Pimozide

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Cat Number

API2062784

CAS Number

2062-78-4

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CAS Number

2062-78-4

EINECS

218-171-7

Storage

Store at room temperature

Synonyms

Orap; Opiran; Pimozidum; McN-JR-6238; pimozida; Neoperidole; R-6238

Molecular Formula

C28H29F2N3O

Molecular Weight

461.5

Smiles

C1CN(CCC1N2C3=CC=CC=C3NC2=O)CCCC(C4=CC=C(C=C4)F)C5=CC=C(C=C5)F

Appearance

White to off-white crystalline powder

Melting Point

214-218°C

Boiling Point

649.0±65.0°C at 760 mmHg

Relative Density

1.2±0.1

General Description

Pimozide is a synthetic diphenylbutylpiperidine derivative, a first-generation antipsychotic with a potent dopamine D2 receptor antagonist activity. Its chemical structure is 1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one. Pimozide is a white to off-white crystalline powder, practically insoluble in water but soluble in organic solvents. It is a highly potent antipsychotic.

Mechanism of Action

Pimozide acts as a selective antagonist of the dopamine D2 receptors, particularly in the mesolimbic and mesocortical pathways, blocking the effects of dopamine and reducing psychotic symptoms. It also has weak antiadrenergic and antihistaminic effects. The drug is effective in reducing the symptoms of schizophrenia, including hallucinations and delusions.

Application

Pimozide is indicated for the treatment of Tourette's syndrome (chronic tic disorder) in patients who have failed to respond to other therapies. It is also used for the treatment of schizophrenia and other psychotic disorders. The drug is associated with a significant risk of QT prolongation and cardiac arrhythmias, requiring careful monitoring of the electrocardiogram.

Pimozide, an antipsychotic agent, inhibited hepatocellular carcinoma cell proliferation, sphere formation, and migration by inducing G0/G1 cell cycle arrest. It also suppressed the maintenance and tumorigenicity of liver cancer stem-like cells (side population and CD133-positive cells). Mechanistically, pimozide attenuated STAT3 activity and downstream gene transcription, reversing IL-6-induced stem-like phenotypes. In a nude mouse xenograft model, pimozide demonstrated antitumor effects. Pimozide may be a novel anti-tumor agent for advanced HCC.

Fig. 1 The neuroleptic drug pimozide inhibits HCC cell proliferation in dose- and time-dependent manners by inducing G0/G1 phase cell cycle arrest. (Chen JJ, et al., 2017)

References

Chen JJ, et al. The neuroleptic drug pimozide inhibits stem-like cell maintenance and tumorigenicity in hepatocellular carcinoma. Oncotarget. 2017;8(11):17593-17609.

Pimozide and loperamide induced ATG5‑ and ATG7‑dependent autophagic cell death in glioblastoma MZ‑54 cells. Proteomic and lipidomic analyses revealed accumulation of cholesterol and sphingolipids, impaired lipid transport, inhibition of sphingomyelin phosphodiesterase 1, and lysosomal membrane permeabilization (LMP) with cathepsin B release. ATG5/7 knockout attenuated LMP and death, while lysophagy receptor VCP depletion enhanced them. Autophagy and lipotoxicity synergize to induce cell death, supporting simultaneous overactivation of autophagy and LMP as a promising GBM treatment approach.

Fig. 2 Whole proteome analysis of loperamide- and pimozide-treated MZ-54 glioma cells. (Meyer N, et al., 2021)

References

Meyer N, et al. Autophagy activation, lipotoxicity and lysosomal membrane permeabilization synergize to promote pimozide- and loperamide-induced glioma cell death. Autophagy. 2021;17(11):3424-3443.

Does Pimozide require protection from light during long‑term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation and discoloration of the benzimidazole ring. Store in light‑resistant containers, preferably amber glass.

What is the recommended storage temperature for Pimozide?

Store at controlled room temperature (15–25°C). Avoid excessive heat above 30°C, which can soften the powder and accelerate oxidative degradation.

Is Pimozide stable in tablet formulations with standard excipients?

Yes, when formulated with standard excipients and protected from moisture.

How is the impurity pimozide N‑oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability‑indicating HPLC method, ensuring it remains within pharmacopoeial limits.