Care transitions represent a common source of drug errors and confusions. The purpose of our prospective observational study was to assess the prevalence of medication discrepancies at care transitions, along with potentially inappropriate medications and potential drug-drug interactions, in an internal medicine unit of an Italian hospital. Adverse drug reactions that occurred in the 30-day period after the discharge from the hospital were included. A related-samples McNemar test was performed for evaluating the effects of hospitalization on the above-mentioned measures of drug prescribing. Medication discrepancies were frequent both on admission (93.4% [95%CI 0.8749, 0.9713]) and at discharge (78.7% [95%CI 0.7035, 0.8558]), with a significant difference between transition times (-14.7% [95%CI -21.82%, -7.69%]; P < .001)]. A high potentially inappropriate medication use prevalence was revealed without differences between care transitions. Potential drug-drug interactions were more frequent at admission to the hospital, with a significant difference of 8.2% in the distribution of patients with potential drug-drug interactions between care transitions. None of the adverse drug reactions recorded on follow-up was related to unintentional discrepancies, and the prevalence rate of patients with potentially inappropriate medication-related adverse drug reactions ranged between 4.9% and 6.9%, and the prevalence rate of patients with drug-drug interaction-related adverse drug reactions was 4.1% of patients. This study is important to raise awareness of the potential dangers medication discrepancies, potentially inappropriate medications, and potential drug-drug interactions could have on older adults. Clinicians and clinical pharmacologists must collaborate to improve patient care and minimize drug-related clinical outcomes.