ref>

Adverse effects

Ziprasidone (and all other second generation antipsychotics (SGAs)) received a boxed warning in the US due to increased mortality in elderly people with dementia-related psychosis.<ref name="Geodon FDA label" />

Sleepiness and headache are very common adverse effects (>10%).<ref name=TGA-Zeldox-IM>{{#invoke:citation/CS1|citation |CitationClass=web }}Template:Dead link</ref><ref name=TGA-Zeldox>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Common adverse effects (1–10%), include producing too much saliva or having dry mouth, runny nose, respiratory disorders or coughing, nausea and vomiting, stomach aches, constipation or diarrhea, loss of appetite, weight gain (but the smallest risk for weight gain compared to other antipsychotics<ref name=PsychDrugsComm>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>), rashes, fast heart beats, blood pressure falling when standing up quickly, muscle pain, weakness, twitches, dizziness, and anxiety.<ref name=TGA-Zeldox-IM/><ref name=TGA-Zeldox/> Extrapyramidal symptoms are also common and include tremor, dystonia (sustained or repetitive muscle contractions), akathisia (the feeling of a need to be in motion), parkinsonism, and muscle rigidity; in a 2013 meta-analysis of 15 antipsychotic drugs, ziprasidone ranked 8th for such side effects.<ref name = "Lancet">Template:Cite journal</ref>

Ziprasidone is known to trigger mania in some bipolar patients.<ref name="pmid12656943">Template:Cite journal</ref><ref name="pmid15795551">Template:Cite journal</ref><ref name="pmid11925314">Template:Cite journal</ref>

This medication can cause birth defects, according to animal studies, although this side effect has not been confirmed in humans.<ref name="Geodon FDA label" />

Recently, the FDA required the manufacturers of some atypical antipsychotics to include a warning about the risk of hyperglycemia and Type II diabetes with atypical antipsychotics. Some evidence suggests that ziprasidone does not cause insulin resistance to the degree of other atypical antipsychotics, such as olanzapine. Weight gain is also less of a concern with ziprasidone compared to other atypical antipsychotics.<ref name="pmid19153944">Template:Cite journal</ref><ref name="pmid17192159">Template:Cite journal</ref><ref name="pmid17712347">Template:Cite journal</ref><ref name="pmid15998156">Template:Cite journal</ref> In fact, in a trial of long term therapy with ziprasidone, overweight patients (BMI > 27) actually had a mean weight loss overall.<ref name="Geodon FDA label" /> According to the manufacturer insert, ziprasidone caused an average weight gain of 2.2 kg (4.8 lbs), which is significantly lower than other atypical antipsychotics, making this medication better for patients that are concerned about their weight. In December 2014, the FDA warned that ziprasidone could cause a potentially fatal skin reaction, Drug Reaction with Eosinophilia and Systemic Symptoms (DRESS), although this was believed to occur only rarely.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}Template:Dead linkTemplate:Cbignore</ref>

Discontinuation

The British National Formulary recommends a gradual withdrawal when discontinuing antipsychotics to avoid acute withdrawal syndrome or rapid relapse.<ref name="Group 2009 192">Template:Cite book</ref> Symptoms of withdrawal commonly include nausea, vomiting, and loss of appetite.<ref name=Had2004>Template:Cite book</ref> Other symptoms may include restlessness, increased sweating, and trouble sleeping.<ref name=Had2004/> Less commonly there may be a feeling of the world spinning, numbness, or muscle pains.<ref name=Had2004/> Symptoms generally resolve after a short period of time.<ref name=Had2004/>

There is tentative evidence that discontinuation of antipsychotics can result in psychosis.<ref>Template:Cite journal</ref> It may also result in reoccurrence of the condition that is being treated.<ref>Template:Cite book</ref> Rarely tardive dyskinesia can occur when the medication is stopped.<ref name=Had2004/>

