ABSTRACT
Apricitabine (BCH-10618, SPD754, and AVX754) is a deoxycytidine nucleoside reverse transcriptase inhibitor (NRTI), the (–)-enantiomer of the heterosubstituted analog 2′-deoxy-3′-oxa-4′-thiocytidine; molecular formula C8H11N3O3S (De Muys et al., 1999; Taylor et al., 2000; Figure 234.1). Apricitabine is structurally similar to lamivudine, but differs in the inversion of the oxygen and sulfur in the furanosyl ring. Apricitabine has a molecular weight of 229.26 (1 μΜ = 0.229 μg/ml) (Wainberg et al., 2007). The drug was developed by Avexa, Ltd. (Melbourne, Australia); development ceased in May 2010 due to lack of funds, after the results from a phase IIb study failed to show apricitabine’s superiority to lamivudine and after unsuccessful partnering negotiations with other companies. The inability of Avexa to obtain further funding for apricitabine development may also have been due to waning commercial interest in drugs of this class, given the spectrum of antiretroviral drugs already available in 2010–2011. Apricitabine also required twice-daily dosing at relatively high drug levels compared to lamivudine. Molecular structure of apricitabine. https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/fig234_1.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>
