Cephamycin

Group of β-lactam antibiotics

Cephamycins are a group of β-lactam antibiotics. They are very similar to cephalosporins, and the cephamycins are sometimes classified as cephalosporins.

Like cephalosporins, cephamycins are based upon the cephem nucleus. Unlike most cephalosporins, cephamycins are a very efficient antibiotic against anaerobic microbes.^{[citation needed]}

Cephamycins were originally produced by Streptomyces, but synthetic ones have been produced as well.^{[citation needed]}

Cephamycins possess a methoxy group at the 7-alpha position.^[1]

In addition, cephamycins have been shown to be stable against extended-spectrum beta-lactamase (ESBL) producing organisms, although their use in clinical practice is lacking for this indication.^{[citation needed]}

Examples

Cephamycins include:

Cefoxitin^[2]
Cefotetan^[3]
Cefmetazole^[4]

References

^ Oreste A. Mascaretti (2003). Bacteria Versus Antibacterial Agents: An Integrated Approach. American Society Microbiology. p. 144. ISBN 1-55581-258-9.
^ Little PJ, Peddie BA (July 1978). "Clinical use of cefoxitin, a new semisynthetic cephamycin". N. Z. Med. J. 88 (616): 46–9. PMID 279853.
^ Clarke AM, Zemcov SJ (January 1983). "Antibacterial activity of the cephamycin cefotetan: an in-vitro comparison with other beta-lactam antibiotics". J. Antimicrob. Chemother. 11. Suppl: 67–72. doi:10.1093/jac/11.suppl_A.67. PMID 6404881.
^ Benlloch M, Torres A, Soriano F (October 1982). "Cefmetazole (CS-1170): a new cephamycin with activity against gram-negative bacilli and staphylococci". J. Antimicrob. Chemother. 10 (4): 347–50. doi:10.1093/jac/10.4.347. PMID 6958672.

Antibacterials active on the cell wall and envelope (J01C-J01D)

Beta-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡
β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Glycopeptides Lipoglycopeptides	Inhibit PG chain elongation: Vancomycin^# (Oritavancin Telavancin) Teicoplanin (Dalbavancin) Ristocetin^‡ Avoparcin Inhibit autolysin: Corbomycin (not approved)
Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Polymyxins	Bind to LPS in the outer bacterial membrane, acting in detergent-like fashion: Colistin Polymyxin B
Other	Inhibits PG elongation and crosslinking: Ramoplanin^§