The case of PMS serves as an illuminating example of the changing characteristics of pharmaceuticalisation and the relationship between pharmaceuticalisation and medicalisation. In this paper, I delineate the changing characteristics of the pharmaceuticals used to treat premenstrual syndrome (PMS), from the physician-centered prescription of progesterone to industry-driven prescription and over-the-counter medications such as Sarafem (an antidepressant) and YAZ (a birthcontrol pill). The medicalization of bodily changes as a new medical category of PMS in gynecology is the starting point of the hormone progesterone as the most popular treatment for almost half a century; while it was promoted by a general practitioner it was never scientifically justified. The pharmaceuticalisation of the mental and emotional aspects of PMS with Prozac marketed as “Sarafem,” motivated by Eli Lilly, leads to a new diagnostic category of premenstrual dysphoric disorder (PMDD), acknowledged by the American Psychiatric Association (APA). Before the 1980s, the medicalization drove the pharmaceuticals used for PMS, while after the early 1980s, the pharmaceuticals drove the medicalizations of the now-multiple syndromes.