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Cefprozil

July 24, 2017
Common Name

Cefprozil Description

Cefprozil is only found in individuals that have used or taken this drug. It is a cephalosporin antibiotic. It can be used to treat bronchitis, ear infections, skin infections, and other bacterial infections.Cefprozil, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefprozil interferes with an autolysin inhibitor. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Cefprozil anhydrousChEBI CefproziloChEBI CefprozilumChEBI CefzilChEBI 7-(2-amino-2-(4-Hydroxyphenyl)acetamido)-3-(propenyl)-3-cephem-4-carboxylic acid monohydrateMeSH ArzimolMeSH BrisoralMeSH ProcefMeSH Cefprozil monohydrateMeSH

Chemical Formlia

C18H19N3O5S Average Molecliar Weight

389.426 Monoisotopic Molecliar Weight

389.104541423 IUPAC Name

(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-(prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Traditional Name

cefprozilo CAS Registry Number

92665-29-7 SMILES

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

InChI Identifier

InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1

InChI Key

WDLWHQDACQUCJR-PBFPGSCMSA-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
  • Alpha amino acid amides
  • Phenylacetamides
  • 1-hydroxy-2-unsubstituted benzenoids
  • Aralkylamines
  • 1,3-thiazines
  • Tertiary carboxylic acid amides
  • Secondary carboxylic acid amides
  • Amino acids
  • Azetidines
  • Thiohemiaminal derivatives
  • Monocarboxylic acids and derivatives
  • Dialkylthioethers
  • Carboxylic acids
  • Azacyclic compounds
  • Carbonyl compounds
  • Hydrocarbon derivatives
  • Monoalkylamines
  • Organic oxides
  • Organopnictogen compounds

    • Substituents

  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Meta-thiazine
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Amino acid
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Hemithioaminal
  • Thioether
  • Azacycle
  • Dialkylthioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxide
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Amine
  • Primary amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • cephalosporin (CHEBI:3506 )
  • semisynthetic derivative (CHEBI:3506 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Cephalosporins

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point218 – 225 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.49e-01 g/LNot Available LogP0.6Not Available

    Predicted Properties

    Property Value Source Water Solubility0.15 mg/mLALOGPS logP0.94ALOGPS logP-1.9ChemAxon logS-3.4ALOGPS pKa (Strongest Acidic)3.53ChemAxon pKa (Strongest Basic)7.43ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area132.96 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity101.27 m3·mol-1ChemAxon Polarizability39.35 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • 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 DB01150

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01150

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01150 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

    4444481 KEGG Compound ID

    C06888 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Cefprozil NuGOwiki Link

    HMDB15281 Metagene Link

    HMDB15281 METLIN ID

    Not Available PubChem Compound

    5281006 PDB ID

    Not Available ChEBI ID

    121681

    Product: DTT

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

    PMID: 23576681

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