Fluphenazine Hydrochloride

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Cat Number

API0232299

CAS Number

146-56-5

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Product Detail Description Scientific Support Customer Q&A

CAS Number

146-56-5

EINECS

205-674-1

Storage

Store at room temperature

Synonyms

Permitil; FLUPHENAZINE HCL; Dapotum; Fluphenazini hydrochloridum; NSC-179197; DTXSID00892922

Molecular Formula

C22H28Cl2F3N3OS

Molecular Weight

510.4

Smiles

C1CN(CCN1CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F)CCO.Cl.Cl

Appearance

White to off-white solid powder

Melting Point

200-202°C

Boiling Point

568.3°C at 760 mmHg

General Description

Fluphenazine hydrochloride is a piperazine phenothiazine derivative with a trifluoromethyl group, a potent antipsychotic of the first-generation class. Its chemical structure is 2-[4-[3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl]piperazin-1-yl]ethanol dihydrochloride. Fluphenazine is a white to off-white crystalline powder, soluble in water. It is a high-potency antipsychotic.

Mechanism of Action

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

Application

Fluphenazine is indicated for the treatment of schizophrenia and other psychotic disorders. It is also used for the management of acute and chronic psychosis, and for the control of agitation and aggression.

Using tumor spheroids under hypoxia as a screening system, fluphenazine (a phenothiazine antipsychotic) was identified as a hit. It functionally inhibits acid sphingomyelinase, causing sphingomyelin accumulation and inducing cancer cell death specifically in hypoxic spheroids. This leads to overactivation of hypoxia stress-response pathways, mediated by ATF4, promoting pro-apoptotic tumor-suppressor functions. Fluphenazine represents a novel approach targeting hypoxic tumor regions through induction of sphingolipid stress.

Fig. 1 Fluphenazine induces HIF overactivation in conditions of high HIF background levels. (Klutzny S, et al., 2017)

References

Klutzny S, et al. Functional inhibition of acid sphingomyelinase by Fluphenazine triggers hypoxia-specific tumor cell death. Cell Death Dis. 2017;8(3):e2709.

Does Fluphenazine Hydrochloride require protection from light during long-term storage?

Yes, it is highly photosensitive. Light exposure causes rapid discoloration and degradation of the phenothiazine ring. Store in light-resistant, tightly sealed containers, preferably amber glass.

What is the recommended storage temperature for Fluphenazine Hydrochloride?

Store at controlled room temperature (15–25°C). Avoid excessive heat above 30°C, which accelerates oxidative degradation and sulfoxide formation.

Is Fluphenazine Hydrochloride stable in solution for injection?

Aqueous solutions require protection from light and the addition of antioxidants (e.g., ascorbic acid) for stability.

How is the impurity fluphenazine sulfoxide (an oxidative degradation product) monitored?

This primary degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within USP/EP limits.