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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]

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.[citation needed]

Synthesis

Cephapirin synthesis:[2] U.S. patent 3,422,100 U.S. patent 3,503,967 U.S. patent 3,578,661

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. ^ “CEFADYL”. U.S. Food and Drug Administration. Archived from the original on September 26, 2006.
  2. ^ a b Crast LB, Graham RG, Cheney LC (December 1973). “Synthesis of cephapirin and related cephalosporins from 7-(alpha-bromoacetamido)cephalosporanic acid”. Journal of Medicinal Chemistry. 16 (12): 1413–5. doi:10.1021/jm00270a025. PMID 4148798.