In Japan, getting prescription medications is a time-consuming and labor-intensive manual process, and purchasing prescription medications through the Internet is highly restrained by the law. In the context of Japan, such a sophisticated process leads to a series of problems for the whole healthcare ecosystem beyond inconvenience. The long-existing National Health Insurance (NHI) system insures every citizen's medical cost with an age-dependent policy, and the elders generally enjoy a high coverage rate. Since Japan has a well-known aging society, this sophisticated process has led to a financial problem for the government. Furthermore, the illicit online pharmacy websites that sell counterfeit medications expose safety risks to the patients, and it is difficult for the government to call to account. To take a measure on these problems, this paper explores digital pharmacies as a solution and evaluates the potential outcomes. Based on the literature review and case study of Computerized Physician Order Entry (CPOE) applications in the U.S., the authors conclude that a regulated digital pharmacy industry (RDP) could improve patients’ outcomes and alleviate the financial pressure. As a result, the paper proposes to implement digital pharmacies with regulations as an innovative change that aligns with the recently developed digitalization technologies.