Ziprasidone

Identification

Name

Ziprasidone

Accession Number

DB00246  (APRD00540)

Type

Small Molecule

Groups

Approved

Description

Disorders such as schizophrenia and bipolar disorder can significantly impair mood, cognition, and behavior.⁶ These mental illnesses can often be accompanied by comorbidities such as depression and substance abuse, and can significantly impact the quality of life of patients and caregivers.⁶ Luckily, several treatment options for psychotic disorders have been introduced to market since the realization of chlorpromazine's antipsychotic properties in 1952.⁶

Second generation antipsychotics (commonly referred to as atypical antipsychotics) include clozapine, quetiapine, olanzapine, aripiprazole and ziprasidone among others, and are generally thought to be as efficacious as first generation antipsychotics but differ in their adverse effect profiles.^6,7 First generation antipsychotics are associated with extrapyramidal adverse effects while atypical antipsychotics are linked to weight gain, impaired glucose tolerance and metabolic syndrome.^7,8

Ziprasidone is used to treat schizophrenia and bipolar disorder.⁵ It can effectively reduce the rate and time of relapses in schizophrenia, and can be used to treat manic episodes in bipolar disorder although the mechanism of action is unknown.⁵ Although ziprasidone is classified as an atypical antipsychotic, it appears to have a lower incidence of metabolic adverse effects compared to other medications in the same class.⁶

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Ziprasidone (DB00246)

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Synonyms

• Ziprasidona
• Ziprasidone
• Ziprasidonum

External IDs

CP 88059

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Ziprasidone hydrochloride	JAL53626GG	122883-93-6	NZDBKBRIBJLNNT-UHFFFAOYSA-N
Ziprasidone mesylate trihydrate	3X6SAX83JZ	199191-69-0	WLQZEFFFIUHSJB-UHFFFAOYSA-N

Product Images

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Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Unlock Additional Data
Geodon	Capsule	20 mg/1	Oral	Unit Dose Services	2001-02-05	2017-12-31
Geodon	Capsule	40 mg/1	Oral	Roerig	2001-02-05	2018-10-31
Geodon	Injection, powder, lyophilized, for solution	20 mg/1mL	Intramuscular	TYA Pharmaceuticals	2003-12-23	Not applicable
Geodon	Capsule	20 mg/1	Oral	Lake Erie Medical DBA Quality Care Products LLC	2010-11-05	2014-12-31
Geodon	Capsule	20 mg/1	Oral	Remedy Repack	2007-04-18	2017-03-17
Geodon	Capsule	80 mg/1	Oral	Physicians Total Care, Inc.	2006-05-25	2011-06-30
Geodon	Injection, powder, lyophilized, for solution	20 mg/1mL	Intramuscular	Roerig	2017-07-24	Not applicable
Geodon	Capsule	60 mg/1	Oral	Physicians Total Care, Inc.	2009-01-19	2011-06-30
Geodon	Capsule	60 mg/1	Oral	Lake Erie Medical &Surgical Supply Dba Quality Care Products Llc	2012-03-27	2014-12-31
Geodon	Injection, powder, lyophilized, for solution	20 mg/1mL	Intramuscular	Remedy Repack	2015-01-29	2016-09-24

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Auro-ziprasidone	Capsule		Oral	Auro Pharma Inc	2018-03-19	Not applicable
Auro-ziprasidone	Capsule		Oral	Auro Pharma Inc	2018-03-19	Not applicable
Auro-ziprasidone	Capsule		Oral	Auro Pharma Inc	2018-03-19	Not applicable
Auro-ziprasidone	Capsule		Oral	Auro Pharma Inc	2018-03-19	Not applicable
Gd-ziprasidone	Capsule		Oral	Genmed A Division Of Pfizer Canada Ulc	Not applicable	Not applicable
Gd-ziprasidone	Capsule		Oral	Genmed A Division Of Pfizer Canada Ulc	Not applicable	Not applicable
Gd-ziprasidone	Capsule		Oral	Genmed A Division Of Pfizer Canada Ulc	Not applicable	Not applicable
Gd-ziprasidone	Capsule		Oral	Genmed A Division Of Pfizer Canada Ulc	Not applicable	Not applicable
Mylan-ziprasidone	Capsule		Oral	Mylan Pharmaceuticals	Not applicable	Not applicable
Mylan-ziprasidone	Capsule		Oral	Mylan Pharmaceuticals	Not applicable	Not applicable

