Ceftiofur

Structural formula
General
Non-proprietary name	Ceftiofur
other names	(6 R , 7 R ) -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-en-2-carboxylic acid ( IUPAC ); Ceftiofurum ( Latin );
Molecular formula	C 19 H 17 N 5 O 7 S 3
Brief description	white solid
External identifiers / databases
PubChem	6328657
ChemSpider	4886668
Wikidata	Q5057296
Drug information
ATC code	J01 DD90
Drug class	β-lactam antibiotic; 3rd generation cephalosporins;
Mechanism of action	Inhibition of cell wall synthesis
properties
Molar mass	523.55 g · mol -1
Physical state	firmly
Melting point	186-198 ° C
pK s value	3.7
solubility	bad in water (23 mg l −1 )
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	2156 mg kg −1 ( LD 50 , rat , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ceftiofur is a semisynthetic antibiotic from the third generation cephalosporin class , which was developed for veterinary medicine and first described in 1987.

indication

Ceftiofur is mainly used to treat bacterial infectious diseases in cattle and pigs .

Working principle

The antibiotic ceftiofur is effective against numerous gram-negative pathogens, e.g. B. Escherichia coli , Pasteurella , streptococci , staphylococci and salmonella by inhibiting the bacterial cell wall biosynthesis . Ceftiofur shows little or no efficacy against Enterococci , Pseudomonas and Camphylobacter strains.

Application

The active ingredient is administered as an injection subcutaneously at the base of the ear (in cattle) or intramuscularly at the neck muscle (in pigs).

Side effects

Local swelling at the injection site and digestive disorders (e.g. diarrhea ) may occur as side effects .

Trade names

Ceftiofur is commercially available as a sterile powder for dissolution in an aqueous solution, as the sodium salt or as the hydrochloride in an oily suspension .

The antibiotic is sold as a monopreparation under the following names:

Active ingredient	Trade names
Ceftiofur	Naxcel Excede
Ceftiofur Sodium	Cefenil (currently not on sale) Cevaxel Cefti Naxcelflex
Ceftiofur hydrochloride	Actionis Cefavex (currently not on sale) Cefenil RTU Cefokel Ceftiocyl Ceftiomax Ceftiosan Cemay (except trade) Cevaxel RTU Eficur Eficur RTU Excel FLOW Excel RTU Spectramast Truleva (except trade)

There is also a combination preparation with ketoprofen (trade name Curacef duo).

Individual evidence

↑ ^a ^b ^c ^d data sheet Ceftiofur at Sigma-Aldrich , accessed on January 9, 2019 ( PDF ).
↑ ^a ^b Entry on Ceftiofur in the Hazardous Substances Data Bank , accessed on December 1, 2019.
↑ ceftiofur: Summary Report (1) . European Medicines Agency , Committee for Veterinary Medicinal Products. 1999. Retrieved January 9, 2019.
↑ RJ Yancey, ML Kinney, BJ Roberts, KR Goodenough, JC Hamel: Ceftiofur sodium, a broad-spectrum cephalosporin: evaluation in vitro and in vivo in mice . In: American Journal of Veterinary Research . tape 48 , no. 7 , 1987, pp. 1050-1053 , PMID 3631686 .
^ ^A ^b Rex E. Hornish, Susan F. Kotarski: Cephalosporins in veterinary medicine - ceftiofur use in food animals . In: Current Topics in Medicinal Chemistry . tape 2 , no. 7 , 2002, p. 717-731 , PMID 12052187 .
↑ ^a ^b ^c Entry on Ceftiofur. In: Römpp Online . Georg Thieme Verlag, accessed on January 9, 2019.
↑ Naxcel | European Medicines Agency. Retrieved January 9, 2019 .
↑ ^a ^b ^c Entry on Ceftiofur at Vetpharm, accessed on November 7, 2019.
↑ ^a ^b vetidata (as of January 11, 2019).

[Sigma-1] ta sheet Ceftiofur at Sigma-Aldrich , accessed on January 9, 2019 ( PDF ).

[HSDB-2] Entry on Ceftiofur in the Hazardous Substances Data Bank , accessed on December 1, 2019.

[3] tiofur: Summary Report (1) . European Medicines Agency , Committee for Veterinary Medicinal Products. 1999. Retrieved January 9, 2019.

[4] RJ Yancey, ML Kinney, BJ Roberts, KR Goodenough, JC Hamel: Ceftiofur sodium, a broad-spectrum cephalosporin: evaluation in vitro and in vivo in mice . In: American Journal of Veterinary Research . tape 48 , no. 7 , 1987, pp. 1050-1053 , PMID 3631686 .

[:0-5] A ^b Rex E. Hornish, Susan F. Kotarski: Cephalosporins in veterinary medicine - ceftiofur use in food animals . In: Current Topics in Medicinal Chemistry . tape 2 , no. 7 , 2002, p. 717-731 , PMID 12052187 .

[:1-6] Entry on Ceftiofur. In: Römpp Online . Georg Thieme Verlag, accessed on January 9, 2019.

[7] Naxcel | European Medicines Agency. Retrieved January 9, 2019 .

[Vetpharm-8] Entry on Ceftiofur at Vetpharm, accessed on November 7, 2019.

[vetidata-9] vetidata (as of January 11, 2019).