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Antiemetics
Pipamazine
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    Pipamazine

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    Pipamazine
    Chemical structure of Pipamazine
    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    • Withdrawn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
    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
     ☒NcheckY (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.

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 It was eventually withdrawn from the U.S. market in 1969, after reports of hepatotoxicity (liver injury).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

    Thieme Patents:

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


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