Antibiotic resistance (ABR) is a serious global health and economic threat that over the last two decades has seen a dramatic increase in the number of antibiotic resistant bacteria being document within clinical and environmental settings. It has long been recognised that to successfully manage ABR, effective antibiotic stewardship is required that takes a 'one health' approach which recognises that the health of individuals is closely linked to the health of animals and the environment. This requires a collaborative effort of multiple disciplines working together locally, nationally and internationally to attain the optimal health for people, animals and the environment. The environmental dimension of antibiotic resistance has until recently been largely overlooked, with recent studies underlying the importance of the non-clinical setting in the emergence and spread of ABR. While advancements in environmental chemistry have led to the discovery of antibiotics in a number of different environmental compartments such as soil, rivers, and wastewater, with their presence thought to be due to anthropogenic use. The presence of antibiotics within the environment alongside antibiotic resistance genes (ARGs) has led to an increasing awareness that these antibiotics may be selecting for antibiotic resistance within the environment. There are several different pathways for antibiotics to enter the environment but through our sewage system is one of major concern leading to antibiotics alongside ARGs being considered emerging contaminants within the wastewater sector. With this in mind, there is a need to develop robust and fit for purpose environmental risk assessments for antibiotics in wastewater. However, to do so, we need to understand their fate within the urban water cycle and their role in the development of antibiotic resistance. It to this knowledge that the research carried out as part of this thesis hopes to add to. First through investigating the fluxes of antibiotics and ARGS in a wastewater catchment level to increase the understanding of the roles WWTPs play in the dissemination and spread of antibiotic resistance. Secondly through exploring the role stereochemistry plays in antibiotic resistance and the fate of antibiotics within the urban water cycle.