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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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
SMILES / InChI / InChIKey
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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
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 - 12
pKi 8.4 [12]
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 - 6,11
pKi 7.7 – 7.8 [6,11]
α2B-adrenoceptor Hs Antagonist Antagonist 7.2 – 8.3 pKi - 1-2
pKi 7.2 – 8.3 [1-2]
5-HT7 receptor Hs Antagonist Inverse agonist 7.6 pKi - 11
pKi 7.6 [11]
5-HT7 receptor Rn Antagonist Inverse agonist 7.6 pKi - 12
pKi 7.6 [12]
D2 receptor Rn Antagonist Antagonist 7.5 pKi - 14
pKi 7.5 [14]
D3 receptor Hs Antagonist Antagonist 7.2 – 7.5 pKi - 4,13
pKi 7.2 – 7.5 [4,13]
D2 receptor Hs Antagonist Antagonist 7.0 – 7.6 pKi - 4,13
pKi 7.0 – 7.6 [4,13]
D3 receptor Rn Antagonist Antagonist 7.2 pKi - 14
pKi 7.2 [14]
α2C-adrenoceptor Hs Antagonist Antagonist 6.9 – 7.4 pKi - 1-2
pKi 6.9 – 7.4 [1-2]
D1 receptor Hs Antagonist Antagonist 7.1 pKi - 15
pKi 7.1 [15]
D5 receptor Hs Antagonist Antagonist 6.9 pKi - 15
pKi 6.9 [15]
α2A-adrenoceptor Hs Antagonist Antagonist 5.9 – 6.6 pKi - 1-2
pKi 5.9 – 6.6 [1-2]
5-HT1A receptor Hs Antagonist Antagonist 6.2 pKi - 9
pKi 6.2 [9]
5-HT7 receptor Mm Antagonist Inverse agonist 5.3 pKi - 10
pKi 5.3 [10]
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPC5 Hs Channel blocker - - - -
Maxi Cl- Hs Activator (extracellular chlorpromazine) - - - -