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...
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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...
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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...
Metformin – Cisplatin Combination Treatment Alters mRNA Expression of Hexokinase II Gene in LNCaP and PC3 Prostate Cancer Cell Lines
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Metformin is an antidiabetic drug with anticancer properties. Cisplatin is known as one of the most potent chemotherapeutics for treatment of various types of cancer. In order to overcome cisplatin resistance and toxicity, the drug can be combined with other chemotherapeutics that sensitize tumour cells to cisplatin. The ability of metformin to potentiate cisplatin-mediated killing of cancer cells in vitro, makes it a plausible candidate for combination with cisplatin-based therapy. The aim of this study is...
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: