ceftiofur

{{Short description|Chemical compound}}

{{Use dmy dates|date=June 2024}}

{{cs1 config |name-list-style=vanc |display-authors=6}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 443443988

| image = Ceftiofur.png

| tradename = Naxcel

| Drugs.com = {{drugs.com|international|ceftiofur}}

| pregnancy_AU =

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| routes_of_administration =

| ATCvet = yes

| ATC_prefix = J01

| ATC_suffix = DD90

| ATC_supplemental = {{ATCvet|J01|DD99}}, {{ATCvet|J51|DD90}}

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| legal_EU = Rx-only

| legal_EU_comment = {{cite web | title=Naxcel EPAR | website=European Medicines Agency | date=20 October 2009 | url=https://www.ema.europa.eu/en/medicines/veterinary/EPAR/naxcel | access-date=29 June 2024}}{{cite web | title=Naxcel PI | website=Union Register of medicinal products | date=24 May 2005 | url=https://ec.europa.eu/health/documents/community-register/html/v053.htm | access-date=26 December 2024}}

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| bioavailability =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 80370-57-6

| PubChem = 6328657

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4886668

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 83JL932I1C

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07657

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 222913

| 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

| C=19 | H=17 | N=5 | O=7 | S=3

| 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ZBHXIWJRIFEVQY-IHMPYVIRSA-N

}}

Ceftiofur is an antibiotic of the cephalosporin type (third generation), licensed for use in veterinary medicine. It was first described in 1987.{{cite journal |vauthors=Yancey RJ, Kinney ML, Roberts BJ, Goodenough KR, Hamel JC, Ford CW |title=Ceftiofur sodium, a broad-spectrum cephalosporin: evaluation in vitro and in vivo in mice |journal=Am. J. Vet. Res. |volume=48 |issue=7 |pages=1050–3 |year=1987 |doi=10.2460/ajvr.1987.48.07.1050 |pmid=3631686 }} It is marketed by pharmaceutical company Zoetis as Excenel,{{cite web |url=http://www.pfizerah.com/index_species.asp?species=DA&country=US&lang=EN |title=Pfizer Animal Health Dairy Information on Products and Solutions |access-date=20 November 2007 |url-status=dead |archive-url=https://web.archive.org/web/20071013221750/http://www.pfizerah.com/index_species.asp?species=DA&country=US&lang=EN |archive-date=13 October 2007 }} 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.{{cn|date=January 2023}}

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.{{cite journal |vauthors=Donaldson SC, Straley BA, Hegde NV, Sawant AA, DebRoy C, Jayarao BM |title=Molecular epidemiology of ceftiofur-resistant Escherichia coli isolates from dairy calves |journal=Appl. Environ. Microbiol. |volume=72 |issue=6 |pages=3940–8 |year=2006 |pmid=16751500 |doi=10.1128/AEM.02770-05 |pmc=1489609|bibcode=2006ApEnM..72.3940D }}

The metabolite desfuroylceftiofur also has antibiotic activity.{{cite journal | vauthors = Salmon SA, Watts JL, Yancey RJ | title = In vitro activity of ceftiofur and its primary metabolite, desfuroylceftiofur, against organisms of veterinary importance | journal = Journal of Veterinary Diagnostic Investigation | volume = 8 | issue = 3 | pages = 332–336 | date = July 1996 | pmid = 8844576 | doi = 10.1177/104063879600800309 | doi-access = free }} The two compounds are measured together to measure for antibiotic activity in milk (alongside other antibiotics).{{cite web | url=http://www.neogen.com/FoodSafety/pdf/ProdInfo/BS-PLUS.pdf | title=BetaStar Plus / For beta-lactam antibiotics / Product information sheet | publisher=Neogen | access-date=9 September 2014}}