Azlocillin

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Azlocillin
Azlocillin skeletal.svg
Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.048.483
Chemical and physical data
Formula C20H23N5O6S
Molar mass 461.491 g/mol
3D model (Jmol)
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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

Synthesis[edit]

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]

References[edit]

  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. ^ Bauer, Victor J.; Safir, S. R. (1966). "Octamethylbiguanide Perchlorate". Journal of Medicinal Chemistry. 9 (6): 980. doi:10.1021/jm00324a056. PMID 4291383.