Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H21ClN4OS.ClH.H2O |
Molecular Weight | 467.412 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.ClC1=CC2=C(CC(=O)N2)C=C1CCN3CCN(CC3)C4=NSC5=C4C=CC=C5
InChI
InChIKey=ZCBZSCBNOOIHFP-UHFFFAOYSA-N
InChI=1S/C21H21ClN4OS.ClH.H2O/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);1H;1H2
DescriptionCurator's Comment: description was created based on several sources, including
https://effectivehealthcare.ahrq.gov/ehc/products/150/786/CER43_Off-LabelAntipsychotics_execsumm_20110928.pdf
Curator's Comment: description was created based on several sources, including
https://effectivehealthcare.ahrq.gov/ehc/products/150/786/CER43_Off-LabelAntipsychotics_execsumm_20110928.pdf
Ziprasidone is atypical antipsychotic, approved by the U.S. Food and Drug Administration for the treatment of schizophrenia, and acute mania and mixed states associated with bipolar disorder. Intramuscilar injections of Ziprasidone are indicated for rapid control of the agitation in schizophrenic patients. Ziprasidone is used off-label for treatment of major depressive disorder, anxiety, obsessive compulsive disorder, borderline personality disorder. Ziprasidone functions as an antagonist at the D2, 5HT2A, and 5HT1D receptors, and as an agonist at the 5HT1A receptor.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL217 |
4.8 nM [Ki] | ||
Target ID: CHEMBL3737 |
3.4 nM [Ki] | ||
Target ID: CHEMBL224 |
0.4 nM [Ki] | ||
Target ID: CHEMBL1983 |
2.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | GEODON Approved UseZiprasidone hydrochloride capsule is an atypical antipsychotic. In choosing among treatments, prescribers should be aware of the capacity of ziprasidone hydrochloride capsule to prolong the QT interval and may consider the use of other drugs first. Launch Date2001 |
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Primary | GEODON Approved UseZiprasidone hydrochloride capsule is an atypical antipsychotic. In choosing among treatments, prescribers should be aware of the capacity of ziprasidone hydrochloride capsule to prolong the QT interval and may consider the use of other drugs first. Ziprasidone intramuscular is indicated for the treatment of acute agitation in schizophrenic patients for whom treatment with ziprasidone is appropriate and who need intramuscular antipsychotic medication for rapid control of the agitation. “Psychomotor agitation” is defined in DSM-IV as “excessive motor activity associated with a feeling of inner tension.” Launch Date2001 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
51 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16721322 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZIPRASIDONE serum | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
457 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16721322 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZIPRASIDONE serum | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16721322 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZIPRASIDONE serum | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
ZIPRASIDONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
4480 mg single, oral Overdose Dose: 4480 mg Route: oral Route: single Dose: 4480 mg Co-administed with:: Clomethiazole(192 mg) Sources: |
unhealthy, 22 years n = 1 Health Status: unhealthy Condition: Paranoid Schizophrenia Age Group: 22 years Sex: M Population Size: 1 Sources: |
Disc. AE: Sedation, Hypotension... AEs leading to discontinuation/dose reduction: Sedation (1 patient) Sources: Hypotension (1 patient) |
20 mg single, oral Overdose |
healthy, 30 month n = 1 Health Status: healthy Age Group: 30 month Sex: F Population Size: 1 Sources: |
Disc. AE: Respiratory depression... AEs leading to discontinuation/dose reduction: Respiratory depression (1 patient) Sources: |
780 mg single, oral Overdose |
unhealthy, 31 years n = 1 Health Status: unhealthy Condition: Mixed personality disorder Age Group: 31 years Sex: M Population Size: 1 Sources: |
Disc. AE: Drowsiness... AEs leading to discontinuation/dose reduction: Drowsiness (1 patient) Sources: |
1120 mg single, oral Overdose Dose: 1120 mg Route: oral Route: single Dose: 1120 mg Sources: |
unhealthy, 35 years n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 35 years Sex: M Population Size: 1 Sources: |
