Identification

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Name
Ziprasidone
Accession Number
DB00246  (APRD00540)
Type
Small Molecule
Groups
Approved
Description

Ziprasidone is classified as an atypical antipsychotic and is used primarily to treat schizophrenia and bipolar disorder.5 It is effective at reducing 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

Structure
Thumb
Synonyms
  • Ziprasidona
  • Ziprasidone
  • Ziprasidonum
External IDs
CP 88059
Product Ingredients
IngredientUNIICASInChI Key
Ziprasidone hydrochlorideJAL53626GG122883-93-6NZDBKBRIBJLNNT-UHFFFAOYSA-N
Ziprasidone mesylate trihydrate3X6SAX83JZ199191-69-0WLQZEFFFIUHSJB-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
GeodonCapsule40 mg/1OralREMEDYREPACK INC.2018-08-14Not applicableUs
GeodonCapsule20 mg/1OralUnit Dose Services2001-02-052018-07-30Us00049 3960 60 nlmimage10 3f159f9c
GeodonCapsule20 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2010-11-052018-04-19Us
GeodonCapsule40 mg/1OralCardinal Health2001-02-052015-06-30Us55154 272620180907 15195 mglf6j
GeodonCapsule40 mg/1OralRemedy Repack2017-06-092017-06-09Us
GeodonInjection, powder, lyophilized, for solution20 mg/1mLIntramuscularRoerig2003-12-23Not applicableUs
GeodonCapsule40 mg/1OralRoerig2001-02-052018-10-31Us0049 397020180814 13942 1425h7p
GeodonCapsule60 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs53808 025420180907 15195 yzfsk
GeodonInjection, powder, lyophilized, for solution20 mg/1mLIntramuscularRemedy Repack2015-01-292016-09-24Us
GeodonCapsule80 mg/1OralRebel Distributors2001-02-05Not applicableUs
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
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-ziprasidoneCapsuleOralAuro Pharma Inc2018-03-19Not applicableCanada
Auro-ziprasidoneCapsuleOralAuro Pharma Inc2018-03-19Not applicableCanada
Auro-ziprasidoneCapsuleOralAuro Pharma Inc2018-03-19Not applicableCanada
Auro-ziprasidoneCapsuleOralAuro Pharma Inc2018-03-19Not applicableCanada
Gd-ziprasidoneCapsuleOralGenmed A Division Of Pfizer Canada UlcNot applicableNot applicableCanada
Gd-ziprasidoneCapsuleOralGenmed A Division Of Pfizer Canada UlcNot applicableNot applicableCanada
Gd-ziprasidoneCapsuleOralGenmed A Division Of Pfizer Canada UlcNot applicableNot applicableCanada
Gd-ziprasidoneCapsuleOralGenmed A Division Of Pfizer Canada UlcNot applicableNot applicableCanada
Mylan-ziprasidoneCapsuleOralMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-ziprasidoneCapsuleOralMylan PharmaceuticalsNot applicableNot applicableCanada
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

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Categories
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 it's 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.7 The injectable formulation is approved only for treatment of acute agitation in schizophrenia.7

Associated Conditions
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 preventing 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 it's 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 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

TargetActionsOrganism
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
U5-hydroxytryptamine receptor 1A
agonist
Humans
U5-hydroxytryptamine receptor 1B
antagonist
Humans
U5-hydroxytryptamine receptor 1D
antagonist
Humans
U5-hydroxytryptamine receptor 1E
antagonist
Humans
U5-hydroxytryptamine receptor 2C
antagonist
Humans
U5-hydroxytryptamine receptor 3A
antagonist
Humans
U5-hydroxytryptamine receptor 6
antagonist
Humans
U5-hydroxytryptamine receptor 7
antagonist
Humans
NHistamine H1 receptor
antagonist
Humans
NAlpha-1A adrenergic receptor
antagonist
Humans
NAlpha-1B adrenergic receptor
antagonist
Humans
NAlpha-2A adrenergic receptor
antagonist
Humans
NAlpha-2B adrenergic receptor
antagonist
Humans
NAlpha-2C adrenergic receptor
antagonist
Humans
NMuscarinic acetylcholine receptor M1
antagonist
Humans
NMuscarinic acetylcholine receptor M2
antagonist
Humans
NMuscarinic acetylcholine receptor M3
antagonist
Humans
NMuscarinic acetylcholine receptor M4
antagonist
Humans
NMuscarinic acetylcholine receptor M5
antagonist
Humans
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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Additional Data Available
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%, while absorption may reach up to 100% if ziprasidone is taken with a meal equal to or greater than 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. 7

