Azlocillin

Azlocillin

Azlocillin
Systematic (IUPAC) name
(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 acid
Clinical data
AHFS/Drugs.com
Identifiers
CAS Registry Number  Y
ATC code J01
PubChem CID:
DrugBank  Y
ChemSpider  Y
UNII  Y
KEGG  Y
ChEBI  Y
ChEMBL  Y
Chemical data
Formula C20H23N5O6S
Molecular mass 461.491 g/mol
 Y   

Azlocillin is an acylampicillin antibiotic with an extended spectrum of activity and greater in vitro potency than the carboxy penicillins. Azlocillin is similar to mezlocillin and piperacillin. It demonstrates antibacterial activity against a broad spectrum of bacteria, including Pseudomonas aeruginosa and, in contrast to most cephalosporins, exhibits activity against enterococci.

Contents

  • Spectrum of bacterial susceptibility 1
  • Synthesis 2
  • See also 3
  • References 4

Spectrum of bacterial susceptibility

Azlocillin is considered a broad spectrum antibiotic and can be used against a number of Gram positive and Gram negative bacteria. The following represents MIC susceptibility data for a few medically significant organisms.[1]

  • Escherichia coli 1 μg/mL - 32 μg/mL
  • Haemophilus spp. 0.03 μg/mL - 2 μg/mL
  • Pseudomonas aeruginosa 4 μg/mL - 6.25 μg/mL

Synthesis

Azlocillin synthesis: FR 2100682  eidem U.S. Patent 3,933,795 [2]
Azlocillin synthesis 2:[2][3]

An interesting alternative synthesis of azlocillin involves activation of the substituted phenylglycine analogue 1 with 1,3-dimethyl-2-chloro-1-imidazolinium chloride (2) and then condensation with 6-APA.

See also

References

  1. ^ http://www.toku-e.com/Assets/MIC/Azlocillin%20sodium%20salt.pdf
  2. ^ a b H. B. Konig et al., Eur. J. Med. Chem. - Chim. Ther. 17, 59 (1982).
  3. ^ doi:10.1021/jm00324a056