// Workers AI · dad joke modeIs Cefapirin an antibiotic? Does it pen for a living?

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.^[1]^[2]

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,^[3] the latter for accute mastitis.^[4]

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.^[5]

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.

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