Cefapirin

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Cefapirin
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Legal status
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Identifiers
JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CSc3ccncc3)COC(=O)C)C(=O)O
  • InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1 checkY
  • Key:UQLLWWBDSUHNEB-CZUORRHYSA-N checkY
  (verify)

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.
  2. ^
    PMID 4148798
    .