{{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 | image_class = skin-invert-image
<!--Clinical data--> | tradename = Naxcel | Drugs.com = {{drugs.com|international|ceftiofur}} | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_category = | routes_of_administration = | ATCvet = yes | ATC_prefix = J01 | ATC_suffix = DD90 | ATC_supplemental = {{ATCvet|J01|DD99}}, {{ATCvet|J51|DD90}}
<!-- Legal status --> | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> | legal_AU_comment = | legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> | legal_BR_comment = | legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA_comment = | legal_DE = <!-- Anlage I, II, III or Unscheduled --> | legal_DE_comment = | legal_NZ = <!-- Class A, B, C --> | legal_NZ_comment = | legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C --> | legal_UK_comment = | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US_comment = | legal_EU = Rx-only | legal_EU_comment = <ref>{{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}}</ref><ref>{{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}}</ref> | legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> | legal_UN_comment = | legal_status = <!-- For countries not listed above -->
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 80370-57-6 | PubChem = 6328657 | DrugBank_Ref = | DrugBank = | 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
<!--Chemical data--> | IUPAC_name = (6''R'',7''R'')-7-[ [(2''Z'')-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.<ref>{{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 }}</ref> It is marketed by pharmaceutical company Zoetis as '''Excenel''',<ref>{{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 }}</ref> 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.<ref>{{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 }}</ref>
The metabolite desfuroylceftiofur also has antibiotic activity.<ref>{{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 }}</ref> The two compounds are measured together to measure for antibiotic activity in milk (alongside other antibiotics).<ref>{{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}}</ref>
==References== {{reflist}}
{{Cell wall disruptive antibiotics}} {{Portal bar | Medicine}} {{Authority control}}
Category:Cephalosporin antibiotics Category:2-Furyl compounds Category:Thiazoles Category:Ketoxime ethers Category:Veterinary drugs