Cephalothin
Title: Cephalothin
CAS Registry Number: 153-61-7
CAS Name: (6R,7R)-3-[(Acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: 3-(hydroxymethyl)-8-oxo-7-[2-(2-thienyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetate; 7-(2-thienylacetamido)cephalosporanic acid; 7-(thiophene-2-acetamido)cephalosporanic acid
Molecular Formula: C16H16N2O6S2
Molecular Weight: 396.44
Percent Composition: C 48.47%, H 4.07%, N 7.07%, O 24.21%, S 16.18%
Literature References: Semi-synthetic cephalosporin antibiotic. Prepn: Chauvette et al., J. Am. Chem. Soc. 84, 3401 (1962); E. H. Flynn, US 3218318 (1965 to Lilly); FR 1384197 (1965 to Glaxo), C.A. 63, 11591c (1965). Bacteriology and pharmacology: Lee, Anderson, Antimicrob. Agents Chemother. 1962, 695; Walters et al., ibid. 706; Naumann, Arzneim.-Forsch. 16, 1099 (1966). Acute toxicity: M. Kuramoto et al., Jpn. J. Antibiot. 27, 746 (1974), C.A. 83, 71972t (1975). Comprehensive description: R. J. Simmons, Anal. Profiles Drug Subs. 1, 319-341 (1972).
Properties: mp 160-160.5°. [a]D20 +50° (c = 1.03 in acetonitrile), see R. B. Woodward et al., J. Am. Chem. Soc. 88, 852 (1966).
Melting point: mp 160-160.5°
Optical Rotation: [a]D20 +50° (c = 1.03 in acetonitrile)
 
Derivative Type: Sodium salt
CAS Registry Number: 58-71-9
Trademarks: Averon-1 (Alfar); Cefalotin; Cemastin (Ist. Vitamine); Cephation (Meiji); Ceporacin (Torii); Cepovenin (Hoechst; Glaxo); Chephalotin (Lilly); Coaxin (Tobishi); Keflin (Lilly); Lospoven (Hoechst); Synclotin (Toyo Jozo); Toricelocin (Torii)
Molecular Formula: C16H15N2NaO6S2
Molecular Weight: 418.42
Percent Composition: C 45.93%, H 3.61%, N 6.70%, Na 5.49%, O 22.94%, S 15.33%
Properties: mp 204-205°. [a]D +135° (c = 1.0 in water). uv max: 236, 260 nm (e 12950, 9350). LD50 in mice, rats (mg/kg): >20000, >10000 orally; 5670, 7716 i.p. (Kuramoto).
Melting point: mp 204-205°
Optical Rotation: [a]D +135° (c = 1.0 in water)
Absorption maximum: uv max: 236, 260 nm (e 12950, 9350)
Toxicity data: LD50 in mice, rats (mg/kg): >20000, >10000 orally; 5670, 7716 i.p. (Kuramoto)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.

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