Protein binding

Ziprasidone is extensively protein bound with over 99% of the drug bound to plasma proteins such as albumin and alpha1-acid glycoprotein. 7

Metabolism

Ziprasidone is heavily metabolized in the liver with less than 5% of the drug excreted unchanged in the urine. There are 2 enzyme systems that are primarily responsible for it's metabolism: aldehyde oxidase catalyzes the primary reductive pathway while CYP3A4 catalyzes 2 other less prominent oxidation pathways. Since they CYP3A4 system is responsible for only 1/3 of ziprasidone metabolism, there is a lower risk of interactions with other CYP3A4 substrates and inhibitors.3

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

7.5 mL/min/kg 7

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. 7

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.
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Ziprasidone.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Ziprasidone.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when Ziprasidone is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when Ziprasidone is combined with 1-benzylimidazole.
1,10-PhenanthrolineThe therapeutic efficacy of Ziprasidone can be decreased when used in combination with 1,10-Phenanthroline.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Ziprasidone.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of Ziprasidone can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of Ziprasidone can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,5-DinitrocatecholThe therapeutic efficacy of 3,5-Dinitrocatechol can be decreased when used in combination with Ziprasidone.
4-Bromo-2,5-dimethoxyamphetamineThe therapeutic efficacy of Ziprasidone can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine.
Additional Data Available
  • Extended Description
    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.

