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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:16:49 UTC
HMDB IDHMDB0015281
Secondary Accession Numbers
  • HMDB15281
Metabolite Identification
Common NameCefprozil
DescriptionCefprozil 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
Thumb
Synonyms
ValueSource
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 FormulaC18H19N3O5S
Average Molecular Weight389.426
Monoisotopic Molecular Weight389.104541423
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 Namecefprozilo
CAS Registry Number92665-29-7
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 KeyWDLWHQDACQUCJR-PBFPGSCMSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
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 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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point218 - 225 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.15 g/LNot Available
LogP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.27 m³·mol⁻¹ChemAxon
Polarizability39.35 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1900000000-fd814e2790d5f453d89bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-0900000000-ec848fcfeb4baef2858aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05gl-1943000000-6526026e86cd6cb96fd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05gr-2920000000-447f3c6096761601c2adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9800000000-275068d6b12d7913192eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0293000000-a70c986a5eaba361d943View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pbc-2962000000-96705de3fccd000e4cefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9510000000-f2fbc8ecdc72ddbe848aView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01150 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01150 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01150
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444481
KEGG Compound IDC06888
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCefprozil
METLIN IDNot Available
PubChem Compound5281006
PDB IDNot Available
ChEBI ID3506
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available