Identification

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

Ziprasidone (marketed as Geodon, Zeldox) was the fifth atypical antipsychotic to gain FDA approval (February 2001). Ziprasidone is Food and Drug Administration (FDA) approved for the treatment of schizophrenia, and the intramuscular injection form of ziprasidone is approved for acute agitation in schizophrenic patients. Ziprasidone has also received approval for acute treatment of mania associated with bipolar disorder. [Wikipedia]

Structure
Thumb
Synonyms
  • Ziprasidona
  • Ziprasidone
  • Ziprasidonum
Product Ingredients
IngredientUNIICASInChI Key
Ziprasidone hydrochlorideJAL53626GG122883-93-6NZDBKBRIBJLNNT-UHFFFAOYSA-N
Ziprasidone mesylate trihydrate3X6SAX83JZ199191-69-0WLQZEFFFIUHSJB-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
GeodonCapsule80 mg/1OralRoerig2013-11-01Not applicableUs
GeodonCapsule60 mg/1OralPhysicians Total Care, Inc.2009-01-192011-06-30Us
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
GeodonCapsule80 mg/1OralCardinal Health2001-02-052015-06-30Us55154 272120180907 15195 1or77a3
GeodonCapsule20 mg/1OralRoerig2013-11-01Not applicableUs
GeodonCapsule40 mg/1OralCardinal Health2001-02-052015-06-30Us55154 272620180907 15195 mglf6j
GeodonCapsule60 mg/1OralRebel Distributors2001-02-05Not applicableUs
GeodonCapsule80 mg/1OralRoerig2001-02-05Not applicableUs0049 399020180814 13942 owbnds
GeodonCapsule80 mg/1OralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2001-02-052014-12-31Us00049 3990 60 nlmimage10 253b12f8
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-ziprasidoneCapsule80 mgOralAuro Pharma Inc2018-03-19Not applicableCanada
Auro-ziprasidoneCapsule20 mgOralAuro Pharma Inc2018-03-19Not applicableCanada
Auro-ziprasidoneCapsule60 mgOralAuro Pharma Inc2018-03-19Not applicableCanada
Auro-ziprasidoneCapsule40 mgOralAuro Pharma Inc2018-03-19Not applicableCanada
Gd-ziprasidoneCapsule80 mgOralGenmed A Division Of Pfizer Canada IncNot applicableNot applicableCanada
Gd-ziprasidoneCapsule20 mgOralGenmed A Division Of Pfizer Canada IncNot applicableNot applicableCanada
Gd-ziprasidoneCapsule60 mgOralGenmed A Division Of Pfizer Canada IncNot applicableNot applicableCanada
Gd-ziprasidoneCapsule40 mgOralGenmed A Division Of Pfizer Canada IncNot applicableNot applicableCanada
Mylan-ziprasidoneCapsule40 mgOralMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-ziprasidoneCapsule80 mgOralMylan PharmaceuticalsNot applicableNot applicableCanada
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

For the treatment of schizophrenia and related psychotic disorders.

Associated Conditions
Pharmacodynamics

Ziprasidone is a psychotropic agent belonging to the chemical class of benzisoxazole derivatives and is indicated for the treatment of schizophrenia. Ziprasidone is a selective monoaminergic antagonist with high affinity for the serotonin Type 2 (5HT2), dopamine Type 2 (D2), 1 and 2 adrenergic, and H1 histaminergic receptors. Ziprasidone acts as an antagonist at other receptors, but with lower potency. Antagonism at receptors other than dopamine and 5HT2 with similar receptor affinities may explain some of the other therapeutic and side effects of Ziprasidone. Ziprasidone's antagonism of muscarinic M1-5 receptors may explain its anticholinergic effects. Ziprasidone's antagonism of histamine H1 receptors may explain the somnolence observed with this drug. Ziprasidone's antagonism of adrenergic a1 receptors may explain the orthostatic hypotension observed with this drug. Ziprasidone functions as an antagonist at the Dopamine D2 , 5HT-2A , and 5HT-1D receptors, and as an agonist at the 5HT-1A receptor. Ziprasidone also inhibits synaptic reuptake of serotonin and norepinephrine.

