Mezlocillin

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Mezlocillin
Mezlocillin.svg
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 Micromedex Detailed Consumer Information
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 51481-65-3 YesY
ATC code J01CA10
PubChem CID: 656511
DrugBank DB00948 YesY
ChemSpider 570894 YesY
UNII OH2O403D1G YesY
KEGG D05021 YesY
ChEBI CHEBI:6919 YesY
ChEMBL CHEMBL1731 YesY
Chemical data
Formula C21H25N5O8S2
Molecular mass 539.584 g/mol
 YesY (what is this?)  (verify)

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.

Mechanism of action[edit]

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[edit]

Gram-negative[edit]

Synthesis[edit]

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[edit]

  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[edit]