Cephalosporin (T3D3492)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-30 17:58:46 UTC
Update Date2014-12-24 20:26:07 UTC
Accession NumberT3D3492
Identification
Common NameCephalosporin
ClassSmall Molecule
DescriptionCeftibuten is a third-generation cephalosporin antibiotic. It is an orally-administered agent. Cefalexin is used to treat acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis.
Compound Type
  • Amide
  • Amine
  • Anti-Bacterial Agent
  • Cephalosporin
  • Drug
  • Ester
  • Ether
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(+)-(6R,7R)-7-((Z)-2-(2-amino-4-Thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
Cedax
Ceftibutene
Ceftibuteno
Ceftibutenum
cis-Ceftibuten
Chemical FormulaC15H14N4O6S2
Average Molecular Mass410.425 g/mol
Monoisotopic Mass410.035 g/mol
CAS Registry Number97519-39-6
IUPAC Name(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Nameceftibuten
SMILES[H]\C(CC(O)=O)=C(\C(O)=N[C@]1([H])C(=O)N2C(=CCS[C@]12[H])C(O)=O)C1=CSC(=N)N1
InChI IdentifierInChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1
InChI KeyInChIKey=UNJFKXSSGBWRBZ-BJCIPQKHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cephalosporins. Cephalosporins 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Meta-thiazine
  • N-acyl-amine
  • Dicarboxylic acid or derivatives
  • 1,3-thiazol-2-amine
  • Azole
  • Tertiary carboxylic acid amide
  • Thiazole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Azetidine
  • Carboxamide group
  • Carboxylic acid derivative
  • Thioether
  • Hemithioaminal
  • Dialkylthioether
  • Azacycle
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.07 g/LALOGPS
logP0.31ALOGPS
logP-1.4ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.99ChemAxon
pKa (Strongest Basic)4.69ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area162.92 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.02 m³·mol⁻¹ChemAxon
Polarizability38.5 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00l6-4429000000-9eb742eca3a39f7f33c72017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-007c-5112290000-67c5009b631f19f5afd32017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-1956200000-fb5911483fe37835ee052016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-1952000000-968eb058db01aac160582016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05py-6900000000-5b91131b300dfce27ffe2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-067i-0197100000-b92f44385691c61e259f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-6497000000-897341155f6550b60c892016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9210000000-0931070d4e68d34816192016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0206900000-56987e3ec4dfee8313a52021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0j5c-0889100000-10c0830632bb6ded71902021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0911000000-451f229108728ac430fd2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-0129000000-5f07301226a0ae9702292021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-1429000000-207cae2f67161059ada92021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-7913000000-5d44774d788cdc748a962021-10-11View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
Toxicity Profile
Route of ExposureRapidly absorbed following oral administration.
Mechanism of ToxicityCeftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.
MetabolismA study with radiolabeled ceftibuten administered to 6 healthy adult male volunteers demonstrated that cis-ceftibuten is the predominant component in both plasma and urine. About 10% of ceftibuten is converted to the trans-isomer is approximately 1/8 as antimicrobially potent as the cis-isomer. Route of Elimination: Ceftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed to treat acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis. It is also indicated for pneumonia, infections of the urinary tract, enteritis and gastroenteritis. [Wikipedia]
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsOverdosage of cephalosporins can cause cerebral irritation leading to convulsions.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01415
HMDB IDNot Available
PubChem Compound ID5282242
ChEMBL IDCHEMBL1605
ChemSpider ID4445418
KEGG IDC08117
UniProt IDNot Available
OMIM ID
ChEBI ID3510
BioCyc IDNot Available
CTD IDNot Available
Stitch IDCephalosporin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkCeftibuten
References
Synthesis ReferenceNot Available
MSDST3D3492.pdf
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Solute carrier family 15 member 1
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory340 uMNot AvailableBindingDB 50370586
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [15567297 ]
  2. Biegel A, Gebauer S, Hartrodt B, Brandsch M, Neubert K, Thondorf I: Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1. J Med Chem. 2005 Jun 30;48(13):4410-9. [15974593 ]