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Economics

Properties

Spectra

Taxonomy

Ziprasidone

Targets (25)Enzymes (5)Biointeractions (31)

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

Similar Structures

Synonyms

Ziprasidona
Ziprasidone
Ziprasidonum

Product Ingredients

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

Product Images

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Geodon	Capsule	20 mg/1	Oral	Unit Dose Services	2001-02-05	Not applicable
Geodon	Capsule	60 mg/1	Oral	Physicians Total Care, Inc.	2009-01-19	2011-06-30
Geodon	Capsule	80 mg/1	Oral	Roerig	2013-11-01	Not applicable
Geodon	Capsule	20 mg/1	Oral	Lake Erie Medical Dba Quality Care Produts Llc	2010-11-05	Not applicable
Geodon	Capsule	20 mg/1	Oral	Roerig	2013-11-01	Not applicable
Geodon	Capsule	80 mg/1	Oral	Cardinal Health	2001-02-05	2015-06-30
Geodon	Capsule	40 mg/1	Oral	Cardinal Health	2001-02-05	2015-06-30
Geodon	Capsule	80 mg/1	Oral	Roerig	2001-02-05	Not applicable
Geodon	Capsule	60 mg/1	Oral	Rebel Distributors	2001-02-05	Not applicable
Geodon	Capsule	80 mg/1	Oral	Lake Erie Medical &Surgical Supply Dba Quality Care Products Llc	2001-02-05	2014-12-31

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Auro-ziprasidone	Capsule	80 mg	Oral	Auro Pharma Inc	2018-03-19	Not applicable
Auro-ziprasidone	Capsule	20 mg	Oral	Auro Pharma Inc	2018-03-19	Not applicable
Auro-ziprasidone	Capsule	60 mg	Oral	Auro Pharma Inc	2018-03-19	Not applicable
Auro-ziprasidone	Capsule	40 mg	Oral	Auro Pharma Inc	2018-03-19	Not applicable
Gd-ziprasidone	Capsule	80 mg	Oral	Genmed A Division Of Pfizer Canada Inc	Not applicable	Not applicable
Gd-ziprasidone	Capsule	20 mg	Oral	Genmed A Division Of Pfizer Canada Inc	Not applicable	Not applicable
Gd-ziprasidone	Capsule	60 mg	Oral	Genmed A Division Of Pfizer Canada Inc	Not applicable	Not applicable
Gd-ziprasidone	Capsule	40 mg	Oral	Genmed A Division Of Pfizer Canada Inc	Not applicable	Not applicable
Mylan-ziprasidone	Capsule	40 mg	Oral	Mylan Pharmaceuticals	Not applicable	Not applicable
Mylan-ziprasidone	Capsule	80 mg	Oral	Mylan Pharmaceuticals	Not applicable	Not applicable

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.

Target	Actions	Organism
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

Ziprasidone
benzisothiazole piperazine

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

Drug	Interaction
(2-benzhydryloxyethyl)diethyl-methylammonium iodide	The risk or severity of adverse effects can be increased when Ziprasidone is combined with (2-benzhydryloxyethyl)diethyl-methylammonium iodide.
(R)-warfarin	The metabolism of (R)-warfarin can be decreased when combined with Ziprasidone.
(S)-Warfarin	The metabolism of (S)-Warfarin can be decreased when combined with Ziprasidone.
1,10-Phenanthroline	The therapeutic efficacy of Ziprasidone can be decreased when used in combination with 1,10-Phenanthroline.
16-Bromoepiandrosterone	The metabolism of 16-Bromoepiandrosterone can be decreased when combined with Ziprasidone.
2,4-thiazolidinedione	The therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Ziprasidone.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of serotonin syndrome can be increased when Ziprasidone is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Ziprasidone.
3-isobutyl-1-methyl-7H-xanthine	The serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Ziprasidone.
3,4-Methylenedioxyamphetamine	The risk or severity of serotonin syndrome can be increased when 3,4-Methylenedioxyamphetamine is combined 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

