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Cephalosporin antibiotics

Drugs & Medication

Cephalosporin antibiotics

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Cephalosporin nucleus
Cephalosporin nucleus

The cephalosporins (IPA: [ˌkɛfəloˈspɔrən, ˌsɛfə-]) are a class of β-lactam antibiotics. Together with cephamycins they belong to a sub-group called cephems.

Contents

History

Cephalosporin compounds were first isolated from cultures of Cephalosporium acremonium from a sewer in Sardinia in 1948 by Italian scientist Giuseppe Brotzu. He noticed that these cultures produced substances that were effective against Salmonella typhi, the cause of typhoid fever. Researchers at the Sir William Dunn School of Pathology at the University of Oxford isolated cephalosporin C, which had stability to β-lactamases but was not sufficiently potent for clinical use. The cephalosporin nucleus, 7-aminocephalosporanic acid (7-ACA), was derived from cephalosporin C and proved to be analogous to the penicillin nucleus 6-aminopenicillanic acid. Modification of the 7-ACA side-chains resulted in the development of useful antibiotic agents, and the first agent cephalothin (cefalotin) was launched by Eli Lilly in 1964.

Mode of action

Cephalosporins are bactericidal and have the same mode of action as other beta-lactam antibiotics (such as penicillins). Cephalosporins disrupt the synthesis of the peptidoglycan layer of bacterial cell walls. The peptidoglycan layer is important for cell wall structural integrity, especially in Gram-positive organisms. The final transpeptidation step in the synthesis of the peptidoglycan is facilitated by transpeptidases known as penicillin binding proteins (PBPs).

Clinical use

Indications

Cephalosporins are indicated for the prophylaxis and treatment of bacterial infections caused by susceptible organisms. First-generation cephalosporins are predominantly active against Gram-positive bacteria, and successive generations have increased activity against Gram-negative bacteria (albeit often with reduced activity against Gram-positive organisms).

Adverse effects

Common adverse drug reactions (ADRs) (≥1% of patients) associated with cephalosporin therapy include: diarrhea, nausea, rash, electrolyte disturbances, and/or pain and inflammation at injection site. Infrequent ADRs (0.1–1% of patients) include: vomiting, headache, dizziness, oral and vaginal candidiasis, pseudomembranous colitis, superinfection, eosinophilia, and/or fever.

Approximately 5–10% of patients with allergic hypersensitivity to penicillins and/or carbapenems will also have cross-reactivity with cephalosporins. Thus, they are contraindicated in patients with a history of severe of immediate allergic reactions (urticaria, anaphylaxis, interstitial nephritis, etc) to penicillins, carbapenems or cephalosporins.[1]

Classification

The cephalosporin nucleus can be modified to gain different properties. Cephalosporins are sometimes grouped into "generations" by their antimicrobial properties. The first cephalosporins were designated first generation while later, more extended spectrum cephalosporins were classified as second generation cephalosporins. Each newer generation of cephalosporins has significantly greater Gram-negative antimicrobial properties than the preceding generation, in most cases with decreased activity against Gram-positive organisms. Fourth generation cephalosporins, however, have true broad spectrum activity.

The classification of cephalosporins into "generations" is commonly practised, although the exact categorisation of cephalosporins is often imprecise. For example, the fourth generation of cephalosporins is not yet recognized in Japan. In Japan, cefaclor is classed as a first generation cephalosporin; and cefbuperazone, cefminox and cefotetan are classed as second generation cephalosporins. Cefbuperazone, cefminox, and cefotetan are classed as second generation cephems. Cefmetazole and cefoxitin are classed as third generation cephems. Flomoxef, latamoxef are in a new class called oxacephems.

Most first generation cephalosporins were originally spelt "ceph-" in English-speaking countries. This continues to be the preferred spelling in North America and Australia, while European countries have adopted International Nonproprietary Names, which are usually spelt "cef-". Newer first-generation cephalosporins and all cephalosporins of later generations are spelt "cef-".

Structure of the classical cephalosporins
Structure of the classical cephalosporins

First generation

First generation cephalosporins are moderate spectrum agents, with a spectrum of activity that includes penicillinase-producing, methicillin-susceptible staphylococci and streptococci, though they are not the drugs of choice for such infections. They also have activity against some Escherichia coli, Klebsiella pneumoniae and Proteus mirabilis, but have no activity against Bacteroides fragilis, enterococci, methicilllin-resistant staphylococci, Pseudomonas, Acinetobacter, Enterobacter, indole-positive Proteus or Serratia.

