Fluphenazine (sold under the brand names Prolixin, Modecate) is a typical antipsychotic drug used for the treatment of chronic psychoses such as schizophrenia. It is a phenothiazine with a piperazine side-chain. It works by antagonising (blocking) the dopamine D2 receptors in the brain. This also leads to some of its side effects like movement disorders (like parkinsonism and akathisia) and prolactin elevation. It is given via an intramuscular or subcutaneous depot injection (as its decanoate salt) or by mouth in the form of tablets. In some countries only the depot formulations are currently available. Compared to other antipsychotics it is less prone to causing sedation, low blood pressure or anticholinergic effects but is associated with a higher frequency of movement disorders.
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.
Medical uses
Its primary uses is in the treatment of schizophrenia. It appears to be about equal in effectiveness to low-potency antipsychotics.
Adverse effects
Information sources:
- Common adverse effects (i.e. those that have an incidence ≥1%) include
- Uncommon side effects (0.1%≤incidence<1%) include
- Rare (incidence<0.1%) side effects include
- Unknown frequency side effects include
- Confusion
- Decreased gag reflex
- Silent pneumonia (likely rare)
Synthesis
Fluphenazine (4-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]-1-piperazineethanol), is synthesized by any of the methods described already for the preparation of trifluoperazine and related antipsychotics.
Alkylation of 2-trifluoromethylphenothiazine using 4-formyl-1-piperazineylpropylchloride in the presence of sodamide synthesizes 2-trifluoromethyl-10-[3-(4-formyl-1-piperazinyl)propyl]phenothiazine. Further alkaline hydrolysis removes the N-formyl group, giving 2-trifluoromethyl-10-[3-(1-piperazinyl)propyl]phenothiazine. This is alkylated by 2-bromoethanol-1 acetate, which upon further acidic hydrolysis removes the protecting acetyl group, yielding fluphenazine.
References
- "Fluphenazine". Davis's Drug Guide for Nurses, Eighth Edition. F.A. Davis Company, 2005. ISBN 0-8036-2455-7.
- Fluphenazine - http://www.minddisorders.com/Flu-Inv/Fluphenazine.html#b#ixzz28etEdxu8 - dose, children, effects, therapy, adults, withdrawal, drug, person