Ion-exchange selectivity of diclofenac, ibuprofen, ketoprofen, and naproxen in ureolyzed human urine

Kelly A. Landry, Peizhe Sun, Ching Hua Huang, Treavor Boyer

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

This research advances the knowledge of ion-exchange of four non-steroidal anti-inflammatory drugs (NSAIDs) - diclofenac (DCF), ibuprofen (IBP), ketoprofen (KTP), and naproxen (NPX) - and one analgesic drug-paracetamol (PCM) - by strong-base anion exchange resin (AER) in synthetic ureolyzed urine. Freundlich, Langmuir, Dubinin-Astakhov, and Dubinin-Radushkevich isotherm models were fit to experimental equilibrium data using nonlinear least squares method. Favorable ion-exchange was observed for DCF, KTP, and NPX, whereas unfavorable ion-exchange was observed for IBP and PCM. The ion-exchange selectivity of the AER was enhanced by van der Waals interactions between the pharmaceutical and AER as well as the hydrophobicity of the pharmaceutical. For instance, the high selectivity of the AER for DCF was due to the combination of Coulombic interactions between quaternary ammonium functional group of resin and carboxylate functional group of DCF, van der Waals interactions between polystyrene resin matrix and benzene rings of DCF, and possibly hydrogen bonding between dimethylethanol amine functional group side chain and carboxylate and amine functional groups of DCF. Based on analysis of covariance, the presence of multiple pharmaceuticals did not have a significant effect on ion-exchange removal when the NSAIDs were combined in solution. The AER reached saturation of the pharmaceuticals in a continuous-flow column at varying bed volumes following a decreasing order of DCF>NPX=KTP>IBP. Complete regeneration of the column was achieved using a 5% (m/m) NaCl, equal-volume water-methanol solution. Results from multiple treatment and regeneration cycles provide insight into the practical application of pharmaceutical ion-exchange in ureolyzed urine using AER.

Original languageEnglish (US)
Pages (from-to)510-521
Number of pages12
JournalWater Research
Volume68
DOIs
StatePublished - Jan 1 2015
Externally publishedYes

Fingerprint

Ketoprofen
Naproxen
Anion Exchange Resins
Diclofenac
Ibuprofen
Ion Exchange
urine
ion exchange
Ion exchange
Urine
resin
drug
Resins
Pharmaceutical Preparations
Negative ions
Drug products
Functional groups
functional group
Acetaminophen
Amines

Keywords

  • Coulombic interactions
  • Ion-exchange
  • Non-steroidal anti-inflammatory drugs
  • Pharmaceuticals
  • Urine source separation
  • Van der Waals forces

ASJC Scopus subject areas

  • Water Science and Technology
  • Waste Management and Disposal
  • Pollution
  • Ecological Modeling
  • Medicine(all)

Cite this

Ion-exchange selectivity of diclofenac, ibuprofen, ketoprofen, and naproxen in ureolyzed human urine. / Landry, Kelly A.; Sun, Peizhe; Huang, Ching Hua; Boyer, Treavor.

In: Water Research, Vol. 68, 01.01.2015, p. 510-521.

Research output: Contribution to journalArticle

Landry, Kelly A. ; Sun, Peizhe ; Huang, Ching Hua ; Boyer, Treavor. / Ion-exchange selectivity of diclofenac, ibuprofen, ketoprofen, and naproxen in ureolyzed human urine. In: Water Research. 2015 ; Vol. 68. pp. 510-521.
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AB - This research advances the knowledge of ion-exchange of four non-steroidal anti-inflammatory drugs (NSAIDs) - diclofenac (DCF), ibuprofen (IBP), ketoprofen (KTP), and naproxen (NPX) - and one analgesic drug-paracetamol (PCM) - by strong-base anion exchange resin (AER) in synthetic ureolyzed urine. Freundlich, Langmuir, Dubinin-Astakhov, and Dubinin-Radushkevich isotherm models were fit to experimental equilibrium data using nonlinear least squares method. Favorable ion-exchange was observed for DCF, KTP, and NPX, whereas unfavorable ion-exchange was observed for IBP and PCM. The ion-exchange selectivity of the AER was enhanced by van der Waals interactions between the pharmaceutical and AER as well as the hydrophobicity of the pharmaceutical. For instance, the high selectivity of the AER for DCF was due to the combination of Coulombic interactions between quaternary ammonium functional group of resin and carboxylate functional group of DCF, van der Waals interactions between polystyrene resin matrix and benzene rings of DCF, and possibly hydrogen bonding between dimethylethanol amine functional group side chain and carboxylate and amine functional groups of DCF. Based on analysis of covariance, the presence of multiple pharmaceuticals did not have a significant effect on ion-exchange removal when the NSAIDs were combined in solution. The AER reached saturation of the pharmaceuticals in a continuous-flow column at varying bed volumes following a decreasing order of DCF>NPX=KTP>IBP. Complete regeneration of the column was achieved using a 5% (m/m) NaCl, equal-volume water-methanol solution. Results from multiple treatment and regeneration cycles provide insight into the practical application of pharmaceutical ion-exchange in ureolyzed urine using AER.

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KW - Pharmaceuticals

KW - Urine source separation

KW - Van der Waals forces

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