Cephalosporin C

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Cephalosporin C
Cephalosporin C.svg
Names
Preferred IUPAC name
(6R,7R)-3-[(Acetyloxy)methyl]-7-[(5R)-5-amino-5-carboxypentanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Other names
7-(5-Amino-5-carboxyvaleramido)cephalosporanic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.456 Edit this at Wikidata
UNII
  • InChI=1S/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/t9-,11-,14-/m1/s1 checkY
    Key: HOKIDJSKDBPKTQ-GLXFQSAKSA-N checkY
  • InChI=1/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/t9-,11-,14-/m1/s1
    Key: HOKIDJSKDBPKTQ-GLXFQSAKBW
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CCC[C@H](C(=O)O)N)COC(=O)C)C(=O)O
Properties
C16H21N3O8S
Molar mass 415.42 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY  (what is checkY☒N ?)
Infobox references

Cephalosporin C is an antibiotic of the cephalosporin class. It was isolated from a fungus of the genus Acremonium and first characterized in 1961.[1] 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.[2] 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.[2] 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.[3]

Mechanism of action[]

Cephalosporin C acts by inhibiting penicillin binding proteins.

Side effects[]

These are allergic reactions to the drug and require medical attention:[3]

  • 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.[2]

Biochemistry[]

Cephalosporin C is the product of the biosynthesis pathway of third generation cephalosporins. This is done by exchanging the acetyl CoA into DAC.[4]

To achieve cephalosporin C as the end product, there are 6 genes reported to be in control of the pathway.[4]

References[]

  1. ^ Abraham, E. P.; Newton, G. G. F. (1961). "Structure of cephalosporin C". Biochemical Journal. 79 (2): 377–393. doi:10.1042/bj0790377. PMC 1205850. PMID 13681080.
  2. ^ a b c Kardos, Nelson; Demain, Arnold L. (November 2011). "Penicillin: the medicine with the greatest impact on therapeutic outcomes". Applied Microbiology and Biotechnology. 92 (4): 677–687. doi:10.1007/s00253-011-3587-6. ISSN 0175-7598. PMID 21964640.
  3. ^ a b "CEPHALOSPORINS - INJECTION side effects, medical uses, and drug interactions". MedicineNet. Retrieved 2019-05-06.
  4. ^ a b Singh, Khusbu; Mohapatra, Pradumna K.; Pati, Sanghamitra; Dwivedi, Gaurav Raj (2019). "Genetics and Molecular Biology of Genes Encoding Cephalosporin Biosynthesis in Microbes". New and Future Developments in Microbial Biotechnology and Bioengineering. pp. 25–34. doi:10.1016/B978-0-444-63503-7.00002-4. ISBN 9780444635037.


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