The steroid 5-alpha reductase type-II (SRD5A2) enzyme converts testosterone to dihydrotestosterone (DHT), a more potent androgen implicated in prostate cancer (PC) progression. This study aimed to evaluate the inhibitory potentials of phytoconstituents, identified from anticancer plants, on the SRD5A2 activity. A systematic review was performed to identify previously reported plants as SRD5A2 inhibitors, including their phytoconstituents. Thirty-four phytoconstituents from nine medicinal plants were selected and evaluated alongside the standard SRD5A2 inhibitors (finasteride and dutasteride) by employing in silico techniques, including molecular docking, pharmacokinetics prediction, and toxicity profiling. Among the bioactive compounds evaluated, five compounds exhibited good docking scores, among which gamma-oryzanol showed the highest binding affinity with SRD5A2, with a binding energy of -11.6 Kcal/mol comparable to finasteride. The pharmacokinetics of the top-five compounds were also predicted to be good, suggesting their therapeutic potential in drug development for PC treatment. However, these compounds were predicted to be toxic, which may affect their therapeutic functions and cause further damage to human health. Hence, additional study is recommended to ascertain their toxicities and validate our findings.