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. Ziprasidone Black Box Warning [Link]
  7. Geodon FDA Label [Link]
  8. Zeldox Pfizer Canada Product Monograph [Link]
External Links
Human Metabolome Database
HMDB0014391
KEGG Drug
D08687
KEGG Compound
C07568
PubChem Compound
60854
PubChem Substance
46507627
ChemSpider
54841
BindingDB
50048803
ChEBI
10119
ChEMBL
CHEMBL708
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
AHFS Codes
  • 28:16.08.04 — Atypical Antipsychotics
MSDS
Download (57.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingPreventionOpioid Abuse, Unspecified / Opioid Dependence1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentHealthy Volunteers2
1Enrolling by InvitationPreventionCardiovascular Heart Disease1
1RecruitingDiagnosticSchizophrenic Disorders1
1, 2RecruitingBasic ScienceSchizophrenic Disorders1
2CompletedTreatmentAutism, Early Infantile1
2CompletedTreatmentBipolar Disorder (BD) / Depression / Depression, Bipolar1
2CompletedTreatmentBipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenic Disorders1
2CompletedTreatmentBorderline Personality Disorder (BPD)1
2CompletedTreatmentCognition Disorders / Delirium1
2CompletedTreatmentMajor Depressive Disorder (MDD)2
2CompletedTreatmentOppositional Defiant Disorder1
2CompletedTreatmentPsychosis Prodrome1
2CompletedTreatmentSchizophrenic Disorders3
2CompletedTreatmentSocial Anxiety Disorder (SAD)1
2TerminatedNot AvailablePost Traumatic Stress Disorder (PTSD)1
2TerminatedTreatmentSchizophrenic Disorders1
2, 3CompletedTreatmentAffective Disorders1
2, 3CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
3CompletedTreatmentBipolar Disorder (BD)5
3CompletedTreatmentBipolar affective disorder, manic / Bipolar Disorder (BD)1
3CompletedTreatmentBipolar Disorder (BD) / Depression, Bipolar1
3CompletedTreatmentBipolar Disorder (BD) / Major Depressive Disorder (MDD) / Psychosis / Schizoaffective Disorders / Schizophreniform Disorder1
3CompletedTreatmentBipolar I Disorder1
3CompletedTreatmentDelirium / Impaired Cognition / Long Term Psychologic Disorders1
3CompletedTreatmentDepression1
3CompletedTreatmentPsychotic Disorder NOS / Schizoaffective Disorders / Schizophrenic Disorders1
3CompletedTreatmentPsychotic Disorder NOS / Schizophrenic Disorders1
3CompletedTreatmentSchizophrenia and Schizoaffective Disorder1
3CompletedTreatmentSchizophrenic Disorders8
3RecruitingTreatmentBipolar Disorder (BD)2
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentBipolar Disorder (BD)1
3TerminatedTreatmentBipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenic Disorders1
3TerminatedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
3TerminatedTreatmentSchizophrenic Disorders3
3Unknown StatusTreatmentPsychosis Nos/Other1
3WithdrawnTreatmentBipolar Disorder (BD)2
4CompletedNot AvailableHealthy Male Volunteers1
4CompletedBasic ScienceDiabetes Mellitus (DM) / Schizophrenic Disorders1
4CompletedDiagnosticPost Traumatic Stress Disorder (PTSD) / Posttraumatic Stress Disorders1
4CompletedTreatmentAcute Exacerbation of Psychosis / Delusional Disorder / Mania / Schizophrenic Disorders1
4CompletedTreatmentAffective Disorders / Psychotic Disorder NOS / Psychotic Mood Disorder / Schizophrenic Disorders1
4CompletedTreatmentBipolar Disorder (BD)3
4CompletedTreatmentBipolar Disorder (BD) / Depression1
4CompletedTreatmentBipolar Disorder (BD) / Generalized Anxiety Disorder (GAD) / Panic Disorders1
4CompletedTreatmentBipolar Disorder (BD) / Mania1
4CompletedTreatmentBipolar Disorder (BD) / Medication Adherence1
4CompletedTreatmentBipolar II Disorder / Major Depressive Episode1
4CompletedTreatmentDepression, Bipolar1
4CompletedTreatmentDepression / Schizoaffective Disorders / Schizophrenic Disorders1
4CompletedTreatmentFirst Episode Psychosis1
4CompletedTreatmentInsulin Resistance / Metabolic Syndromes / Schizophrenic Disorders1
4CompletedTreatmentPsychotic Disorder NOS2
4CompletedTreatmentPsychotic Disorder NOS / Schizophrenic Disorders4
4CompletedTreatmentPyschotic Disorders1
4CompletedTreatmentSchizoaffective Disorders / Schizophrenia and Disorders With Psychotic Features / Schizophrenic Disorders1
4CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders6
4CompletedTreatmentSchizophrenia, Schizoaffective Disorder1
4CompletedTreatmentSchizophrenic Disorders8
4Not Yet RecruitingTreatmentSchizophrenic Disorders1
4RecruitingTreatmentBipolar Disorder (BD)1
4RecruitingTreatmentSchizophrenic Disorders1
4TerminatedNot AvailableHigh Risk MC4R Genotype / Low Risk MC4R Genotype / One Week or Less Antipsychotic Lifetime Exposure1
4TerminatedTreatmentAcute Mania / Bipolar Disorder, Manic1
4TerminatedTreatmentBipolar Disorder (BD) / Generalized Anxiety Disorder (GAD)1
4TerminatedTreatmentSchizophrenia and Disorders With Psychotic Features1
4Unknown StatusTreatmentSchizophrenia or Schizoaffective Disorder1
4Unknown StatusTreatmentSchizophrenic Disorders1
4WithdrawnTreatmentAgitation / Delirium / Psychosis1
Not AvailableCompletedNot AvailableAffective Psychosis, Bipolar / Mania / Psychoses, Manic-Depressive1
Not AvailableCompletedNot AvailableBipolar Disorder (BD)1
Not AvailableCompletedNot AvailableBipolar Disorder (BD) / Psychotic Disorder NOS / Schizoaffective Disorders / Schizophrenic Disorders / Type 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableBipolar Disorder (BD) / Schizophrenic Disorders1
Not AvailableCompletedNot AvailablePsychomotor Agitation2
Not AvailableCompletedNot AvailableSchizophrenic Disorders2
Not AvailableCompletedDiagnosticObsessive Compulsive Disorder (OCD) / Schizophrenic Disorders1
Not AvailableCompletedPreventionHyperglycemia / Hyperlipidemias1
Not AvailableCompletedTreatmentBipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenic Disorders2
Not AvailableCompletedTreatmentHyperglycemia / Schizoaffective Disorders / Schizophrenic Disorders / Type 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentPsychomotor Agitation1
Not AvailableCompletedTreatmentSchizophrenic Disorders3
Not AvailableCompletedTreatmentSchizophrenic Disorders / Type 2 Diabetes Mellitus1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / 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 / Cardiac Dysrhythmia / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Chronic Kidney Disease (CKD) / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infection / Convulsions / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / 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 / Hospital-acquired bacterial pneumonia / 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 / Opioid Addiction / Pain / Plague / Pneumonia / Prophylaxis / Psittacosis / Pulmonary Arterial Hypertension (PAH) / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue 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 / Withdrawal1
Not AvailableRecruitingNot AvailableAdverse Drug Effect of Antipsychotics and Neuroleptics / Efficacy / Individualed Opitmal Therapy / Schizophrenic Disorders1
Not AvailableRecruitingNot AvailableMicrognathia / Schizophrenic Disorders1

