Azlocillin

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.

Azlocillin
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.048.483
Chemical and physical data
FormulaC20H23N5O6S
Molar mass461.49 g·mol−1
3D model (JSmol)
SMILES
  • O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)NC(=O)N2C(=O)NCC2)[C@H]4SC3(C)C
InChI
  • InChI=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 Y
  • Key:JTWOMNBEOCYFNV-NFFDBFGFSA-N Y
  (verify)

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. "Azlocillin sodium salt Susceptibility and Minimum Inhibitory and Concentration (MIC) Data" (PDF). The Antimicrobial Index. toku-e.com.
  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.
  3. Bauer VJ, Safir SR (November 1966). "Octamethylbiguanide perchlorate". Journal of Medicinal Chemistry. 9 (6): 980–1. doi:10.1021/jm00324a056. PMID 4291383.
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