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Categories

• Adrenergic alpha-1 Receptor Antagonists
• Adrenergic alpha-Antagonists
• Adrenergic Antagonists
• Agents that produce hypertension
• Anticholinergic Agents
• Antidepressive Agents
• Antipsychotic Agents
• Antipsychotic Agents (Second Generation [Atypical])
• Central Nervous System Agents
• Central Nervous System Depressants
• Cytochrome P-450 CYP2D6 Inhibitors
• Cytochrome P-450 CYP2D6 Inhibitors (weak)
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (moderate)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A4 Substrates (strength unknown)
• Cytochrome P-450 CYP3A5 Substrates
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Dopamine Agents
• Dopamine Antagonists
• Dopamine D2 Receptor Antagonists
• Highest Risk QTc-Prolonging Agents
• Histamine Antagonists
• Histamine H1 Antagonists
• Hyperglycemia-Associated Agents
• Indole Derivatives
• Muscarinic Antagonists
• Nervous System
• Neurotoxic agents
• Neurotransmitter Agents
• Psycholeptics
• Psychotropic Drugs
• QTc Prolonging Agents
• Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
• Serotonin 5-HT1 Receptor Agonists
• Serotonin 5-HT1 Receptor Antagonists
• Serotonin 5-HT1D Receptor Antagonists
• Serotonin 5-HT2 Receptor Antagonists
• Serotonin 5-HT2A Receptor Antagonists
• Serotonin 5-HT2C Receptor Antagonists
• Serotonin Agents
• Serotonin Receptor Agonists
• Serotonin Receptor Antagonists
• Sulfur Compounds
• Tranquilizing Agents

UNII

6UKA5VEJ6X

CAS number

146939-27-7

Weight

Average: 412.936
Monoisotopic: 412.112459711

Chemical Formula

C₂₁H₂₁ClN₄OS

InChI Key

MVWVFYHBGMAFLY-UHFFFAOYSA-N

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)

IUPAC Name

5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one

SMILES

ClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C1

Pharmacology

Indication

In its oral form, ziprasidone is approved for the treatment of schizophrenia, as monotherapy for acute treatment of manic or mixed episodes related to bipolar I disorder, and as adjunctive therapy to lithium or valproate for maintenance treatment of bipolar I disorder.¹³ The injectable formulation is approved only for treatment of acute agitation in schizophrenia.¹³

Associated Conditions

• Acute Agitation
• Agitation
• Bipolar I
• Psychosis
• Schizophrenia
• Treatment Resistant Major Depressive Disorder
• Acute Manic episode
• Acute Mixed manic depressive episode

Pharmacodynamics

Ziprasidone is classified as a "second generation" or "atypical" antipsychotic and is a dopamine and 5HT2A receptor antagonist with a unique receptor binding profile. As previously mentioned, ziprasidone has a very high 5-HT2A/D2 affinity ratio, binds to multiple serotonin receptors in addition to 5-HT2A, and blocks monoamine transporters which prevents 5HT and NE reuptake. On the other hand, ziprasidone has a low affinity for muscarinic cholinergic M1, histamine H1, and alpha1-adrenergic receptors.⁴

Mechanism of action

The effects of ziprasidone are differentiated from other antispychotics based on its preference and affinity for certain receptors. Ziprasidone binds to serotonin-2A (5-HT2A) and dopamine D2 receptors in a similar fashion to other atypical antipsychotics; however, one key difference is that ziprasidone has a higher 5-HT2A/D2 receptor affinity ratio when compared to other antipsychotics such as olanzapine, quetiapine, risperidone, and aripiprazole.¹ Ziprasidone offers enhanced modulation of mood, notable negative symptom relief, overall cognitive improvement and reduced motor dysfunction which is linked to it's potent interaction with 5-HT2C, 5-HT1D, and 5-HT1A receptors in brain tissue.¹ Ziprasidone can bind moderately to norepinephrine and serotonin reuptake sites which may contribute to its antidepressant and anxiolytic activity.¹ Patient's taking ziprasidone will likely experience a lower incidence of orthostatic hypotension, cognitive disturbance, sedation, weight gain, and disruption in prolactin levels since ziprasidone has a lower affinity for histamine H1, muscarinic M1, and alpha1-adrenoceptors.¹

