This study evaluated the chronic impact and biodegradability of sulfamethoxazole under anaerobic conditions. For this purpose, a lab-scale anaerobic sequencing batch reactor was operated in a sequence of different phases with gradually increasing sulfamethoxazole doses of 1 to 45 mg/L. Conventional parameters, such as COD, VFA, and methane generation, were monitored with corresponding antimicrobial concentrations in the reactor and the methanogenic activity of the sludge. The results revealed that anaerobic treatment was suitable for pharmaceutical industry wastewater with concentrations of up to 40 mg/L of sulfamethoxazole. Higher levels exerted toxic effects on themicrobial community under anaerobic conditions, causing the inhibition of substrate/COD utilization and biogas generation and leading to a total collapse of the reactor. The adverse long-term impact was quite variable for fermentative bacteria and methanogenic achaea fractions of the microbial community based on changes inflicted on the composition of the residual organic substrate and mRNA expression of the key enzymes. (C) 2015 Elsevier B.V. All rights reserved.