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.
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2D Structure
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Physico-chemical Properties
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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
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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
Bioactivity Comments
Haloperidol is one of a number of drugs that are cationic amphiphilic in nature, for which anti-SARS-CoV-2 activity has been identified in drug repurposing screens. Tummino et al. (2021; bioRxiv preprint PMID: 33791693 target="_blank") suggest that this antiviral activity is most likely a result of the drug promoting phospholipidosis via disruption of lipid homeostasis.
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
D4 receptor Primary target of this compound Hs Antagonist Antagonist 8.7 – 8.8 pKi - 8,18,22
pKi 8.7 – 8.8 [8,18,22]
D2 receptor Rn Antagonist Antagonist 8.3 pKi - 20
pKi 8.3 [20]
D2 receptor Primary target of this compound Hs Antagonist Antagonist 7.4 – 8.8 pKi - 2,10-11,19,22
pKi 7.4 – 8.8 [2,10-11,19,22]
D3 receptor Primary target of this compound Hs Antagonist Antagonist 7.5 – 8.6 pKi - 2,18-19,22
pKi 7.5 – 8.6 [2,18-19,22]
D1 receptor Hs Antagonist Antagonist 7.6 – 8.2 pKi - 18,21
pKi 7.6 – 8.2 [18,21]
5-HT2A receptor Rn Antagonist Antagonist 7.4 pKi - 1
pKi 7.4 [1]
5-HT2A receptor Primary target of this compound Hs Antagonist Antagonist 6.7 – 7.3 pKi - 7,12,17-18,23
pKi 6.7 – 7.3 [7,12,17-18,23]
D3 receptor Rn Antagonist Antagonist 7.0 pKi - 20
pKi 7.0 [20]
5-HT1D receptor Hs Antagonist Antagonist 6.6 pKi - 17
pKi 6.6 [17]
5-HT7 receptor Hs Antagonist Antagonist 6.3 – 6.6 pKi - 4
pKi 6.3 – 6.6 [4]
5-HT7 receptor Rn Antagonist Antagonist 6.3 – 6.6 pKi - 6,15-16
pKi 6.3 – 6.6 [6,15-16]
5-HT7 receptor Mm Antagonist Antagonist 6.3 pKi - 14
pKi 6.3 [14]
D5 receptor Hs Antagonist Antagonist 6.3 pKi - 21
pKi 6.3 [21]
5-HT2B receptor Hs Antagonist Antagonist 5.8 – 6.4 pKi - 24
pKi 5.8 – 6.4 [24]
H1 receptor Hs Antagonist Antagonist 5.7 – 6.1 pKi - 7,17
pKi 5.7 – 6.1 [7,17]
5-HT1A receptor Hs Antagonist Antagonist 5.7 – 5.8 pKi - 9,12-13,17
pKi 5.7 – 5.8 [9,12-13,17]
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Kir3.2 Mm Gating inhibitor Antagonist 4.1 pEC50 - 5
pEC50 4.1 [5]
Voltage: -70.0 mV
Kv10.1 Hs Channel blocker - 6.2 pIC50 - 3
pIC50 6.2 [3]
Ligand mentioned in the following text fields