Target	Actions	Organism
ADopamine D2 receptor	antagonist	Humans
UDopamine D1 receptor	antagonist	Humans
UDopamine D5 receptor	antagonist	Humans
A5-hydroxytryptamine receptor 2A	antagonist	Humans
UDopamine D3 receptor	antagonist	Humans
UDopamine D4 receptor	antagonist	Humans
A5-hydroxytryptamine receptor 1A	agonist	Humans
U5-hydroxytryptamine receptor 1B	antagonist	Humans
A5-hydroxytryptamine receptor 1D	antagonist	Humans
U5-hydroxytryptamine receptor 1E	antagonist	Humans
A5-hydroxytryptamine receptor 2C	antagonist	Humans
U5-hydroxytryptamine receptor 6	antagonist	Humans
U5-hydroxytryptamine receptor 7	antagonist	Humans
UHistamine H1 receptor	antagonist	Humans
UAlpha-1A adrenergic receptor	antagonist	Humans
UAlpha-1B adrenergic receptor	antagonist	Humans
UAlpha-2A adrenergic receptor	antagonist	Humans
UAlpha-2B adrenergic receptor	antagonist	Humans
UAlpha-2C adrenergic receptor	antagonist	Humans
UMuscarinic acetylcholine receptor M1	antagonist	Humans
UMuscarinic acetylcholine receptor M2	antagonist	Humans
UMuscarinic acetylcholine receptor M3	antagonist	Humans
UMuscarinic acetylcholine receptor M4	antagonist	Humans
UMuscarinic acetylcholine receptor M5	antagonist	Humans
U5-hydroxytryptamine 3 receptor	antagonist	Humans
U5-hydroxytryptamine receptor 5A	antagonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

In the absence of food, ziprasidone's oral bioavailability is 60%, and absorption may reach 100% if ziprasidone is taken with a meal containing at least 500 kcal. The difference in bioavailability has little to do with the fat content of the food and appears to be related to the bulk of the meal since more absorption occurs the longer ziprasidone remains in the stomach.⁴

Volume of distribution

The mean apparent volume of distribution of Ziprasidone is 1.5 L/kg.¹³

Protein binding

Ziprasidone is extensively protein bound with over 99% of the drug bound to plasma proteins, primarily albumin and alpha1-acid glycoprotein.^11,13

Metabolism

Ziprasidone is heavily metabolized in the liver with less than 5% of the drug excreted unchanged in the urine.³ The primary reductive pathway is catalyzed by aldehyde oxidase, while 2 other less prominent oxidative pathways are catalyzed by CYP3A4.³ Ziprasidone is unlikely to interact with other medications metabolized by CYP3A4 since only 1/3 of the antipsychotic is metabolized by the CYP3A4 system.³

There are 12 identified ziprasidone metabolites (abbreviations italicized): Ziprasidone sulfoxide, ziprasidone sulfone, (6-chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetic acid (OX-COOH), OX-COOH glucuronide, 3-(piperazine-1-yl)-1,2-benzisothiazole (BITP), BITP sulfoxide, BITP sulfone, BITP sulfone lactam, S-Methyl-dihydro-ziprasidone, S-Methyl-dihydro-ziprasidone-sulfoxide, 6-chloro-5-(2-piperazin-1-yl-ethyl)-1,3-dihydro-indol-2-one (OX-P), and dihydro-ziprasidone-sulfone.¹⁰

As suggested by the quantity of metabolites, ziprasidone is metabolized through several different pathways. Ziprasidone is sequentially oxidized to ziprasidone sulfoxide and ziprasidone sulfone, and oxidative N-dealkylation of ziprasidone produces OX-COOH and BITP.¹⁰ OX-COOH undergoes phase II metabolism to yield a glucuronidated metabolite while BITP is sequentially oxidized into BITP sulfoxide, BITP sulfone, then BITP sulfone lactam.¹⁰ Ziprasidone can also undergo reductive cleavage and methylation to produce S-Methyl-dihydro-ziprasidone and then further oxidation to produce S-Methyl-dihydro-ziprasidone-sulfoxide.¹⁰ Finally dearylation of ziprasidone produces OX-P, and the process of hydration and oxidation transforms the parent drug into dihydro-ziprasidone-sulfone.¹⁰

Although CYP3A4 and aldehyde oxidase are the primary enzymes involved in ziprasidone metabolism³, the pathways associated with each enzyme have not been specified.

