Biotransformation of the Fluorinated Nonsteroidal Anti-Inflammatory Pharmaceutical Flurbiprofen in Activated Sludge Results in Accumulation of a Recalcitrant Fluorinated Aromatic Metabolite

Yanac, Kadir
Murdoch, Robert Waller
Flurbiprofen is a fluorinated, nonsteroidal, anti-inflammatory pharmaceutical with potential application in a wide range of maladies. Currently, there is no information regarding its environmental fate. To address this, flurbiprofen is spiked at 500 and 50 ppm into activated sewage sludge taken from the municipal treatment plant of Ankara, Turkey. Flurbiprofen is partially degraded after 80 days, with removal proportion varying from 33% to 48%. Isolation of organisms able to use flurbiprofen as a sole carbon and energy source is unsuccessful. A transient, acid-labile yellow coloration appears in supernatants after addition of flurbiprofen. During disappearance, a novel potential metabolite is detected by high-performance liquid chromatography (HPLC) analyses, a chemical that does not appear in killed controls or in nonflurbiprofen-amended controls. Mass spectra of the novel chemical obtained at low and high collision energies are consistent with 4-(1-carboxyethyl)-2-fluorobenzoic acid, suggesting the application of a canonical metabolic paradigm for halogenated biphenyl metabolism by bacteria in which the nonhalogenated ring is metabolized by dioxygenation and metacleavage, leaving the halogenated aromatic ring behind. This metabolite shows no signs of disappearance after the 80-day monitoring period, implying that the environmental release of flurbiprofen might be of concern.


Biodegradation of the fluorinated non-steroidal anti-inflammatory pharmaceutical flurbiprofen
Yanaç, Kadir; Murdoch, Robert W.; Kentel Erdoğan, Elçin; Department of Environmental Engineering (2016)
Flurbiprofen (FLB) is a fluorinated aromatic acid non-steroidal anti-inflammatory pharmaceutical which is widely consumed in Turkey. However, nothing is known regarding its environmental fate. The aim of this master thesis study was to contribute to the understanding of the biodegradation of flurbiprofen (FLB) by environmental bacteria and to gain understanding of the biological activities of fluorinated aromatics and their tendencies to result in toxic byproducts. FLB was spiked into aerobic sewage sludge ...
Biodegradation of the fluorinated non-steroidal anti-inflammatory pharmaceutical Flurbiprofen by environmental bacterial isolates
Murdoch, Robert Waller(2015-12-31)
Flurbiprofen is a fluorinated non-steroidal anti-inflammatory pharmaceutical. While flurbiprofen is quite popular in Turkey, there is at the present time no information as to how environmental bacteria degrade this chemical. Organisms capable of using flurbiprofen as sole carbon and energy source will be enriched from Ankara municipal sewage treatment plant. Strains will be isolated and identified using molecular methods. The general features of degradation pathways employed by unique strains will be cha...
Biomechanical and histological outcome of combined raloxifene-estrogen therapy on skeletal and reproductive tissues
Tasci, Arzu; BİLGİLİ, HASAN; Altunay, Hikmet; Gecit, Mehmet Rusen; Keskin, Dilek (Elsevier BV, 2010-02-10)
Estrogen replacement is a potent therapy for postmenopausal osteoporosis. However, its carcinogenic effects on breasts and the uterus limit its utilization. Raloxifene has estrogen-like effects on bones without the carcinogenic symptoms on breast or uterine tissue. Their individual effects are well characterized, but the results of their interaction remains elusive. In this work, we investigate the consequences of a combined raloxifene/estrogen therapy on bone and uterus with experimental osteoporosis. 40 W...
Structural and functional effects of non-steroidal anti-inflammatory drugs rofecoxib and valdecoxib on DSPC model membranes
Rachkauska, Richardas; Banerjee, Sreeparna; Severcan, Feride; Department of Biology (2014)
Celecoxib (CLX), rofecoxib (RFX) and valdecoxib (VLX) belong to a family of Non-steroidal anti-inflammatory drugs (NSAIDs), which are selective COX-2 inhibitors. While these drugs are established analgesics, they also have a number of pleiotropic effects such as cancer chemoprevention, occasionally in a COX-2 independent manner. RFX and VLX were withdrawn from the market after clinical trials indicated that use of these drugs enhanced the risk of heart attack and stroke. CLX is currently FDA approved for pa...
Design, synthesis, molecular docking studies and biological evaluation of thiazole carboxamide derivatives as COX inhibitors
Hawash, Mohammed; Jaradat, Nidal; Abualhasan, Murad; ŞÜKÜROĞLU, MURAT KADİR; Qaoud, Mohammed T.; Kahraman, Deniz Cansen; Daraghmeh, Heba; Maslamani, Leen; Sawafta, Mais; Ratrout, Ala; Issa, Linda (2023-12-01)
Background: Nonsteroidal anti-inflammatory drugs (NSAIDs) have been the most commonly used class of medications worldwide for the last three decades. Objectives: This study aimed to design and synthesize a novel series of methoxyphenyl thiazole carboxamide derivatives and evaluate their cyclooxygenase (COX) suppressant and cytotoxic properties. Methods: The synthesized compounds were characterized using 1H, 13C-NMR, IR, and HRMS spectrum analysis and were evaluated for their selectivity towards COX-1 and CO...
Citation Formats
K. Yanac and R. W. Murdoch, “Biotransformation of the Fluorinated Nonsteroidal Anti-Inflammatory Pharmaceutical Flurbiprofen in Activated Sludge Results in Accumulation of a Recalcitrant Fluorinated Aromatic Metabolite,” GLOBAL CHALLENGES, pp. 0–0, 2019, Accessed: 00, 2020. [Online]. Available: