ABSTRACT

Eravacycline (also known as TP-434) is a novel fluorocycline antibiotic developed via a totally synthetic methodology, initially reported by Charest et al. (2005) and subsequently expanded by Tetraphase Pharmaceuticals (Xiao et al., 2012; Clark et al., 2012; Ronin et al., 2013). The term fluorocycline has been used to represent the broader class of 7-fluoro-6-demethyl-6-deoxytetracyclines. Eravacycline is a synthetic analog of the molecules of this class, made via modifications on the D-ring of the core tetracycline scaffold (four benzene rings), including incorporation of a fluorine atom at position C-7 and a pyrrolidinoacetamido group at C-9. Consequently, eravacycline has a chemical formula of 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline, a molecular formula of C27H31FN4O8, and a molecular weight of 558.6. The chemical structure of eravacycline is shown in Figure 72.1. Chemical structure of eravacycline. https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/fig72_1.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>