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Amphenichols synthesis and antibacterial activity

Chloramphenicol was one of the first therapeutically useful antibiotics to appear from systematic screening of Streptomyces strains in the 1940s. Although it is a naturally occurring compound it is a relatively simple molecule that can readily be synthesized. Attempts to modify the structure have generally resulted in a marked loss of activity, but thiamphenicol, a compound in which a sulphomethyl group replaces the nitro group of chloramphenicol, displays comparable antibacterial activity.

Pure chloramphenicol is insoluble in water and tastes extremely bitter. These problems have been overcome preparing prodrugs of the antibiotic: chloramphenicol palmitate and stearate to improve palatability and chloramphenicol succinate to improve solubility for injection.

 

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