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Ceftiofur

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Ceftiofur
Clinical data
Trade namesNaxcel
AHFS/Drugs.comInternational Drug Names
ATCvet code
Legal status
Legal status
Identifiers
  • (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
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H17N5O7S3
Molar mass523.55 g·mol−1
3D model (JSmol)
  • 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=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 anantibiotic of thecephalosporin type (third generation), licensed for use inveterinary medicine. It was first described in 1987.[3] It is marketed bypharmaceutical companyZoetis asExcenel,[4] 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]

It is resistant to theantibiotic resistance enzymebeta-lactamase, and has activity against bothGram-positive andGram-negative bacteria.Escherichia coli strains resistant to ceftiofur have been reported.[5]

The metabolite desfuroylceftiofur also has antibiotic activity.[6] The two compounds are measured together to measure for antibiotic activity in milk (alongside other antibiotics).[7]

References

[edit]
  1. ^"Naxcel EPAR".European Medicines Agency. 20 October 2009. Retrieved29 June 2024.
  2. ^"Naxcel PI".Union Register of medicinal products. 24 May 2005. Retrieved26 December 2024.
  3. ^Yancey RJ, Kinney ML, Roberts BJ, Goodenough KR, Hamel JC, Ford CW (1987). "Ceftiofur sodium, a broad-spectrum cephalosporin: evaluationin vitro andin vivo in mice".Am. J. Vet. Res.48 (7):1050–3.doi:10.2460/ajvr.1987.48.07.1050.PMID 3631686.
  4. ^"Pfizer Animal Health Dairy Information on Products and Solutions". Archived fromthe original on 13 October 2007. Retrieved20 November 2007.
  5. ^Donaldson SC, Straley BA, Hegde NV, Sawant AA, DebRoy C, Jayarao BM (2006)."Molecular epidemiology of ceftiofur-resistantEscherichia 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.
  6. ^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.
  7. ^"BetaStar Plus / For beta-lactam antibiotics / Product information sheet"(PDF). Neogen. Retrieved9 September 2014.
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases
)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems /Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking:Ramoplanin§
Intracellular
Other
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