Pipamazine

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Pipamazine
Pipamazine.svg
Systematic (IUPAC) name
1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperidine-4-carboxamide
Clinical data
Pregnancy cat. Formerly used for morning sickness
Legal status Withdrawn
Routes Oral, intramuscular injection
Identifiers
CAS number 84-04-8 YesY
ATC code None
PubChem CID 6761
ChemSpider 6503 YesY
UNII 653552FH1N YesY
KEGG D02606 YesY
ChEMBL CHEMBL1909072 N
Chemical data
Formula C21H24ClN3OS 
Mol. mass 401.95 g/mol
 N (what is this?)  (verify)

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.[1]

Pipamazine was introduced to the U.S. market in 1959 by G. D. Searle & Company. It was advertised for morning sickness[2] and postoperative nausea and vomiting, and was claimed to reduce the need for postoperative analgesia.[3] It was eventually withdrawn from the U.S. market in 1969, after reports of hepatotoxicity (liver injury).[4][5]

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.[1]

Adverse effects[edit]

Mornidine advertisements for postoperative recovery claimed "unusually low side effects".[3] However, contemporary comparative trials found that hypotension (low blood pressure) was a substantial concern when the drug was given at normal dosages for this indication; blood pressure reductions of up to 70 mmHg were reported.[6] 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.[7]

References[edit]

  1. ^ a b Frota LH (2003). Cinqüenta anos de medicamentos antipsicóticos em psiquiatria (in Portuguese) (1st ed.). Rio de Janeiro: UFRJ. p. 486. ISBN 85-903827-1-0. 
  2. ^ [No authors listed] (July 1959). "Now she can cook breakfast again..." (PDF). Canadian Medical Association Journal 81 (1): 59. PMC 1830735.  Advertisement.
  3. ^ a b [No authors listed] (April 1960). "Lessened postoperative vomiting with MORNIDINE" (PDF). Annals of Surgery 151 (4). PMC 1613578.  Advertisement.
  4. ^ 34 F.R. 12051. July 17, 1969.
  5. ^ Wysowski DK, Swartz L (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 165 (12): 1363–9. doi:10.1001/archinte.165.12.1363. PMID 15983284. 
  6. ^ Blatchford E (March 1961). "Studies of anti-emetic drugs: A comparative study of cyclizine (Marzine), pipamazine (Mornidine), trimethobenzamide (Tigan), and hyoscine". Canadian Journal of Anesthesia 8 (2): 159–65. doi:10.1007/BF03021345. 
  7. ^ Healy D (2002). "Explorations in a new world". The creation of psychopharmacology. Cambridge: Harvard University Press. pp. 123–4. ISBN 0-674-01599-1.