trifluoperazine   Click here for help

GtoPdb Ligand ID: 214

Synonyms: Eskazinyl® | Stelazine® | trifluoperazine hydrochloride
Approved drug PDB Ligand
trifluoperazine is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: Trifluoperazine is a phenothiazine class typical antipsychotic drug, acting principally as a dopamine D2 receptor antagonist.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 35.02
Molecular weight 407.16
XLogP 4.87
No. Lipinski's rules broken 0
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Canonical SMILES CN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(cc2)C(F)(F)F
Isomeric SMILES CN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(cc2)C(F)(F)F
InChI InChI=1S/C21H24F3N3S/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24/h2-3,5-8,15H,4,9-14H2,1H3
Bioactivity Comments
Trifluoperazine 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
D2 receptor Primary target of this compound Hs Antagonist Antagonist 8.9 – 9.0 pKi - 1-2
pKi 8.9 – 9.0 (Ki 1.3x10-9 – 9.6x10-10 M) [1-2]
5-HT2A receptor Hs Antagonist Antagonist 7.9 pKi - 1
pKi 7.9 [1]
D4 receptor Hs Antagonist Antagonist 7.4 pKi - 2
pKi 7.4 (Ki 4.4x10-8 M) [2]
H1 receptor Hs Antagonist Antagonist 7.2 pKi - 1
pKi 7.2 [1]
5-HT2C receptor Hs Antagonist Antagonist 6.4 pKi - 1
pKi 6.4 [1]