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
FormRouteStrength
CapsuleOral20 mg/1
CapsuleOral40 mg/1
CapsuleOral60 mg/1
CapsuleOral80 mg/1
Injection, powder, lyophilized, for solutionIntramuscular20 mg/1mL
CapsuleOral
Prices
Unit descriptionCostUnit
Zoladex 10.8 mg Implant Syringe1407.72USD syringe
Geodon 20 mg vial16.22USD vial
Geodon 60 mg capsule9.88USD capsule
Geodon 80 mg capsule9.88USD capsule
Geodon 20 mg capsule8.14USD capsule
Geodon 40 mg capsule8.14USD capsule
Zeldox 40 mg Capsule2.13USD capsule
Zeldox 60 mg Capsule2.13USD capsule
Zeldox 80 mg Capsule2.13USD capsule
Zeldox 20 mg Capsule1.86USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5134127No1992-07-282010-01-23Us
CA2256227No2003-07-012018-12-16Canada
CA2105114No2000-02-152013-08-30Canada
US6245766No2001-06-122018-12-18Us
US6150366No2000-11-212019-05-27Us
US6232304No2001-05-152017-04-01Us
US6399777No2002-06-042017-04-01Us
US6110918No2000-08-292017-03-26Us
US7175855No2007-02-132020-05-18Us
Additional Data Available
  • Filed On
    Filed On

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

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>276°C (Ziprasidone Hydrochloride Monohydrate)https://www.trc-canada.com/product-detail/?CatNum=Z485000
logP3.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00718 mg/mLALOGPS
logP4.64ALOGPS
logP4.3ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.18ChemAxon
pKa (Strongest Basic)7.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area48.47 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity116.72 m3·mol-1ChemAxon
Polarizability44.96 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9759
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.7167
P-glycoprotein inhibitor IInhibitor0.8052
P-glycoprotein inhibitor IIInhibitor0.6419
Renal organic cation transporterInhibitor0.5325
CYP450 2C9 substrateNon-substrate0.7972
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateSubstrate0.7408
CYP450 1A2 substrateInhibitor0.6576
CYP450 2C9 inhibitorInhibitor0.6329
CYP450 2D6 inhibitorNon-inhibitor0.7151
CYP450 2C19 inhibitorInhibitor0.8086
CYP450 3A4 inhibitorNon-inhibitor0.7723
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9567
Ames testNon AMES toxic0.6273
CarcinogenicityNon-carcinogens0.8672
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5877 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6826
hERG inhibition (predictor II)Inhibitor0.7753
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ox-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 compounds
show 8 more
Substituents
N-arylpiperazine / 1,2-benzothiazole / Indole / Indole or derivatives / Phenethylamine / Dialkylarylamine / N-alkylpiperazine / Aralkylamine / Imidolactam / Benzenoid
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, indolones, piperazines, 1,2-benzisothiazole (CHEBI:10119)

