Pipotiazine

Pipotiazine (Piportil), also known as pipothiazine, is a typical antipsychotic of the phenothiazine class used in the United Kingdom and other countries for the treatment of schizophrenia. Its properties are similar to those of chlorpromazine. A 2004 systematic review investigated its efficacy for people with schizophrenia:

Medical uses
Pipotiazine palmitate is used to treat schizophrenia.

Contraindications
Pipotiazine palmitate is contraindicated in people with circulatory collapse (shock), altered states of consciousness, including drug intoxication, or other serious health conditions (liver disease, kidney disease, pheochromocytoma, severe cardiovascular disease, or blood dyscrasias). It is contraindicated in people with severe depression. Pipotiazine palmitate should not be used in people who have a history of allergic reactions to any component of the medicine or to chemically similar medicines (phenothiazines).

Pharmacokinetics
Pipotiazine was available as a long-acting injectable formulation (pipotiazine palmitate). After deep intramuscular injection, pipotiazine palmitate reaches maximum plasma concentration in 7-14 days, has an elimination half-life of 15 days, and reaches steady-state levels after 2 months of usual dosing (given every 4 weeks).

Synthesis
The alkylation of 2-Dimethylaminosulfonylphenthiazine [1090-78-4] (1) with 1-Bromo-3-chloropropane (2) gives 10-(3-chloropropyl)-N,N-dimethylphenothiazine-2-sulfonamide [40051-12-5] (3). Alkylation with 4-Piperidineethanol [622-26-4] (4) completes the synthesis of Pipothiazine (5).

History
The long-acting injectable formulation of pipotiazine (pipotiazine palmitate) was withdrawn from all markets globally in March 2015 due to a shortage of the active ingredient.