Cephalosporin C

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

CAS Number

* 61-24-5 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:15776 Y

ChEMBL |

* ChEMBL482858 Y

ChemSpider |

* 58980 Y

PubChem CID

* 65536

UNII |

* 3XIY7HJT5L Y

InChI

* 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 Y

Key: HOKIDJSKDBPKTQ-GLXFQSAKSA-N Y

* 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

SMILES

* 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

Chemical formula

| 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).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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.

## Contents

* 1 Uses
* 2 Mechanism of action
* 3 Side effects
* 4 Chemistry
* 5 Biochemistry
* 6 References

## 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. PMID 13681080.
2. ↑ 2.0 2.1 2.2 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. ↑ 3.0 3.1 "CEPHALOSPORINS - INJECTION side effects, medical uses, and drug interactions.". https://www.medicinenet.com/cephalosporins-injection/article.htm.
4. ↑ 4.0 4.1 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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*[CID]: Compound ID