• Ziprasidone
  Ziprasidone Sulfoxide
  • Ziprasidone Sulfoxide
    Ziprasidone Sulfone
• Ziprasidone
  (6-chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetic acid
  • (6-chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetic acid
    (6-chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetic acid glucuronide
• Ziprasidone
  3-(piperazine-1-yl)-1,2-benzisothiazole
  • 3-(piperazine-1-yl)-1,2-benzisothiazole
    3-(piperazine-1-yl)-1,2-benzisothiazole sulfoxide
    • 3-(piperazine-1-yl)-1,2-benzisothiazole sulfoxide
      3-(piperazine-1-yl)-1,2-benzisothiazole sulfone
      • 3-(piperazine-1-yl)-1,2-benzisothiazole sulfone
        3-(piperazine-1-yl)-1,2-benzisothiazole sulfone lactam
• Ziprasidone
  S-Methyl-dihydro-ziprasidone
  • S-Methyl-dihydro-ziprasidone
    S-Methyl-dihydro-ziprasidone-sulfoxide
• Ziprasidone
  6-chloro-5-(2-piperazin-1-yl-ethyl)-1,3-dihydro-indol-2-one
• Ziprasidone
  dihydro-ziprasidone-sulfone

Route of elimination

Ziprasidone is extensively metabolized after oral administration with only a small amount excreted in the urine (<1%) or feces (<4%) as unchanged drug.

Half life

The half life of ziprasidone is 6-7 hours.⁴

Clearance

The mean apparent systemic clearance is 7.5 mL/min/kg.¹³

Toxicity

The most common adverse reactions reported with ziprasidone include somnolence, respiratory tract infections, extrapyramidal symptoms, dizziness, akathisia, abnormal vision, asthenia, vomiting, headache and nausea. ¹³

Affected organisms

• Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
Unlock Additional Data
(R)-warfarin	The serum concentration of (R)-warfarin can be increased when it is combined with Ziprasidone.
(S)-Warfarin	The serum concentration of (S)-Warfarin can be increased when it is combined with Ziprasidone.
1-benzylimidazole	The risk or severity of hypertension can be increased when Ziprasidone is combined with 1-benzylimidazole.
1,10-Phenanthroline	The therapeutic efficacy of Ziprasidone can be decreased when used in combination with 1,10-Phenanthroline.
2,4-thiazolidinedione	The therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Ziprasidone.
2,5-Dimethoxy-4-ethylamphetamine	The therapeutic efficacy of Ziprasidone can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Ziprasidone.
3,5-Dinitrocatechol	The therapeutic efficacy of 3,5-Dinitrocatechol can be decreased when used in combination with Ziprasidone.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Ziprasidone.
4-Bromo-2,5-dimethoxyphenethylamine	The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Ziprasidone.

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Extended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
A severity rating for each drug interaction, from minor to major.
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Evidence Level
Evidence Level
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Action
Action
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Food Interactions

• Avoid alcohol.
• Take with food.

References

Synthesis Reference

Frank R. Busch, Carol A. Rose, "Mesylate trihydrate salt of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihy dro-2(1H)-indol-2-one (=ziprasidone), its preparation and its use as dopamine D2 antagonist." U.S. Patent US6110918, issued January, 1995.