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]
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

Phase	Status	Purpose	Conditions	Count
1	Completed	Basic Science	Healthy Volunteers	1
1	Completed	Treatment	Healthy Volunteers	2
1	Enrolling by Invitation	Prevention	Cardiovascular Disease (CVD)	1
1, 2	Recruiting	Basic Science	Schizophrenic Disorders	1
2	Completed	Treatment	Autism, Early Infantile	1
2	Completed	Treatment	Bipolar Disorder (BD) / Depression / Depression, Bipolar	1
2	Completed	Treatment	Bipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenic Disorders	1
2	Completed	Treatment	Borderline Personality Disorder (BPD)	1
2	Completed	Treatment	Cognition Disorders / Delirium	1
2	Completed	Treatment	Major Depressive Disorder (MDD)	2
2	Completed	Treatment	Oppositional Defiant Disorder	1
2	Completed	Treatment	Psychosis Prodrome	1
2	Completed	Treatment	Schizophrenic Disorders	1
2	Completed	Treatment	Social Anxiety Disorder (SAD)	1
2	Recruiting	Treatment	Schizophrenic Disorders	1
2	Terminated	Not Available	Post-Traumatic Stress Disorder (PTSD)	1
2	Terminated	Treatment	Schizophrenic Disorders	1
2, 3	Completed	Treatment	Affective Disorders	1
2, 3	Completed	Treatment	Schizoaffective Disorders / Schizophrenic Disorders	1
3	Active Not Recruiting	Treatment	Delirium / Impaired Cognition / Long Term Psychologic Disorders	1
3	Completed	Treatment	Bipolar Disorder (BD)	5
3	Completed	Treatment	Bipolar affective disorder, manic / Bipolar Disorder (BD)	1
3	Completed	Treatment	Bipolar Disorder (BD) / Depression, Bipolar	1
3	Completed	Treatment	Bipolar Disorder (BD) / Major Depressive Disorder (MDD) / Psychosis / Schizoaffective Disorders / Schizophreniform Disorder	1
3	Completed	Treatment	Depression	1
3	Completed	Treatment	Psychotic Disorder NOS / Schizophrenic Disorders	1
3	Completed	Treatment	Schizophrenia and Schizoaffective Disorder	1
3	Completed	Treatment	Schizophrenic Disorders	8
3	Recruiting	Treatment	Bipolar Disorder (BD)	1
3	Terminated	Treatment	Anxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders	1
3	Terminated	Treatment	Bipolar Disorder (BD)	1
3	Terminated	Treatment	Bipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenic Disorders	1
3	Terminated	Treatment	Schizoaffective Disorders / Schizophrenic Disorders	1
3	Terminated	Treatment	Schizophrenic Disorders	3
3	Unknown Status	Treatment	Psychosis Nos/Other	1
3	Withdrawn	Treatment	Bipolar Disorder (BD)	2
4	Active Not Recruiting	Treatment	Schizoaffective Disorders / Schizophrenia and Disorders With Psychotic Features / Schizophrenic Disorders	1
4	Completed	Basic Science	Diabetes Mellitus (DM) / Schizophrenic Disorders	1
4	Completed	Diagnostic	Post-Traumatic Stress Disorder (PTSD) / Posttraumatic Stress Disorders / PTSD	1
4	Completed	Treatment	Acute Exacerbation of Psychosis / Delusional Disorder / Mania / Schizophrenic Disorders	1
4	Completed	Treatment	Affective Disorders / Psychotic Disorder NOS / Psychotic Mood Disorder / Schizophrenic Disorders	1
4	Completed	Treatment	Bipolar Disorder (BD)	3
4	Completed	Treatment	Bipolar Disorder (BD) / Depression	1
4	Completed	Treatment	Bipolar Disorder (BD) / Generalized Anxiety Disorder (GAD) / Panic Disorders	1
4	Completed	Treatment	Bipolar Disorder (BD) / Mania	1
4	Completed	Treatment	Bipolar Disorder (BD) / Medication Adherence	1
