THC Science

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
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). verify (what is ?) 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[edit]

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[edit]

Cephalosporin C acts by inhibiting penicillin binding proteins.^{[citation needed]}

Side effects[edit]

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[edit]

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[edit]

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[edit]

^ 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.
^ ^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. S2CID 91263634.

[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.

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