Cephalosporins

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Cephalosporins

A large class antibiotics related to penicillin; examples include cephalexin, cefazolin and others.

Information about Cephalosporins

The cephalosporins are a family of bactericidal antibiotics structurally related to penicillin which were first derived from the fungus, Cephalosporum acremonium. Their basic structure is similar to penicillin with a thiazolidine and beta-lactam ring, which has a variable side chain.

Mechanism of action of Cephalosporins

Cephalosporins bind to the penicillin-binding proteins on bacteria and inhibit synthesis of the bacterial cell wall, causing cell lysis particularly in rapidly growing organisms. Their differences in activity relate to the range of penicillin-binding proteins that they inhibit. They have a broader activity than the standard penicillins, but are also sensitive to some extent to beta-lactamase.

Types of Cephalosporins

Five generations of cephalosporins have been developed with varying antibacterial activity. Cephalosporins are indicated for infections with susceptible organisms. Cephalosporins have variable oral absorption and many must be given parenterally. In the lists below, formulations that are available in oral and parenteral forms are shown separately.

First generation cephalosporins include cefadroxil, cefazolin, cephalexin, and cephradine, and these are active against many gram-positive cocci, including penicillinase-producing Staphylococcus aureus.

Second generation cephalosporins include cefaclor, cefoxitin, cefprozil, cefonicid, and cefuroxime; these have broader antibacterial activity, and additional sensitive organisms including Citrobacter, Enterobacter, Haemophilus influenzae, Neisseria and Serratia species.

Third generation cephalosporins include cefdinir, cefditoren, cefixime, cefoperazone, cefotaxime, cefpodoxime, ceftazidime, ceftibuten, ceftizoxime, and ceftriaxone, which are less active than first- and second generation drugs against gram-positive bacteria, but more active against gram-negative organisms and have greater stability against beta-lactamases.

Fourth generation cephalosporins include cefepime, which are active against a wide range of both gram-positive and gram-negative organisms.

Fifth generation cephalosporins include ceftaroline and ceftolozane/tazabactam, which are active against a wide range of both gram-positive and gram-negative organisms including methicillin resistant Staphylococcus aureus (MRSA). These agents are sometimes referred to as advanced generation rather than fifth generation cephalosporins.

Side effects of Cephalosporins

Cephalosporins have side effects similar to penicillin, and drug-allergy and hypersensitivity are often (but not always) shared. The cephalosporins in general have been associated with little hepatotoxicity and only rare instances of drug induced liver injury due to these agents have been published. A special exception is ceftriaxone, a third generation cephalosporin which, when given parenterally, can cause biliary sludge with symptoms of cholecystitis and cholestatic jaundice. For these reasons, other than for ceftriaxone, the cephalosporins will be discussed as a general class rather than individual agents, and separately for the intravenous and oral forms.

Liver safety of Cephalosporins

A few cephalosporins have been implicated in only a few cases, but in general the liver injury from cephalosporins is similar from case to case. The typical case of liver injury from cephalosporins is a self-limited cholestatic hepatitis with mild if any immunoallergic features that arises 1 to 3 weeks after starting therapy, sometimes occurring after a single parenteral dose.


Oral Cephalosporins

Parenteral Cephalosporins

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