Cephalosporin

Cephalosporins are a class of β-lactam antibiotics. Together with cephamycins they belong to a subgroup called cephems.

Cephalosporin - History

Cephalosporin was first isolated from cultures of Cephalosporium acremonium from a sewer in Sardinia in 1948 by an Italian scientist Giuseppe Brotzu. He noted that these cultures produced a substance that was effective against Salmonella typhi, the cause of typhoid fever. Cephalosporins were developed as a medicine in the Sir William Dunn School of Pathology at the University of Oxford and Keflin (cephalothin) was launched by Eli Lilly in 1964.

Cephalosporin - Mode of action

Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for cross-links. This effect is bactericidal.

Cephalosporins - The generations

Cephalosporin core can be modified to achieve different properties. Cephalosporins are 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 previous generation; currently four generations of cephalosporins are recognized. Conversely, the "older" generations of cephalosporins has greater gram positive (Staphylococcus and Streptococcus) coverage than the "newer" generations. 

There is some disagreement about the definition of generations. Fourth-generation cephalosporins are not yet recognized in Japan, and is included in the third generation instead. In Japan, classified Cefaclor 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 classified as third-generation cephems. Flomoxef, latamoxef is a new class called oxacephems.

Cephalosporins - First-generation cephalosporins

First-generation cephalosporins, generally contains "ph" in their names (except cefadroxil, cefaloridine, cefazolin and newer varieties) in the U.S.. In other nations, 'f' are commonly used. They have a range of activities involving penicillinase-producing, methicillin-sensitive staphylococci and streptococci, although they are not the substances are chosen from such infections. They also have activity against some Escherichia coli, Klebsiella pneumoniae, and Proteus mirabilis, but has no activity against Bacteroides fragilis, enterococci, methicilllin-resistant staphylococci, Pseudomonas, Acinetobacter, Enterobacter, indole-positive Proteus and Serratia.

cefacetrile / cephacetrile (Celospor, Celtol, Cristacef)

• cefadroxil / cefadroxyl (Baxan, Bidocef, Cefadril, Cefadrox, Cefroxil, Ceoxil, Cephos, Crenodyn, Duracef, Duricef, Kefroxil, Longacef, Moxacef, Oradroxil, Sumacef, Ultracef) 

• cefalexin / cefalexin / cephalexin (Cefanox, Ceporex, Keflet, Keflex, Keforal, keftab, Keftal, Lopilexin) 

• cefaloglycin / cephaloglycin (Kafocin, Kefglycin) 

• Cefalonium / cephalonium (Cepravin) (veterinary use) 

• cefaloridine / cephaloradine (Cefaclox, Cepalorin, Ceporan, Ceporin, Ceporine, Coporin, Dinasint, Danger Dina Floridin, Keflodin, Kefloridin, Kefspor, Latorex, Lauridin, Loridine, Sasperin) 

• cefalothin / cefalotin / cephalothin / cephalotin (Ceporacin, Keflin, Seffin) 

• cephapirin / cephapirin (Cefadyl, Lopitrex) 

• cefatrizine (Cefaperos, Zanitrin) 

• cefazaflur 

• cefazedone (Refosporin) 

• cefazolin / cefazolin / cephazolin (Ancef, Cefacidal, Cefamezin, Cefrina, Elzogram, Gramaxin, Kefazol, Kefol, Kefzol, Kefzolan, Kezolin, Novaporin, Zolicef) 

• cefradine / cephradine (Promotion, Askacef, Velosef) 

• cefroxadine (Cefthan-DS, Oraspor) 

• ceftezole (Celoslin, Cefthan-DS, Falomesin) 

Cephalosporins - Second generation cephems 

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

  

• Cefaclor / cefachlor (Alenfral, Ceclor, Distaclor, Keflor, Kefral, Panacef, Panoral) 

• cefonicid / cefonicide (Monocid) 

• cefprozil (Cefzil) 

• Cefuroxime axetil (Ceftin, Elobact, Kefurox, Oracef, Oraxim, Zinacef, Zinadol, zināt) 

• cefuzonam (Cosmosin) 

