Ziprasidone (CED0003679)

Record Information
Version1.0
Creation Date2016-05-22 03:48:13 UTC
Update Date2026-08-21 18:33:53 UTC
SynCED IDCED0003679
Secondary Accession Numbers
  • CHEM016940
Identification
Common NameZiprasidone
ClassSmall Molecule
Description
Ziprasidone is an organic compound with the chemical formula C21H21ClN4OS and an average molecular weight of 412.94 g/mol. Ziprasidone belongs to the piperazines, a subclass of diazinanes within the organic compounds. This compound is identified in six recorded sources, including healthcare, pharmaceuticals and veterinary products as antipsychotics, as well as electrical and electronic equipment such as radio transmission systems and electrically stimulated smoking devices. It is also found in household cleaning and consumer products, specifically other smoking requisites, non electric simulated smoking devices, and cigar cigarettes. Recorded routes of exposure for the compound include oral and intramuscular administration. Ziprasidone interacts with 28 recorded protein targets. It acts as an agonist, antagonist, or binder for the D(2) dopamine receptor (DRD2), the Alpha-1A adrenergic receptor (ADRA1A), the D(3) dopamine receptor (DRD3), and the 5-hydroxytryptamine receptor 2C (HTR2C), along with 24 other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
ZiprasidonaChEBI
ZiprasidonumChEBI
ZipradonKegg
Ziprasidone mesylate trihydrateHMDB
5-(2-(4-(3-Benzisothiazolyl)piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-oneHMDB
Ziprasidone hydrochlorideHMDB
ZiprazidoneHMDB
Ziprasidone hydrochloride, monohydrateHMDB
GeodonHMDB
Chemical FormulaC21H21ClN4OS
Average Molecular Mass412.936 g/mol
Monoisotopic Mass412.112 g/mol
CAS Registry Number146939-27-7
IUPAC Name5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one
Traditional Nameziprasidone
SMILESClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C1
InChI IdentifierInChI=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 KeyMVWVFYHBGMAFLY-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentN-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0072 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity116.72 m³·mol⁻¹ChemAxon
Polarizability44.96 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00lr-2963000000-73cfc43e5f403e3ecc3cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ox-0900400000-0a17dd0e237f50ba91c5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ox-0900400000-f48ae3c72fd303348090Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-af32fe00a14db315cf8bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900200000-4a3f1cc15848e67e20a4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0000900000-a6bfb6420e00cb948710Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0100900000-c6778b116b9686acf160Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05mo-0900000000-7fa49aa5ae170ec5d44dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0100900000-729ef7c784ed6b441be2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0102900000-fa5da81fd10bba242977Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01po-0977400000-7e1cc88e25385239ddceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01r6-0910000000-cf9cd1eba914ad67bfd4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0001900000-6744a80d8f97817dd4d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03xu-1239400000-c4b9e0aa1e6ecda282adNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9771000000-b7a94f6b2c87097c90abNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0000900000-a39ff6e23c7d3ae58642Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-9200700000-1c46f9707ae8ff17a567Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-6923100000-63bd8cda1809361ef1d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0000900000-eee450689fc3c8c5f739Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0100900000-9282980f21fd87d87ec4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-3925600000-35b0278722002948c536Not AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
827.0 Log mg/kg [470:1500]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Health Effects
Health EffectRelationshipDirectionDescriptionReference
schizophreniaNot AvailableNot AvailableA psychotic disorder that is characterized by a disintegration of thought processes and of emotional responsiveness. (DO)PMC8596611
psychiatric disorderNot AvailableNot AvailableNot AvailablePMC8596611
Exposure Sources
Source IDSourceSectorReference
CEDs000010Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.Agriculture & land managementPubChem
CEDs000374Antipsychotics?Antipsychotics are a class of synthetic chemicals used primarily for the treatment of psychiatric disorders, including schizophrenia and bipolar disorder.Healthcare, pharmaceuticals & veterinary productsNot Available
CEDs000518Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.Electrical & Electronic EquipmentPubChem
CEDs000530Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.Electrical & Electronic EquipmentPubChem
CEDs000545Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.Food, food processing & cookwarePubChem
CEDs000556Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.Household cleaning & consumer productsPubChem
CEDs000559Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.Household cleaning & consumer productsPubChem
CEDs000560Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.Household cleaning & consumer productsPubChem
CEDs000569Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.Household cleaning & consumer productsPubChem
CEDs000580Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.Industrial manufacturing & chemical processingPubChem
CEDs000596Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.Agriculture & land managementPubChem
CEDs000600Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.Agriculture & land managementPubChem
CEDs000611Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000615Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.Personal care & cosmeticsPubChem
CEDs000632Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.Textiles, leather & furnishingsPubChem
CEDs000642Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.Textiles, leather & furnishingsPubChem