  • Cefacetrile (cephacetrile)
    Cefadroxil (cefadroxyl; Duricef®)
    Cefalexin (cephalexin; Keflex®)
    Cephaloglycin
    Cefalonium (cephalonium)
    Cefaloridine (cephaloradine)
    Cefalotin (cephalothin; Keflin®)
    Cefapirin (cephapirin; Cefadryl®)
    Cefatrizine
    Cefazaflur
    Cefazedone
    Cefazolin (cephazolin; Ancef®, Kefzol®)
    Cefradine (cephradine; Velosef®)
    Cefroxadine
    Ceftezole

Second generation

The second generation cephalosporins have a greater Gram-negative spectrum while retaining some activity against Gram-positive cocci. They are also more resistant to beta-lactamase.

  • Cefaclor (Ceclor®)
    Cefonicid (Monocid®)
    Cefprozil (cefproxil; Cefzil®)
    Cefuroxime (Zinnat®, Zinacef®, Ceftin®)
    Cefuzonam

Second generation cephalosporins with antianaerobe activity

  • Cefamandole
    Ceforanide
    Cefotiam

The following cephems are also sometimes grouped with second-generation cephalosporins:

  • Carbacephems: loracarbef (Lorabid®)
    Cephamycins: cefbuperazone, cefmetazole (Zefazone®), cefminox, cefotetan (Cefotan®), cefoxitin (Mefoxin®)

Third generation

Third generation cephalosporins have a broad spectrum of activity and further increased activity against Gram-negative organisms. Some members of this group (particularly those available in an oral formulation, and those with anti-pseudomonal activity) have decreased activity against Gram-positive organisms. They may be particularly useful in treating hospital-acquired infections, although increasing levels of extended-spectrum beta-lactamases are reducing the clinical utility of this class of antibiotics.

  • Cefcapene
    Cefdaloxime
    Cefdinir (Omnicef®)
    Cefditoren
    Cefetamet
    Cefixime (Suprax®)
    Cefmenoxime
    Cefodizime
    Cefoperazone (Cefobid®)
    Cefotaxime (Claforan®)
    Cefpimizole
    Cefpodoxime (Vantin®)
    Cefteram
    Ceftibuten (Cedax®)
    Ceftiofur
    Ceftiolene
    Ceftizoxime (Cefizax®)
    Ceftriaxone (Rocephin®)

Third generation cephalosporins with antipseudomonal activity

  • Ceftazidime (Fortum®, Fortaz®)
    Cefpiramide
    Cefsulodin

The following cephems are also sometimes grouped with third-generation cephalosporins:

  • Oxacephems: latamoxef (moxalactam)

Fourth generation

Fourth generation cephalosporins are extended-spectrum agents with similar activity against Gram-positive organisms as first-generation cephalosporins. They also have a greater resistance to beta-lactamases than the third generation cephalosporins. Many can cross blood brain barrier and are effective in meningitis.

  • Cefclidine
    Cefepime (Maxipime®)
    Cefluprenam
    Cefoselis
    Cefozopran
    Cefpirome
    Cefquinome

The following cephems are also sometimes grouped with third-generation cephalosporins:

  • Oxacephems: flomoxef

Yet to be classified

These cephems have progressed far enough to be named, but have not been assigned to a particular generation. Ceftobiprole (and the oral medocaril version) are on the FDA fast track. Ceftobiprole has powerful antipseudomonal characteristics and appears to be less susceptible to development of resistance.

  • Cefaclomezine
    Cefaloram
    Cefaparole
    Cefcanel
    Cefedrolor
    Cefempidone
    Cefetrizole
    Cefivitril
    Cefmatilen
    Cefmepidium
    Cefovecin
    Cefoxazole
    Cefrotil
    Cefsumide
    Ceftioxide
    Ceftobiprole (previously BAL 9141 and RO 63-9141)
    Ceftobiprole (previously BAL 5788)
    Cefuracetime

References

  1. ^ Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006.

See also

External links


Home | Up | Carbapenem antibiotics | Cephalosporin antibiotics | AGG01 | Amoxicillin | Ampicillin | Co-amoxiclav | Penicillin

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This guide is licensed under the GNU Free Documentation License. It uses material from the Wikipedia.


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