Ceftiofur

Ceftiofur is an antibiotic of the cephalosporin type (third generation), licensed for use in veterinary medicine. It was first described in 1987.^[2] It is marketed by pharmaceutical company Zoetis as Excenel,^[3] Naxcel, and Excede and is also the active ingredient in that company's Spectramast LC (lactating cow formulation) and Spectramast DC (dry cow formulation) product.^{[citation needed]}

Ceftiofur

Clinical data
Trade names	Naxcel
AHFS/Drugs.com	International Drug Names
ATCvet code	QJ01DD90 (WHO) QJ51DD90 (WHO)
Legal status
Legal status	EU: Rx-only[1]
Identifiers
IUPAC name (6R,7R)-7-[ [(2Z)-2-(2-Amino-1,3-thiazol-4-yl)- 2-methoxyiminoacetyl]amino]-3-(furan-2- carbonylsulfanylmethyl)-8-oxo-5-thia-1- azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number	80370-57-6 Y
PubChem CID	6328657
ChemSpider	4886668 Y
UNII	83JL932I1C
KEGG	D07657 Y
ChEMBL	ChEMBL222913 Y
CompTox Dashboard (EPA)	DTXSID7046702
Chemical and physical data
Formula	C19H17N5O7S3
Molar mass	523.55 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3nc(sc3)N)CSC(=O)c4occc4)C(=O)O
InChI InChI=1S/C19H17N5O7S3/c1-30-23-11(9-7-34-19(20)21-9)14(25)22-12-15(26)24-13(17(27)28)8(5-32-16(12)24)6-33-18(29)10-3-2-4-31-10/h2-4,7,12,16H,5-6H2,1H3,(H2,20,21)(H,22,25)(H,27,28)/b23-11-/t12-,16-/m1/s1 Y Key:ZBHXIWJRIFEVQY-IHMPYVIRSA-N Y
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It is resistant to the antibiotic resistance enzyme beta-lactamase, and has activity against both Gram-positive and Gram-negative bacteria. Escherichia coli strains resistant to ceftiofur have been reported.^[4]

The metabolite desfuroylceftiofur also has antibiotic activity.^[5] The two compounds are measured together to measure for antibiotic activity in milk (alongside other antibiotics).^[6]

References

1. "Naxcel EPAR". European Medicines Agency. 20 October 2009. Retrieved 29 June 2024.
2. Yancey RJ, Kinney ML, Roberts BJ, Goodenough KR, Hamel JC, Ford CW (1987). "Ceftiofur sodium, a broad-spectrum cephalosporin: evaluation in vitro and in vivo in mice". Am. J. Vet. Res. 48 (7): 1050–3. PMID 3631686.
3. "Pfizer Animal Health Dairy Information on Products and Solutions". Archived from the original on 13 October 2007. Retrieved 20 November 2007.
4. Donaldson SC, Straley BA, Hegde NV, Sawant AA, DebRoy C, Jayarao BM (2006). "Molecular epidemiology of ceftiofur-resistant Escherichia coli isolates from dairy calves". Appl. Environ. Microbiol. 72 (6): 3940–8. Bibcode:2006ApEnM..72.3940D. doi:10.1128/AEM.02770-05. PMC 1489609. PMID 16751500.
5. Salmon SA, Watts JL, Yancey RJ (July 1996). "In vitro activity of ceftiofur and its primary metabolite, desfuroylceftiofur, against organisms of veterinary importance". Journal of Veterinary Diagnostic Investigation. 8 (3): 332–336. doi:10.1177/104063879600800309. PMID 8844576.
6. "BetaStar Plus / For beta-lactam antibiotics / Product information sheet" (PDF). Neogen. Retrieved 9 September 2014.