The original lincosamide, lincomycin, a naturally occurring product of Streptomyces lincolnensis, has been superseded by clindamycin (7-chloro-7-deoxylincomycin; Fig. 1), which exhibits improved antibacterial activity.
This class include: Clindamycin, Lincomycin, Pirlimycin.
Figure 1. Chemical structure of clindamycin
Lincosamides interfere with the process of peptide elongation in a way that has not been precisely defined. The ribosomal binding site is probably similar to that of erythromycin, since resistance to erythromycin caused by methylation of the ribosomal binding site affects lincosamides as well.
Lincomycin and clindamycin possess good antistaphylococcal and antistreptococcal activity and have proved therapeutically useful in the treatment of infections due to Bacteroides fragilis and some other anaerobes. Enterobacteria and P. aeruginosa are not affected. Clindamycin exhibits some activity against parasitic protozoa and has been used in toxoplasmosis, malaria, and babesiosis.
Clindamycin hydrochloride, like chloramphenicol, is extremely bitter. For oral administration the drug is formulated in capsules or as the biologically inactive palmitate, which liberates the parent compound in vivo. Clindamycin phosphate is the soluble prodrug used for intravenous administration.
Patients treated with clindamycin (or lincomycin) may develop Clostrdium difficile associated diarrhoea. Other antibiotics, like ampicillin and broad-spectrum cephalosporins, may also cause this side effect, but the incidence of toxin-associated colitis appears to be higher following clindamycin therapy.
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