The cephalosporins, are a class of β-lactam antibiotics. Together with cephamycins they belong to a sub-group called cephems. β-lactam antibiotics are a broad class of antibiotics including penicillin derivatives, cephalosporins, monobactams, carbapenems and β-lactamase inhibitors; basically any antibiotic agent which contains a β-lactam nucleus in its molecular structure. ... Cephamycins are a group of beta-lactam antibiotics, very similar to cephalosporins. ... Cephems are a sub-group of beta-lactam antibiotics including cephalosporins and cephamycins. ...

Cephalosporin nucleus

Cephalosporin nucleus I drew this. ... Cephalosporin nucleus I drew this. ...

History

Cephalosporin was first isolated from cultures of Cephalosporium acremonium from a sewer in Sardinia in 1948 by an Italian scientist Giuseppe Brotzu. He noticed that these cultures produced a substance that was effective against Salmonella typhi, the cause of typhoid. The cephalosporins were developed as drugs at the Sir William Dunn School of Pathology at the University of Oxford and Keflin (cephalothin) was launched by Eli Lilly in 1964. Sardinia (Sardigna, Sardinna or Sardinnia in the Sardinian language, Sardegna in Italian, Sardenya in Catalan), is the second largest island in the Mediterranean Sea (Sicily is the largest), between Italy, Spain and Tunisia, south of Corsica. ... 1948 (MCMXLVIII) is a leap year starting on Thursday (link will take you to calendar). ... Binomial name Salmonella enterica Salmonella enterica is a species of Salmonella bacterium. ... This is about the disease typhoid fever. ... One of the worlds largest corporations, Eli Lilly and Company (NYSE: LLY) is a global pharmaceutical company with headquarters in Indianapolis,Indiana, USA. A Fortune 500 corporation, the company had revenues of $12. ... For the Nintendo 64 emulator, see 1964 (Emulator). ...

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 the cross-links. This effect is bactericidal. Penicillin is a β-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms. ... Peptidoglycan, also known as murein, is a substance that forms a homogeneous layer lying outside the plasma membrane in prokaryotes. ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ...

The generations

The cephalosporin nucleus can be modified to gain 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 preceding generation; currently, four generations of cephalosporins are recognized.. Conversely, the "older" generations of cephalosporins have greater gram positive (staphylococcus and streptococcus) coverage than the "newer" generations. An antimicrobial is a substance that kills or slows the growth of microbes like bacteria (antibacterial activity), fungi (antifungal activity), viruses (antiviral activity), or parasites (antiparasitic activity). ... In most modern usages of the word spectrum, there is a unifying theme of a variety of possible cases between extremes at either end. ... Bacteria that are Gram-negative are not stained dark blue or violet by Gram staining, in contrast to Gram-positive bacteria. ... Species S. aureus S. caprae S. epidermidis S. haemolyticus S. hominis S. lugdunensis S. saprophyticus S. warneri S. xylosus Staphylococcus (in Greek staphyle means bunch of grapes and coccos means granule) is a genus of gram-positive bacteria. ... Species S. faecalis S. pneumoniae S. pyogenes S. suis S. viridans Streptococcus is a genus of spherical, Gram-positive bacteria of the phylum Firmicutes. ...

There is some disagreement on the definition of generations. The fourth generation of cephalosporins is not yet recognized in Japan, and are they included in the third generation instead. Cefaclor is classed as a first generation cephalosporin; and cefbuperazone, cefminox and cefotetan are classed as second generation cephalosporins in Japan.

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 of oxacephems.