|
4400 mg single, oral Overdose Dose: 4400 mg Route: oral Route: single Dose: 4400 mg Co-administed with:: Clomethiazole(768 mg) Sources: flunitrazepam(4 mg) |
unhealthy, 57 years n = 1 Health Status: unhealthy Condition: Manic-depressive disorder Age Group: 57 years Sex: F Population Size: 1 Sources: |
Disc. AE: Drowsiness, Tremor... AEs leading to discontinuation/dose reduction: Drowsiness (1 patient) Sources: Tremor (1 patient) Anxiety (1 patient) |
20 mg 2 times / day steady, intramuscular Studied dose Dose: 20 mg, 2 times / day Route: intramuscular Route: steady Dose: 20 mg, 2 times / day Sources: |
unhealthy, 60 – 81 years n = 21 Health Status: unhealthy Condition: Schizophrenia Age Group: 60 – 81 years Sex: M+F Population Size: 21 Sources: |
Other AEs: Blurred vision, Sedation... Other AEs: Blurred vision (1 patient) Sources: Sedation (1 patient) |
40 mg 1 times / day steady, oral Studied dose Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, 7 – 17 years n = 28 Health Status: unhealthy Condition: Tourette's syndrome Age Group: 7 – 17 years Sex: M+F Population Size: 28 Sources: |
Other AEs: Somnolence, Akathisia... Other AEs: Somnolence (1 patient) Sources: Akathisia (1 patient) |
20 mg single, oral |
unhealthy, 7-16 years n = 24 Health Status: unhealthy Condition: Tourette's disorder or chronic tic disorder Age Group: 7-16 years Sex: M+F Population Size: 24 Sources: |
Other AEs: Somnolence, Syncope hypotensive... Other AEs: Somnolence (16 patients) Sources: Syncope hypotensive (2 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypotension | 1 patient Disc. AE |
4480 mg single, oral Overdose Dose: 4480 mg Route: oral Route: single Dose: 4480 mg Co-administed with:: Clomethiazole(192 mg) Sources: |
unhealthy, 22 years n = 1 Health Status: unhealthy Condition: Paranoid Schizophrenia Age Group: 22 years Sex: M Population Size: 1 Sources: |
Sedation | 1 patient Disc. AE |
4480 mg single, oral Overdose Dose: 4480 mg Route: oral Route: single Dose: 4480 mg Co-administed with:: Clomethiazole(192 mg) Sources: |
unhealthy, 22 years n = 1 Health Status: unhealthy Condition: Paranoid Schizophrenia Age Group: 22 years Sex: M Population Size: 1 Sources: |
Respiratory depression | 1 patient Disc. AE |
20 mg single, oral Overdose |
healthy, 30 month n = 1 Health Status: healthy Age Group: 30 month Sex: F Population Size: 1 Sources: |
Drowsiness | 1 patient Disc. AE |
780 mg single, oral Overdose |
unhealthy, 31 years n = 1 Health Status: unhealthy Condition: Mixed personality disorder Age Group: 31 years Sex: M Population Size: 1 Sources: |
Anxiety | 1 patient Disc. AE |
4400 mg single, oral Overdose Dose: 4400 mg Route: oral Route: single Dose: 4400 mg Co-administed with:: Clomethiazole(768 mg) Sources: flunitrazepam(4 mg) |
unhealthy, 57 years n = 1 Health Status: unhealthy Condition: Manic-depressive disorder Age Group: 57 years Sex: F Population Size: 1 Sources: |
Drowsiness | 1 patient Disc. AE |
4400 mg single, oral Overdose Dose: 4400 mg Route: oral Route: single Dose: 4400 mg Co-administed with:: Clomethiazole(768 mg) Sources: flunitrazepam(4 mg) |
unhealthy, 57 years n = 1 Health Status: unhealthy Condition: Manic-depressive disorder Age Group: 57 years Sex: F Population Size: 1 Sources: |
Tremor | 1 patient Disc. AE |
4400 mg single, oral Overdose Dose: 4400 mg Route: oral Route: single Dose: 4400 mg Co-administed with:: Clomethiazole(768 mg) Sources: flunitrazepam(4 mg) |
unhealthy, 57 years n = 1 Health Status: unhealthy Condition: Manic-depressive disorder Age Group: 57 years Sex: F Population Size: 1 Sources: |
Blurred vision | 1 patient | 20 mg 2 times / day steady, intramuscular Studied dose Dose: 20 mg, 2 times / day Route: intramuscular Route: steady Dose: 20 mg, 2 times / day Sources: |
unhealthy, 60 – 81 years n = 21 Health Status: unhealthy Condition: Schizophrenia Age Group: 60 – 81 years Sex: M+F Population Size: 21 Sources: |
Sedation | 1 patient | 20 mg 2 times / day steady, intramuscular Studied dose Dose: 20 mg, 2 times / day Route: intramuscular Route: steady Dose: 20 mg, 2 times / day Sources: |
unhealthy, 60 – 81 years n = 21 Health Status: unhealthy Condition: Schizophrenia Age Group: 60 – 81 years Sex: M+F Population Size: 21 Sources: |
