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Ceftibuten

July 24, 2017
Common Name

Ceftibuten Description

Ceftibuten is only found in individuals that have used or taken this drug. It 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.Ceftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+)-(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 acidChEBI CeftibuteneChEBI CeftibutenoChEBI CeftibutenumChEBI cis-CeftibutenChEBI (+)-(6R,7R)-7-((Z)-2-(2-amino-4-Thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateGenerator CedaxMeSH CedexMeSH 7-(2-(2-amino-4-Thiazolyl)-4-carboxy-2-butenoylamino)-3-cephem-4-carboxylic acidMeSH

Chemical Formlia

C15H14N4O6S2 Average Molecliar Weight

410.425 Monoisotopic Molecliar Weight

410.03547558 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 Name

ceftibuten CAS Registry Number

97519-39-6 SMILES

[H][C@]12SCC=C(N1C(=O)[C@H]2NC(=O)C(=C/CC(O)=O)C1=CSC(N)=N1)C(O)=O

InChI Identifier

InChI=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 Key

UNJFKXSSGBWRBZ-BJCIPQKHSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Lactams Direct Parent

Cephalosporins Alternative Parents

  • N-acyl-alpha amino acids and derivatives
  • 2,4-disubstituted thiazoles
  • 1,3-thiazines
  • Primary aromatic amines
  • 2-amino-1,3-thiazoles
  • Dicarboxylic acids and derivatives
  • N-acyl amines
  • Tertiary carboxylic acid amides
  • Heteroaromatic compounds
  • Secondary carboxylic acid amides
  • Amino acids
  • Azetidines
  • Carboxylic acids
  • Azacyclic compounds
  • Thiohemiaminal derivatives
  • Dialkylthioethers
  • Carbonyl compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Meta-thiazine
  • Dicarboxylic acid or derivatives
  • N-acyl-amine
  • 1,3-thiazol-2-amine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Azole
  • Tertiary carboxylic acid amide
  • Thiazole
  • Amino acid or derivatives
  • Amino acid
  • Azetidine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkylthioether
  • Hemithioaminal
  • Azacycle
  • Thioether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • cephalosporin (CHEBI:3510 )
  • dicarboxylic acid (CHEBI:3510 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Cephalosporins

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility7.05e-02 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.07 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity97.02 m3·mol-1ChemAxon Polarizability38.5 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01415

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01415

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01415 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4445419 KEGG Compound ID

    C08117 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Ceftibuten NuGOwiki Link

    HMDB15485 Metagene Link

    HMDB15485 METLIN ID

    Not Available PubChem Compound

    5282242 PDB ID

    Not Available ChEBI ID

    3510

    Product: DUBs-IN-4

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Transporters

    General function:
    Involved in 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:
    78805.3
    References
    1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716 ]
    2. 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. [PubMed:15567297 ]
    3. Saito H, Okuda M, Terada T, Sasaki S, Inui K: Cloning and characterization of a rat H+/peptide cotransporter mediating absorption of beta-lactam antibiotics in the intestine and kidney. J Pharmacol Exp Ther. 1995 Dec;275(3):1631-7. [PubMed:8531138 ]
    4. Terada T, Saito H, Mukai M, Inui K: Characterization of stably transfected kidney epithelial cell line expressing rat H+/peptide cotransporter PEPT1: localization of PEPT1 and transport of beta-lactam antibiotics. J Pharmacol Exp Ther. 1997 Jun;281(3):1415-21. [PubMed:9190878 ]
    5. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
    6. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677 ]
    General function:
    Involved in transporter activity
    Specific function:
    Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
    Gene Name:
    SLC15A2
    Uniprot ID:
    Q16348
    Molecular weight:
    81782.8
    References
    1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716 ]
    2. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
    3. 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. [PubMed:15567297 ]

    PMID: 8555236

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