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Ziprasidone

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Ziprasidone
Clinical data
Trade namesGeodon, Zeldox, Zipwell, other
AHFS/Drugs.comMonograph
MedlinePlusa699062
License data
Pregnancy
category
  • AU:C
Routes of
administration		By mouth,intramuscular injection(IM)
Drug classAtypical antipsychotic
ATC code
Legal status
Legal status
Pharmacokineticdata
Bioavailability60% (oral)[3]
100% (IM)
MetabolismLiver (aldehyde reductase)
Eliminationhalf-life7 to 10 hours[4]
ExcretionUrine and feces
Identifiers
  • 5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.106.954Edit this at Wikidata
Chemical and physical data
FormulaC21H21ClN4OS
Molar mass412.94g·mol−1
3D model (JSmol)
  • O=C1Cc2c(N1)cc(Cl)c(c2)CCN3CCN(CC3)c4nsc5ccccc45
  • 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)checkY
  • Key:MVWVFYHBGMAFLY-UHFFFAOYSA-NcheckY
(verify)
3D-animation of a ziprasidone molecule.
Ziprasidon Krka brand medicine.
Wikimedia Commons has media related toZiprasidone.

Ziprasidone,sold under the brand nameGeodonamong others, is anatypical antipsychoticused to treatschizophreniaandbipolar disorder.[5]It may be usedby mouthand byinjection into a muscle(IM).[5]The IM form may be used for acuteagitationin people with schizophrenia.[5]

Common side effects includedizziness,drowsiness,dry mouth,andtwitches.[6][7]Although it can also causeweight gain,the risk is much lower than for other atypical antipsychotics.[8]How it works is not entirely clear but is believed to involve effects onserotoninanddopaminein thebrain.[5]

Ziprasidone was approved for medical use in the United States in 2001.[5]The pills are made up of the hydrochloride salt, ziprasidone hydrochloride. The intramuscular form is themesylate,ziprasidone mesylate trihydrate, and is provided as alyophilizedpowder. In 2020, it was the 282nd most commonly prescribed medication in the United States, with more than 1million prescriptions.[9][10]

Medical uses[edit]

Ziprasidone is approved by the U.S.Food and Drug Administration(FDA) for the treatment ofschizophreniaas well as acutemaniaandmixed statesassociated withbipolar disorder.Its intramuscular injection form is approved for acute agitation in schizophrenic patients for whom treatment with just ziprasidone is appropriate.[11]

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 thanlurasidoneandiloperidone,approximately as effective aschlorpromazineandasenapine,and 9–13% less effective thanhaloperidol,quetiapine,andaripiprazole.[12]Ziprasidone is effective in the treatment of schizophrenia, though evidence from the CATIE trials suggests it is less effective thanolanzapine,and equally as effective compared toquetiapine.There are higher discontinuation rates for lower doses of ziprasidone, which are also less effective than higher doses.[13]

Adverse effects[edit]

Ziprasidone (and all other second generation antipsychotics (SGAs)) received ablack box warningdue to increased mortality in elderly patients withdementia-relatedpsychosis.[14]

Sleepiness and headache are very common adverse effects (>10%).[6][7]

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[8]), rashes, fast heart beats, blood pressure falling when standing up quickly, muscle pain, weakness, twitches, dizziness, and anxiety.[6][7]Extrapyramidal symptomsare 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.[15]

Ziprasidone is known to trigger mania in some bipolar patients.[16][17][18]

This medication can cause birth defects, according to animal studies, although this side effect has not been confirmed in humans.[14]

Recently, the FDA required the manufacturers of some atypical antipsychotics to include a warning about the risk ofhyperglycemiaandType II diabeteswith atypical antipsychotics. Some evidence suggests that ziprasidone does not causeinsulin resistanceto the degree of other atypical antipsychotics, such asolanzapine.Weight gain is also less of a concern with ziprasidone compared to other atypical antipsychotics.[19][20][21][22]In fact, in a trial of long term therapy with ziprasidone, overweight patients (BMI> 27) actually had a mean weight loss overall.[14]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.[23]

Discontinuation[edit]

TheBritish National Formularyrecommends a gradual withdrawal whendiscontinuing antipsychoticsto avoid acute withdrawal syndrome or rapid relapse.[24]Symptoms of withdrawal commonly include nausea, vomiting, and loss of appetite.[25]Other symptoms may include restlessness, increased sweating, and trouble sleeping.[25]Less commonly there may be a feeling of the world spinning, numbness, or muscle pains.[25]Symptoms generally resolve after a short period of time.[25]

There is tentative evidence that discontinuation of antipsychotics can result in psychosis.[26]It may also result in reoccurrence of the condition that is being treated.[27]Rarelytardive dyskinesiacan occur when the medication is stopped.[25]

Pharmacology[edit]

Pharmacodynamics[edit]

