Cefapirin

Basic Info

Common NameCefapirin(F05998)
2D Structure
FRCD IDF05998
CAS Number21593-23-7
PubChem CID30699
FormulaC17H17N3O6S2
IUPAC Name

(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

InChI Key

UQLLWWBDSUHNEB-CZUORRHYSA-N

InChI

InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1

Canonical SMILES

CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O

Isomeric SMILES

CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O

Synonyms
        
            cephapirin
        
            Cefapirin
        
            Cephapirine
        
            Cefaprin
        
            Cefapirina
        
            Cefapirine
        
            Cefapirinum
        
            Cefadyl
        
            21593-23-7
        
            Cefapirine [INN-French]
Classifies
                

                  
                    Predicted: Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives - Alpha amino acids and derivatives
Direct ParentN-acyl-alpha amino acids and derivatives
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsN-acyl-alpha amino acid or derivatives - Cephem - Aryl thioether - Alkylarylthioether - Meta-thiazine - Dicarboxylic acid or derivatives - Pyridine - Heteroaromatic compound - Beta-lactam - Tertiary carboxylic acid amide - Carboxamide group - Carboxylic acid ester - Lactam - Azetidine - Azacycle - Organoheterocyclic compound - Carboximidic acid - Carboximidic acid derivative - Dialkylthioether - Carboxylic acid - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Sulfenyl compound - Thioether - Hemithioaminal - Hydrocarbon derivative - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Organopnictogen compound - Carbonyl group - Organic oxide - Organic nitrogen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Properties

Property NameProperty Value
Molecular Weight423.458
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count8
Complexity707
Monoisotopic Mass423.056
Exact Mass423.056
XLogP-1.1
Formal Charge0
Heavy Atom Count28
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9971
Human Intestinal AbsorptionHIA-0.9590
Caco-2 PermeabilityCaco2-0.7523
P-glycoprotein SubstrateSubstrate0.8491
P-glycoprotein InhibitorNon-inhibitor0.6578
Non-inhibitor0.8382
Renal Organic Cation TransporterNon-inhibitor0.8236
Distribution
Subcellular localizationMitochondria0.4553
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7333
CYP450 2D6 SubstrateNon-substrate0.8159
CYP450 3A4 SubstrateSubstrate0.5132
CYP450 1A2 InhibitorNon-inhibitor0.7695
CYP450 2C9 InhibitorNon-inhibitor0.7348
CYP450 2D6 InhibitorNon-inhibitor0.8753
CYP450 2C19 InhibitorNon-inhibitor0.7075
CYP450 3A4 InhibitorNon-inhibitor0.8003
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5917
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9946
Non-inhibitor0.7588
AMES ToxicityNon AMES toxic0.6996
CarcinogensNon-carcinogens0.9010
Fish ToxicityHigh FHMT0.9644
Tetrahymena Pyriformis ToxicityHigh TPT0.8757
Honey Bee ToxicityLow HBT0.6860
BiodegradationNot ready biodegradable0.9955
Acute Oral ToxicityIV0.6182
Carcinogenicity (Three-class)Non-required0.5586
Model Value Unit
Absorption
Aqueous solubility-2.9577LogS
Caco-2 Permeability-0.0483LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.4439LD50, mol/kg
Fish Toxicity1.2779pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5338pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.03ppm
Cattle,Edible OffalJapan0.03ppm
Cattle,KidneyJapan0.03ppm
Cattle,LiverJapan0.03ppm
Cattle,FatJapan0.03ppm
Cattle,MuscleJapan0.03ppm

References

TitleJournalDatePubmed ID
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
Use of Preservative Agents and Antibiotics for Increased Poliovirus Survival onPositively Charged Filters.Food Environ Virol2017 Dec28616833
Multiresidue analysis of cephalosporin antibiotics in bovine milk based onmolecularly imprinted polymer extraction followed by liquid chromatography-tandemmass spectrometry.J Chromatogr A2016 Nov 2527816225
Randomized clinical trial of intrauterine cephapirin infusion in dairy cows forthe treatment of purulent vaginal discharge and cytological endometritis.J Dairy Sci2015 Oct26210270
Comparison of pharmacokinetics and milk elimination of flunixin in healthy cowsand cows with mastitis.J Am Vet Med Assoc2015 Jan 125517334
High resolution mass spectrometry in the identification of transformationproducts and metabolites from β-lactam antibiotics in thermally treated milk.J Chromatogr A2014 Nov 1425441345
Pharmacokinetics in foremilk and antimicrobial activity of cephapirin followingintramammary administration in healthy and Staphylococcus aureus-infected cows.N Z Vet J2014 May24224523
Impact of intramammary treatment on gene expression profiles in bovineEscherichia coli mastitis.PLoS One2014 Jan 1424454893
Ion-paired extraction of cephalosporins in acetone prior to their analysis bycapillary liquid chromatography in environmental water and meat samples.Talanta2013 Oct 1524054686
Development of a direct ELISA based on carboxy-terminal of penicillin-bindingprotein BlaR for the detection of β-lactam antibiotics in foods.Anal Bioanal Chem2013 Nov24013636
Evaluation of the Charm maximum residue limit β-lactam and tetracycline test for the detection of antibiotics in ewe and goat milk.J Dairy Sci2013 May23453521
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 Sci2013 Jul 1523747425
Elimination kinetics of cephapirin sodium in milk after an 8-day extended therapyprogram of daily intramammary infusion in healthy lactating Holstein-Friesiancows.J Dairy Sci2013 Jul23684021
Development of a rapid multi-residue assay for detecting β-lactams usingpenicillin binding protein 2x*.Biomed Environ Sci2013 Feb23336133
Hot topic: investigating the risk of violative meat residues in bob veal calvesfed colostrum from cows treated at dry-off with cephapirin benzathine.J Dairy Sci2013 Apr23415519
Validation study of the BetaStar plus lateral flow assay for detection ofbeta-lactam antibiotics in milk.J AOAC Int2012 Jul-Aug22970593
Validation of a rapid lateral flow test for the simultaneous determination ofβ-lactam drugs and flunixin in raw milk.J Food Prot2012 Jul22980011
A broadly applicable approach to prepare monoclonal anti-cephalosporin antibodiesfor immunochemical residue determination in milk.Anal Bioanal Chem2012 Apr22362272
Effect of heat treatments on stability of β-lactams in milk.J Dairy Sci2011 Mar21338781
Analysis of veterinary drugs and metabolites in milk using quadrupoletime-of-flight liquid chromatography-mass spectrometry.J Agric Food Chem2011 Jul 2721284383