chlorpromazine   Click here for help

GtoPdb Ligand ID: 83

Synonyms: chlorpromazine HCl | Largactil® | Thorazine®
Approved drug PDB Ligand
chlorpromazine is an approved drug (FDA (1957))
Compound class: Synthetic organic
Comment: Chlorpromazine was the first antipsychotic drug to be discovered. It is one of the most sedating of the typical antipsychotics and also causes antimuscarinic effects.
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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: chlorpromazine

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 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.

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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 31.78
Molecular weight 318.1
XLogP 4.92
No. Lipinski's rules broken 0
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.

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Canonical SMILES CN(CCCN1c2ccccc2Sc2c1cc(Cl)cc2)C
Isomeric SMILES CN(CCCN1c2ccccc2Sc2c1cc(Cl)cc2)C
InChI InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3
InChI Key ZPEIMTDSQAKGNT-UHFFFAOYSA-N
Bioactivity Comments
Chlorpromazine 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
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT2A receptor Rn Antagonist Inverse agonist 8.7 pKi - 3
⤷ pKi 8.7 [3]
5-HT6 receptor Rn Antagonist Inverse agonist 8.4 pKi - 13
⤷ pKi 8.4 [13]
H1 receptor Hs Antagonist Antagonist 8.2 pKi - 7
⤷ pKi 8.2 [7]
5-HT2A receptor Primary target of this compound Hs Antagonist Inverse agonist 8.1 pKi - 7
⤷ pKi 8.1 [7]
5-HT2C receptor Hs Antagonist Antagonist 7.6 – 8.2 pKi - 5,7
⤷ pKi 7.6 – 8.2 [5,7]
D4 receptor Hs Antagonist Antagonist 7.8 pKi - 8
⤷ pKi 7.8 [8]
5-HT6 receptor Hs Antagonist Inverse agonist 7.7 – 7.8 pKi - 6,12
⤷ pKi 7.7 – 7.8 [6,12]
5-HT7 receptor Hs Antagonist Inverse agonist 7.6 pKi - 12
⤷ pKi 7.6 [12]
5-HT7 receptor Rn Antagonist Inverse agonist 7.6 pKi - 13
⤷ pKi 7.6 [13]
D2 receptor Rn Antagonist Antagonist 7.5 pKi - 15
⤷ pKi 7.5 [15]
α2B-adrenoceptor Hs Antagonist Antagonist 6.6 – 8.3 pKi - 1-2,11
⤷ pKi 6.6 – 8.3 [1-2,11]
D3 receptor Hs Antagonist Antagonist 7.2 – 7.5 pKi - 4,14
⤷ pKi 7.2 – 7.5 [4,14]
D2 receptor Hs Antagonist Antagonist 7.0 – 7.6 pKi - 4,14
⤷ pKi 7.0 – 7.6 [4,14]
D3 receptor Rn Antagonist Antagonist 7.2 pKi - 15
⤷ pKi 7.2 [15]
D1 receptor Hs Antagonist Antagonist 7.1 pKi - 16
⤷ pKi 7.1 [16]
D5 receptor Hs Antagonist Antagonist 6.9 pKi - 16
⤷ pKi 6.9 [16]
α2C-adrenoceptor Hs Antagonist Antagonist 5.9 – 7.4 pKi - 1-2,11
⤷ pKi 5.9 – 7.4 [1-2,11]
5-HT1A receptor Hs Antagonist Antagonist 6.2 pKi - 9
⤷ pKi 6.2 [9]
α2A-adrenoceptor Hs Antagonist Antagonist 5.5 – 6.6 pKi - 1-2,11
⤷ pKi 5.5 – 6.6 [1-2,11]
5-HT7 receptor Mm Antagonist Inverse agonist 5.3 pKi - 10
⤷ pKi 5.3 [10]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPC5 Hs Channel blocker - - - -
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Maxi Cl- Hs Activator (extracellular chlorpromazine) - - - -
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