Mechanism of action

Ziprasidone's antipsychotic activity is likely due to a combination of its antagonistic function at D2 receptors in the mesolimbic pathways and at 5HT2A receptors in the frontal cortex. Alleviation of positive symptoms is due to antagonism at D2 receptors while relief of negative symptoms are due to 5HT2A antagonism.

TargetActionsOrganism
AD(2) dopamine receptor
antagonist
Human
A5-hydroxytryptamine receptor 2A
antagonist
Human
UD(1A) dopamine receptor
antagonist
Human
UD(1B) dopamine receptor
antagonist
Human
UD(3) dopamine receptor
antagonist
Human
UD(4) dopamine receptor
antagonist
Human
U5-hydroxytryptamine receptor 1A
agonist
Human
U5-hydroxytryptamine receptor 1B
antagonist
Human
U5-hydroxytryptamine receptor 1D
antagonist
Human
U5-hydroxytryptamine receptor 1E
antagonist
Human
U5-hydroxytryptamine receptor 2C
antagonist
Human
U5-hydroxytryptamine receptor 3A
antagonist
Human
U5-hydroxytryptamine receptor 6
antagonist
Human
U5-hydroxytryptamine receptor 7
antagonist
Human
NHistamine H1 receptor
antagonist
Human
NAlpha-1A adrenergic receptor
antagonist
Human
NAlpha-1B adrenergic receptor
antagonist
Human
NAlpha-2A adrenergic receptor
antagonist
Human
NAlpha-2B adrenergic receptor
antagonist
Human
NAlpha-2C adrenergic receptor
antagonist
Human
NMuscarinic acetylcholine receptor M1
antagonist
Human
NMuscarinic acetylcholine receptor M2
antagonist
Human
NMuscarinic acetylcholine receptor M3
antagonist
Human
NMuscarinic acetylcholine receptor M4
antagonist
Human
NMuscarinic acetylcholine receptor M5
antagonist
Human
Absorption

~60%

Volume of distribution
  • 1.5 L/kg
Protein binding

99%

Metabolism

Hepatic

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. Approximately 20% of the dose is excreted in the urine, with approximately 66% being eliminated in the feces.

