Ceftiofur

Ceftiofur

Systematic (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
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	80370-57-6
ATCvet code	QJ01DD90(WHO) QJ51DD90
PubChem	CID 6328657
ChemSpider	4886668
UNII	83JL932I1C
KEGG	D07657
ChEMBL	CHEMBL222913
Chemical data
Formula	C19H17N5O7S3
Molar mass	523.56 g/mol
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
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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] and is the active ingredient in that company's Specramast LC (lactating cow formula) 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". 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. doi:10.1177/104063879600800309. PMID 8844576.
5. "BetaStar Plus / For beta-lactam antibiotics / Product information sheet" (PDF). Neogen. Retrieved 9 September 2014.

External links

• Official website