Cefoxitin Chemische Eigenschaften,Einsatz,Produktion Methoden
Beschreibung
Cefoxitin contains the same C-7 side chain as cephalothin and the same C-3 side chain as cefuroxime. The
most novel chemical feature of cefoxitin is the possession of an α-oriented methoxyl group in place of the
normal H-atom at C-7. This increased steric bulk conveys very significant stability against β-lactamases. The
inspiration for these functional groups was provided by the discovery of the naturally occurring antibiotic
cephamycin C
derived from fermentation of Streptomyces lactamdurans. Cephamycin C itself has not seen clinical use but,
rather, has provided the structural clue that led to useful agents such as cefoxitin. Agents that contain this
7α methoxy group are commonly referred to as cephamycins. Ingenious chemical transformations now enable
synthetic introduction of such a methoxy group into cephalosporins lacking this feature.
Verwenden
Cefoxitinis a semisynthetic, broad-spectrum second-generation cephalosporin with antibacterial activity. The activity of cefoxitin results in the weakening of the bacterial cell wall and causes cell lysis. Cefoxitin acts by interfering with cell wall synthesis. Its activity spectrum includes a broad range of gram-negative and gram-positive bacteria including anaerobes.
Antimicrobial activity
Most Gram-positive bacilli are susceptible, but L. monocytogenes is resistant. It is resistant to many Gramnegative
β-lactamases and is active against organisms elaborating
them, including some Citrobacter, Providencia, Serratia
and Acinetobacter spp. Enterobacter spp. are resistant. It is moderately
active against Bacteroides spp., but considerable strain
variation in susceptibility occurs.
Acquired resistance
Resistant strains of Bacteroides, some of which produce
β-lactamases that hydrolyze cefoxitin, have been described.
Resistance may be transferable to other Bacteroides spp. It is a
potent inducer of chromosomal cephalosporinases of certain
Gram-negative bacilli and can antagonize the effect
of cefotaxime and other β-lactam agents.
Clinical Use
As for other group 3 cephalosporins, with particular emphasis
on mixed infections including anaerobes, notably abdominal
and pelvic sepsis. In considering its use, its low activity against
aerobic Gram-positive cocci should be noted.
Nebenwirkungen
Reactions are those common to cephalosporins. Pain on
intramuscular, and thrombophlebitis on intravenous, injection
occur. Substantial changes can occur in the fecal flora,
with virtual eradication of susceptible enterobacteria and
non-
fragilis Bacteroides, and appearance of, or increase in,
yeasts, enterococci and other resistant bacteria including
C. difficile. Development of meningitis due to H. influenzae and
Str. pneumoniae in patients treated for other infections has been
observed.
Cefoxitin Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