Half life

7 hours

Clearance
  • 7.5 mL/min/kg
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Ziprasidone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Ziprasidone.
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 risk or severity of serotonin syndrome can be increased when Ziprasidone is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Ziprasidone is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Ziprasidone.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Ziprasidone is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Ziprasidone.
3,5-DinitrocatecholThe therapeutic efficacy of 3,5-Dinitrocatechol can be decreased when used in combination with Ziprasidone.
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]
External Links
Human Metabolome Database
HMDB0014391
KEGG Compound
C07568
PubChem Compound
60854
PubChem Substance
46507627
ChemSpider
54841
BindingDB
50048803
ChEBI
10119
ChEMBL
CHEMBL708
Therapeutic Targets Database
DAP000079
PharmGKB
PA451974
IUPHAR
59
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
FDA label
Download (75 KB)
MSDS
Download (57.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentHealthy Volunteers2
1Enrolling by InvitationPreventionCardiovascular Disease (CVD)1
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 Disorders1
2CompletedTreatmentSocial Anxiety Disorder (SAD)1
2RecruitingTreatmentSchizophrenic Disorders1
2TerminatedNot AvailablePost Traumatic Stress Disorder (PTSD)1
2TerminatedTreatmentSchizophrenic Disorders1
2, 3CompletedTreatmentAffective Disorders1
2, 3CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
3Active Not RecruitingTreatmentDelirium / Impaired Cognition / Long Term Psychologic 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
3CompletedTreatmentDepression1
3CompletedTreatmentPsychotic Disorder NOS / Schizophrenic Disorders1
3CompletedTreatmentSchizophrenia and Schizoaffective Disorder1
3CompletedTreatmentSchizophrenic Disorders8
3RecruitingTreatmentBipolar Disorder (BD)1
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
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
4CompletedTreatmentHyperglycemias / Schizoaffective Disorders / Schizophrenic Disorders / Type 2 Diabetes Mellitus1
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
4CompletedTreatmentSchizophrenic Disorders / Type 2 Diabetes Mellitus1
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
4WithdrawnTreatmentAcute Agitation / 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 AvailableCompletedPreventionHyperglycemias / Hyperlipidemias1
Not AvailableCompletedTreatmentBipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenic Disorders1
Not AvailableCompletedTreatmentPsychomotor Agitation1
Not AvailableCompletedTreatmentSchizophrenic Disorders1
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 / Anxiolysis / Arterial Hypotension / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infections / Convulsions / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Edema / Epilepsies / Feeling Anxious / Flu caused by Influenza / Gastroparesis / Gynaecological infection / Headaches / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hospital-acquired bacterial pneumonia / Hyperlipidemias / Infantile Hemangiomas / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Migraines / Muscle Spasms / Nausea / Opioid Addiction / Pain NOS / Plague / Pneumonia / Prophylaxis / Psittacosis / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation therapy / 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 Infections (UTIs) / 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
CapsuleOral20 mg/1
CapsuleOral40 mg/1
CapsuleOral60 mg/1
CapsuleOral80 mg/1
Injection, powder, lyophilized, for solutionIntramuscular20 mg/1mL
CapsuleOral20.0 mg
CapsuleOral40 mg
CapsuleOral60 mg
CapsuleOral80 mg
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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>300 °CNot Available
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. D(2) dopamine receptor
Kind
Protein
Organism
Human
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  5. 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]
  6. 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
Human
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
3. D(1A) dopamine receptor
Kind
Protein
Organism
Human
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
Human
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]
Details
5. D(3) dopamine receptor
Kind
Protein
Organism
Human
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]
Details
6. D(4) dopamine receptor
Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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
Human
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
Human
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
Human
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
Human
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. Stark AD, Jordan S, Allers KA, Bertekap RL, Chen R, Mistry Kannan T, Molski TF, Yocca FD, Sharp T, Kikuchi T, Burris KD: Interaction of the novel antipsychotic aripiprazole with 5-HT1A and 5-HT 2A receptors: functional receptor-binding and in vivo electrophysiological studies. Psychopharmacology (Berl). 2007 Feb;190(3):373-82. Epub 2006 Nov 25. [PubMed:17242925]
  2. Meltzer HY: The role of serotonin in antipsychotic drug action. Neuropsychopharmacology. 1999 Aug;21(2 Suppl):106S-115S. [PubMed:10432496]
  3. Meltzer HY: Role of serotonin in the action of atypical antipsychotic drugs. Clin Neurosci. 1995;3(2):64-75. [PubMed:7583621]
Details
15. Histamine H1 receptor
Kind
Protein
Organism
Human
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. Arnt J: Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine. Eur J Pharmacol. 1995 Sep 5;283(1-3):55-62. [PubMed:7498321]
Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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
Human
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
Human
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
Human
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
Human
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
Human
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
Human
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
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Nakamura H, Nakasa H, Ishii I, Ariyoshi N, Igarashi T, Ohmori S, Kitada M: Effects of endogenous steroids on CYP3A4-mediated drug metabolism by human liver microsomes. Drug Metab Dispos. 2002 May;30(5):534-40. [PubMed:11950784]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Curator comments
The FDA label states that CYP1A2 may have a minor contribution to ziprasidone metabolism.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Ziprasidone FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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]

Drug created on June 13, 2005 07:24 / Updated on November 18, 2018 13:32