Cefapirin

Cefapirin (INN, also spelled cephapirin) is an injectable, first-generation cephalosporin antibiotic. It is marketed under the trade name Cefadyl. Production for use in humans has been discontinued in the United States.[1]

Cefapirin
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa601206
Pregnancy
category
  • US: B (No risk in non-human studies)
    Routes of
    administration
    Intravenous, intramuscular
    ATC code
    Legal status
    Legal status
    Identifiers
    CAS Number
    PubChem CID
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard100.040.409
    Chemical and physical data
    FormulaC17H17N3O6S2
    Molar mass423.466 g/mol g·mol−1
    3D model (JSmol)
      (verify)

    It also has a role in veterinary medicine as Metricure, an intrauterine preparation, and combined with prednisolone in Mastiplan, an intramammary preparation. Both are licensed in cattle.

    Synthesis

    In one of the syntheses, 7-aminocephalosporanic acid (7-ACA) is reacted with bromoacetyl chloride to give the amide. The halo group is then displaced by 4-thiopyridine.[2]

    References

    1. http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=CEFADYL
    2. Crast, L. B.; Graham, R. G.; Cheney, L. C. (1973). "Synthesis of cephapirin and related cephalosporins from 7-(.alpha.-bromoacetamido)cephalosporanic acid". Journal of Medicinal Chemistry. 16 (12): 1413. doi:10.1021/jm00270a025.
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