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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:36 UTC
HMDB IDHMDB0014391
Secondary Accession Numbers
  • HMDB14391
Metabolite Identification
Common NameZiprasidone
DescriptionZiprasidone (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
Data?1582753174
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 Weight412.936
Monoisotopic Molecular Weight412.112459711
IUPAC Name5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one
Traditional Nameziprasidone
CAS Registry Number146939-27-7
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 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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0072 g/LNot Available
LogP3.8Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM192.630932474
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-221.01730932474
DeepCCS[M+Na]+196.42230932474
AllCCS[M+H]+195.732859911
AllCCS[M+H-H2O]+193.332859911
AllCCS[M+NH4]+197.832859911
AllCCS[M+Na]+198.532859911
AllCCS[M-H]-191.732859911
AllCCS[M+Na-2H]-191.532859911
AllCCS[M+HCOO]-191.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ZiprasidoneClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C14649.7Standard polar33892256
ZiprasidoneClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C13628.7Standard non polar33892256
ZiprasidoneClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C14055.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ziprasidone,1TMS,isomer #1C[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C213651.1Semi standard non polar33892256
Ziprasidone,1TMS,isomer #1C[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C213582.0Standard non polar33892256
Ziprasidone,1TMS,isomer #1C[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C214792.9Standard polar33892256
Ziprasidone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C213820.6Semi standard non polar33892256
Ziprasidone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C213807.5Standard non polar33892256
Ziprasidone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C214825.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ziprasidone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-2963000000-73cfc43e5f403e3ecc3c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ziprasidone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ziprasidone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ziprasidone LC-ESI-QFT , positive-QTOFsplash10-01ox-0900400000-0a17dd0e237f50ba91c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ziprasidone 35V, Positive-QTOFsplash10-01ox-0900400000-f48ae3c72fd3033480902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ziprasidone 40V, Positive-QTOFsplash10-0006-0900000000-af32fe00a14db315cf8b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ziprasidone 30V, Positive-QTOFsplash10-0006-0900200000-4a3f1cc15848e67e20a42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ziprasidone 10V, Positive-QTOFsplash10-03di-0000900000-a6bfb6420e00cb9487102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ziprasidone 20V, Positive-QTOFsplash10-03di-0100900000-c6778b116b9686acf1602021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ziprasidone 50V, Positive-QTOFsplash10-05mo-0900000000-7fa49aa5ae170ec5d44d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ziprasidone 20V, Positive-QTOFsplash10-03di-0100900000-729ef7c784ed6b441be22021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 10V, Negative-QTOFsplash10-03di-0001900000-6744a80d8f97817dd4d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 20V, Negative-QTOFsplash10-03xu-1239400000-c4b9e0aa1e6ecda282ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 40V, Negative-QTOFsplash10-0006-9771000000-b7a94f6b2c87097c90ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 10V, Negative-QTOFsplash10-03di-0000900000-a39ff6e23c7d3ae586422021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 20V, Negative-QTOFsplash10-01q9-9200700000-1c46f9707ae8ff17a5672021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 40V, Negative-QTOFsplash10-001i-6923100000-63bd8cda1809361ef1d92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 10V, Positive-QTOFsplash10-03di-0102900000-fa5da81fd10bba2429772016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 20V, Positive-QTOFsplash10-01po-0977400000-7e1cc88e25385239ddce2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 40V, Positive-QTOFsplash10-01r6-0910000000-cf9cd1eba914ad67bfd42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 10V, Positive-QTOFsplash10-03di-0000900000-eee450689fc3c8c5f7392021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 20V, Positive-QTOFsplash10-03di-0100900000-9282980f21fd87d87ec42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ziprasidone 40V, Positive-QTOFsplash10-03di-3925600000-35b0278722002948c5362021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00246 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00246 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00246
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54841
KEGG Compound IDC07568
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkZiprasidone
METLIN IDNot Available
PubChem Compound60854
PDB IDNot Available
ChEBI ID10119
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (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. [PubMed:14728084 ]

Only showing the first 10 proteins. There are 30 proteins in total.

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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 ]
General function:
Involved in monooxygenase 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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
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 ]
General function:
Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
General function:
Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
General function:
Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 is mediated by G proteins that stimulate adenylate cyclase
Gene Name:
HTR7
Uniprot ID:
P34969
Molecular weight:
53554.4
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
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 ]

Only showing the first 10 proteins. There are 30 proteins in total.