Akathisia | 1 patient | 40 mg 1 times / day steady, oral Studied dose Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, 7 – 17 years n = 28 Health Status: unhealthy Condition: Tourette's syndrome Age Group: 7 – 17 years Sex: M+F Population Size: 28 Sources: |
Somnolence | 1 patient | 40 mg 1 times / day steady, oral Studied dose Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, 7 – 17 years n = 28 Health Status: unhealthy Condition: Tourette's syndrome Age Group: 7 – 17 years Sex: M+F Population Size: 28 Sources: |
Somnolence | 16 patients | 20 mg single, oral |
unhealthy, 7-16 years n = 24 Health Status: unhealthy Condition: Tourette's disorder or chronic tic disorder Age Group: 7-16 years Sex: M+F Population Size: 24 Sources: |
Syncope hypotensive | 2 patients | 20 mg single, oral |
unhealthy, 7-16 years n = 24 Health Status: unhealthy Condition: Tourette's disorder or chronic tic disorder Age Group: 7-16 years Sex: M+F Population Size: 24 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-825_Geodan_pharmr_P2.pdf#page=16 Page: 16.0 |
no [IC50 >100 uM] | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-825_Geodan_pharmr_P2.pdf#page=16 Page: 16.0 |
no [IC50 >100 uM] | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-825_Geodan_pharmr_P2.pdf#page=16 Page: 16.0 |
no [IC50 >100 uM] | |||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no | ||||
Page: 16, (ClinPharm) 16, (ClinPharm4) 58-60 |
yes [IC50 5.8 uM] | no (co-administration study) Comment: Estimated Cfree,plasma = 0.29-0.73 nM (80mg BID); Coadministration of Ziprasidone had no effect on the urinary Dextromethorphan/Dextrophan ratio. Page: 16, (ClinPharm) 16, (ClinPharm4) 58-60 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-825_Geodan_pharmr_P2.pdf#page=16 Page: 16.0 |
yes [Ki 64 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-825_Geodan_biopharmr_P3.pdf#page=68 Page: (ClinPharm3) 68 |
likely | |||
Page: 15-16, (ClinPhar) 15-16, (ClinPharm3) 65-66, (ClinPharm4) 35-38, 64-66 |
major | yes (co-administration study) Comment: Ketoconazole inhibited formation of Ziprasidone sulfoxide by 77% in vitro.; Coadministration of Ketoconazoke (strong CYP3A4 inhibitor) increased Ziprasidone AUC and Cmax by about 30%. Coadministration of Carbamazepine (strong CYP3A4 inducer) decreased Ziprasidone AUC by 36% and Cmax by 27%. Page: 15-16, (ClinPhar) 15-16, (ClinPharm3) 65-66, (ClinPharm4) 35-38, 64-66 |
||
Page: 15-16, (ClinPharm3) 65-66, 68 |
minor | |||
Sources: https://go.drugbank.com/drugs/DB00246 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors. | 2000 Oct |
|
Emerging options in the treatment of bipolar disorders. | 2001 |
|
Antipsychotic medications and the elderly: effects on cognition and implications for use. | 2001 |
|
Atypical antipsychotics: new directions and new challenges in the treatment of schizophrenia. | 2001 |
|
Ziprasidone: a novel antipsychotic agent with a unique human receptor binding profile. | 2001 Aug 17 |
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Cost effectiveness of the newer atypical antipsychotics: a review of the pharmacoeconomic research evidence. | 2001 Jan |
|
Antipsychotic drugs classified by their effects on the release of dopamine and noradrenaline in the prefrontal cortex and striatum. | 2001 Jan 26 |
|
Ziprasidone: a new atypical antipsychotic. | 2001 Jun |
|
Ziprasidone, a new atypical antipsychotic drug. | 2001 Jun |
|
Antipsychotic medication: effects on regulation of glucose and lipids. | 2001 Oct |
|
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor. | 2001 Oct |
|
Efficacy of antipsychotic agents at human 5-HT(1A) receptors determined by [3H]WAY100,635 binding affinity ratios: relationship to efficacy for G-protein activation. | 2001 Oct 5 |
|
Inverse agonist properties of antipsychotic agents at cloned, human (h) serotonin (5-HT)(1B) and h5-HT(1D) receptors. | 2001 Sep |
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Advances in atypical antipsychotics for the treatment of schizophrenia: new formulations and new agents. | 2002 |
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Pharmacological treatment of psychotic agitation. | 2002 |
|
Psychotropic drugs and adverse events in the treatment of bipolar disorders revisited. | 2002 |
|
Ziprasidone induction of hypomania in depression? | 2002 Apr |
|
The anxiolytic effect of the novel antipsychotic ziprasidone compared with diazepam in subjects anxious before dental surgery. | 2002 Apr |
