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(1989) Mechanistic studies of the metabolic chiral inversion of (R)-ibuprofen in humans. J
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165. Hao H, Wang G, Sun J (2005) Enantioselective pharmacokinetics of ibuprofen and involved
mechanisms. Drug Metab Rev 37:215–234. https://doi.org/10.1081/dmr-200047999
166. Buser HR, Poiger T, Muller MD (1999) Occurrence and environmental behavior of the chiral
pharmaceutical drug ibuprofen in surface waters and in wastewater. Environ Sci Technol
33:2529–2535. https://doi.org/10.1021/es981014w
167. Khan SJ, Wang L, Hashim NH, Mcdonald JA (2014) Distinct enantiomeric signals of
ibuprofen and naproxen in treated wastewater and sewer overflow. Chirality 26:739–746.
https://doi.org/10.1002/chir.22258
168. Camacho-Muñoz D, Kasprzyk-Hordern B (2015) Multi-residue enantiomeric analysis of
human and veterinary pharmaceuticals and their metabolites in environmental samples by
chiral liquid chromatography coupled with tandem mass spectrometry detection. Anal Bioanal
Chem 407:9085–9104. https://doi.org/10.1007/s00216-015-9075-6
169. Moeder M, Schrader S, Winkler M, Popp P (2000) Solid-phase microextraction-gas
chromatography-mass spectrometry of biologically active substances in water samples. J
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170. Winkler M, Lawrence JR, Neu TR (2001) Selective degradation of ibuprofen and clofibric acid
in two model river biofilm systems. Water Res 35:3197–3205. https://doi.org/10.1016/S00431354(01)00026-4
171. Żur J, Piński A, Marchlewicz A, Hupert-Kocurek K, Wojcieszyńska D, Guzik U (2018)
Organic micropollutants paracetamol and ibuprofen – toxicity, biodegradation, and genetic
background of their utilization by bacteria. Environ Sci Pollut Res 25:21498–21524. https://
doi.org/10.1007/s11356-018-2517-x
172. Chen Y, Rosazza JPN (1994) Microbial transformation of ibuprofen by a Nocardia species.
Appl Environ Microbiol 60:1292–1296. https://doi.org/10.1128/aem.60.4.1292-1296.1994
173. Marco-Urrea E, Pérez-Trujillo M, Vicent T, Caminal G (2009) Ability of white-rot fungi to
remove selected pharmaceuticals and identification of degradation products of ibuprofen by
Trametes versicolor. Chemosphere 74:765–772. https://doi.org/10.1016/j.chemosphere.2008.
10.040
174. Lin AY-C, Plumlee MH, Reinhard M (2006) Natural attenuation of pharmaceuticals and
alkylphenol polyethoxylate metabolites during river transport: photochemical and biological
transformation. Environ Toxicol Chem 25:1458. https://doi.org/10.1897/05-412R.1
175. Ashfaq M, Nawaz Khan K, Saif Ur Rehman M, Mustafa G, Faizan Nazar M, Sun Q, Iqbal J,
Mulla SI, Yu CP (2017) Ecological risk assessment of pharmaceuticals in the receiving
environment of pharmaceutical wastewater in Pakistan. Ecotoxicol Environ Saf 136:31–39.
https://doi.org/10.1016/j.ecoenv.2016.10.029
176. Calderón-Preciado D, Matamoros V, Bayona JM (2011) Occurrence and potential crop uptake
of emerging contaminants and related compounds in an agricultural irrigation network. Sci
Total Environ 412–413:14–19. https://doi.org/10.1016/j.scitotenv.2011.09.057
177. Sanyal AK, Roy D, Chowdhury B, Banerjee AB (1993) Ibuprofen, a unique anti-inflammatory
compound with antifungal activity against dermatophytes. Lett Appl Microbiol 17:109–111.
https://doi.org/10.1111/j.1472-765X.1993.tb01436.x
178. Elvers KT, Wright SJL (1995) Antibacterial activity of the anti-inflammatory compound
ibuprofen. Lett Appl Microbiol 20:82–84. https://doi.org/10.1111/j.1472-765X.1995.
tb01291.x
179. Hussein A, AL-Janabi S (2010) In Vitro antibacterial activity of ibuprofen and acetaminophen.
J Glob Infect Dis 2:105. https://doi.org/10.4103/0974-777x.62880
180. Lawrence JR, Swerhone GDW, Wassenaar LI, Neu TR (2005) Effects of selected pharmaceuticals on riverine biofilm communities. Can J Microbiol 51:655–669. https://doi.org/10.
