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Cephalosporin C

Cephalosporin C is an antibiotic of the cephalosporin class. It was isolated from a fungus of the genus Acremonium and first characterized in 1961. Although not a very active antibiotic itself, synthetic analogs of cephalosporin C, such as cefalotin, became some of the first marketed cephalosporin antibiotic drugs.

Cephalosporin C strongly absorbs ultraviolet light, is stable to acid, is non-toxic and has in vivo activity in mice. Cephalosporin C, which has a similar structure to penicillin N, was never commercialized.

Cephalosporin C was a lead compound for the discovery and production of many other cephalosporins. Cephalosporins are drugs used for some people who are allergic to penicillin.

Uses

Cephalosporins are used to treat bacterial infections such as respiratory tract infections, skin infections and urinary tract infections. When a cephalosporin or any other antibiotic is given as a treatment, the medication should be taken for the fully prescribed time even if symptoms disappear.

Mechanism of action

Cephalosporin C acts by inhibiting penicillin binding proteins.

Side effects

These are allergic reactions to the drug and require medical attention:

  • itching
  • swelling
  • dizziness
  • rash
  • trouble breathing
  • vomiting
  • severe stomach cramps
  • bloody diarrhea
  • fever
  • weakness
  • fast heartbeat

Chemistry

Cephalosporin C has weak activity to the staphylococci infection, which was 0.1% activity. This decrease in activity was due to the replacement of the D-α-aminoadipic acid side chain with phenylacetic acid.

Biochemistry

Cephalosporin C is the product of a natural biosynthesis pathway that starts with penicillin N (also called adicillin).

Industrial production uses a strain of the fungus Acremonium chrysogenum which has been optimised by molecular biology techniques to give a high yield of cephalosporin C. The enzymes involved are deacetoxycephalosporin-C synthase (DAOCS), deacetoxycephalosporin-C hydroxylase (DACS) and deacetylcephalosporin-C acetyltransferase (DAC-AT).

References