First generation cephalosporins

First generation cephalosporins generally contain 'ph' in their names (except cefadroxil, cefaloridine, cefazolin and newer varieties) in the United States. In other nations, 'f' is commonly used. They have 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. The spectrum of activity of a drug is the range of diseases which it can treat. ... Species S. aureus S. caprae S. epidermidis S. haemolyticus S. hominis S. lugdunensis S. saprophyticus S. warneri S. xylosus Staphylococcus (in Greek staphyle means bunch of grapes and coccos means granule) is a genus of gram-positive bacteria. ... Species S. faecalis S. pneumoniae S. pyogenes S. suis S. viridans Streptococcus is a genus of spherical, Gram-positive bacteria of the phylum Firmicutes. ... Binomial name Escherichia coli T. Escherich, 1885 E. coli at 10,000x magnification Escherichia coli (usually abbreviated to E. coli) is one of the main species of bacteria that live in the lower intestines of warm-blooded animals (including birds and mammals) and are necessary for the proper digestion of... Binomial name Klebsiella pneumoniae (Schroeter 1886) Klebsiella pneumoniae is a gram-negative rod-shaped bacteria, and clinically the most important member of the Klebsiella genus of Enterobacteriaceae. ... In biology, Proteus is a genus of Gram-negative Proteobacteria, which includes pathogens responsible for many human urinary tract infections. ... Species P. fluorescens P. putida etc. ... Acinetobacter is a genus of Proteobacteria. ... Enterobacter is a genus of common gram-negative facultatively-anaerobic bacteria of the family Enterobacteriaceae. ... In biology, Proteus is a genus of Gram-negative Proteobacteria, which includes pathogens responsible for many human urinary tract infections. ... Serratia marcescens is a Gram negative bacterium, a human pathogen of the family Enterobacteriaceae. ...

• cefacetrile (Celtol®)
• cefadroxil/cefadroxyl (Baxan®, Bidocef®, Cefadril®, Cefadrox®, Cefroxil®, Ceoxil®, Cephos®, Crenodyn®, Duracef®, Duricef®, Kefroxil®, Longacef®, Moxacef®, Oradroxil®, Ultracef®)
• cefaloridine/cephaloradine (Cefaclox®, Cepalorin®, Ceporan®, Ceporin®, Ceporine®, Dinasint®, Faredina®, Floridin®, Keflodin®, Kefspor®, Latorex®, Lauridin®, Loridine®, Sasperin®)
• cefalexin/cefalexine/cephalexin (Cefanox®, Ceporex®, Keflet®, Keflex®, Keforal®, Keftab®, Keftal®, Lopilexin®)
• cefalothin/cefalotin/cephalothin/cephalotin (Ceporacin®, Keflin®, Seffin®)
• cefapirin/cephapirin (Cefadyl®, Lopitrex®)
• cefatrizine (Cefaperos®, Zanitrin®)
• cefazaflur
• cefazedone (Refosporin®)
• cefazolin/cefazolinecephazolin (Ancef®, Cefacidal®, Cefamezin®, Elzogram®, Gramaxin®, Kefzol®, Zolicef®)
• cefradine/cephradine (Anspor®, Askacef®, Velosef®)
• cefroxadine (Cefthan-DS®, Oraspor®)
• ceftezole (Celoslin®)

Categories: Stub | Cephalosporin antibiotics ... Cefazolin is an antibiotic in the chemical family of Cephalosporin. ... Cefazolin is an antibiotic in the chemical family of Cephalosporin. ...

Second generation cephalosporins

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. Bacteria that are Gram-negative are not stained dark blue or violet by Gram staining, in contrast to Gram-positive bacteria. ... Gram-positive bacteria are those that are stained dark blue or violet by gram staining, in contrast to gram-negative bacteria, which are not affected by the stain. ... Beta-lactamase is a type of enzyme (EC 3. ...

• cefaclor (Ceclor®, Distaclor®, Keflor®, Kefral®, Panacef®, Panoral®)
• cefbuperazone (Keiperazon®, Tomiporan®)
• cefminox (Meicelin®)
• cefonicid/cefonicide (Monocid®)
• cefprozil (Cefzil®)
• cefuroxime axetil (Ceftin®, Elobact®, Kefurox®, Oracef®, Oraxim®, Zinacef®, Zinadol®, Zinat®)
• cefuzonam (Cosmosin®)
• loracarbef (Lorabid®)

Second generation antianaerobe Cephalosporins Cefaclor (brand name Raniclor®) is a 2nd generation cephalosporin antibiotic used to treat certain infections caused by bacteria such as pneumonia and ear, lung, skin, throat, and urinary tract infections. ... Cefprozil, sometimes spelled cefproxil and sold under the brand name Cefzil, is a cephalosporin antibiotic. ... Cefuroxime is an cephalosporin antibiotic that has been widely available in the USA since 1977. ... Loracarbef is a second-generation cephalosporin antibiotic, also called Lorabid. ...

