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Pipamazine

Chemical compound

Pipamazine

Chemical compound

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Pipamazine (INN; trade names Mornidine, Mometine, Nausidol) is a drug of the phenothiazine class formerly used as an antiemetic. It is chemically related to chlorpromazine, but has negligible antipsychotic activity and produces few extrapyramidal side effects.

Pipamazine was introduced to the U.S. market in 1959 by G. D. Searle & Company. It was advertised for morning sickness and postoperative nausea and vomiting, and was claimed to reduce the need for postoperative analgesia. It was eventually withdrawn from the U.S. market in 1969, after reports of hepatotoxicity (liver injury).

There is very little published information on pipamazine; it is mostly absent from modern-day sources, apart from a few passing mentions in the pharmacological literature.

Adverse effects

Mornidine advertisements for postoperative recovery claimed "unusually low side effects". Reductions in dosage mitigated hypotension while maintaining antiemetic efficacy.

In his book The Creation of Psychopharmacology, Irish psychiatrist David Healy states that the failure of pipamazine to perform as a neuroleptic and its negative side effect profile helped Searle lose interest in the antipsychotic sector, and contributed to the company's refusal to market haloperidol in the United States.

Synthesis

2957870}} (1960 to Searle & Co).</ref>

The alkylation of 2-chloro-10-(3-chloropropyl)phenothiazine [2765-59-5] (1) with Isonipecotamide [39546-32-2] (2) gives pipamazine (3).

References

References

  1. (2003). "Cinqüenta anos de medicamentos antipsicóticos em psiquiatria". UFRJ.
  2. [No authors listed]. (July 1959). "Now she can cook breakfast again...". [[Canadian Medical Association Journal]].
  3. [No authors listed]. (April 1960). "Lessened postoperative vomiting with MORNIDINE". [[Annals of Surgery]].
  4. {{Federal Register. 34. 12051. July 17, 1969.
  5. (June 2005). "Adverse drug event surveillance and drug withdrawals in the United States, 1969-2002: the importance of reporting suspected reactions". Archives of Internal Medicine.
  6. (March 1961). "Studies of anti-emetic drugs: A comparative study of cyclizine (Marzine), pipamazine (Mornidine), trimethobenzamide (Tigan), and hyoscine". Canadian Journal of Anesthesia.
  7. (2002). "The creation of psychopharmacology". Harvard University Press.
  8. John W Cusic, Dr Henry William Sause, {{Cite patent. DE. 1089386 (1960 to Searle & Co).
  9. John W Cusic, Sause Henry William, {{US patent. 2957870 (1960 to Searle & Co).
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antiemetics hepatotoxins phenothiazines piperidines withdrawn-drugs
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