4	Completed	Treatment	Bipolar II Disorder / Major Depressive Episode	1
4	Completed	Treatment	Depression, Bipolar	1
4	Completed	Treatment	Depression / Schizoaffective Disorders / Schizophrenic Disorders	1
4	Completed	Treatment	First Episode Psychosis	1
4	Completed	Treatment	Hyperglycemias / Schizoaffective Disorders / Schizophrenic Disorders / Type 2 Diabetes Mellitus	1
4	Completed	Treatment	Insulin Resistance / Metabolic Syndromes / Schizophrenic Disorders	1
4	Completed	Treatment	Psychotic Disorder NOS	2
4	Completed	Treatment	Psychotic Disorder NOS / Schizophrenic Disorders	4
4	Completed	Treatment	Pyschotic Disorders	1
4	Completed	Treatment	Schizoaffective Disorders / Schizophrenic Disorders	6
4	Completed	Treatment	Schizophrenia, Schizoaffective Disorder	1
4	Completed	Treatment	Schizophrenic Disorders	8
4	Completed	Treatment	Schizophrenic Disorders / Type 2 Diabetes Mellitus	1
4	Not Yet Recruiting	Treatment	Schizophrenic Disorders	1
4	Recruiting	Treatment	Bipolar Disorder (BD)	1
4	Recruiting	Treatment	Schizophrenic Disorders	1
4	Terminated	Not Available	High Risk MC4R Genotype / Low Risk MC4R Genotype / One Week or Less Antipsychotic Lifetime Exposure	1
4	Terminated	Treatment	Acute Mania / Bipolar Disorder, Manic	1
4	Terminated	Treatment	Bipolar Disorder (BD) / Generalized Anxiety Disorder (GAD)	1
4	Terminated	Treatment	Schizophrenia and Disorders With Psychotic Features	1
4	Unknown Status	Treatment	Schizophrenia or Schizoaffective Disorder	1
4	Unknown Status	Treatment	Schizophrenic Disorders	1
4	Withdrawn	Treatment	Acute Agitation / Delirium / Psychosis	1
Not Available	Completed	Not Available	Affective Psychosis, Bipolar / Mania / Psychoses, Manic-Depressive	1
Not Available	Completed	Not Available	Bipolar Disorder (BD)	1
Not Available	Completed	Not Available	Bipolar Disorder (BD) / Psychotic Disorder NOS / Schizoaffective Disorders / Schizophrenic Disorders / Type 2 Diabetes Mellitus	1
Not Available	Completed	Not Available	Bipolar Disorder (BD) / Schizophrenic Disorders	1
Not Available	Completed	Not Available	Psychomotor Agitation	2
Not Available	Completed	Not Available	Schizophrenic Disorders	2
Not Available	Completed	Diagnostic	Obsessive Compulsive Disorder (OCD) / Schizophrenic Disorders	1
Not Available	Completed	Prevention	Hyperglycemias / Hyperlipidemias	1
Not Available	Completed	Treatment	Bipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenic Disorders	1
Not Available	Completed	Treatment	Psychomotor Agitation	1
Not Available	Completed	Treatment	Schizophrenic Disorders	1
Not Available	Completed	Treatment	Schizophrenic Disorders / Type 2 Diabetes Mellitus	1
Not Available	Enrolling by Invitation	Not Available	Bipolar Disorder (BD)	1
Not Available	Recruiting	Not Available	Acute 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 / Cyanide Poisoning / 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 Cholesterol Level / High Blood Pressure (Hypertension) / 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 / 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 / Thrombosis / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal	1
Not Available	Recruiting	Not Available	Adverse Drug Effect of Antipsychotics and Neuroleptics / Efficacy / Individualed Opitmal Therapy / Schizophrenic Disorders	1
Not Available	Recruiting	Not Available	Micrognathia / Schizophrenic Disorders	1

