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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View more information in the IUPHAR Pharmacology Education Project: chlorpromazine

2D Structure
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Physico-chemical Properties
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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
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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
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Summary of Clinical Use Click here for help
Antipsychotic used in the treatment of schizophrenia and the manic phase of bipolar disorder. May also be used to treat porphyria, tetanus, nausea and vomiting, hiccups and some behavioural problems in children.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Chlorpromazine has antagonistic action across a variety of CNS postsysnaptic receptor systems, including dopamine, serotonin, histamine, adrenergic and muscarinic receptors. Each of these receptor pathways accounts for different aspects of the drug action. For example, sedative and antiemetic actions may arise via antagonism of histamine receptors and anxiolytic, antidepressive and antiaggressive properties may be attributable to antagonism of serotonin 5HT1 and 5HT2 receptors. More detail is available in the DrugBank entry for this ligand, accessible on the Summary tab of this ligand page.