Chemistry:Ceftiofur

Short description: Chemical compound

Ceftiofur

Clinical data
Trade names	Naxcel
AHFS/Drugs.com	International Drug Names
ATCvet code	QJ01DD90 (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 Y
PubChem CID	6328657
ChemSpider	4886668 Y
UNII	83JL932I1C
KEGG	D07657 Y
ChEMBL	ChEMBL222913 Y
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 Y Key:ZBHXIWJRIFEVQY-IHMPYVIRSA-N Y
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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. It is marketed by pharmaceutical company Zoetis as Excenel, 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.

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