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Mezlocillin is a broad-spectrum
Mezlocillin can be made in a variety of ways including reaction of
Duke
{{PenicillinAntiBiotics Penicillins Enantiopure drugs Imidazolidinones
penicillin
Penicillins (P, PCN or PEN) are a group of beta-lactam antibiotic, β-lactam antibiotics originally obtained from ''Penicillium'' Mold (fungus), moulds, principally ''Penicillium chrysogenum, P. chrysogenum'' and ''Penicillium rubens, P. ru ...
antibiotic
An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting pathogenic bacteria, bacterial infections, and antibiotic medications are widely used in the therapy ...
. It is active against both Gram-negative
Gram-negative bacteria are bacteria that, unlike gram-positive bacteria, do not retain the crystal violet stain used in the Gram staining method of bacterial differentiation. Their defining characteristic is that their cell envelope consists ...
and some Gram-positive
In bacteriology, gram-positive bacteria are bacteria that give a positive result in the Gram stain test, which is traditionally used to quickly classify bacteria into two broad categories according to their type of cell wall.
The Gram stain is ...
bacteria
Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of Prokaryote, prokaryotic microorganisms. Typically a few micr ...
. Unlike most other extended spectrum penicillins, it is excreted by the liver, therefore it is useful for biliary tract infections, such as ascending cholangitis.
Mechanism of action
Like all other beta-lactam antibiotics, mezlocillin inhibits the third and last stage of bacterialcell wall
A cell wall is a structural layer that surrounds some Cell type, cell types, found immediately outside the cell membrane. It can be tough, flexible, and sometimes rigid. Primarily, it provides the cell with structural support, shape, protection, ...
synthesis by binding to penicillin binding proteins. This ultimately leads to cell lysis
Lysis ( ; from Greek 'loosening') is the breaking down of the membrane of a cell, often by viral, enzymic, or osmotic (that is, "lytic" ) mechanisms that compromise its integrity. A fluid containing the contents of lysed cells is called a ...
.
Susceptible organisms
Gram-negative
* ''Bacteroides
''Bacteroides'' is a genus of Gram-negative, obligate anaerobic bacteria. ''Bacteroides'' species are non endospore–forming bacilli, and may be either motile or nonmotile, depending on the species. The DNA base composition is 40–48% GC. Un ...
'' spp., including '' B. fragilis''
* ''Enterobacter
''Enterobacter'' is a genus of common Gram-negative, Facultative anaerobic organism, facultatively anaerobic, bacillus (shape), rod-shaped, non-spore-forming bacteria of the family Enterobacteriaceae. Cultures are found in soil, water, sewage, ...
'' spp.
* ''Escherichia coli
''Escherichia coli'' ( )Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. is a gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus '' Escherichia'' that is commonly fo ...
''
* ''Haemophilus influenzae
''Haemophilus influenzae'' (formerly called Pfeiffer's bacillus or ''Bacillus influenzae'') is a Gram-negative, Motility, non-motile, Coccobacillus, coccobacillary, facultative anaerobic organism, facultatively anaerobic, Capnophile, capnophili ...
''
* ''Klebsiella
''Klebsiella'' is a genus of Gram-negative, oxidase-negative, rod-shaped bacteria with a prominent polysaccharide-based capsule.
''Klebsiella'' is named after German-Swiss microbiologist Edwin Klebs (1834–1913). Carl Friedlander described ' ...
'' species
* '' Morganella morganii''
* ''Neisseria gonorrhoeae
''Neisseria gonorrhoeae'', also known as ''gonococcus'' (singular) or ''gonococci'' (plural), is a species of Gram-negative diplococci bacteria first isolated by Albert Ludwig Sigesmund Neisser, Albert Neisser in 1879. An obligate human pathog ...
''
* ''Proteus mirabilis
''Proteus mirabilis'' is a Gram-negative, facultatively Anaerobic organism, anaerobic, rod-shaped bacterium. It shows swarming motility and urease activity. ''P. mirabilis'' causes 90% of all ''Proteus (bacterium), Proteus'' infections in human ...
''
* ''Proteus vulgaris
''Proteus vulgaris'' is a rod-shaped, nitrate-reducing, indole-positive and catalase-positive, hydrogen sulfide-producing, Gram-negative bacterium that inhabits the intestinal tracts of humans and animals. It can be found in soil, water, and ...
''
* ''Providencia rettgeri
''Providencia rettgeri'' (commonly ''P. rettgeri''), is a Gram negative bacterium that is commonly found in both water and land environments. ''P. rettgeri'' is in the genus Providencia (bacterium), Providencia, along with ''Providencia stuartii ...
''
* ''Pseudomonas
''Pseudomonas'' is a genus of Gram-negative bacteria belonging to the family Pseudomonadaceae in the class Gammaproteobacteria. The 348 members of the genus demonstrate a great deal of metabolic diversity and consequently are able to colonize a ...
'' spp., including '' P. aeruginosa''
* ''Serratia marcescens
''Serratia marcescens'' () is a species of bacillus (shape), rod-shaped, Gram-negative bacteria in the family Yersiniaceae. It is a facultative anaerobe and an opportunistic pathogen in humans. It was discovered in 1819 by Bartolomeo Bizio in Pa ...
''
Gram-positive
* ''Enterococcus faecalis
''Enterococcus faecalis'' – formerly classified as part of the group D '' Streptococcus,'' is a Gram-positive, commensal bacterium naturally inhabiting the gastrointestinal tracts of humans. Like other species in the genus '' Enterococcus'', ' ...
''
* ''Peptococcus
''Peptococcus'' is a Gram-positive bacterium genus in the family Peptococcaceae.
Species in the genus are part of the human microbiome, especially in the bacteria that form the gut flora. They are part of the flora of the mouth, upper respirato ...
'' spp.
* ''Peptostreptococcus
''Peptostreptococcus'' is a genus of anaerobic, Gram-positive, non-spore forming bacteria. The cells are small, spherical, and can occur in short chains, in pairs or individually. They typically move using cilia. ''Peptostreptococcus'' are slow- ...
'' spp.
Synthesis
Mezlocillin can be made in a variety of ways including reaction of ampicillin
Ampicillin is an antibiotic belonging to the aminopenicillin class of the penicillin family. The drug is used to prevent and treat several bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, s ...
with chlorocarbamate 1 in the presence of triethylamine. Chlorocarbamate 1 itself is made from ethylenediamine
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately ...
by reaction with phosgene to form the cyclic urea followed by monoamide formation with methanesulfonyl chloride
Methanesulfonyl chloride (mesyl chloride) is an organosulfur compound with the formula . Using the organic pseudoelement symbol Ms for the methanesulfonyl (or mesyl) group –, it is frequently abbreviated MsCl in reaction schemes or equations. It ...
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
Further reading
* * *External links
*Duke
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