Cephalosporin C

Cephalosporin C
Names
	IUPAC name 3-[(Acetyloxy)methyl]-7β-(N6-L-homoglutamino)-3,4-didehydrocepham-4-carboxylic acid
	Systematic 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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15776 ;
ChEMBL	ChEMBL482858 ;
ChemSpider	58980 ;
ECHA InfoCard	100.000.456
KEGG	C00916;
PubChem CID	65536;
UNII	3XIY7HJT5L ;
CompTox Dashboard (EPA)	DTXSID90960427 ;
	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 Key: HOKIDJSKDBPKTQ-GLXFQSAKSA-N ; 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). 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 a natural biosynthesis pathway that starts with penicillin N (also called adicillin).^[4]

penicillin N

DAOCS

deacetoxycephalosporin C

DACS

deacetylcephalosporin C

DAC-AT

cephalosporin C

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).^[5]

References

^ 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.
^ ^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. S2CID 39223087.
^ ^a ^b "CEPHALOSPORINS - INJECTION side effects, medical uses, and drug interactions". MedicineNet. Retrieved 2019-05-06.
^ 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. S2CID 91263634.
^ Liu, Ling; Chen, Zhen; Liu, Wuyi; et al. (2022). "Cephalosporin C biosynthesis and fermentation in Acremonium chrysogenum". Applied Microbiology and Biotechnology. 106 (19–20): 6413–6426. doi:10.1007/s00253-022-12181-w. PMID 36114850.

[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.

[:0-2] 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. S2CID 39223087.

[:1-3] "CEPHALOSPORINS - INJECTION side effects, medical uses, and drug interactions". MedicineNet. Retrieved 2019-05-06.

[:2-4] 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. S2CID 91263634.

[5] Liu, Ling; Chen, Zhen; Liu, Wuyi; et al. (2022). "Cephalosporin C biosynthesis and fermentation in Acremonium chrysogenum". Applied Microbiology and Biotechnology. 106 (19–20): 6413–6426. doi:10.1007/s00253-022-12181-w. PMID 36114850.

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