US6110918

General References

1. Stahl SM, Shayegan DK: The psychopharmacology of ziprasidone: receptor-binding properties and real-world psychiatric practice. J Clin Psychiatry. 2003;64 Suppl 19:6-12. [PubMed:14728084]
2. Schmidt AW, Lebel LA, Howard HR Jr, Zorn SH: Ziprasidone: a novel antipsychotic agent with a unique human receptor binding profile. Eur J Pharmacol. 2001 Aug 17;425(3):197-201. [PubMed:11513838]
3. Beedham C, Miceli JJ, Obach RS: Ziprasidone metabolism, aldehyde oxidase, and clinical implications. J Clin Psychopharmacol. 2003 Jun;23(3):229-32. doi: 10.1097/01.jcp.0000084028.22282.f2. [PubMed:12826984]
4. Mattei C, Rapagnani MP, Stahl SM: Ziprasidone hydrocloride: what role in the management of schizophrenia? J Cent Nerv Syst Dis. 2011 Feb 15;3:1-16. doi: 10.4137/JCNSD.S4138. Print 2011. [PubMed:23861634]
5. Bouchette D, Marwaha R: Ziprasidone . [PubMed:28846230]
6. Kutcher S, Brooks SJ, Gardner DM, Honer B, Kopala L, Labelle A, Lalonde P, Malla A, Milliken H, Soni J, Williams R: Expert Canadian consensus suggestions on the rational, clinical use of ziprasidone in the treatment of schizophrenia and related psychotic disorders. Neuropsychiatr Dis Treat. 2005 Jun;1(2):89-108. doi: 10.2147/nedt.1.2.89.61042. [PubMed:18568067]
7. Murray R, Correll CU, Reynolds GP, Taylor D: Atypical antipsychotics: recent research findings and applications to clinical practice: Proceedings of a symposium presented at the 29th Annual European College of Neuropsychopharmacology Congress, 19 September 2016, Vienna, Austria. Ther Adv Psychopharmacol. 2017 Mar;7(1 Suppl):1-14. doi: 10.1177/2045125317693200. Epub 2017 Mar 1. [PubMed:28344764]
8. Dayabandara M, Hanwella R, Ratnatunga S, Seneviratne S, Suraweera C, de Silva VA: Antipsychotic-associated weight gain: management strategies and impact on treatment adherence. Neuropsychiatr Dis Treat. 2017 Aug 22;13:2231-2241. doi: 10.2147/NDT.S113099. eCollection 2017. [PubMed:28883731]
9. Wilner KD, Demattos SB, Anziano RJ, Apseloff G, Gerber N: Ziprasidone and the activity of cytochrome P450 2D6 in healthy extensive metabolizers. Br J Clin Pharmacol. 2000;49 Suppl 1:43S-47S. [PubMed:10771453]
10. Prakash C, Kamel A, Gummerus J, Wilner K: Metabolism and excretion of a new antipsychotic drug, ziprasidone, in humans. Drug Metab Dispos. 1997 Jul;25(7):863-72. [PubMed:9224781]
11. Uzelac TN, Nikolic-Kokic AL, Spasic SD, Macvanin MT, Nikolic MR, Mandic LM, Jovanovic VB: Opposite clozapine and ziprasidone effects on the reactivity of plasma albumin SH-group are the consequence of their different binding properties dependent on protein fatty acids content. Chem Biol Interact. 2019 Sep 25;311:108787. doi: 10.1016/j.cbi.2019.108787. Epub 2019 Aug 7. [PubMed:31400341]
12. Ziprasidone Black Box Warning [Link]
13. FDA Approved Drug Products: Geodon (ziprasidone HCl) [Link]
14. Zeldox Pfizer Canada Product Monograph [Link]
15. FDA Approved Drug Products: Geodon (ziprasidone) [Link]

External Links

Human Metabolome Database

HMDB0014391

KEGG Drug

D08687

KEGG Compound

C07568

PubChem Compound

60854

PubChem Substance

46507627

ChemSpider

54841

BindingDB

50048803

RxNav

115698

ChEBI

10119

ChEMBL

CHEMBL708

ZINC

ZINC000000538550

Therapeutic Targets Database

DAP000079

PharmGKB

PA451974

Guide to Pharmacology

GtP Drug Page

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Ziprasidone

ATC Codes

N05AE04 — Ziprasidone

• N05AE — Indole derivatives
• N05A — ANTIPSYCHOTICS
• N05 — PSYCHOLEPTICS
• N — NERVOUS SYSTEM

