ABSTRACT
The lincosamides were discovered in the late 1950s (DeBoer et al., 1955). Lincomycin was isolated in 1962 via fermentation from a strain of Streptomyces lincolnensis obtained from a soil sample near Lincoln, Nebraska (Lewis et al., 1962). Although many synthetic and semisynthetic derivatives of the lincosamides exist, only two of them—lincomycin (Lincocin, Lincorex, L-Mycin) and clindamycin (Cleocin, Cleocin Phosphate, Dalacin, Sobelin, Evoclin, Clindesse, Clindagel, Cleocin T)—were developed for clinical practice. Clindamycin, a derivative of lincomycin, is 7-chloro-7-chlorodeoxylin-comyin and differs from lincomycin by the presence of a methoxy group as a replacement for a hydroxyl group at position 7 on the molecule. Pirlimycin hydrochloride (Pirsue), the 4-cis-ethyl-l-pipecolic derivative of clindamycin, is another lincosamide and is currently used in veterinary medicine. The lincosamides are composed of an amino acid unit connected to a sugar via an amide bond. The molecular weights of lincomycin and clindamycin are 406.54 g/mol and 424.98 g/mol, respectively. The chemical formula for lincomycin is C18H34N2O6S and for clindamycin is C18H33CIN2O5S. Their chemical structures are shown in Figure 85.1. Molecular structure of (a) lincomycin and (b) clindamycin. https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/fig85_1.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>
