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- W2166220054 abstract "The kinetics and mechanism of degradation of the antibiotic clindamycin were studied in buffered aqueous solution in the pH range 0.4-12. Clindamycin showed maximum stability at pH 3-5; however, high temperature studies indicated that not more than 10% degradation will occur in the pH range 1-6.5 after two years at 25°. In the pH range 0.4-4 the major degradative pathway was hydrolysis of the thioglycoside linkage to form 1-dethiomethyl-1-hydroxy clindamycin and methyl mercaptan. The major degradative pathway in the pH range 5-10 was scission of the 7-(S)-Cl of clindamycin to form the 7-(R)-OH analog, lincomycin. Evidence was obtained that supports the hypothesis that this conversion to lincomycin proceeds through an oxazolonium intermediate and that the extent of conversion depends on the degree of protonation of the amine function of clindamycin. The activation energy for clindamycin degradation in 0.1 M HCl, where thioglycoside hydrolysis is predominant, is 38.0 ± 1.2 kcal./mole, and the activation energy in 0.2 M citrate buffer adjusted to pH 5, where conversion to lincomycin is predominant, is 29.1 ± 0.6 kcal./mole." @default.
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- W2166220054 date "1970-01-01" @default.
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- W2166220054 title "Aqueous Stability of Clindamycin" @default.
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- W2166220054 doi "https://doi.org/10.1002/jps.2600590110" @default.
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