haloperidol   Click here for help

GtoPdb Ligand ID: 86

Synonyms: Haldol® | MCN-JR-1625 | R-1625 | Serenace®
Approved drug PDB Ligand
haloperidol is an approved drug (FDA (1967))
Compound class: Synthetic organic
Comment: Haloperidol is a typical antipsychotic drug.
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: haloperidol

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 CDK toolkit. 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 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 40.54
Molecular weight 375.14
XLogP 4.02
No. Lipinski's rules broken 0
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.

✖
Canonical SMILES Fc1ccc(cc1)C(=O)CCCN1CCC(CC1)(O)c1ccc(cc1)Cl
Isomeric SMILES Fc1ccc(cc1)C(=O)CCCN1CCC(CC1)(O)c1ccc(cc1)Cl
InChI InChI=1S/C21H23ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2
InChI Key LNEPOXFFQSENCJ-UHFFFAOYSA-N
References
1. Egan CT, Herrick-Davis K, Teitler M. (1998)
Creation of a constitutively activated state of the 5-hydroxytryptamine2A receptor by site-directed mutagenesis: inverse agonist activity of antipsychotic drugs.
J Pharmacol Exp Ther, 286 (1): 85-90. [PMID:9655845]
2. 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]
3. Gessner G, Heinemann SH. (2003)
Inhibition of hEAG1 and hERG1 potassium channels by clofilium and its tertiary analogue LY97241.
Br J Pharmacol, 138 (1): 161-71. [PMID:12522086]
4. Jasper JR, Kosaka A, To ZP, Chang DJ, Eglen RM. (1997)
Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b).
Br J Pharmacol, 122 (1): 126-32. [PMID:9298538]
5. 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]
6. Kongsamut S, Roehr JE, Cai J, Hartman HB, Weissensee P, Kerman LL, Tang L, Sandrasagra A. (1996)
Iloperidone binding to human and rat dopamine and 5-HT receptors.
Eur J Pharmacol, 317 (2-3): 417-23. [PMID:8997630]
7. 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]
8. Lahti RA, Evans DL, Stratman NC, Figur LM. (1993)
Dopamine D4 versus D2 receptor selectivity of dopamine receptor antagonists: possible therapeutic implications.
Eur J Pharmacol, 236 (3): 483-6. [PMID:8102973]
9. Lejeune F, Newman-Tancredi A, Audinot V, Millan MJ. (1997)
Interactions of (+)- and (-)-8- and 7-hydroxy-2-(di-n-propylamino)tetralin at human (h)D3, hD2 and h serotonin1A receptors and their modulation of the activity of serotoninergic and dopaminergic neurones in rats.
J Pharmacol Exp Ther, 280 (3): 1241-9. [PMID:9067310]
10. MacKenzie RG, VanLeeuwen D, Pugsley TA, Shih YH, Demattos S, Tang L, Todd RD, O'Malley KL. (1994)
Characterization of the human dopamine D3 receptor expressed in transfected cell lines.
Eur J Pharmacol, 266 (1): 79-85. [PMID:7907989]
11. Meyerhof W, Batram C, Kuhn C, Brockhoff A, Chudoba E, Bufe B, Appendino G, Behrens M. (2010)
The molecular receptive ranges of human TAS2R bitter taste receptors.
Chem Senses, 35 (2): 157-70. [PMID:20022913]
12. Mierau J, Schneider FJ, Ensinger HA, Chio CL, Lajiness ME, Huff RM. (1995)
Pramipexole binding and activation of cloned and expressed dopamine D2, D3 and D4 receptors.
Eur J Pharmacol, 290 (1): 29-36. [PMID:7664822]
13. Millan MJ, Gobert A, Newman-Tancredi A, Audinot V, Lejeune F, Rivet JM, Cussac D, Nicolas JP, Muller O, Lavielle G. (1998)
S 16924 ((R)-2-[1-[2-(2,3-dihydro-benzo[1,4] dioxin-5-Yloxy)-ethyl]-pyrrolidin-3yl]-1-(4-fluoro-phenyl)-ethanone), a novel, potential antipsychotic with marked serotonin (5-HT)1A agonist properties: I. Receptorial and neurochemical profile in comparison with clozapine and haloperidol.
J Pharmacol Exp Ther, 286 (3): 1341-55. [PMID:9732398]
14. 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]
15. Plassat JL, Amlaiky N, Hen R. (1993)
Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase.
Mol Pharmacol, 44 (2): 229-36. [PMID:8394987]
16. 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]
17. Ruat M, Traiffort E, Leurs R, Tardivel-Lacombe J, Diaz J, Arrang JM, Schwartz JC. (1993)
Molecular cloning, characterization, and localization of a high-affinity serotonin receptor (5-HT7) activating cAMP formation.
Proc Natl Acad Sci USA, 90 (18): 8547-51. [PMID:8397408]
18. 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]
19. 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]
20. 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]
21. 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]
22. Sunahara RK, Guan HC, O'Dowd BF, Seeman P, Laurier LG, Ng G, George SR, Torchia J, Van Tol HH, Niznik HB. (1991)
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
Nature, 350 (6319): 614-9. [PMID:1826762]
23. Tice MA, Hashemi T, Taylor LA, Duffy RA, McQuade RD. (1994)
Characterization of the binding of SCH 39166 to the five cloned dopamine receptor subtypes.
Pharmacol Biochem Behav, 49 (3): 567-71. [PMID:7862709]
24. Vanover KE, Harvey SC, Son T, Bradley SR, Kold H, Makhay M, Veinbergs I, Spalding TA, Weiner DM, Andersson CM et al.. (2004)
Pharmacological characterization of AC-90179 [2-(4-methoxyphenyl)-N-(4-methyl-benzyl)-N-(1-methyl-piperidin-4-yl)-acetamide hydrochloride]: a selective serotonin 2A receptor inverse agonist.
J Pharmacol Exp Ther, 310 (3): 943-51. [PMID:15102927]
25. Wainscott DB, Sasso DA, Kursar JD, Baez M, Lucaites VL, Nelson DL. (1998)
[3H]Rauwolscine: an antagonist radioligand for the cloned human 5-hydroxytryptamine2b (5-HT2B) receptor.
Naunyn Schmiedebergs Arch Pharmacol, 357 (1): 17-24. [PMID:9459568]