Ceftiofur

Ceftiofur
Clinical data
Trade names	Naxcel
AHFS/Drugs.com	International Drug Names
ATCvet code	QJ01DD90 (WHO) QJ01DD99 (WHO), QJ51DD90 (WHO);
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	80370-57-6 ;
PubChem CID	6328657;
ChemSpider	4886668 ;
UNII	83JL932I1C;
KEGG	D07657 ;
ChEMBL	ChEMBL222913 ;
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 ; Key:ZBHXIWJRIFEVQY-IHMPYVIRSA-N ;
	(verify)

Ceftiofur is an antibiotic of the cephalosporin type (third generation), licensed for use in veterinary medicine. It was first described in 1987.^[3] It is marketed by pharmaceutical company Zoetis as Excenel,^[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 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.^[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

^ "Naxcel EPAR". European Medicines Agency. 20 October 2009. Retrieved 29 June 2024.
^ "Naxcel PI". Union Register of medicinal products. 24 May 2005. Retrieved 26 December 2024.
^ 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.
^ "Pfizer Animal Health Dairy Information on Products and Solutions". Archived from the original on 13 October 2007. Retrieved 20 November 2007.
^ 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.
^ 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.
^ "BetaStar Plus / For beta-lactam antibiotics / Product information sheet" (PDF). Neogen. Retrieved 9 September 2014.

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[1] "Naxcel EPAR". European Medicines Agency. 20 October 2009. Retrieved 29 June 2024.

[2] "Naxcel PI". Union Register of medicinal products. 24 May 2005. Retrieved 26 December 2024.

[3] 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.

[4] "Pfizer Animal Health Dairy Information on Products and Solutions". Archived from the original on 13 October 2007. Retrieved 20 November 2007.

[5] 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.

[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. Retrieved 9 September 2014.

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