AHFS Codes

• 28:16.08.04 — Atypical Antipsychotics

MSDS

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Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Recruiting	Prevention	Opioid Abuse, Unspecified / Opioid Dependence	1
1	Completed	Basic Science	Healthy Volunteers	1
1	Completed	Treatment	Healthy Volunteers	2
1	Recruiting	Diagnostic	Schizophrenia	1
1	Terminated	Prevention	Cardiovascular Heart Disease	1
1, 2	Recruiting	Basic Science	Schizophrenia	1
2	Completed	Treatment	Autism, Early Infantile	1
2	Completed	Treatment	Bipolar Disorder (BD) / Depression / Depression, Bipolar	1
2	Completed	Treatment	Bipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenia	1
2	Completed	Treatment	Borderline Personality Disorder (BPD)	1
2	Completed	Treatment	Cognition Disorders / Delirium	1
2	Completed	Treatment	Major Depressive Disorder (MDD)	2
2	Completed	Treatment	Oppositional Defiant Disorder	1
2	Completed	Treatment	Psychosis Prodrome	1
2	Completed	Treatment	Schizophrenia	3
2	Completed	Treatment	Social Anxiety Disorder (SAD)	1
2	Terminated	Treatment	Schizophrenia	1
2, 3	Completed	Treatment	Affective Disorders	1
2, 3	Completed	Treatment	Schizoaffective Disorders / Schizophrenia	1
3	Completed	Treatment	Bipolar Disorder (BD)	5
3	Completed	Treatment	Bipolar affective disorder, manic / Bipolar Disorder (BD)	1
3	Completed	Treatment	Bipolar Disorder (BD) / Depression, Bipolar	1
3	Completed	Treatment	Bipolar Disorder (BD) / Major Depressive Disorder (MDD) / Psychosis / Schizoaffective Disorders / Schizophreniform Disorder	1
3	Completed	Treatment	Bipolar I Disorder	1
3	Completed	Treatment	Delirium / Impaired Cognition / Long Term Psychologic Disorders	1
3	Completed	Treatment	Depression	1
3	Completed	Treatment	Psychotic Disorder NOS / Schizoaffective Disorders / Schizophrenia	1
3	Completed	Treatment	Psychotic Disorder NOS / Schizophrenia	1
3	Completed	Treatment	Schizophrenia	8
3	Completed	Treatment	Schizophrenia and Schizoaffective Disorder	1
3	Recruiting	Treatment	Bipolar Disorder (BD)	2
3	Terminated	Treatment	Anxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenia	1
3	Terminated	Treatment	Bipolar Disorder (BD)	1
3	Terminated	Treatment	Bipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenia	1
3	Terminated	Treatment	Schizoaffective Disorders / Schizophrenia	1
3	Terminated	Treatment	Schizophrenia	3
3	Unknown Status	Treatment	Psychosis Nos/Other	1
3	Withdrawn	Treatment	Bipolar Disorder (BD)	2
4	Completed	Not Available	Healthy Male Volunteers	1
4	Completed	Basic Science	Diabetes / Schizophrenia	1
4	Completed	Diagnostic	Post Traumatic Stress Disorder (PTSD)	1
4	Completed	Treatment	Acute Exacerbation of Psychosis / Delusional Disorder / Mania / Schizophrenia	1
4	Completed	Treatment	Affective Disorders / Psychotic Disorder NOS / Psychotic Mood Disorder / Schizophrenia	1
4	Completed	Treatment	Bipolar Disorder (BD)	3
4	Completed	Treatment	Bipolar Disorder (BD) / Depression	1
4	Completed	Treatment	Bipolar Disorder (BD) / Generalized Anxiety Disorder (GAD) / Panic Disorders	1
4	Completed	Treatment	Bipolar Disorder (BD) / Mania	1
4	Completed	Treatment	Bipolar Disorder (BD) / Medication Adherence	1
4	Completed	Treatment	Bipolar II Disorder / Major Depressive Episode	1
4	Completed	Treatment	Depression, Bipolar	1
4	Completed	Treatment	Depression / Schizoaffective Disorders / Schizophrenia	1
4	Completed	Treatment	First Episode Psychosis	1
4	Completed	Treatment	Insulin Resistance / Metabolic Syndromes / Schizophrenia	1
4	Completed	Treatment	Psychotic Disorder NOS	2
4	Completed	Treatment	Psychotic Disorder NOS / Schizophrenia	4
4	Completed	Treatment	Pyschotic Disorders	1
4	Completed	Treatment	Schizoaffective Disorders / Schizophrenia	6
4	Completed	Treatment	Schizoaffective Disorders / Schizophrenia / Schizophrenia and Disorders With Psychotic Features	1
4	Completed	Treatment	Schizophrenia	8
4	Completed	Treatment	Schizophrenia, Schizoaffective Disorder	1