Pharmacology

Pharmacodynamics

citation

CitationClass=web }}</ref>
Site	Ki (nM)	Action	Ref
Template:Abbrlink	112	Blocker	<ref name="PDSP" />
Template:Abbrlink	44	Blocker	<ref name="PDSP" />
Template:Abbrlink	10000+	Template:Abbr	<ref name="PDSP" />
5-HT1A	2.5–76	Partial agonist	<ref name="pmid11513838">Template:Cite journal</ref><ref name="pmid8935801">Template:Cite journal</ref><ref name="pmid12629531">Template:Cite journal</ref>
5-HT1B	0.99–4.0	Partial agonist	<ref name="pmid8935801" /><ref name="PDSP" />
5-HT1D	5.1–9.0	Partial agonist	<ref name="pmid8935801" /><ref name="PDSP" />
5-HT1E	360–1279	Template:Abbr	<ref name="pmid8935801" /><ref name="PDSP" />
5-HT2A	0.08–1.4	Antagonist	<ref name="pmid18160289">Template:Cite journal</ref><ref name="pmid11513838" /><ref name="pmid8935801" />
5-HT2B	27.2	Antagonist	<ref name="PDSP" />
5-HT2C	0.72–13	Antagonist	<ref name="pmid11513838" />
5-HT3	10000+	Template:Abbr	<ref name="PDSP" />
5-HT5A	291	Template:Abbr	<ref name="PDSP" />
5-HT6	61–76	Antagonist	<ref name="pmid12629531" /><ref name="pmid11513838" />
5-HT7	6.0–9.3	Antagonist	<ref name="PDSP" /><ref name="pmid12629531" /><ref name="pmid11513838" />
α1A	18	Antagonist	<ref name="PDSP" /><ref name="pmid12629531" />
α1B	9.0	Antagonist	<ref name="PDSP" />
α2A	160	Antagonist	<ref name="PDSP" /><ref name="pmid8935801" /><ref name="pmid12629531" />
α2B	48	Antagonist	<ref name="PDSP" /><ref name="pmid8935801" /><ref name="pmid12629531" />
α2C	59–77	Antagonist	<ref name="PDSP" /><ref name="pmid8935801" /><ref name="pmid12629531" />
β1	2570+	Template:Abbr	<ref name="pmid8935801" /><ref name="PDSP" />
β2	10000+	Template:Abbr	<ref name="pmid8935801" /><ref name="PDSP" />
D1	30–130	Template:Abbr	<ref name="PDSP" /><ref name="pmid11513838" />
D2	4.8	Antagonist	<ref name="pmid9577836">Template:Cite journal</ref><ref name="pmid11513838" /><ref name="pmid12629531" />
D2L	4.6	Antagonist	<ref name="pmid8935801" /><ref name="pmid9430133">Template:Cite journal</ref>
D2S	4.2	Antagonist	<ref name="pmid8935801" />
D3	7.2	Antagonist	<ref name="pmid9577836" /><ref name="pmid11513838" /><ref name="pmid8935801" />
D4	0.8–105	Antagonist	<ref name="pmid9577836" /><ref name="pmid11513838" /><ref name="PDSP" />
D4.2	28–39	Antagonist	<ref name="pmid9430133" />
D4.4	14.9	Antagonist	<ref name="pmid9223553">Template:Cite journal</ref>
D5	152	Template:Abbr	<ref name="PDSP" />
H1	15–130	Antagonist	<ref name="pmid8935801" /><ref name="pmid11513838" /><ref name="PDSP" />
H2	3500+	Template:Abbr	<ref name="PDSP" />
H3	10000+	Template:Abbr	<ref name="PDSP" />
H4	10000+	Template:Abbr	<ref name="PDSP" />
M1	300+	Template:Abbr	<ref name="pmid14642972">Template:Cite journal</ref><ref name="PDSP" /><ref name="pmid11513838" />
M2	3000+	Template:Abbr	<ref name="pmid14642972" /><ref name="PDSP" />
M3	1300+	Template:Abbr	<ref name="pmid14642972" /><ref name="pmid12629531" /><ref name="PDSP" />
M4	1600+	Template:Abbr	<ref name="pmid14642972" /><ref name="PDSP" />
M5	1600+	Template:Abbr	<ref name="pmid14642972" /><ref name="PDSP" />
σ1	110	Template:Abbr	<ref name="pmid8935801" />
σ2	Template:Abbr	Template:Abbr	Template:Abbr
Opioid	1000+	Template:Abbr	<ref name="pmid8935801" />
Template:Abbrlink	10000+	Template:Abbr	<ref name="PDSP" />
[[NMDA receptor|Template:Abbr (Template:Abbr)]]	10000+	Template:Abbr	<ref name="PDSP" />
Template:Abbrlink	10000+	Template:Abbr	<ref name="PDSP" /><ref name="pmid8935801" />
Template:Abbrlink	2620	Template:Abbr	<ref name="pmid8935801" />
Template:Abbrlink	169	Blocker	<ref name="pmid12176106">Template:Cite journal</ref>
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site. All data are for human cloned proteins, except H3 (guinea pig), σ1 (guinea pig), opioid (rodent), Template:Abbr/Template:Abbr (rat), Template:Abbr, and Template:Abbr.<ref name="PDSP" />