CEDs000650Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.Textiles, leather & furnishingsPubChem
CEDs000651Purses Money Bags Wallets?Purses, money bags, and wallets are often manufactured using synthetic materials, including plastics, polyurethanes, and various treated fabrics.Textiles, leather & furnishingsPubChem
CEDs000671Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.Aviation & AerospacePubChem
CEDs000685Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.Building & ConstructionPubChem
CEDs000696Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.Industrial manufacturing & chemical processingPubChem
CEDs000735Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.Defense & military infrastructurePubChem
CEDs000741Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.Paper, pulp & fiber productsPubChem
CEDs000744Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.Wastewater, sanitation & biosolidsPubChem
Pathways
7 pathwaysPathway Source: PathBank
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)
Prediction Confidence Score
0.583
Applicability Domain
1.0
Statistical Significance
0.0016
Supporting Reference Compounds
955
E-value
12.4559
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)
Prediction Confidence Score
0.583
Applicability Domain
1.0
Statistical Significance
0.0031
Supporting Reference Compounds
1103
E-value
24.4447
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)
Prediction Confidence Score
0.571
Applicability Domain
1.0
Statistical Significance
0.0025
Supporting Reference Compounds
528
E-value
19.7737
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)
Prediction Confidence Score
0.562
Applicability Domain
1.0
Statistical Significance
0.0032
Supporting Reference Compounds
953
E-value
24.6004
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)
Prediction Confidence Score
0.521
Applicability Domain
1.0
Statistical Significance
0.0046
Supporting Reference Compounds
1498
E-value
35.5771
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.517
Applicability Domain
1.0
Statistical Significance
8.50e-04
Supporting Reference Compounds
208
E-value
6.61718
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)
Prediction Confidence Score
0.509
Applicability Domain
1.0
Statistical Significance
0.0026
Supporting Reference Compounds
565
E-value
20.1629
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)
Prediction Confidence Score
0.484
Applicability Domain
1.0
Statistical Significance
0.0025
Supporting Reference Compounds
536
E-value
19.6959
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)
Prediction Confidence Score
0.479
Applicability Domain
1.0
Statistical Significance
0.0064
Supporting Reference Compounds
861
E-value
49.59
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.466
Applicability Domain
1.0
Statistical Significance
0.0035
Supporting Reference Compounds
380
E-value
27.6365
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)
Prediction Confidence Score
0.463
Applicability Domain
1.0
Statistical Significance
0.0035
Supporting Reference Compounds
376
E-value
27.0137
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)
Prediction Confidence Score
0.456
Applicability Domain
1.0
Statistical Significance
0.0061
Supporting Reference Compounds
823
E-value
47.3323
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)
Prediction Confidence Score
0.456
Applicability Domain
1.0
Statistical Significance
0.004
Supporting Reference Compounds
686
E-value
31.2175
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)
Prediction Confidence Score
0.453
Applicability Domain
1.0
Statistical Significance
0.0058
Supporting Reference Compounds
524
E-value
45.0747
D(1A) dopamine receptor structureClick to view 3D structureD(1A) dopamine receptorP21728HumansPredicted (SEA)
Prediction Confidence Score
0.449
Applicability Domain
1.0
Statistical Significance
0.0045
Supporting Reference Compounds
425
E-value
34.9543
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)
Prediction Confidence Score
0.443
Applicability Domain
1.0
Statistical Significance
0.0057
Supporting Reference Compounds
593
E-value
44.3741
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansPredicted (SEA)
Prediction Confidence Score
0.438
Applicability Domain
1.0
Statistical Significance
0.0049
Supporting Reference Compounds
507
E-value
38.3018
Click to view 3D structureHistamine H1 receptorP31390Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.426
Applicability Domain
1.0
Statistical Significance
5.30e-04
Supporting Reference Compounds
63
E-value
4.12601
Click to view 3D structureHistamine H1 receptorP31389Cavia porcellusPredicted (SEA)
Prediction Confidence Score
0.423
Applicability Domain
1.0
Statistical Significance
0.0014
Supporting Reference Compounds
101
E-value
10.821
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.423
Applicability Domain
0.5
Statistical Significance
0.0099
Supporting Reference Compounds
541
E-value
77.46
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)
Prediction Confidence Score
0.421
Applicability Domain
1.0
Statistical Significance
0.0027
Supporting Reference Compounds
385
E-value
21.4085
Click to view 3D structureTransporterQ63380Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.395
Applicability Domain
1.0
Statistical Significance
7.10e-04
Supporting Reference Compounds
54
E-value
5.52729
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)
Prediction Confidence Score
0.326
Applicability Domain
0.417
Statistical Significance
0.0165
Supporting Reference Compounds
298
E-value
128.529
Aspartate aminotransferase, cytoplasmic structureClick to view 3D structureAspartate aminotransferase, cytoplasmicP17174HumansPredicted (SEA)
Prediction Confidence Score
0.32
Applicability Domain
1.0
Statistical Significance
2.00e-05
Supporting Reference Compounds
4
E-value
0.155698
Click to view 3D structureD(1A) dopamine receptorP18901Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.312
Applicability Domain
0.44
Statistical Significance
0.0182
Supporting Reference Compounds
206
E-value
141.452
Concentrations
Not Available
External Links
DrugBank IDDB00246
HMDB IDHMDB0014391
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkZiprasidone
Chemspider ID54841
ChEBI ID10119
PubChem Compound ID60854
Kegg Compound IDC07568
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available