• cefamandole nafate (Kefdole®, Mandol®, Mandokef®)
• cefmetazole/sefmetazole (Cefmeazon®, Cefmetazon®, Zefazone®)
• ceforanide (Precef®)
• cefotetan (Apacef®, Cefotan®, Yamatetan®)
• cefotiam (Cefapicol®, Halospor, Pansporin®, Spizef®)
• cefoxitin/cefoxitine (Mefoxin®, Mefoxitin®)

Cefotetan is an injectable antibiotic of the cephamycin type for prophylaxis and treatment of bacterial infections. ...

Third generation cephalosporins

Third generation cephalosporins have a broad spectrum of activity against enteric gram-negative rods and thus are particularly useful in treating hospital-acquired infections. A nosocomial infection is an infection that is caused by staying in a hospital. ...

• cefcapene pivoxil (Flomox®)
• cefdinir (Cefzon®, Omnicef®)
• cefditoren pivoxil (Spectracef®)
• cefetamet pivoxil (Globocef®)
• cefixime (Cefspan®, Suprax®)
• cefmenoxime (Bestcall®, Tacef®)
• cefodizim/cefodizime (Kenicef®, Opticef®, Timecef®)
• cefoperazone (Cefobid®, Cefoperazin®, Sulperazon®)
• cefotaxime (Cefotax®, Claforan®)
• cefpimizole (Ajicef®)
• cefpodoxime proxetil (Banan®, Vantin®)
• cefsulodin (Pseudocef®, Pseudomonil®, Takesulin®, Tilmapor®)
• cefteram pivoxil (Tomiron®)
• ceftibuten (Cedax®, Procef®, Seftem®)
• ceftiofur (Excenel®, Naxcel®) (*veterinary use*)
• ceftiolene
• ceftizoxime (Cefizox®, Epocelin®)
• ceftriaxone (Rocephin®)
• moxalactam (also called latamoxef) (Latamoxef®, Moxam®, Shiomarin®)

cefoperazone combined with Sulbactam is sold as Sulperazon®. Cefixime is an oral third generation cephalosporin antibiotic. ... Cefotaxime is a third generation intravenous cephalosporin antibiotic. ... Ceftriaxone (trade name Rocephin®) is a third-generation cephalosporin antibiotic. ... Sulbactam is a molecule which is given in combination with beta-lactam antibiotics to overcome beta-lactamase, an enzyme produced by bacteria that destroys the antibiotics. ...

Third generation antipseudomonal Cephalosporins

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

Ceftazidime is an antibiotic which eliminates bacteria that cause many kinds of infections, including lung, skin, bone, joint, stomach, blood, gynecological, and urinary tract infections. ...

Fourth generation cephalosporins

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

• cefepime (Maxipime®)
• cefetecol
• cefoselis sulfate (Wincef®)
• cefozopran (Firstcin®)
• cefpirome (Broact®, Cefrom®, Keiten®)
• cefquinome (Cephaguard®) (*veterinary use*)
• flomoxef (Flumarin®)

This article needs to be cleaned up to conform to a higher standard of quality. ...

Unknown generation cephalosporins

Unknown generation - help needed to place in the correct generation.

• cefaloglycin/cephaloglycin (Kafocin®)
• cefcanel and cefcanel daloxate
• cefluprenam
• cefmatilen

Caution - Possible name confusion

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

• cefcamate (Flomox) <-> flomoxef (Flumarin)

External links

• Cephalosporins College of Health and Life Sciences, Fort Hays State University.

• Cephalosporins "Family Practice Notebook" page on Cephalosporins.

• [1] Chemical Land 21 Cephalosporin class antibiotics