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Azlocillin skeletal.svg
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/ International Drug Names
CAS Number 37091-66-0 YesY
ATC code J01CA09 (WHO)
PubChem CID 6479523
DrugBank DB01061 YesY
ChemSpider 4980416 YesY
KEGG D02339 YesY
Chemical data
Formula C20H23N5O6S
Molar mass 461.491 g/mol

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.

Spectrum of bacterial susceptibility[edit]

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


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[edit]


  1. ^
  2. ^ a b H. B. Konig et al., Eur. J. Med. Chem. - Chim. Ther. 17, 59 (1982).
  3. ^ Bauer, Victor J.; Safir, S. R. (1966). "Octamethylbiguanide Perchlorate". Journal of Medicinal Chemistry. 9 (6): 980. doi:10.1021/jm00324a056. PMID 4291383.