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Azlocillin

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Beta-lactam antibiotic
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Pharmaceutical compound
Azlocillin
Clinical data
Trade namesSecuropen
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (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
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.048.483Edit this at Wikidata
Chemical and physical data
FormulaC20H23N5O6S
Molar mass461.49 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:JTWOMNBEOCYFNV-NFFDBFGFSA-N checkY
  (verify)

Azlocillin is anacylampicillinantibiotic with an extended spectrum of activity and greaterin vitro potency than the carboxypenicillins.Azlocillin is similar tomezlocillin andpiperacillin. It demonstrates antibacterial activity against a broad spectrum ofbacteria, includingPseudomonas aeruginosa, and, in contrast to mostcephalosporins, exhibits activity againstenterococci.

Spectrum of bacterial susceptibility

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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

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Azlocillin synthesis:FR 2100682  eidemU.S. patent 3,933,795[2]
Azlocillin synthesis 2:[2][3]

An interesting alternative synthesis of azlocillin involves activation of the substitutedphenylglycine analogue1 with 1,3-dimethyl-2-chloro-1-imidazolinium chloride (2) and then condensation with6-APA.

See also

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References

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  1. ^"Azlocillin sodium salt Susceptibility and Minimum Inhibitory and Concentration (MIC) Data"(PDF).The Antimicrobial Index. toku-e.com.
  2. ^abKoenig 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.
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases
)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
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Extended
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  • Inhibits PG elongation and crosslinking:Ramoplanin§
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