Cefapirin

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Cefapirin
Cefapirin.svg
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a601206
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
ECHA InfoCard 100.040.409
Chemical and physical data
Formula C17H17N3O6S2
Molar mass 423.466 g/mol
3D model (JSmol)
  (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.

Synthesis[edit]

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[edit]

  1. ^ http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=CEFADYL
  2. ^ a b 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.