4	Not Yet Recruiting	Treatment	Schizophrenia	2
4	Recruiting	Treatment	Bipolar Disorder (BD)	1
4	Recruiting	Treatment	Schizophrenia	1
4	Terminated	Not Available	High Risk MC4R Genotype / Low Risk MC4R Genotype / One Week or Less Antipsychotic Lifetime Exposure	1
4	Terminated	Treatment	Acute Mania / Bipolar Disorder, Manic	1
4	Terminated	Treatment	Bipolar Disorder (BD) / Generalized Anxiety Disorder (GAD)	1
4	Terminated	Treatment	Schizophrenia and Disorders With Psychotic Features	1
4	Unknown Status	Treatment	Schizophrenia	1
4	Unknown Status	Treatment	Schizophrenia or Schizoaffective Disorder	1
4	Withdrawn	Treatment	Agitation / Delirium / Psychosis	1
Not Available	Completed	Not Available	Acute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiety / Anxiolysis / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Bradycardia / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest (CA) / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Chronic Kidney Disease (CKD) / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infection / Convulsions / Cytomegalovirus Retinitis / Decompensated Heart Failure / Drug hypersensitivity reaction / Dysrhythmia, Cardiac / Early-onset Schizophrenia Spectrum Disorders / Edema / Endocarditis / Epilepsies / Fibrinolytic Bleeding / Flu caused by Influenza / Gastroparesis / Gram-negative Infection / Gynaecological infection / Headache / Heart Failure / Heavy Menstrual Bleeding / Hemophilia / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hyperaldosteronism / Hyperlipidemias / Hypokalemia / Hypotension / Infantile Hemangiomas / Infection / Infection caused by staphylococci / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Insomnia / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Methicillin Resistant Staphylococcus Aureus (MRSA) / Migraine / Muscle Spasms / Nausea / Neuromuscular Blockade / Neutropenia / Nosocomial Pneumonia / Opioid Addiction / Pain / Plague / Pneumonia / Prophylaxis / Psittacosis / Pulmonary Arterial Hypertension (PAH) / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenia / Sedation / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and skin-structure infections / Skin and Subcutaneous Tissue Bacterial Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombotic events / Toxic effect of hydrocyanic acid and cyanides / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infection / Vomiting / Withdrawal	1
Not Available	Completed	Not Available	Affective Psychosis, Bipolar / Mania / Mixed affective disorder (psychosis) / Psychoses, Manic-Depressive	1
Not Available	Completed	Not Available	Bipolar Disorder (BD)	1
Not Available	Completed	Not Available	Bipolar Disorder (BD) / Psychotic Disorder NOS / Schizoaffective Disorders / Schizophrenia / Type 2 Diabetes Mellitus	1
Not Available	Completed	Not Available	Bipolar Disorder (BD) / Schizophrenia	1
Not Available	Completed	Not Available	Psychomotor Agitation	2
Not Available	Completed	Not Available	Schizophrenia	2
Not Available	Completed	Diagnostic	Obsessive Compulsive Disorder (OCD) / Schizophrenia	1
Not Available	Completed	Prevention	Hyperglycemia / Hyperlipidemias	1
Not Available	Completed	Treatment	Bipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenia	2
Not Available	Completed	Treatment	Hyperglycemia / Schizoaffective Disorders / Schizophrenia / Type 2 Diabetes Mellitus	1
Not Available	Completed	Treatment	Psychomotor Agitation	1
Not Available	Completed	Treatment	Schizophrenia	3
Not Available	Completed	Treatment	Schizophrenia / Type 2 Diabetes Mellitus	1
Not Available	Enrolling by Invitation	Not Available	Bipolar Disorder (BD)	1
Not Available	Recruiting	Not Available	Adverse Drug Effect of Antipsychotics and Neuroleptics / Efficacy / Individualed Opitmal Therapy / Schizophrenia	1
Not Available	Recruiting	Not Available	Micrognathia / Schizophrenia	1
Not Available	Terminated	Not Available	Post Traumatic Stress Disorder (PTSD)	1