Targets

Details
1. Dopamine D2 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706]
  2. Kopecek M, Bares M, Mohr P: Ziprasidone-induced galactorrhea: a case report. Neuro Endocrinol Lett. 2005 Feb;26(1):69-70. [PubMed:15726024]
  3. Seeger TF, Seymour PA, Schmidt AW, Zorn SH, Schulz DW, Lebel LA, McLean S, Guanowsky V, Howard HR, Lowe JA 3rd, et al.: Ziprasidone (CP-88,059): a new antipsychotic with combined dopamine and serotonin receptor antagonist activity. J Pharmacol Exp Ther. 1995 Oct;275(1):101-13. [PubMed:7562537]
  4. 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]
  5. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Details
2. Dopamine D1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name
DRD1
Uniprot ID
P21728
Uniprot Name
D(1A) dopamine receptor
Molecular Weight
49292.765 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name
DRD5
Uniprot ID
P21918
Uniprot Name
D(1B) dopamine receptor
Molecular Weight
52950.5 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Mansbach RS, Carver J, Zorn SH: Blockade of drug-induced deficits in prepulse inhibition of acoustic startle by ziprasidone. Pharmacol Biochem Behav. 2001 Jul-Aug;69(3-4):535-42. [PubMed:11509214]
  2. Ichikawa J, Li Z, Dai J, Meltzer HY: Atypical antipsychotic drugs, quetiapine, iloperidone, and melperone, preferentially increase dopamine and acetylcholine release in rat medial prefrontal cortex: role of 5-HT1A receptor agonism. Brain Res. 2002 Nov 29;956(2):349-57. [PubMed:12445705]
  3. Lu BY, Lundgren R, Escalona PR, Roberts BB: A case of ziprasidone-induced mania and the role of 5-HT2A in mood changes induced by atypical antipsychotics. J Clin Psychiatry. 2002 Dec;63(12):1185-6. [PubMed:12530423]
  4. Mamo D, Kapur S, Shammi CM, Papatheodorou G, Mann S, Therrien F, Remington G: A PET study of dopamine D2 and serotonin 5-HT2 receptor occupancy in patients with schizophrenia treated with therapeutic doses of ziprasidone. Am J Psychiatry. 2004 May;161(5):818-25. [PubMed:15121646]
  5. Kast RE, Focosi D, Petrini M, Altschuler EL: Treatment schedules for 5-HT2A blocking in progressive multifocal leukoencephalopathy using risperidone or ziprasidone. Bone Marrow Transplant. 2007 Jun;39(12):811-2. Epub 2007 Apr 23. [PubMed:17450180]
  6. 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]
  7. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Details
5. Dopamine D3 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name
DRD3
Uniprot ID
P35462
Uniprot Name
D(3) dopamine receptor
Molecular Weight
44224.335 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Details
6. Dopamine D4 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Sh3 domain binding
Specific Function
Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Its activity is mediated by G proteins ...
Gene Name
DRD4
Uniprot ID
P21917
Uniprot Name
D(4) dopamine receptor
Molecular Weight
48359.86 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Sprouse JS, Reynolds LS, Braselton JP, Rollema H, Zorn SH: Comparison of the novel antipsychotic ziprasidone with clozapine and olanzapine: inhibition of dorsal raphe cell firing and the role of 5-HT1A receptor activation. Neuropsychopharmacology. 1999 Nov;21(5):622-31. [PubMed:10516958]
  2. Rollema H, Lu Y, Schmidt AW, Sprouse JS, Zorn SH: 5-HT(1A) receptor activation contributes to ziprasidone-induced dopamine release in the rat prefrontal cortex. Biol Psychiatry. 2000 Aug 1;48(3):229-37. [PubMed:10924666]
  3. Richelson E, Souder T: Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds. Life Sci. 2000 Nov 24;68(1):29-39. [PubMed:11132243]
  4. Wilner KD, Anziano RJ, Johnson AC, Miceli JJ, Fricke JR, Titus CK: The anxiolytic effect of the novel antipsychotic ziprasidone compared with diazepam in subjects anxious before dental surgery. J Clin Psychopharmacol. 2002 Apr;22(2):206-10. [PubMed:11910268]
  5. Newman-Tancredi A, Rivet JM, Cussac D, Touzard M, Chaput C, Marini L, Millan MJ: Comparison of hippocampal G protein activation by 5-HT(1A) receptor agonists and the atypical antipsychotics clozapine and S16924. Naunyn Schmiedebergs Arch Pharmacol. 2003 Sep;368(3):188-99. Epub 2003 Aug 16. [PubMed:12923612]
  6. 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]
  7. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1B
Uniprot ID
P28222
Uniprot Name
5-hydroxytryptamine receptor 1B
Molecular Weight
43567.535 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1D
Uniprot ID
P28221
Uniprot Name
5-hydroxytryptamine receptor 1D
Molecular Weight
41906.38 Da
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. Wilner KD, Anziano RJ, Johnson AC, Miceli JJ, Fricke JR, Titus CK: The anxiolytic effect of the novel antipsychotic ziprasidone compared with diazepam in subjects anxious before dental surgery. J Clin Psychopharmacol. 2002 Apr;22(2):206-10. [PubMed:11910268]