|
Rhabdomyolysis, pancreatitis, and hyperglycemia with ziprasidone. | 2002 Aug |
|
Ziprasidone and migraine headache. | 2002 Aug |
|
Recent developments in pharmacotherapy for the acutely psychotic patient. | 2002 Dec |
|
New drugs 2002, part 1. | 2002 Jan |
|
Experience with ziprasidone. | 2002 May |
|
Ziprasidone: the fifth atypical antipsychotic. | 2002 May |
|
Effects of typical and atypical antipsychotics and receptor selective compounds on acetylcholine efflux in the hippocampus of the rat. | 2002 May |
|
Clinical issues associated with maintenance treatment of patients with schizophrenia. | 2002 Sep 1 |
|
Continuum of care: stabilizing the acutely agitated patient. | 2002 Sep 1 |
|
Ziprasidone-associated galactorrhea in a female teenager. | 2003 Jan |
|
Constitutive coupling of a chimeric dopamine D2/alpha 1B receptor to the phospholipase C pathway: inverse agonism to silent antagonism by neuroleptic drugs. | 2003 Jan |
Sample Use Guides
For treatment of schizophrenia, GEODON capsules should be administered at an initial daily dose of 20 mg BID with food. Daily dosage may subsequently be adjusted on the basis of individual clinical status up to 80 mg BID. Systematic evaluation of ziprasidone has shown that its efficacy in schizophrenia is maintained for periods of up to 52 weeks at a dose of 20 to 80 mg BID. For treatment of bipolar mania, oral ziprasidone should be administered at an initial daily dose of 40 mg BID with food. The dose should then be increased to 60 mg or 80 mg BID on the second day of treatment and subsequently adjusted on the basis of toleration and efficacy within the range 40-80 mg BID. The recommended dose for intramuscular administration is 10 to 20 mg administered as required up to a maximum dose of 40 mg per day. Doses of 10 mg may be administered every two hours; doses of 20 mg may be administered every four hours up to a maximum of 40 mg/day.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8568801
Standard receptor-binding methods were used to label dopamine D2 receptors using [3H]spiperone. Briefly, rats were sacrificed by decapitation and the brains rapidly removed. The corpus striatum was dissected and homogenized in 20 vol at 50 mM Tris HCl (pH 7.2) buffer using a Brinkman Polytron homogenizer (setting 7 for 15 s). The homogenate was centrifuged for 10 min at 40000g. The pellet was resuspended in fresh ice-cold 50 mM Tris (pH 7.2) buffer with the Polytron homogenizer and recentrifuged. The final pellet was resuspended in 50 mM Tris HCl buffer (pH 7.2) containing 1 mM MgCl2 and 100 mM NaCl. Assays were initiated by the addition of tissue to tubes containing [3H]spiperone (0.2 nM) and drug or buffer in a final volume of 1 mL. Blocking agents (500 nM cinanserin and 1 mM prazosin) were present to prevent [3H]spiperone from labeling 5-HT2 and R1 noradrenergic receptors. Nonspecific binding was defined as the radioligand bound in the presence of 10 uM (+)-butaclamol. After a 15 min incubation at 37 °C, tissue samples were filtered onto Whatman GF/B glass fiber filters using a Brandel harvester and rinsed two times with 5 mL of ice-cold 50 mM Tris HCl (pH 7.4) buffer. Filters were soaked in 10 mL of Ready-Safe (Beckman Instruments), and the radioactivity was quantified using liquid scintillation counting. Ziprasidone binds to D2 receptors with pKi of 8.32 nM.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29710
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216X081ORU
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DBSALT000810
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1294533
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EE-54
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m11641
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100000092710
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32314
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C48031
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60853
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SUB05189MIG
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CHEMBL708
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1724408
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SUB28840
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ACTIVE MOIETY
SUBSTANCE RECORD