Cefuroxime

Basic Info

Common NameCefuroxime(F05956)
2D Structure
FRCD IDF05956
CAS Number55268-75-2
PubChem CID5479529
FormulaC16H16N4O8S
IUPAC Name

(6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

InChI Key

JFPVXVDWJQMJEE-IZRZKJBUSA-N

InChI

InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1

Canonical SMILES

CON=C(C1=CC=CO1)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O

Isomeric SMILES

CO/N=C(/C1=CC=CO1)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O

Synonyms
        
            Zinacef Danmark
        
            cefuroxime
        
            Cephuroxime
        
            Cefuroximo
        
            Cefuroxim
        
            Cefuroximum
        
            55268-75-2
        
            Zinacef
        
            Sharox
        
            Cefuroximum [INN-Latin]
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassLactams
SubclassBeta lactams
Intermediate Tree NodesCephems - Cephalosporins
Direct ParentCephalosporin 3'-carbamates
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsCephalosporin 3'-carbamate - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Meta-thiazine - Furan - Heteroaromatic compound - Carbamic acid ester - Tertiary carboxylic acid amide - Azetidine - Carboxamide group - Carbonic acid derivative - Secondary carboxylic acid amide - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Oxacycle - Azacycle - Dialkylthioether - Hemithioaminal - Thioether - Hydrocarbon derivative - Organopnictogen compound - Carbonyl group - Organonitrogen compound - Organooxygen compound - Organic oxide - Organic nitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as cephalosporin 3'-carbamates. These are cephalosporins that are substituted at the 3'-position by a carbamate group.

Properties

Property NameProperty Value
Molecular Weight424.384
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count10
Rotatable Bond Count8
Complexity798
Monoisotopic Mass424.069
Exact Mass424.069
XLogP-0.2
Formal Charge0
Heavy Atom Count29
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-0.9863
Human Intestinal AbsorptionHIA+0.6504
Caco-2 PermeabilityCaco2-0.7051
P-glycoprotein SubstrateSubstrate0.7253
P-glycoprotein InhibitorNon-inhibitor0.8621
Non-inhibitor0.8383
Renal Organic Cation TransporterNon-inhibitor0.8688
Distribution
Subcellular localizationLysosome0.3989
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8686
CYP450 2D6 SubstrateNon-substrate0.8196
CYP450 3A4 SubstrateSubstrate0.5051
CYP450 1A2 InhibitorNon-inhibitor0.6957
CYP450 2C9 InhibitorNon-inhibitor0.7771
CYP450 2D6 InhibitorNon-inhibitor0.8707
CYP450 2C19 InhibitorNon-inhibitor0.7064
CYP450 3A4 InhibitorNon-inhibitor0.8308
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8916
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9724
Non-inhibitor0.8292
AMES ToxicityNon AMES toxic0.7525
CarcinogensNon-carcinogens0.8816
Fish ToxicityHigh FHMT0.9467
Tetrahymena Pyriformis ToxicityHigh TPT0.9658
Honey Bee ToxicityHigh HBT0.5146
BiodegradationNot ready biodegradable0.9759
Acute Oral ToxicityIV0.6099
Carcinogenicity (Three-class)Non-required0.5040
Model Value Unit
Absorption
Aqueous solubility-2.5611LogS
Caco-2 Permeability-0.0274LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.6593LD50, mol/kg
Fish Toxicity1.2734pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5136pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.02ppm
Cattle,Edible OffalJapan0.08ppm
Cattle,KidneyJapan0.02ppm
Cattle,LiverJapan0.02ppm
Cattle,FatJapan0.02ppm
Cattle,MuscleJapan0.02ppm

References

TitleJournalDatePubmed ID
[Clinical observation on effect of shaogen decoction for the prevention and treatment of acute radiation esophagitis].Zhongguo Zhong Xi Yi Jie He Za Zhi2010 Dec21302489
High incidence of enteroaggregative Escherichia coli among food handlers in three areas of Kenya: a possible transmission route of travelers' diarrhea.J Travel Med2008 Jan-Feb18217867
Antimicrobial resistance patterns of Shiga toxin-producing Escherichia coli O157:H7 and O157:H7- from different origins.Microb Drug Resist2007 Spring17536933
Isolation, molecular characterization and antimicrobial resistance patterns of Salmonella and Escherichia coli isolates from meat-based fast food in Lebanon.Sci Total Environ2005 Apr 115833239
Characteristics of antibiotic-resistant Escherichia coli O157:H7 in Washington State, 1984-1991.J Infect Dis1994 Dec7996005
[Yersinia enterocolitica strains of bovine origin isolated in San Luis, Argentina: virulence, enterotoxigenicity, and antibiotic sensitivity].Rev Latinoam Microbiol1991 Apr-Sep1670473