One of the most recognized methods to evaluate usability in software applications is the heuristic evaluation. In this inspection method, Nielsen's heuristics, are the most widely used evaluation instrument. However, there is evidence in the literature which establishes that these heuristics are not appropriate when they are used to measure the level of usability of new emerging categories of software applications. This paper presents a case study where this concept is verified for Transactional Web Sites. Therefore, given the present limitations, a new set of usability heuristics was proposed following a structured and systematic methodology. Finally, fifteen new usability heuristics were obtained as final product of this research. A validation phase allowed to contrast this new proposal with the Nielsen's principles under a real context, where a heuristic evaluation was performed to a Transactional Web Site. The results established that the new set of usability heuristics, which is presented in this study, provides more accurate and promising results than the current proposal of Nielsen. © 2014 IEEE.