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.com	International Drug Names
MedlinePlus	a601206
Routes of administration	Intravenous, intramuscular
ATC code	J01DB08 (WHO) QG51AA05 (WHO) QJ51DB08 (WHO)
Legal status
Legal status	US: ℞-only
Identifiers
CAS Number	21593-23-7
PubChem CID	30699
DrugBank	DB01139
ChemSpider	28486
UNII	89B59H32VN
KEGG	D07636
ChEBI	CHEBI:554446
ChEMBL	ChEMBL1599
CompTox Dashboard (EPA)	DTXSID9022784
ECHA InfoCard	100.040.409
Chemical and physical data
Formula	C17H17N3O6S2
Molar mass	423.46 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CSc3ccncc3)COC(=O)C)C(=O)O
InChI 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 Key:UQLLWWBDSUHNEB-CZUORRHYSA-N
(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

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. 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.