Azlocillin (CHEM022227)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:24:42 UTC
Update Date2016-11-09 01:17:27 UTC
Accession NumberCHEM022227
Identification
Common NameAzlocillin
ClassSmall Molecule
DescriptionA semisynthetic penicillin having a 6beta-{(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl}amino side-group. It is an antibiotic used in treating infections caused by Pseudomonas aeruginosa, Escherichia coli and Haemophilus influenzae.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
AzlocilinaChEBI
AzlocillineChEBI
AzlocillinumChEBI
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
Azlocillin sodium saltHMDB
Azlocillin, sodiumHMDB
Baye 6905HMDB
Bayer brand OF azlocillinHMDB
SecuropenHMDB
Azlocillin sodiumHMDB
AzlinHMDB
Sodium azlocillinHMDB
Sodium, azlocillinHMDB
Azlocillin bayer brandHMDB
Bay e 6905HMDB
Bay-e 6905HMDB
Chemical FormulaC20H23N5O6S
Average Molecular Mass461.492 g/mol
Monoisotopic Mass461.137 g/mol
CAS Registry Number37091-66-0
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP0.2ALOGPS
logP-0.33ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area148.15 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity111.71 m³·mol⁻¹ChemAxon
Polarizability45.02 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-9770100000-8492b9b1630f98f790e8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-2090000000-7ac30823250a688befa1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9211100000-386db4fc343ba0cb9fe4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9100000000-e2e66b83eab9cb055d8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-9000000000-227c79047a0dfcc73d8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1009100000-a664da387030dc08745fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014l-4119100000-f877d479d0e5f892a5e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-66f3e846633855262d34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0924300000-a8929cfd6ecdfa5c7b6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-9652100000-beb18aca53a37bb14d86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4901100000-a09421560a7ba18c3b01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0203900000-b8104d8386d5f1e5e300Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-4319200000-9d0bf49e9f38fa74d970Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-b8e310b7abfb83cddd4fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01061
HMDB IDHMDB0015194
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAzlocillin
Chemspider ID4980416
ChEBI ID2956
PubChem Compound ID6479523
Kegg Compound IDC06839
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11036013
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11397088
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19292999
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20363776
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=2068466
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21219695
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21360610
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21883661
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=6212725
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6231603
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=6289737
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6810286
14. Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307.