Mezlocillin

Mezlocillin

Mezlocillin
Systematic (IUPAC) name
(2S,5R,6R)-3,3-dimethyl-6-[[(2R)-2-[(3-methylsulfonyl-
2-oxo-imidazolidine-1-carbonyl)amino]-2-phenyl-acetyl]
amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-
carboxylic acid
Clinical data
AHFS/Drugs.com
Pregnancy
category
  • B
Routes of
administration
Intravenous, intramuscular
Pharmacokinetic data
Protein binding 16–59%
Metabolism Hepatic (20–30%)
Biological half-life 1.3–4.4 hours
Excretion Renal (50%) and biliary
Identifiers
CAS Registry Number  YesY
ATC code J01
PubChem CID:
DrugBank  YesY
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEBI  YesY
ChEMBL  YesY
Chemical data
Formula C21H25N5O8S2
Molecular mass 539.584 g/mol
 YesY   

Mezlocillin is a broad-spectrum penicillin antibiotic. It is active against both Gram-negative and some Gram-positive bacteria. Unlike most other extended spectrum penicillins, it is excreted by the liver, therefore it is useful for biliary tract infections, such as ascending colangitis.

Contents

  • Mechanism of action 1
  • Susceptible organisms 2
    • Gram-negative 2.1
    • Gram-positive 2.2
  • Synthesis 3
  • References 4
  • External links 5

Mechanism of action

Like all other beta-lactam antibiotics, mezlocillin inhibits the third and last stage of bacterial cell wall synthesis by binding to penicillin binding proteins. This ultimately leads to cell lysis.

Susceptible organisms

Gram-negative

Synthesis

Mezlocillin synthesis:[1][2]

Mezlocillin can be made in a variety of ways including reaction of ampicillin with chlorocarbamate 1 in the presence of triethylamine. Chlorocarbamate 1 itself is made from ethylenediamine by reaction with phosgene to form the cyclic urea followed by monoamide formation with methanesulfonyl chloride and then reaction of the other nitrogen atom with phosgene and trimethylsilylchloride.

The closely related analogue azlocillin is made in essentially the same manner as mezlocillin. but with omission of the methylation step.

References

  1. ^ W. Schroeck, H. R. Furtwaengier, H. B. Koenig, and K. G.Metzer, German Offen. 2,318,955 (1973); Chem. Abstr., 82,31313b (1975).
  2. ^ H. B. Koenig, K. G. Metzer, H. A. Offe, and W. Schroeck, Eur. J_. Med. Chem., 17, 59 (1982).

External links