  3. Seeger TF, Seymour PA, Schmidt AW, Zorn SH, Schulz DW, Lebel LA, McLean S, Guanowsky V, Howard HR, Lowe JA 3rd, et al.: Ziprasidone (CP-88,059): a new antipsychotic with combined dopamine and serotonin receptor antagonist activity. J Pharmacol Exp Ther. 1995 Oct;275(1):101-13. [PubMed:7562537]
  4. Richelson E, Souder T: Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds. Life Sci. 2000 Nov 24;68(1):29-39. [PubMed:11132243]
  5. Sprouse JS, Reynolds LS, Braselton JP, Rollema H, Zorn SH: Comparison of the novel antipsychotic ziprasidone with clozapine and olanzapine: inhibition of dorsal raphe cell firing and the role of 5-HT1A receptor activation. Neuropsychopharmacology. 1999 Nov;21(5):622-31. [PubMed:10516958]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that trig...
Gene Name
HTR1E
Uniprot ID
P28566
Uniprot Name
5-hydroxytryptamine receptor 1E
Molecular Weight
41681.57 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 Da
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. Sanchez C, Arnt J: In-vivo assessment of 5-HT2A and 5-HT2C antagonistic properties of newer antipsychotics. Behav Pharmacol. 2000 Jun;11(3-4):291-8. [PubMed:11103883]
  3. Seeger TF, Seymour PA, Schmidt AW, Zorn SH, Schulz DW, Lebel LA, McLean S, Guanowsky V, Howard HR, Lowe JA 3rd, et al.: Ziprasidone (CP-88,059): a new antipsychotic with combined dopamine and serotonin receptor antagonist activity. J Pharmacol Exp Ther. 1995 Oct;275(1):101-13. [PubMed:7562537]
  4. Richelson E, Souder T: Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds. Life Sci. 2000 Nov 24;68(1):29-39. [PubMed:11132243]
  5. Wood MD, Scott C, Clarke K, Cato KJ, Patel N, Heath J, Worby A, Gordon L, Campbell L, Riley G, Davies CH, Gribble A, Jones DN: Pharmacological profile of antipsychotics at monoamine receptors: atypicality beyond 5-HT2A receptor blockade. CNS Neurol Disord Drug Targets. 2006 Aug;5(4):445-52. [PubMed:16918396]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Voltage-gated potassium channel activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
Gene Name
HTR3A
Uniprot ID
P46098
Uniprot Name
5-hydroxytryptamine receptor 3A
Molecular Weight
55279.835 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
Gene Name
HTR6
Uniprot ID
P50406
Uniprot Name
5-hydroxytryptamine receptor 6
Molecular Weight
46953.625 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
Gene Name
HTR7
Uniprot ID
P34969
Uniprot Name
5-hydroxytryptamine receptor 7
Molecular Weight
53554.43 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Details
15. Histamine H1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Richelson E, Souder T: Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds. Life Sci. 2000 Nov 24;68(1):29-39. [PubMed:11132243]
  2. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Andersohn F, Schmedt N, Weinmann S, Willich SN, Garbe E: Priapism associated with antipsychotics: role of alpha1 adrenoceptor affinity. J Clin Psychopharmacol. 2010 Feb;30(1):68-71. doi: 10.1097/JCP.0b013e3181c8273d. [PubMed:20075651]
  2. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Epinephrine binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
Molecular Weight
49565.8 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Protein homodimerization activity
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name
ADRA2C
Uniprot ID
P18825
Uniprot Name
Alpha-2C adrenergic receptor
Molecular Weight
49521.585 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Prakash C, Kamel A, Cui D, Whalen RD, Miceli JJ, Tweedie D: Identification of the major human liver cytochrome P450 isoform(s) responsible for the formation of the primary metabolites of ziprasidone and prediction of possible drug interactions. Br J Clin Pharmacol. 2000;49 Suppl 1:35S-42S. [PubMed:10771452]
  2. Prior TI, Baker GB: Interactions between the cytochrome P450 system and the second-generation antipsychotics. J Psychiatry Neurosci. 2003 Mar;28(2):99-112. [PubMed:12670127]
  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]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
General Function
Xanthine dehydrogenase activity
Specific Function
Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide and N-methylphthalazinium, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal...
Gene Name
AOX1
Uniprot ID
Q06278
Uniprot Name
Aldehyde oxidase
Molecular Weight
147916.735 Da
References
  1. Spina E, de Leon J: Metabolic drug interactions with newer antipsychotics: a comparative review. Basic Clin Pharmacol Toxicol. 2007 Jan;100(1):4-22. doi: 10.1111/j.1742-7843.2007.00017.x. [PubMed:17214606]

Drug created on June 13, 2005 07:24 / Updated on December 11, 2019 03:24