1139/w05-047
292
S. Gallego and F. Martin-Laurent
(1989) Mechanistic studies of the metabolic chiral inversion of (R)-ibuprofen in humans. J
Pharmacol Exp Ther 249:517–523
165. Hao H, Wang G, Sun J (2005) Enantioselective pharmacokinetics of ibuprofen and involved
mechanisms. Drug Metab Rev 37:215–234. https://doi.org/10.1081/dmr-200047999
166. Buser HR, Poiger T, Muller MD (1999) Occurrence and environmental behavior of the chiral
pharmaceutical drug ibuprofen in surface waters and in wastewater. Environ Sci Technol
33:2529–2535. https://doi.org/10.1021/es981014w
167. Khan SJ, Wang L, Hashim NH, Mcdonald JA (2014) Distinct enantiomeric signals of
ibuprofen and naproxen in treated wastewater and sewer overflow. Chirality 26:739–746.
https://doi.org/10.1002/chir.22258
168. Camacho-Muñoz D, Kasprzyk-Hordern B (2015) Multi-residue enantiomeric analysis of
human and veterinary pharmaceuticals and their metabolites in environmental samples by
chiral liquid chromatography coupled with tandem mass spectrometry detection. Anal Bioanal
Chem 407:9085–9104. https://doi.org/10.1007/s00216-015-9075-6
169. Moeder M, Schrader S, Winkler M, Popp P (2000) Solid-phase microextraction-gas
chromatography-mass spectrometry of biologically active substances in water samples. J
Chromatogr A 873:95–106. https://doi.org/10.1016/S0021-9673(99)01256-X
170. Winkler M, Lawrence JR, Neu TR (2001) Selective degradation of ibuprofen and clofibric acid
in two model river biofilm systems. Water Res 35:3197–3205. https://doi.org/10.1016/S00431354(01)00026-4
171. Żur J, Piński A, Marchlewicz A, Hupert-Kocurek K, Wojcieszyńska D, Guzik U (2018)
Organic micropollutants paracetamol and ibuprofen – toxicity, biodegradation, and genetic
background of their utilization by bacteria. Environ Sci Pollut Res 25:21498–21524. https://
doi.org/10.1007/s11356-018-2517-x
172. Chen Y, Rosazza JPN (1994) Microbial transformation of ibuprofen by a Nocardia species.
Appl Environ Microbiol 60:1292–1296. https://doi.org/10.1128/aem.60.4.1292-1296.1994
173. Marco-Urrea E, Pérez-Trujillo M, Vicent T, Caminal G (2009) Ability of white-rot fungi to
remove selected pharmaceuticals and identification of degradation products of ibuprofen by
Trametes versicolor. Chemosphere 74:765–772. https://doi.org/10.1016/j.chemosphere.2008.
10.040
174. Lin AY-C, Plumlee MH, Reinhard M (2006) Natural attenuation of pharmaceuticals and
alkylphenol polyethoxylate metabolites during river transport: photochemical and biological
transformation. Environ Toxicol Chem 25:1458. https://doi.org/10.1897/05-412R.1
175. Ashfaq M, Nawaz Khan K, Saif Ur Rehman M, Mustafa G, Faizan Nazar M, Sun Q, Iqbal J,
Mulla SI, Yu CP (2017) Ecological risk assessment of pharmaceuticals in the receiving
environment of pharmaceutical wastewater in Pakistan. Ecotoxicol Environ Saf 136:31–39.
https://doi.org/10.1016/j.ecoenv.2016.10.029
176. Calderón-Preciado D, Matamoros V, Bayona JM (2011) Occurrence and potential crop uptake
of emerging contaminants and related compounds in an agricultural irrigation network. Sci
Total Environ 412–413:14–19. https://doi.org/10.1016/j.scitotenv.2011.09.057
177. Sanyal AK, Roy D, Chowdhury B, Banerjee AB (1993) Ibuprofen, a unique anti-inflammatory
compound with antifungal activity against dermatophytes. Lett Appl Microbiol 17:109–111.
https://doi.org/10.1111/j.1472-765X.1993.tb01436.x
178. Elvers KT, Wright SJL (1995) Antibacterial activity of the anti-inflammatory compound
ibuprofen. Lett Appl Microbiol 20:82–84. https://doi.org/10.1111/j.1472-765X.1995.
tb01291.x
179. Hussein A, AL-Janabi S (2010) In Vitro antibacterial activity of ibuprofen and acetaminophen.
J Glob Infect Dis 2:105. https://doi.org/10.4103/0974-777x.62880
180. Lawrence JR, Swerhone GDW, Wassenaar LI, Neu TR (2005) Effects of selected pharmaceuticals on riverine biofilm communities. Can J Microbiol 51:655–669. https://doi.org/10.
1139/w05-047
292
S. Gallego and F. Martin-Laurent