Azlocillin

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Azlocillin
Azlocillin skeletal.svg
Clinical data
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Chemical and physical data
Formula C20H23N5O6S
Molar mass 461.49 g·mol−1
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Azlocillin is an acyl ampicillin 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. Azlocillin has been identified as a potential candidate against Lyme disease. [1]

Contents

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. [2]

Synthesis

Azlocillin synthesis: FR 2100682 eidem U.S. Patent 3,933,795 Azlocillin synthesis.svg
Azlocillin synthesis: FR 2100682   eidem U.S. Patent 3,933,795
Azlocillin synthesis 2: Azlocillin synthesis2.svg
Azlocillin synthesis 2:

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

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References

  1. https://scopeblog.stanford.edu/2020/03/30/lyme-disease-bacteria-eradicated-by-new-drug-in-early-tests/
  2. "Azlocillin sodium salt Susceptibility and Minimum Inhibitory and Concentration (MIC) Data" (PDF). The Antimicrobial Index. toku-e.com.
  3. 1 2 Koenig HB, Metzer KG, Offe HA, Schroeck W (1982). "Azlocillin. Ein Neues Penicillin aus der Acylureidoreihe: Synthese und Chemische Eigenschaften". Eur. J. Med. Chem. - Chim. Ther. (in German). 17 (1): 59–63.
  4. Bauer VJ, Safir SR (November 1966). "Octamethylbiguanide perchlorate". Journal of Medicinal Chemistry. 9 (6): 980–1. doi:10.1021/jm00324a056. PMID   4291383.