Correspondence to clinical effects

Ziprasidone mostly affects the receptors of dopamine (D₂), serotonin (5-HT_2A, partially 5-HT_1A, 5-HT_2C, and 5-HT_1D)<ref name=2011rev/><ref name="pmid7562537">Template:Cite journal</ref><ref name=Goodman>Template:Cite book</ref> and epinephrine/norepinephrine (α₁) to a high degree, while of histamine (H₁) - moderately.<ref name="AkiskalTohen2011">Template:Cite book</ref><ref name="pmid16381088">Template:Cite journal</ref> It also somewhat inhibits reuptake of serotonin and norepinephrine, though not dopamine.<ref name="AkiskalTohen2011" /><ref name="pmid10193665">Template:Cite journal</ref>

Ziprasidone's efficacy in treating the positive symptoms of schizophrenia is believed to be mediated primarily via antagonism of the dopamine receptors, specifically D₂. Blockade of the 5-HT_2A receptor may also play a role in its effectiveness against positive symptoms, though the significance of this property in antipsychotic drugs is still debated among researchers.<ref name="LüllmannMohr2006">Template:Cite book</ref> Blockade of 5-HT_2A and 5-HT_2C and activation of 5-HT_1A as well as inhibition of the reuptake of serotonin and norepinephrine may all contribute to its ability to alleviate negative symptoms.;<ref name="SchatzbergNemeroff2006">Template:Cite book</ref> however, its effects on the 5-HT_1A receptor may be limited as a study<ref>Template:Cite journal</ref> found ziprasidone would likely "produce detectable occupancy [of 5-HT_1A receptors] only at higher doses that would produce unacceptable levels of side effects in man, although lower doses are sufficient to produce pharmacological effects." The relatively weak antagonistic actions of ziprasidone on the α₁-adrenergic receptor likely in part explains some of its side effects, such as orthostatic hypotension. Unlike many other antipsychotics, ziprasidone has no significant affinity for the mACh receptors, and as such lacks any anticholinergic side effects. Like most other antipsychotics, ziprasidone is sedating due primarily to serotonin and dopamine blockade.<ref name="pmid20467592">Template:Cite journal</ref><ref name="pmid10817605">Template:Cite journal</ref>

Pharmacokinetics

The systemic bioavailability of ziprasidone is 100% when administered intramuscularly and 60% when administered orally without food.<ref name=2011rev/>

After a single dose intramuscular administration, the peak serum concentration typically occurs at about 60 minutes after the dose is administered, or earlier.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Steady state plasma concentrations are achieved within one to three days. Exposure increases in a dose-related manner and following three days of intramuscular dosing, little accumulation is observed.

The bioavailability of the drug is reduced by approximately 50% if a meal is not eaten before Ziprasidone ingestion.<ref name="Geodon FDA label" /><ref name="pmid18007569">Template:Cite journal</ref>

Ziprasidone is hepatically metabolized by aldehyde oxidase; minor metabolism occurs via cytochrome P450 3A4 (CYP3A4).<ref name=Sandson>Template:Cite journal</ref> Medications that induce (e.g. carbamazepine) or inhibit (e.g. ketoconazole) CYP3A4 have been shown to decrease and increase, respectively, blood levels of ziprasidone.<ref name="pmid10771457">Template:Cite journal</ref><ref name="pmid10771458">Template:Cite journal</ref>

Its biological half-life time is 10 hours at doses of 80–120 milligrams.<ref name=2007rev/>

History

Ziprasidone is chemically similar to risperidone,<ref>Template:Cite book</ref> of which it is a structural analogue.<ref>Template:Cite journal</ref> It was first synthesized in 1987 at the Pfizer central research campus in Groton, Connecticut.<ref>Template:Cite book</ref>

Phase I trials started in 1995.<ref name="fda.gov1">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> In 1998 ziprasidone was approved in Sweden.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> After the FDA raised concerns about long QT syndrome, more clinical trials were conducted and submitted to the FDA, which approved the drug on February 5, 2001.<ref name="fda.gov1"/><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Society and culture

Lawsuit

In September 2009, the U.S. Justice Department announced that Pfizer had been ordered to pay a historic fine of $2.3 billion as a penalty for fraudulent marketing of several drugs, including Geodon.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Brand names

In the US, Geodon is marketed by Viatris after Upjohn was spun off from Pfizer.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Research

Ziprasidone has been studied in and reported to be effective in the treatment of borderline personality disorder, but findings are mixed.<ref name="DelCasaleBonanniBargagna2021">Template:Cite journal</ref><ref name="StoffersVöllmRücker2010">Template:Cite journal</ref><ref name="PascualSolerPuigdemont2008">Template:Cite journal</ref><ref name="PascualOllerSoler2004">Template:Cite journal</ref>

Further reading

• Template:Cite book