Cephalosporin C

Title: Cephalosporin C
CAS Registry Number: 61-24-5
CAS Name: (6R,7R)-3-[(Acetyloxy)methyl]-7-[[(5R)-5-amino-5-carboxy-1-oxopentyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: 7-(D-5-amino-5-carboxyvaleramido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetate
Molecular Formula: C16H21N3O8S
Molecular Weight: 415.42
Percent Composition: C 46.26%, H 5.10%, N 10.12%, O 30.81%, S 7.72%
Literature References: Antibiotic substance produced along with penicillin N by a Cephalosporium sp. cultivated from sea water near a sewage outlet on the coast of Sardinia: G. Brotzu, Lav. Ist. Igiene Cagliari (1948); Newton, Abraham, Nature 175, 548 (1955); eidem, Biochem. J. 62, 651 (1956); eidem, DE 1014711 (1957 to Natl. Res. Dev. Corp.); GB 810196 (1959); Kelly et al., US 3082155 (1963 to Natl. Res. Dev. Corp.); Demain, US 3116216; US 3116217 (both 1963 to Merck & Co.). Biosynthesis: Demain, Newkirk, Appl. Microbiol. 10, 321 (1962). Has the same side chain as penicillin N, but the nucleus is different and is named 7-aminocephalosporanic acid: Jago, Heatley, Br. J. Pharmacol. 16, 170 (1961). Structure: Abraham, Newton, Biochem. J. 79, 377 (1961); Hodgkin, Maslen, ibid. 393. In cephalosporin CA the acetoxy group is replaced by a pyridinium group: Hale et al., ibid. 403. Transformation to cephalosporin CC for which greater activity is claimed: Abraham et al., US 3049541 (1962 to Natl. Res. Dev. Corp.). Total synthesis: Woodward et al., J. Am. Chem. Soc. 88, 852 (1966). Review of cephalosporin C and related compounds: Abraham, Q. Rev. Chem. Soc. 21, 231 (1967); Abraham, Loder, in Cephalosporins and Penicillins, E. H. Flynn, Ed. (Academic Press, New York, 1972) pp 1-26.
Derivative Type: Sodium salt, dihydrate
Molecular Formula: C16H20N3NaO8S.2H2O
Molecular Weight: 473.43
Percent Composition: C 40.59%, H 5.11%, N 8.88%, Na 4.86%, O 33.79%, S 6.77%
Properties: Monoclinic crystals from dil alc. [a]D20 +103° (H2O). uv max: 260 nm (E1%1cm 200). pKa values: <2.6, 3.1, 9.8. Sol in water. Practically insol in ethanol, ether. Aq solns are stable at pH 2.5 to 8. Low toxicity. Shows in vitro activity against penicillin-resistant staphylococci.
pKa: pKa values: <2.6, 3.1, 9.8
Optical Rotation: [a]D20 +103° (H2O)
Absorption maximum: uv max: 260 nm (E1%1cm 200)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cephalosporin P1 Cephamycins Cephapirin Sodium Cepharanthine Cephradine

Cephalosporin C
Cephalosporin C.svg
Identifiers
CAS number 61-24-5 YesY
PubChem 65536
ChemSpider 58980 YesY
ChEBI CHEBI:15776 YesY
ChEMBL CHEMBL482858 YesY
Jmol-3D images Image 1
Properties
Molecular formula C16H21N3O8S
Molar mass 415.42 g mol−1
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Except where noted otherwise, 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 fungi 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.