Cited by 66Water Treatment and DisinfectionPharmaceutical and Antibiotic Environmental ImpactsAdvanced oxidation water treatment

Transformation of Tamoxifen and its Major Metabolites During Water Chlorination: Identification and in Silico Toxicity Assessment of Their Disinfection Byproducts

Negreira, Noelia, Regueiro, Jorge, López de Alda, Miren, Barceló, Damià·2015·Water Research

Abstract

The selective estrogen receptor modulator tamoxifen is the most commonly used drug for the treatment and prevention of breast cancer. Tamoxifen is considered as a pro-drug since it is known to exert its pharmacological effect through its major active metabolites, 4-hydroxy-tamoxifen and 4-hydroxy-N-desmethyl-tamoxifen, which are mainly excreted in the urine in the days following administration. In the present work, the reactivity of tamoxifen and its major active metabolites in free chlorine-containing water was investigated for the first time. Under the studied chlorination conditions, tamoxifen was fairly stable whereas its metabolites were quickly degraded. A total of thirteen chlorinated byproducts were tentatively identified by ultra-high performance liquid chromatography coupled to high-resolution hybrid quadrupole-Orbitrap tandem mass spectrometry. Time-course profiles of the identified byproducts were followed in real wastewater samples under conditions that simulate wastewater disinfection. A preliminary assessment of their acute aquatic toxicity at two trophic levels by means of quantitative structure-activity relationship models showed that the identified byproducts were up to 110-fold more toxic than the parent compounds.

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Crossref · 10.1016/j.watres.2015.08.036

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Authors
Negreira, N., Regueiro, J., López de Alda, M., & Barceló, D.
Affiliations
  • Institute of Environmental Assessment and Water Research (ES)
  • Universidade de Vigo (ES)
  • Universitat de Girona (ES)
Venue
Water Research
Publisher
Elsevier BV
Published
2015-11
Volume
85
Pages
199-207
ISSN
0043-1354 (ISSN-L)
OpenAlex
W1661314417
Cited by
66
References
39
Citations by year
2026: 1 · 2025: 5 · 2024: 4 · 2023: 4 · 2022: 6 · 2021: 8 · 2020: 13 · 2019: 3 · 2018: 4 · 2017: 9 · 2016: 7 · 2015: 1
FWCI
4.38
Type
journal article
Language
en
Open access
closed
Locations
  • Water Research (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • CYTOTHREAT (265264)
  • SOLUTIONS (603437)
  • Generalitat de Catalunya (2014 SGR 418—Water and Soil Quality Unit, 2014 SGR 291—ICRA)
Topics
  • Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Water Treatment and Disinfection
  • Physical Sciences › Environmental Science › Pollution › Pharmaceutical and Antibiotic Environmental Impacts
  • Physical Sciences › Environmental Science › Water Science and Technology › Advanced oxidation water treatment
Keywords
tamoxifen, chlorination by-products, free chlorine, drug degradation, wastewater disinfection, aquatic toxicity, QSAR, estrogen receptor modulators, drug metabolites
MeSH terms
Chromatography, High Pressure Liquid, Disinfection, Tamoxifen, Water Pollutants, Chemical, Water Purification, Quantitative Structure-Activity Relationship, Tandem Mass Spectrometry, Halogenation

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