See also:Atypical antipsychotic § Pharmacodynamics,andAntipsychotic § Comparison of medications
Ziprasidone[28]
Site Ki(nM) Action Ref
SERTTooltip Serotonin transporter 112 Blocker [28]
NETTooltip Norepinephrine transporter 44 Blocker [28]
DATTooltip Dopamine transporter >10,000 ND [28]
5-HT1A 2.5–76 Partial agonist [29][30][31]
5-HT1B 0.99–4.0 Partial agonist [30][28]
5-HT1D 5.1–9.0 Partial agonist [30][28]
5-HT1E 360–1,279 ND [30][28]
5-HT2A 0.08–1.4 Antagonist [32][29][30]
5-HT2B 27.2 Antagonist [28]
5-HT2C 0.72–13 Antagonist [29]
5-HT3 >10,000 ND [28]
5-HT5A 291 ND [28]
5-HT6 61–76 Antagonist [31][29]
5-HT7 6.0–9.3 Antagonist [28][31][29]
α1A 18 Antagonist [28][31]
α1B 9.0 Antagonist [28]
α2A 160 Antagonist [28][30][31]
α2B 48 Antagonist [28][30][31]
α2C 59–77 Antagonist [28][30][31]
β1 ≥2,570 ND [30][28]
β2 >10,000 ND [30][28]
D1 30–130 ND [28][29]
D2 4.8 Antagonist [33][29][31]
D2L 4.6 Antagonist [30][34]
D2S 4.2 Antagonist [30]
D3 7.2 Antagonist [33][29][30]
D4 0.8–105 Antagonist [33][29][28]
D4.2 28–39 Antagonist [34]
D4.4 14.9 Antagonist [35]
D5 152 ND [28]
H1 15–130 Antagonist [30][29][28]
H2 3,500 ND [28]
H3 >10,000 ND [28]
H4 >10,000 ND [28]
M1 ≥300 ND [36][28][29]
M2 ≥3,000 ND [36][28]
M3 ≥1,300 ND [36][31][28]
M4 ≥1,600 ND [36][28]
M5 ≥1,600 ND [36][28]
σ1 110 ND [30]
σ2 ND ND ND
Opioid >1,000 ND [30]
nAChTooltip Nicotinic acetylcholine receptor >10,000 ND [28]
NMDA
(PCP)		 >10,000 ND [28]
VDCCTooltip Voltage-dependent calcium channel >10,000 ND [28][30]
VGSCTooltip Voltage-gated sodium channel 2,620 ND [30]
hERGTooltip Human Ether-à-go-go-Related Gene 169 Blocker [37]
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),NMDA/PCP(rat),VDCC,andVGSC.[28]

Correspondence to clinical effects[edit]

Ziprasidone mostlyaffectsthe receptors ofdopamine(D2),serotonin(5-HT2A,partially5-HT1A,5-HT2C,and5-HT1D)[3][38][39]andepinephrine/norepinephrine(α1) to a high degree, while ofhistamine (H1)- moderately.[40][41]It also somewhatinhibitsreuptakeofserotoninandnorepinephrine,though notdopamine.[40][42]

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-HT2Areceptor 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.[43]Blockade of 5-HT2Aand 5-HT2Cand activation of 5-HT1Aas well as inhibition of the reuptake of serotonin and norepinephrine may all contribute to its ability to alleviate negative symptoms.[44];however, its effects on the 5-HT1Areceptor may be limited as a study[45]found ziprasidone would likely "produce detectable occupancy [of 5-HT1Areceptors] 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 asorthostatic hypotension.Unlike many other antipsychotics, ziprasidone has no significant affinity for the mACh receptors, and as such lacks anyanticholinergicside effects. Like most other antipsychotics, ziprasidone is sedating due primarily to serotonin and dopamine blockade.[46][47]

Pharmacokinetics[edit]

The systemicbioavailabilityof ziprasidone is 100% when administered intramuscularly and 60% when administered orally without food.[3]

After a single dose intramuscular administration, the peak serum concentration typically occurs at about 60 minutes after the dose is administered, or earlier.[48]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.[14][49]

Ziprasidone is hepatically metabolized byaldehyde oxidase;minor metabolism occurs viacytochrome P450 3A4(CYP3A4).[50]Medications that induce (e.g.carbamazepine) or inhibit (e.g.ketoconazole) CYP3A4 have been shown to decrease and increase, respectively, blood levels of ziprasidone.[51][52]

Its biological half-life time is 10 hours at doses of 80–120 milligrams.[4]

History[edit]

Ziprasidone is chemically similar torisperidone,[53]of which it is astructural analogue.[54] It was first synthesized in 1987 at thePfizercentral research campus inGroton, Connecticut.[55]

Phase I trials started in 1995.[56]In 1998 ziprasidone was approved in Sweden.[57][58]After the FDA raised concerns aboutlong QT syndrome,more clinical trials were conducted and submitted to the FDA, which approved the drug on February 5, 2001.[56][59][60]

Society and culture[edit]

Lawsuit[edit]

In September 2009, theU.S. Justice Departmentannounced 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.[61]Pfizer had illegally promoted Geodon and submitted false claims to government health care programs for uses that were not medically accepted indications. The civil settlement also resolves allegations that Pfizer paid kickbacks to health care providers to induce them to prescribe Geodon, as well as other drugs. This was the largest civil fraud settlement in history against a pharmaceutical company.[citation needed]

Brand names[edit]

In the US, Geodon is marketed byViatrisafter Upjohn was spun off from Pfizer.[62][63][64]

References[edit]

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Further reading[edit]

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