Cefquinome
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Basic Info
| Common Name | Cefquinome(F05643) |
| 2D Structure | |
| FRCD ID | F05643 |
| CAS Number | 84957-30-2 |
| PubChem CID | 5464355 |
| Formula | C23H24N6O5S2 |
| IUPAC Name | (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(5,6,7,8-tetrahydroquinolin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate |
| InChI Key | YWKJNRNSJKEFMK-PQFQYKRASA-N |
| InChI | InChI=1S/C23H24N6O5S2/c1-34-27-16(14-11-36-23(24)25-14)19(30)26-17-20(31)29-18(22(32)33)13(10-35-21(17)29)9-28-8-4-6-12-5-2-3-7-15(12)28/h4,6,8,11,17,21H,2-3,5,7,9-10H2,1H3,(H3-,24,25,26,30,32,33)/b27-16-/t17-,21-/m1/s1 |
| Canonical SMILES | CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCCC5)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)C[N+]4=CC=CC5=C4CCCC5)C(=O)[O-] |
| Synonyms |
Cefquinoma
Cefquinoma [INN-Spanish]
Cefquinome (INN)
Cefquinome
UNII-Z74S078CWP
84957-30-2
Cefquinomum
Z74S078CWP
Cefquinome [INN:BAN]
Cefquinomum [INN-Latin]
|
| Classifies |
Predicted: Veterinary Drug
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Lactams |
| Subclass | Beta lactams |
| Intermediate Tree Nodes | Cephems |
| Direct Parent | Cephalosporins |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Cephalosporin - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Tetrahydroquinoline - 2,4-disubstituted 1,3-thiazole - Meta-thiazine - Pyridine - Pyridinium - 1,3-thiazol-2-amine - Heteroaromatic compound - Tertiary carboxylic acid amide - Thiazole - Azole - Amino acid - Amino acid or derivatives - Azetidine - Secondary carboxylic acid amide - Carboxylic acid salt - Carboxamide group - Azacycle - Dialkylthioether - Carboxylic acid derivative - Carboxylic acid - Hemithioaminal - Thioether - Monocarboxylic acid or derivatives - Organic zwitterion - Organic oxide - Organic oxygen compound - Carbonyl group - Organic salt - Amine - Hydrocarbon derivative - Organic nitrogen compound - Primary amine - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound |
| Description | This 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 Name | Property Value |
|---|---|
| Molecular Weight | 528.602 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 6 |
| Complexity | 971 |
| Monoisotopic Mass | 528.125 |
| Exact Mass | 528.125 |
| XLogP | 1.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 36 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Cattle,Muscle | Japan | 0.04ppm | |||
| Milk | Japan | 0.02ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.1ppm | |||
| Pig,Edible Offal | Japan | 0.1ppm | |||
| Cattle,Edible Offal | Japan | 0.04ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.2ppm | |||
| Pig,Kidney | Japan | 0.2ppm | |||
| Cattle,Kidney | Japan | 0.04ppm | |||
| Other Terrestrial Mammals,Liver | Japan | 0.1ppm | |||
| Pig,Liver | Japan | 0.1ppm | |||
| Cattle,Liver | Japan | 0.04ppm | |||
| Other Terrestrial Mammals,Fat | Japan | 0.05ppm | |||
| Pig,Fat | Japan | 0.05ppm | |||
| Cattle,Fat | Japan | 0.04ppm | |||
| Other Terrestrial Mammals,Muscle | Japan | 0.05ppm | |||
| Pig,Muscle | Japan | 0.05ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Detection of tetracycline and other antimicrobial residues in milk from cows withclinical mastitis treated by combination therapy. | J Dairy Res | 2018 Jul 3:1-6 | 29969084 |
| Residue concentration of cefquinome after intramammary dry cow therapy and short dry periods. | J Dairy Sci | 2018 Aug | 29859692 |
| Development and validation of a quantitative confirmatory method for 30 β-lactam antibiotics in bovine muscle using liquid chromatography coupled to tandem massspectrometry. | J Chromatogr A | 2017 Jun 2 | 28449875 |
| Infection-stage adjusted dose of beta-lactams for parsimonious and efficientantibiotic treatments: A Pasteurella multocida experimental pneumonia in mice. | PLoS One | 2017 Aug 4 | 28777819 |
| Modelling concentrations of antimicrobial drugs: comparative pharmacokinetics of cephalosporin antimicrobials and accuracy of allometric scaling in food-producingand companion animals. | BMC Vet Res | 2016 Sep 6 | 27596044 |
| Susceptibility to cephalosporins of bacteria causing intramammary infections indairy cows with a high somatic cell count in Germany. | Prev Vet Med | 2016 Sep 1 | 27401227 |
| CTX-M-15-Type Extended-Spectrum Beta-Lactamase-Producing Escherichia coli asCausative Agent of Bovine Mastitis. | Foodborne Pathog Dis | 2016 Sep | 27182838 |
| Multiresidue analysis of cephalosporin antibiotics in bovine milk based onmolecularly imprinted polymer extraction followed by liquid chromatography-tandemmass spectrometry. | J Chromatogr A | 2016 Nov 25 | 27816225 |
| Degradation of cefquinome in spiked milk as a model for bioremediation of dairyfarm waste milk containing cephalosporin residues. | J Appl Microbiol | 2015 Apr | 25627038 |
| Low or high doses of cefquinome targeting low or high bacterial inocula cureKlebsiella pneumoniae lung infections but differentially impact the levels ofantibiotic resistance in fecal flora. | Antimicrob Agents Chemother | 2014 | 24395228 |
| Ion-paired extraction of cephalosporins in acetone prior to their analysis bycapillary liquid chromatography in environmental water and meat samples. | Talanta | 2013 Oct 15 | 24054686 |
| Development of a direct ELISA based on carboxy-terminal of penicillin-bindingprotein BlaR for the detection of β-lactam antibiotics in foods. | Anal Bioanal Chem | 2013 Nov | 24013636 |
| Evaluation of the Charm maximum residue limit β-lactam and tetracycline test for the detection of antibiotics in ewe and goat milk. | J Dairy Sci | 2013 May | 23453521 |
| Development and validation of an ultra high performance liquid chromatographytandem mass spectrometry method for determination of 10 cephalosporins anddesacetylcefapirin in milk. | J Chromatogr B Analyt Technol Biomed Life Sci | 2013 Jul 15 | 23747425 |
| Development of a rapid multi-residue assay for detecting β-lactams usingpenicillin binding protein 2x*. | Biomed Environ Sci | 2013 Feb | 23336133 |
| Efficacy of extended cefquinome treatment of clinical Staphylococcus aureusmastitis. | J Dairy Sci | 2013 Aug | 23706485 |
| A broadly applicable approach to prepare monoclonal anti-cephalosporin antibodiesfor immunochemical residue determination in milk. | Anal Bioanal Chem | 2012 Apr | 22362272 |
| Antibiotic resistance of Escherichia coli isolated from a poultry slaughterhouse. | Ann Agric Environ Med | 2012 | 22462449 |
| Development of an enzyme immunoassay for the antibiotic cefquinome and itsapplication for residue determination in cow's milk after therapeutical mastitis treatment. | Anal Bioanal Chem | 2011 Jan | 21103866 |
| A comparison of broad-spectrum and narrow-spectrum dry cow therapy used alone andin combination with a teat sealant. | J Dairy Sci | 2011 Feb | 21257038 |