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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:53 UTC
HMDB IDHMDB0015194
Secondary Accession Numbers
  • HMDB15194
Metabolite Identification
Common NameAzlocillin
DescriptionAzlocillin is only found in individuals that have used or taken this drug. It is a semisynthetic ampicillin-derived acylureido penicillin.By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, azlocillin 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 azlocillin interferes with an autolysin inhibitor.
Structure
Thumb
Synonyms
Chemical FormulaC20H23N5O6S
Average Molecular Weight461.492
Monoisotopic Molecular Weight461.136904183
IUPAC Name(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Nameazlocillin
CAS Registry Number37091-66-0
SMILES
[H][C@](NC(=O)N1CCNC1=O)(C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@]12[H])C1=CC=CC=C1
InChI Identifier
InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1
InChI KeyJTWOMNBEOCYFNV-NFFDBFGFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • N-carbamoyl-alpha-amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Penam
  • Imidazolidinone
  • Monocyclic benzene moiety
  • Benzenoid
  • Imidazolidine
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Azetidine
  • Urea
  • Carbonic acid derivative
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Hemithioaminal
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Thioether
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.23 g/LNot Available
LogP0.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available205.791http://allccs.zhulab.cn/database/detail?ID=AllCCS00001271
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01061 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01061 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01061
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4980416
KEGG Compound IDC06839
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAzlocillin
METLIN IDNot Available
PubChem Compound6479523
PDB IDNot Available
ChEBI ID2956
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 References
  1. Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. [PubMed:10090000 ]