Ceftiofur

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 checkY
  • Key:ZBHXIWJRIFEVQY-IHMPYVIRSA-N checkY
  (verify)

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.

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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