Chlorprothixene (CPTX) is an antipsychotic drug of the thioxanthene class. Although it is widely used as a tranquillizer in psychiatry, anesthesiology, pediatrics, and in general medical practice, there is a gap in knowledge regarding its occurrence and fate in the environment. Therefore, we provide for the first-time data on the environmental fate and ecotoxicity of CPTX and its potential photo-transformations products (PTPs). Firstly, two standardized biodegradation tests (Closed Bottle test (CBT) and Manometric Respiratory test (MRT)) were performed to assess CPTX's environmental biodegradability. Then, its photodegradability was studied using Xenon and UV lamps. Effects of different conditions (initial drug concentration, pH, and temperature) were applied during UV-photodegradation. Subsequently, the time courses of CPTX and dissolved organic carbon (DOC) concentrations were monitored throughout the photodegradation tests. After that, high-resolution mass spectrometry was employed to elucidate the structures of the formed photo-transformation products (PTPs). In addition, biodegradation tests were performed for the photolytic mixtures to assess the biodegradability of the PTPs. Finally, the (eco)toxicity assessment for CPTX and its photolytic mixtures was predicted using different (quantitative) structure-activity relationship ((Q)SAR) software. CPTX was found to be not readily biodegradable in CBT and MRT. CPTX was not eliminated by irradiation with the Xenon lamp, however primarily eliminated using the UV-lamp. The CPTX elimination during UV-irradiation was faster at lower concentrations. CPTX UV-photodegradation was affected by pH value, while not affected by the temperature of the irradiated solution. 13 PTPs were detected in UV-photolysis mixtures. One additional product was detected in CPTX standard solution, and it was degraded simultaneously with CPTX during UV-irradiation. On one hand, Biodegradation assays revealed that UV-photolytic mixtures of CPTX, containing its PTPs, were not better biodegradable than CPTX itself. On the other hand, LC-MS analysis showed some PTPs which were eliminated after the biodegradation tests indicating possible biodegradability of these PTPs. This because those PTPs are present in low concentrations in the photolysis mixture and their effect can be hindered by the effect of CPTX and other non-biodegradable PTPs. QSAR analysis revealed that CPTX and some of its PTPs may have some human and/or eco-toxic properties. In conclusion, the release of CPTX into aquatic environments could be harmful. Therefore, further research focusing on CPTX and its PTPs are strongly recommended.