Ceftiofur

Basic Info

Common NameCeftiofur(F05965)
2D Structure
FRCD IDF05965
CAS Number80370-57-6
PubChem CID6328657
FormulaC19H17N5O7S3
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

InChI Key

ZBHXIWJRIFEVQY-IHMPYVIRSA-N

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

Canonical SMILES

CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)CSC(=O)C4=CC=CO4)C(=O)O

Isomeric SMILES

CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)CSC(=O)C4=CC=CO4)C(=O)O

Synonyms
        
            UNII-83JL932I1C
        
            Ceftiofur Hydrochloride [USAN]
        
            Ceftiofur
        
            80370-57-6
        
            Excenel
        
            Ceftiofur hydrochloride
        
            Ceftiofurum
        
            83JL932I1C
        
            Ceftiofur (INN)
        
            C19H17N5O7S3.HCl
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassLactams
SubclassBeta lactams
Intermediate Tree NodesCephems
Direct ParentCephalosporins
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsCephalosporin - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Furoic acid or derivatives - 2,4-disubstituted 1,3-thiazole - Meta-thiazine - 1,3-thiazol-2-amine - Azole - Furan - Heteroaromatic compound - Tertiary carboxylic acid amide - Thiazole - Amino acid or derivatives - Azetidine - Carboxamide group - Amino acid - Secondary carboxylic acid amide - Carbothioic s-ester - Thiocarboxylic acid ester - Dialkylthioether - Sulfenyl compound - Hemithioaminal - Thioether - Thiocarboxylic acid or derivatives - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Oxacycle - Azacycle - Organic oxygen compound - Amine - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Primary amine - Organic nitrogen compound - Organopnictogen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.

Properties

Property NameProperty Value
Molecular Weight523.553
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count13
Rotatable Bond Count9
Complexity945
Monoisotopic Mass523.029
Exact Mass523.029
XLogP0.2
Formal Charge0
Heavy Atom Count34
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9878
Human Intestinal AbsorptionHIA-0.5082
Caco-2 PermeabilityCaco2-0.7558
P-glycoprotein SubstrateSubstrate0.6906
P-glycoprotein InhibitorNon-inhibitor0.8663
Non-inhibitor0.6473
Renal Organic Cation TransporterNon-inhibitor0.8558
Distribution
Subcellular localizationPlasma membrane0.3490
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8599
CYP450 2D6 SubstrateNon-substrate0.8235
CYP450 3A4 SubstrateSubstrate0.5116
CYP450 1A2 InhibitorNon-inhibitor0.7839
CYP450 2C9 InhibitorNon-inhibitor0.7864
CYP450 2D6 InhibitorNon-inhibitor0.8856
CYP450 2C19 InhibitorNon-inhibitor0.7604
CYP450 3A4 InhibitorNon-inhibitor0.7138
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8066
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9798
Non-inhibitor0.8522
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.8700
Fish ToxicityHigh FHMT0.8678
Tetrahymena Pyriformis ToxicityHigh TPT0.9406
Honey Bee ToxicityLow HBT0.6200
BiodegradationNot ready biodegradable0.9930
Acute Oral ToxicityIV0.5369
Carcinogenicity (Three-class)Non-required0.4771
Model Value Unit
Absorption
Aqueous solubility-2.6947LogS
Caco-2 Permeability-0.2154LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.6899LD50, mol/kg
Fish Toxicity1.3107pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5404pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.1ppm
Pig,KidneyJapan6.0ppm
Milk Of CattleUnited States0.1ppm
Muscle Of CattleUnited States1ppm
Liver Of CattleUnited States2ppm
Kidney Of CattleUnited States0.4ppm
Muscle Of SwineUnited States2ppm
Liver Of SwineUnited States3ppm
Kidney Of SwineUnited States0.25ppm
Edible Tissues Of SheepUnited States0.t required
Edible Tissues Of PoultryUnited States0.t required
Other Terrestrial Mammals,Edible OffalJapan2ppm
Pig,Edible OffalJapan2ppm
Cattle,Edible OffalJapan2ppm
Other Terrestrial Mammals,LiverJapan2ppm
Other Terrestrial Mammals,FatJapan2ppm
Other Terrestrial Mammals,MuscleJapan1ppm
Cattle,KidneyJapan6.0ppm
Pig,LiverJapan2. oppm
Cattle,LiverJapan2. oppm

References

TitleJournalDatePubmed ID
Comparative Study on Antibiotic Resistance and DNA Profiles of Salmonellaenterica Serovar Typhimurium Isolated from Humans, Retail Foods, and theEnvironment in Shanghai, China.Foodborne Pathog Dis2018 May 929741928
Validation of the BetaStar® Advanced for Beta-lactams Test Kit for the Screening of Bulk Tank and Tanker Truck Milks for the Presence of Beta-lactam DrugResidues.J AOAC Int2018 May 1829776460
Changes in feeding, social, and lying behaviors in dairy cows with metritisfollowing treatment with a nonsteroidal anti-inflammatory drug as adjunctivetreatment to an antimicrobial.J Dairy Sci2018 May29477521
Prevalence of Salmonella enterica, Listeria monocytogenes, and pathogenicEscherichia coli in bulk tank milk and milk filters from US dairy operations inthe National Animal Health Monitoring System Dairy 2014 study.J Dairy Sci2018 Mar29274964
Decrease in the prevalence of extended-spectrum cephalosporin-resistantSalmonella following cessation of ceftiofur use by the Japanese poultry industry.Int J Food Microbiol2018 Jun 229626788
Effects of Ceftiofur and Chlortetracycline on the Resistomes of Feedlot Cattle.Appl Environ Microbiol2018 Jun 1829728379
High prevalence of ESBLs in retail chicken meat despite reduced use ofantimicrobials in chicken production, France.Int J Food Microbiol2017 Sep 1828728058
Prevalence and antimicrobial susceptibility of Mannheimia haemolytica,Pasteurella multocida, and Histophilus somni isolated from the lower respiratory tract of healthy feedlot cattle and those diagnosed with bovine respiratorydisease.Vet Microbiol2017 Sep28888626
Effect of ceftiofur and enrofloxacin on E. coli sub-population in piggastrointestinal tract.J Glob Antimicrob Resist2017 Sep28732789
Population dynamics of enteric Salmonella in response to antimicrobial use inbeef feedlot cattle.Sci Rep2017 Oct 3029085049
Effects of feeding pasteurized waste milk to dairy calves on phenotypes andgenotypes of antimicrobial resistance in fecal Escherichia coli isolates beforeand after weaning.J Dairy Sci2017 Oct28755935
Elimination kinetics of ceftiofur hydrochloride in milk after an 8-day extendedintramammary administration in healthy and infected cows.PLoS One2017 Nov 229095869
Surveillance of antimicrobial resistance among Escherichia coli from chicken and swine, China, 2008-2015.Vet Microbiol2017 May28619166
Determinants of virulence and of resistance to ceftiofur, gentamicin, andspectinomycin in clinical Escherichia coli from broiler chickens in Québec,Canada.Vet Microbiol2017 May28619137
A Whole-Genome Sequencing Approach To Study Cefoxitin-Resistant Salmonellaenterica Serovar Heidelberg Isolates from Various Sources.Antimicrob Agents Chemother2017 Mar 2428137797
Isolation and characterization of Avibacterium paragallinarum with differentnicotinamide adenine dinucleotide requirements.Vet Microbiol2017 Jun28622864
Normal milk microbiome is reestablished following experimental infection withEscherichia coli independent of intramammary antibiotic treatment with athird-generation cephalosporin in bovines.Microbiome2017 Jul 1228701174
Models of antimicrobial pressure on intestinal bacteria of the treated hostpopulations.Epidemiol Infect2017 Jul28462738
Carbapenemase-Producing Enterobacteriaceae Recovered from the Environment of aSwine Farrow-to-Finish Operation in the United States.Antimicrob Agents Chemother2017 Jan 2427919894
Prevalence and antimicrobial resistance of Salmonella isolated from two porkprocessing plants in Alberta, Canada.Int J Food Microbiol2017 Jan 1627750110