ContaminantDB: Ziprasidone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:48:13 UTC

Update Date

2016-11-09 01:15:30 UTC

Accession Number

CHEM016940

Identification

Common Name

Ziprasidone

Class

Small Molecule

Description

Disorders such as schizophrenia and bipolar disorder can significantly impair mood, cognition, and behavior. These mental illnesses can often be accompanied by comorbidities such as depression and substance abuse, and can significantly impact the quality of life of patients and caregivers. Luckily, several treatment options for psychotic disorders have been introduced to market since the realization of chlorpromazine's antipsychotic properties in 1952. Second generation antipsychotics (commonly referred to as atypical antipsychotics) include , , , and among others, and are generally thought to be as efficacious as first generation antipsychotics but differ in their adverse effect profiles. First generation antipsychotics are associated with extrapyramidal adverse effects while atypical antipsychotics are linked to weight gain, impaired glucose tolerance and metabolic syndrome. Ziprasidone is used to treat schizophrenia and bipolar disorder. It can effectively reduce the rate and time of relapses in schizophrenia, and can be used to treat manic episodes in bipolar disorder although the mechanism of action is unknown. Although ziprasidone is classified as an atypical antipsychotic, it appears to have a lower incidence of metabolic adverse effects compared to other medications in the same class.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ziprasidona	ChEBI
Ziprasidonum	ChEBI
Zipradon	Kegg
Ziprasidone mesylate trihydrate	HMDB
5-(2-(4-(3-Benzisothiazolyl)piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one	HMDB
Ziprasidone hydrochloride	HMDB
Ziprazidone	HMDB
Ziprasidone hydrochloride, monohydrate	HMDB
Geodon	HMDB

Chemical Formula

C₂₁H₂₁ClN₄OS

Average Molecular Mass

412.936 g/mol

Monoisotopic Mass

412.112 g/mol

CAS Registry Number

146939-27-7

IUPAC Name

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

Traditional Name

ziprasidone

SMILES

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

InChI Identifier

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)

InChI Key

MVWVFYHBGMAFLY-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

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

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0072 g/L	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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-2963000000-73cfc43e5f403e3ecc3c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01ox-0900400000-0a17dd0e237f50ba91c5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-01ox-0900400000-f48ae3c72fd303348090	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0900000000-af32fe00a14db315cf8b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-0900200000-4a3f1cc15848e67e20a4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000900000-a6bfb6420e00cb948710	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0100900000-c6778b116b9686acf160	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-05mo-0900000000-7fa49aa5ae170ec5d44d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0100900000-729ef7c784ed6b441be2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0102900000-fa5da81fd10bba242977	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01po-0977400000-7e1cc88e25385239ddce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01r6-0910000000-cf9cd1eba914ad67bfd4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0001900000-6744a80d8f97817dd4d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xu-1239400000-c4b9e0aa1e6ecda282ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9771000000-b7a94f6b2c87097c90ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-a39ff6e23c7d3ae58642	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-9200700000-1c46f9707ae8ff17a567	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-6923100000-63bd8cda1809361ef1d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000900000-eee450689fc3c8c5f739	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0100900000-9282980f21fd87d87ec4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-3925600000-35b0278722002948c536	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00246

HMDB ID

HMDB0014391

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

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.

Ziprasidone (CHEM016940)

Structure for CHEM016940: Ziprasidone