To assess the effectiveness of the use of dexketoprofen, tamsulosin, silodosin, and tadalafil in medical expulsive therapy for distal ureteral stones in male patients. Cohort study. Department of Urology, Gazi Hospital, Samsun, Turkey, from March 2020 to March 2021. Adult males satisfying the inclusion criteria were randomly assigned into dexketoprofen (Group 1), tamsulosin (Group 2), silodosin (Group 3), or tadalafil (Group 4) treatment arms. The primary endpoint consisted of the stone expulsion rate at the end of four weeks, while the secondary endpoints were the expulsion rate after two weeks and the occurrence of adverse events. Clinical findings were then compared among the study groups. Altogether 193 patients, 50 (25.9%) in group 1, 48 (24.9%) in group 2, 49 (25.4%) in group 3, and 46 (23.8%) in group 4, were enrolled in the study. No significant difference was determined in terms of age, body mass index, stone characteristics, expulsion time, pain episodes, or total analgesic consumption among the four groups. Expulsion rates in the fourth week were 48%, 79.2%, 81.6%, and 78.3% in groups 1, 2, 3, and 4, respectively. Stone expulsion rates were significantly greater in groups 2, 3, and 4 compared to group 1 (p <0.001), but no significant differences were determined between groups 2, 3, and 4. No severe adverse effects occurred throughout the study period. Tamsulosin, silodosin and tadalafil exhibited higher expulsion rates for distal ureteral stones in male patients, although none was significantly superior to the others. All three are safe, efficacious, and well-tolerated, with only very minor side-effects. Key Words: Dexketoprofen, Distal ureteral stones, Medical expulsive therapy, Silodosin, Tadalafil, Tamsulosin.