Pharmacoeconomics

Manufacturers

• Pfizer inc

Packagers

• Ben Venue Laboratories Inc.
• Cardinal Health
• Comprehensive Consultant Services Inc.
• Kaiser Foundation Hospital
• Lake Erie Medical and Surgical Supply
• Nucare Pharmaceuticals Inc.
• Pfizer Inc.
• Pharmacia Inc.
• Physicians Total Care Inc.
• Prepackage Specialists
• Rebel Distributors Corp.
• Remedy Repack
• Resource Optimization and Innovation LLC
• Stat Rx Usa
• US Pharmaceutical Group

Dosage forms

Form	Route	Strength
Capsule	Oral	20 mg/1
Capsule	Oral	40 mg/1
Capsule	Oral	60 mg/1
Capsule	Oral	80 mg/1
Injection, powder, lyophilized, for solution	Intramuscular	20 mg/1mL
Capsule	Oral

Prices

Unit description	Cost	Unit
Zoladex 10.8 mg Implant Syringe	1407.72USD	syringe
Geodon 20 mg vial	16.22USD	vial
Geodon 60 mg capsule	9.88USD	capsule
Geodon 80 mg capsule	9.88USD	capsule
Geodon 20 mg capsule	8.14USD	capsule
Geodon 40 mg capsule	8.14USD	capsule
Zeldox 40 mg Capsule	2.13USD	capsule
Zeldox 60 mg Capsule	2.13USD	capsule
Zeldox 80 mg Capsule	2.13USD	capsule
Zeldox 20 mg Capsule	1.86USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
Unlock Additional Data
US5134127	No	1992-07-28	2010-01-23
CA2256227	No	2003-07-01	2018-12-16
CA2105114	No	2000-02-15	2013-08-30
US6245766	No	2001-06-12	2018-12-18
US6150366	No	2000-11-21	2019-05-27
US6232304	No	2001-05-15	2017-04-01
US6399777	No	2002-06-04	2017-04-01
US6110918	No	2000-08-29	2017-03-26
US7175855	No	2007-02-13	2020-05-18

Additional Data Available

Filed On
Filed On
The date on which a patent was filed with the relevant government.
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Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	>276°C (Ziprasidone Hydrochloride Monohydrate)	https://www.trc-canada.com/product-detail/?CatNum=Z485000
logP	3.8	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00718 mg/mL	ALOGPS
logP	4.64	ALOGPS
logP	4.3	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	7.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	48.47 Å2	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.72 m3·mol-1	ChemAxon
Polarizability	44.96 Å3	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9759
Caco-2 permeable	+	0.8867
P-glycoprotein substrate	Substrate	0.7167
P-glycoprotein inhibitor I	Inhibitor	0.8052
P-glycoprotein inhibitor II	Inhibitor	0.6419
Renal organic cation transporter	Inhibitor	0.5325
CYP450 2C9 substrate	Non-substrate	0.7972
CYP450 2D6 substrate	Non-substrate	0.9117
CYP450 3A4 substrate	Substrate	0.7408
CYP450 1A2 substrate	Inhibitor	0.6576
CYP450 2C9 inhibitor	Inhibitor	0.6329
CYP450 2D6 inhibitor	Non-inhibitor	0.7151
CYP450 2C19 inhibitor	Inhibitor	0.8086
CYP450 3A4 inhibitor	Non-inhibitor	0.7723
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.9567
Ames test	Non AMES toxic	0.6273
Carcinogenicity	Non-carcinogens	0.8672
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.5877 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.6826
hERG inhibition (predictor II)	Inhibitor	0.7753

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-01ox-0900400000-0a17dd0e237f50ba91c5

Taxonomy

Description

This compound belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

N-arylpiperazines

Alternative Parents

Benzothiazoles / Phenethylamines / Indoles / Dialkylarylamines / Aralkylamines / N-alkylpiperazines / Aminothiazoles / Aryl chlorides / Imidolactams / Heteroaromatic compoundsCyclic carboximidic acids / Trialkylamines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Hydrocarbon derivatives / Organopnictogen compounds / Organooxygen compounds / Organochlorides

show 8 more

Substituents

N-arylpiperazine / 1,2-benzothiazole / Indole / Indole or derivatives / Phenethylamine / Dialkylarylamine / N-alkylpiperazine / Aralkylamine / Imidolactam / Benzenoid1,2-thiazolamine / Aryl chloride / Aryl halide / Cyclic carboximidic acid / Heteroaromatic compound / Thiazole / Azole / Tertiary aliphatic amine / Tertiary amine / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Azacycle / Amine / Organohalogen compound / Organopnictogen compound / Organic oxygen compound / Organic nitrogen compound / Organochloride / Organonitrogen compound / Organooxygen compound / Hydrocarbon derivative / Aromatic heteropolycyclic compound

show 22 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound, indolones, piperazines, 1,2-benzisothiazole (CHEBI:10119)

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Drug created on June 13, 2005 07:24 / Updated on July 11, 2020 00:05