Pharmacoeconomics

Manufacturers

Pfizer inc

Packagers

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

Dosage forms

Form	Route	Strength
Capsule	Oral	20 mg
Capsule	Oral	20 mg/1
Capsule	Oral	40 mg/1
Capsule	Oral	60 mg/1
Capsule	Oral	80 mg/1
Injection, powder, lyophilized, for solution	Intramuscular	20 mg/1mL
Capsule	Oral	20.0 mg
Capsule	Oral	40 mg
Capsule	Oral	60 mg
Capsule	Oral	80 mg

Prices

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

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

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5134127	No	1993-01-23	2010-01-23
CA2256227	No	2003-07-01	2018-12-16
CA2105114	No	2000-02-15	2013-08-30
US6245766	No	1998-12-18	2018-12-18
US6150366	No	1999-05-27	2019-05-27
US6232304	No	1997-04-01	2017-04-01
US6399777	No	1997-04-01	2017-04-01
US6110918	No	1997-03-26	2017-03-26
US7175855	No	2000-05-18	2020-05-18

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	>300 °C	Not Available
logP	3.8	Not Available

Predicted Properties

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

Predicted ADMET features

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

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

Spectra

Mass Spec (NIST)

Not Available

Spectra

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

Taxonomy

Description: This compound belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
Kingdom: Organic compounds
Super Class: Organoheterocyclic compounds
Class: Diazinanes
Sub Class: Piperazines
Direct Parent: N-arylpiperazines
Alternative Parents: Benzothiazoles / Phenethylamines / Indoles / Dialkylarylamines / Aralkylamines / N-alkylpiperazines / Aminothiazoles / Aryl chlorides / Imidolactams / Heteroaromatic 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

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	5	N/A	N/A	16220969
Ki (nM)	2.8	N/A	N/A	11170639
Ki (nM)	3.1	N/A	N/A	18595716
Ki (nM)	5	N/A	N/A	18160289
Ki (nM)	8.5	N/A	N/A	23043306
Ki (nM)	9.7	N/A	N/A	14998318

Details1. 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

Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706]
Kopecek M, Bares M, Mohr P: Ziprasidone-induced galactorrhea: a case report. Neuro Endocrinol Lett. 2005 Feb;26(1):69-70. [PubMed:15726024]
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]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
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]
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]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	0.42	N/A	N/A	16220969
Ki (nM)	0.08	N/A	N/A	18160289
Ki (nM)	0.12	N/A	N/A	11132243
Ki (nM)	0.25	N/A	N/A	11170639
Ki (nM)	0.3	N/A	N/A	12629531 / 14998318
Ki (nM)	0.39	N/A	N/A	18595716
Ki (nM)	0.5	N/A	N/A	12176106
Ki (nM)	1.4	N/A	N/A	8935801

Details2. 5-hydroxytryptamine receptor 2A

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

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]
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]
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]
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]
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]
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]
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	130	N/A	N/A	18595716
Ki (nM)	330	N/A	N/A	14998318
Ki (nM)	9.5	N/A	N/A	11170639

Details3. 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

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]

Details4. D(1B) 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: DRD5
Uniprot ID: P21918
Uniprot Name: D(1B) dopamine receptor
Molecular Weight: 52950.5 Da

References

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	10	N/A	N/A	11170639
Ki (nM)	7.2	N/A	N/A	18595716
Ki (nM)	7.5	N/A	N/A	14998318

Details5. 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

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]
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	32	N/A	N/A	18595716
Ki (nM)	39	N/A	N/A	11170639 / 14998318

