ziprasidone   Click here for help

GtoPdb Ligand ID: 59

Synonyms: CP-88059 | CP-88059-27 | CP-880591 | CP-8805927 | Geodon®
Approved drug PDB Ligand
ziprasidone is an approved drug (FDA (2001))
Compound class: Synthetic organic
Comment: Ziprasidone is a monoaminergic antagonist with affinity for a range of receptors including dopamine receptors, alpha 1 and 2 adrenoceptors, the histamine H1 receptor, and serotonin 5-HT receptors. Marketed formulations may contain ziprasidone hydrochloride (PubChem CID 219099).
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: ziprasidone

ziprasidone is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 76.71
Molecular weight 412.11
XLogP 3.89
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES O=C1Nc2c(C1)cc(c(c2)Cl)CCN1CCN(CC1)c1nsc2c1cccc2
Isomeric SMILES O=C1Nc2c(C1)cc(c(c2)Cl)CCN1CCN(CC1)c1nsc2c1cccc2
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)
InChI Key MVWVFYHBGMAFLY-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Ablordeppey SY, Altundas R, Bricker B, Zhu XY, Kumar EV, Jackson T, Khan A, Roth BL. (2008)
Identification of a butyrophenone analog as a potential atypical antipsychotic agent: 4-[4-(4-chlorophenyl)-1,4-diazepan-1-yl]-1-(4-fluorophenyl)butan-1-one.
Bioorg Med Chem, 16 (15): 7291-301. [PMID:18595716]
2. Arnt J, Skarsfeldt T. (1998)
Do novel antipsychotics have similar pharmacological characteristics? A review of the evidence.
Neuropsychopharmacology, 18 (2): 63-101. [PMID:9430133]
3. Herrick-Davis K, Grinde E, Teitler M. (2000)
Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors.
J Pharmacol Exp Ther, 295 (1): 226-32. [PMID:10991983]
4. Kongsamut S, Kang J, Chen XL, Roehr J, Rampe D. (2002)
A comparison of the receptor binding and HERG channel affinities for a series of antipsychotic drugs.
Eur J Pharmacol, 450 (1): 37-41. [PMID:12176106]
5. Kroeze WK, Hufeisen SJ, Popadak BA, Renock SM, Steinberg S, Ernsberger P, Jayathilake K, Meltzer HY, Roth BL. (2003)
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs.
Neuropsychopharmacology, 28 (3): 519-26. [PMID:12629531]
6. Newman-Tancredi A, Gavaudan S, Conte C, Chaput C, Touzard M, Verrièle L, Audinot V, Millan MJ. (1998)
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.
Eur J Pharmacol, 355 (2-3): 245-56. [PMID:9760039]
7. Purohit A, Smith C, Herrick-Davis K, Teitler M. (2005)
Stable expression of constitutively activated mutant h5HT6 and h5HT7 serotonin receptors: inverse agonist activity of antipsychotic drugs.
Psychopharmacology (Berl), 179 (2): 461-9. [PMID:15821958]
8. Schotte A, Janssen PF, Gommeren W, Luyten WH, Van Gompel P, Lesage AS, De Loore K, Leysen JE. (1996)
Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding.
Psychopharmacology (Berl.), 124 (1-2): 57-73. [PMID:8935801]
9. Shahid M, Walker GB, Zorn SH, Wong EH. (2009)
Asenapine: a novel psychopharmacologic agent with a unique human receptor signature.
J Psychopharmacol (Oxford), 23 (1): 65-73. [PMID:18308814]