• Second generation carbacephem 

• loracarbef (Lorabid) 

Second-generation cephalosporins antianaerobe 

• cefamandole NAFAT (Kefdole, Mandol, Mandokef) 

• ceforanide (Precef) 

• cefotiam (Cefapicol, Ceradon, Halo Track Pansporin, Spizef) 

Antianaerobe Second generation cephamycins 

• cefbuperazone (Keiperazon, Tomiporan) 

• cefmetazole / sefmetazole (Cefmeazon, Cefmetazon, Zefazone) 

• cefminox (Meicelin) 

• cefotetan (Apacef, Cefotan, Yamatetan) 

• cefoxitin / cefoxitine (Mefoxin, Mefoxitin) 

Cephalosporins - Third generation cephalosporins 

Third generation cephalosporins have a broad spectrum of activity against enteric gram-negative rods and are therefore particularly suitable for treating infections acquired in hospitals. 

• cefcapene pivoxil (Flomox) 

• cefdaloxime pentexil TOSILATE 

• cefdinir (Cefzon, omnicef) 

• cefditoren pivoxil (Meiact, Spectracef) 

• cefetamet pivoxil (Cefyl, Globocef) 

• cefixime (Cefspan, Suprax) 

• cefmenoxime (Best Call, Cefmax, Tacef) 

• cefodizim / cefodizime (Kenicef, Opticef, Timecef) 

• cefoperazone (Cefobid, Cefoperazin, Sulperazon) 

• cefotaxime (Cefotax, Claforan) 

• cefpimizole (Ajicef) 

• cefpodoxime proxetil (Banan, vantin) 

• cefteram pivoxil (Tomiron) 

• ceftibuten (Cedax, Procef, Seftem) 

• ceftiofur (Excenel, Naxcel) (veterinary use) 

• ceftiolene 

• ceftizoxime (Ceftix, Cefizox, Epocelin) 

• ceftriaxone (rocephine) 

• moxalactam (also called latamoxef) (Latamoxef, Moxam, Shiomarin) 

cefoperazone combined with Sulbactam sold as Sulperazon. 

Antipseudomonal third generation cephalosporins 

• ceftazidime (Cefortime, Ceptaz, Fortaz, Fortum, Glazidim, Kefadim, Modacin, Tazicef, Tazidime, Tanicef) 

• cefpiramide (Suncefal) 

• cefsulodin (Pseudocef, Pseudomonil, Takesulin, Tilmapor) 

Cephalosporin - fourth generation cephalosporins 

Fourth generation cephalosporins have a greater spectrum of activity against Gram-positive organisms than third-generation cephalosporins. They also have a greater resistance to beta-lactamases than third-generation cephalosporins. 

• cefquinome (Cephaguard) (veterinary use) 

• flomoxef (Flumarin) 

• catecholic cephalosporin 

• cefetecol (Cefcatacol) 

• fourth-generation cephalosporins, antipseudomonal 

• cefclidin, cefclidine 

• cefepime (Maxipime) 

• cefluprenam 

• cefoselis sulfate (Wincef) 

• cefozopran (Firstcin) 

• cefpirome (Broact, Cefrom, Keiten) 

Cephalosporins - Unknown generation cephems 

These cephems has developed sufficiently to be named, but has not been assigned a particular generation. Ceftobiprole (and oral medocaril version) is on the FDA's Fast Track. Ceftobiprole has powerful antipseudomonal characteristics and appear to be less sensitive to the development of resistance. 

• cefaclomezine / cephachlomezine 

• cefaloram 

• cefaparole 

• cefcanel and cefcanel daloxate 

• cefedrolor 

• cefempidone 

• cefetrizole 

• cefivitril 

• cefmatilen 

• cefmepidium 

• cefovecin 

• cefoxazole / cephoxazole 

• cefrotil 

• cefsumide 

• ceftioxide 

• ceftobiprole (BAL 9141 and earlier RO 63-9141) 

• ceftobiprole medocaril (formerly BAL 5788) 

• cefuracetime 

Cephalosporins - Caution - Possible name confusion 

The names of many cephalosporins are very similar and easily confused.