Details6. 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

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]
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1.9	N/A	N/A	11132243
Ki (nM)	12	N/A	N/A	8935801
Ki (nM)	2.5	N/A	N/A	18595716
Ki (nM)	37	N/A	N/A	11170639
Ki (nM)	4	N/A	N/A	18160289
Ki (nM)	76	N/A	N/A	12629531

Details7. 5-hydroxytryptamine receptor 1A

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

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]
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]
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]
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]
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]
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]
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	0.99	N/A	N/A	8935801

Details8. 5-hydroxytryptamine receptor 1B

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	2.4	N/A	N/A	11132243
Ki (nM)	5.1	N/A	N/A	8935801

Details9. 5-hydroxytryptamine receptor 1D

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

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]
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]
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]
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]
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	360	N/A	N/A	8935801

Details10. 5-hydroxytryptamine receptor 1E

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	0.55	N/A	N/A	11170639
Ki (nM)	0.72	N/A	N/A	18595716
Ki (nM)	0.9	N/A	N/A	11132243
Ki (nM)	13	N/A	N/A	12629531 / 14998318 / 20719507
Ki (nM)	4.1	N/A	N/A	10991983

Details11. 5-hydroxytryptamine receptor 2C

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

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]
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]
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]
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]
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]

Details12. 5-hydroxytryptamine receptor 3A

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	60.9	N/A	N/A	12629531
Ki (nM)	61	N/A	N/A	20719507
Ki (nM)	76	N/A	N/A	18595716

Details13. 5-hydroxytryptamine receptor 6

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

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]

Details14. 5-hydroxytryptamine receptor 7

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

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]
Meltzer HY: The role of serotonin in antipsychotic drug action. Neuropsychopharmacology. 1999 Aug;21(2 Suppl):106S-115S. [PubMed:10432496]
Meltzer HY: Role of serotonin in the action of atypical antipsychotic drugs. Clin Neurosci. 1995;3(2):64-75. [PubMed:7583621]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	15	N/A	N/A	8935801
Ki (nM)	4.6	N/A	N/A	11132243
Ki (nM)	43	N/A	N/A	12629531
Ki (nM)	47	N/A	N/A	18595716
Ki (nM)	5.3	N/A	N/A	14998318
Ki (nM)	510	N/A	N/A	11170639

Details15. 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

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]
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]

Details16. Alpha-1A adrenergic receptor

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

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]
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]

Details17. Alpha-1B adrenergic receptor

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	154	N/A	N/A	11132243
Ki (nM)	160	N/A	N/A	8935801 / 12629531

Details18. Alpha-2A adrenergic receptor

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	48	N/A	N/A	8935801 / 12629531

Details19. Alpha-2B adrenergic receptor

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	59	N/A	N/A	12629531
Ki (nM)	77	N/A	N/A	8935801

Details20. Alpha-2C adrenergic receptor

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	>10000	N/A	N/A	11170639
Ki (nM)	300	N/A	N/A	14642972
Ki (nM)	5100	N/A	N/A	18595716

Details21. Muscarinic acetylcholine receptor M1

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	2440	N/A	N/A	11132243
Ki (nM)	3000	N/A	N/A	14642972

Details22. Muscarinic acetylcholine receptor M2

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	>10000	N/A	N/A	12629531
Ki (nM)	1300	N/A	N/A	14642972

Details23. Muscarinic acetylcholine receptor M3

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1600	N/A	N/A	14642972

Details24. Muscarinic acetylcholine receptor M4

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

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]

Details25. Muscarinic acetylcholine receptor M5

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

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

Details1. Cytochrome P450 3A4

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

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]
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]
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]

Details2. Cytochrome P450 3A5

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

Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Details3. Cytochrome P450 3A7

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

Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Details4. Cytochrome P450 1A2

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Substrate

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

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]

Details5. Cytochrome P450 2D6

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

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]
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 September 23, 2018 19:37

Ziprasidone

Identification

Structure for Ziprasidone (DB00246)

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Enzymes

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