Surotomycin

Surotomycin (CB-183,315; MK-4261) belongs to the lipopeptides and is a semisynthetic derivate cyclic tail analogue of daptomycin (see Chapter 45, Daptomycin) designed specifically to improve the activity against Clostridium difficile (Yin et al., 2015). It has the same peptide sequence as daptomycin but has an aromatic ring containing an unsaturated lipid tail, (E)-3-(4-pentylphenyl) but-2-enoic acid tail. The molecular formula for surotomycin is C₇₇H₁₀1N₁₇O₂₆ with a corresponding molecular weight of 1680.7 g/mol (PubChem, 2016). The molecular structure of surotomycin is depicted in Figure 50.1. Its mechanism of action is similar to that of daptomycin, cell membrane depolarization leading ultimately to cell death (Mascio et al., 2012). It was developed by Cubist Pharmaceuticals but is now owned by Merck & Co. (North Wales, PA). Figure 50.1 Molecular structure of surotomycin. https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/fig50_1.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>