Ceftiofur

Ceftiofur is an antibiotic of the cephalosporin type (third generation), licensed for use in veterinary medicine. It was first described in 1987.[1] It is marketed by pharmaceutical company Zoetis as Excenel,[2] 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.

Ceftiofur
Clinical data
Trade namesNaxcel
AHFS/Drugs.comInternational Drug Names
ATCvet code
Legal status
Legal status
  • EU: Rx-only
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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H17N5O7S3
Molar mass523.55 g·mol−1
3D model (JSmol)
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
  (verify)

It is resistant to the antibiotic resistance enzyme beta-lactamase, and has activity against both Gram-positive and Gram-negative bacteria. E. coli strains resistant to ceftiofur have been reported.[3]

The metabolite desfurolyceftiofur also has antibiotic activity.[4] The two compounds are measured together to measure for antibiotic activity in milk (alongside other antibiotics).[5]

References
  1. 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.
  2. "Pfizer Animal Health Dairy Information on Products and Solutions". Archived from the original on 2007-10-13. Retrieved 2007-11-20.
  3. 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. doi:10.1128/AEM.02770-05. PMC 1489609. PMID 16751500.
  4. Salmon, S. A.; Watts, J. L.; Yancey, R. J. (1996). "In Vitro Activity of Ceftiofur and its Primary Metabolite, Desfuroylceftiofur, against Organisms of Veterinary Importance". Journal of Veterinary Diagnostic Investigation. 8 (3): 332–6. doi:10.1177/104063879600800309. PMID 8844576.
  5. "BetaStar Plus / For beta-lactam antibiotics / Product information sheet" (PDF). Neogen. Retrieved 9 September 2014.


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