Cefoperazone

Basic Info

Common NameCefoperazone(F05932)
2D Structure
FRCD IDF05932
CAS Number62893-19-0
PubChem CID44187
FormulaC25H27N9O8S2
IUPAC Name

(6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

InChI Key

GCFBRXLSHGKWDP-XCGNWRKASA-N

InChI

InChI=1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16-,22-/m1/s1

Canonical SMILES

CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=C(C=C2)O)C(=O)NC3C4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O

Isomeric SMILES

CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=C(C=C2)O)C(=O)N[C@H]3[C@@H]4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O

Synonyms
        
            Cefobid
        
            Cefoperazone dihydrate
        
            cefoperazone
        
            62893-19-0
        
            Cefoperazine
        
            Cefoperazono
        
            Cefoperazonum
        
            UNII-7U75I1278D
        
            Cefoperazone (Cefobid)
        
            biocefazon
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 NodesNot available
Direct ParentPeptides
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsAlpha peptide - Cephalosporin - N-acyl-alpha amino acid or derivatives - N-carbamoyl-alpha-amino acid or derivatives - Alpha-amino acid amide - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Phenylacetamide - Cephem - Piperazine-1-carboxamide - Dioxopiperazine - Aryl thioether - Alkylarylthioether - 1-hydroxy-2-unsubstituted benzenoid - N-acyl urea - N-alkylpiperazine - Ureide - Phenol - Benzenoid - 1,4-diazinane - Piperazine - Meta-thiazine - Monocyclic benzene moiety - Dicarboximide - Azole - Tertiary carboxylic acid amide - Tetrazole - Beta-lactam - Heteroaromatic compound - Azetidine - Urea - Carboxamide group - Secondary carboxylic acid amide - Lactam - Carbonic acid derivative - Azacycle - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Hemithioaminal - Sulfenyl compound - Thioether - Carboxylic acid - Dialkylthioether - Organonitrogen compound - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organopnictogen compound - Organic oxide - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Properties

Property NameProperty Value
Molecular Weight645.666
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count13
Rotatable Bond Count9
Complexity1250
Monoisotopic Mass645.142
Exact Mass645.142
XLogP-0.7
Formal Charge0
Heavy Atom Count44
Defined Atom Stereocenter Count3
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-0.9886
Human Intestinal AbsorptionHIA+0.5526
Caco-2 PermeabilityCaco2-0.7049
P-glycoprotein SubstrateSubstrate0.9460
P-glycoprotein InhibitorNon-inhibitor0.8782
Non-inhibitor0.9759
Renal Organic Cation TransporterNon-inhibitor0.8099
Distribution
Subcellular localizationMitochondria0.6121
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7919
CYP450 2D6 SubstrateNon-substrate0.8101
CYP450 3A4 SubstrateSubstrate0.5899
CYP450 1A2 InhibitorNon-inhibitor0.8022
CYP450 2C9 InhibitorNon-inhibitor0.7458
CYP450 2D6 InhibitorNon-inhibitor0.8502
CYP450 2C19 InhibitorNon-inhibitor0.7271
CYP450 3A4 InhibitorNon-inhibitor0.8690
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6906
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8021
Inhibitor0.5570
AMES ToxicityNon AMES toxic0.6584
CarcinogensNon-carcinogens0.9099
Fish ToxicityHigh FHMT0.9982
Tetrahymena Pyriformis ToxicityHigh TPT0.9546
Honey Bee ToxicityLow HBT0.6774
BiodegradationNot ready biodegradable0.6674
Acute Oral ToxicityIII0.5690
Carcinogenicity (Three-class)Non-required0.5275
Model Value Unit
Absorption
Aqueous solubility-2.9764LogS
Caco-2 Permeability-0.0886LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4703LD50, mol/kg
Fish Toxicity1.3134pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5468pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.05ppm

References

TitleJournalDatePubmed ID
Structure-toxicity relationship of cefoperazone and its impurities to developing zebrafish by transcriptome and Raman analysis.Toxicol Appl Pharmacol2017 Jul 1528465218
Phenotypic Characters and Molecular Epidemiology of Campylobacter Jejuni in East China.J Food Sci2016 Jan26565657
Prevalence and Characterization of Cronobacter sakazakii in Retail Milk-Based Infant and Baby Foods in Shaanxi, China.Foodborne Pathog Dis2016 Apr26886843
Isolation and Antibiogram of Clostridium tetani from Clinically Diagnosed Tetanus Patients.Am J Trop Med Hyg2015 Oct26175031
Prevalence, toxin gene profiles, and antimicrobial resistance of Staphylococcus aureus isolated from quick-frozen dumplings.J Food Prot2015 Jan25581200
Comparative analysis of virulence and resistance profiles of Salmonella Enteritidis isolates from poultry meat and foodborne outbreaks in northern Jordan.Virulence2014 Jul 124780883
Antimicrobial susceptibility testing and genotypic characterization of Staphylococcus aureus from food and food animals.Foodborne Pathog Dis2012 Feb22044289