The role-play for pharmacological education has been developed by Yanagita et al. since 2010. This case and communication based active learning course provides the fundamental skills for pharmacotherapy including appropriate drug prescriptions and communication to achieve behavioral modification in patients, through a role playing of medical professionals and patients in simulated clinical settings. The conventional role-play requires a face-to-face environment to run the course based on direct communication and interaction between students. However, COVID-19 forces us to transit from on-campus classes to off-campus online courses from April 2020. We performed an online role-play for the first time at Tohoku Medical and Pharmaceutical University Faculty of Medicine during the state of emergency in Japan. In this presentation, we will describe the course design, preparation, and operation of the online role-play for pharmacological education. We will explain how it was transformed and developed from the conventional composition to the online setting. We will also describe the differences, advantages, and disadvantages of the online setting. Finally, we give examples of on-going challenges to the effective use of the online role-play as a core curricular model of pharmacological and pharmacotherapeutic education.