Cephalothin: hydrolysis of the C-3'-acetoxy moiety of a 7-aminocephalosporanic acid; observation of both acyl-oxygen bond cleavage and reversible alkyl-oxygen bond cleavage

The aqueous solution chemistry of the C-3'-acetoxy moiety of cephalothin sodium (1b) was examined with the use of isotopically labeled H2(18)O and [2-13C]acetate anion. The 18O incorporation studies indicate that the hydrolysis (at pH 4.7 +/- 0.1) of 1b to the deacetyl derivative of cephalothin...

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Bibliographic Details
Published inJournal of pharmaceutical sciences Vol. 74; no. 11; p. 1162
Main Authors Indelicato, J M, Engel, G L, Occolowitz, J L
Format Journal Article
LanguageEnglish
Published United States 01.11.1985
Subjects
Cephalosporins - analysis
Cephalothin - analysis
Chemical Phenomena
Chemistry
Crystallization
Dealkylation
Hydrolysis
Magnetic Resonance Spectroscopy
Mass Spectrometry
Oxygen - analysis
Oxygen Radioisotopes
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Summary:The aqueous solution chemistry of the C-3'-acetoxy moiety of cephalothin sodium (1b) was examined with the use of isotopically labeled H2(18)O and [2-13C]acetate anion. The 18O incorporation studies indicate that the hydrolysis (at pH 4.7 +/- 0.1) of 1b to the deacetyl derivative of cephalothin (2b) proceeds via two pathways: alkyl-oxygen bond cleavage (55-63%) and acyl-oxygen bond cleavage accounting for the remainder. The incorporation of [2-13C]acetate into 1b suggests that the alkyl-oxygen cleavage pathway is a reversible reaction.
ISSN:0022-3549
DOI:10.1002/jps.2600741106