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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 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 monohydrateHMDB
ArzimolHMDB
BrisoralHMDB
ProcefHMDB
Cefprozil monohydrateHMDB
7-(2-Amino-2-(p-hydroxyphenyl)acetamido)-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHMDB
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
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 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point218 - 225 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.15 g/LNot Available
LogP0.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01150 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID56685
KEGG Compound IDC06888
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCefprozil
METLIN IDNot Available
PubChem Compound5281006
PDB IDNot Available
ChEBI ID3506
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available