Pipamazine

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Pipamazine
Pipamazine.svg
Clinical data
Pregnancy
category
Routes of
administration 		Oral, intramuscular injection
ATC code
  • None
Legal status
Legal status
  • Withdrawn
Identifiers
  • 1-[3-(2-chlorophenothiazin-10-yl)propyl]piperidine-4-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.375 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H24ClN3OS
Molar mass 401.95 g·mol−1
3D model (JSmol)
  • C1CN(CCC1C(=O)N)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)Cl
  • InChI=1S/C21H24ClN3OS/c22-16-6-7-20-18(14-16)25(17-4-1-2-5-19(17)27-20)11-3-10-24-12-8-15(9-13-24)21(23)26/h1-2,4-7,14-15H,3,8-13H2,(H2,23,26)
  • Key:OSJJYEUEJRVVOD-UHFFFAOYSA-N
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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. [1]

Contents

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 [3] It was eventually withdrawn from the U.S. market in 1969, after reports of hepatotoxicity (liver injury).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

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]

Synthesis

Thieme Patents: Pipamazine synthesis.svg
Thieme Patents:

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

Related Research Articles

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<span class="mw-page-title-main">Haloperidol</span> Typical antipsychotic medication

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<span class="mw-page-title-main">Promethazine</span> Sedating antihistamine

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<span class="mw-page-title-main">Acepromazine</span> Antipsychotic medication

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<span class="mw-page-title-main">Dopamine antagonist</span> Drug which blocks dopamine receptors

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<span class="mw-page-title-main">Prochlorperazine</span> Medication for nausea, psychosis, and anxiety

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<span class="mw-page-title-main">Amisulpride</span> Atypical antipsychotic and antiemetic medication

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<span class="mw-page-title-main">Droperidol</span> Antidopaminergic drug

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<span class="mw-page-title-main">Promazine</span> Chemical compound

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<span class="mw-page-title-main">Thiethylperazine</span> Chemical compound

Thiethylperazine (Torecan, Norzine) is an antiemetic of the phenothiazine class. It is an antagonist of dopamine receptors (DRD1, DRD2, DRD4) as well as of 5-HT2A, 5-HT2C receptors, mAChRs (1 through 5), α1 adrenergic receptor and H1 receptor.

<span class="mw-page-title-main">Asenapine</span> Medication to treat schizophrenia

Asenapine, sold under the brand name Saphris among others, is an atypical antipsychotic medication used to treat schizophrenia and acute mania associated with bipolar disorder as well as the medium to long-term management of bipolar disorder.

<span class="mw-page-title-main">Melperone</span> Antipsychotic drug

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<span class="mw-page-title-main">Metopimazine</span> Chemical compound

Metopimazine, sold under the brand names Vogalen and Vogalene, is an antiemetic of the phenothiazine group which is used to treat nausea and vomiting. It is marketed in Europe, Canada, and South America. As of August 2020, metopimazine has been repurposed and is additionally under development for use in the United States for the treatment of gastroparesis.

<span class="mw-page-title-main">Cyamemazine</span> Antipsychotic medication

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References

  1. 1 2 Frota LH (2003). Cinqüenta anos de medicamentos antipsicóticos em psiquiatria (PDF) (in Portuguese) (1st ed.). Rio de Janeiro: UFRJ. p. 486. ISBN   85-903827-1-0. Archived from the original (PDF) on 2011-07-06. Retrieved 2010-09-28.
  2. ↑ [No authors listed] (July 1959). "Now she can cook breakfast again..." Canadian Medical Association Journal . 81 (1): 59. PMC   1830735 . Advertisement.
  3. 1 2 [No authors listed] (April 1960). "Lessened postoperative vomiting with MORNIDINE". Annals of Surgery . 151 (4). PMC   1613578 . Advertisement.
  4. ↑ 34 FR 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.
  8. ↑ John W Cusic, Dr Henry William Sause, DE 1089386 (1960 to Searle & Co).
  9. ↑ John W Cusic, Sause Henry William, U.S. patent 2,957,870 (1960 to Searle & Co).
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