Cefapirin

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)

Cefapirin (INN, also spelled cephapirin) is an injectable, first-generation cephalosporin antibiotic. It was marketed in the United States for human use under the trade name Cefadyl, but has since been discontinued in all forms for human use.

Veterinary Use

Although it is no longer used in Humans, Cefapirin remains an important veterinary medication. For cattle, it is sold as ToDAY and ToMORROW by Merial, the prior as a treatment for mammary inflammation, the latter for accute mastitis.

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.

References

↑ "CEFADYL". U.S. Food and Drug Administration. Archived from the original on September 26, 2006.
↑ "Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations (NDA 050446 Details)". U.S. Food and Drug Administration. Retrieved August 5, 2026.
↑ "Animal Drugs @ FDA: ToDAY (cephapirin sodium) Intramammary Infusion (NADA 097-222)". U.S. Food and Drug Administration. Retrieved August 5, 2026.
↑ "Animal Drugs @ FDA: Cefa-Lak (cephapirin sodium) Intramammary Infusion (NADA 108-114)". U.S. Food and Drug Administration. Retrieved August 5, 2026.
1 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.

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[1] "CEFADYL". U.S. Food and Drug Administration. Archived from the original on September 26, 2006.

[2] "Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations (NDA 050446 Details)". U.S. Food and Drug Administration. Retrieved August 5, 2026.

[3] "Animal Drugs @ FDA: ToDAY (cephapirin sodium) Intramammary Infusion (NADA 097-222)". U.S. Food and Drug Administration. Retrieved August 5, 2026.

[4] "Animal Drugs @ FDA: Cefa-Lak (cephapirin sodium) Intramammary Infusion (NADA 108-114)". U.S. Food and Drug Administration. Retrieved August 5, 2026.

[Crast-5] 1 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.