pimozide   Click here for help

GtoPdb Ligand ID: 90

Synonyms: haldol decanoate | Orap® | R-6238
Approved drug PDB Ligand
pimozide is an approved drug (FDA (1984))
Compound class: Synthetic organic
Comment: Pimozide is a typical antipsychotic drug.
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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.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: pimozide

pimozide is commercially available from our sponsors

2D Structure
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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.

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Physico-chemical Properties
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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.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 41.03
Molecular weight 461.23
XLogP 5.61
No. Lipinski's rules broken 1

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
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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/)

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Canonical SMILES Fc1ccc(cc1)C(c1ccc(cc1)F)CCCN1CCC(CC1)n1c(=O)[nH]c2c1cccc2
Isomeric SMILES Fc1ccc(cc1)C(c1ccc(cc1)F)CCCN1CCC(CC1)n1c(=O)[nH]c2c1cccc2
InChI InChI=1S/C28H29F2N3O/c29-22-11-7-20(8-12-22)25(21-9-13-23(30)14-10-21)4-3-17-32-18-15-24(16-19-32)33-27-6-2-1-5-26(27)31-28(33)34/h1-2,5-14,24-25H,3-4,15-19H2,(H,31,34)
InChI Key YVUQSNJEYSNKRX-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. Freedman SB, Patel S, Marwood R, Emms F, Seabrook GR, Knowles MR, McAllister G. (1994)
Expression and pharmacological characterization of the human D3 dopamine receptor.
J Pharmacol Exp Ther, 268 (1): 417-26. [PMID:8301582]
2. Kasanami Y, Ishikawa C, Kino T, Chonan M, Toyooka N, Takashima Y, Iba Y, Sekiguchi F, Tsubota M, Ohkubo T et al.. (2022)
Discovery of pimozide derivatives as novel T-type calcium channel inhibitors with little binding affinity to dopamine D2 receptors for treatment of somatic and visceral pain.
Eur J Med Chem, 243: 114716. [PMID:36075145]
3. Kobayashi T, Ikeda K, Kumanishi T. (2000)
Inhibition by various antipsychotic drugs of the G-protein-activated inwardly rectifying K(+) (GIRK) channels expressed in xenopus oocytes.
Br J Pharmacol, 129 (8): 1716-22. [PMID:10780978]
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.
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H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs.
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6. Lang R, Lee G, Liu W, Tian S, Rafi H, Orias M, Segal AS, Desir GV. (2000)
KCNA10: a novel ion channel functionally related to both voltage-gated potassium and CNG cation channels.
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7. 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.
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8. Roth BL, Craigo SC, Choudhary MS, Uluer A, Monsma Jr FJ, Shen Y, Meltzer HY, Sibley DR. (1994)
Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors.
J Pharmacol Exp Ther, 268 (3): 1403-10. [PMID:7908055]
9. Santi CM, Cayabyab FS, Sutton KG, McRory JE, Mezeyova J, Hamming KS, Parker D, Stea A, Snutch TP. (2002)
Differential inhibition of T-type calcium channels by neuroleptics.
J Neurosci, 22 (2): 396-403. [PMID:11784784]
10. Sokoloff P, Andrieux M, Besançon R, Pilon C, Martres MP, Giros B, Schwartz JC. (1992)
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.
Eur J Pharmacol, 225 (4): 331-7. [PMID:1354163]
11. Sokoloff P, Giros B, Martres MP, Bouthenet ML, Schwartz JC. (1990)
Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics.
Nature, 347 (6289): 146-51. [PMID:1975644]