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Characterization of naproxen salts with amino acid esters and their application in topical skin preparations.
Swiatek, Ewelina; Janus, Ewa; Ossowicz-Rupniewska, Paula; Nowak, Anna; Duchnik, Wiktoria; Kucharski, Lukasz; Adamiak-Giera, Urszula; Lendzion-Bielun, Zofia.
Afiliación
  • Swiatek E; Ossowicz-Rupniewska, Faculty of Chemical Technology and Engineering, Department of Chemical Organic Technology and Polymeric Materials, West Pomeranian University of Technology in, Szczecin, Pulaskiego, 10, PL-70322 Szczecin, Poland. Electronic address: ewelina.swiatek@zut.edu.pl.
  • Janus E; Ossowicz-Rupniewska, Faculty of Chemical Technology and Engineering, Department of Chemical Organic Technology and Polymeric Materials, West Pomeranian University of Technology in, Szczecin, Pulaskiego, 10, PL-70322 Szczecin, Poland.
  • Ossowicz-Rupniewska P; Ossowicz-Rupniewska, Faculty of Chemical Technology and Engineering, Department of Chemical Organic Technology and Polymeric Materials, West Pomeranian University of Technology in, Szczecin, Pulaskiego, 10, PL-70322 Szczecin, Poland.
  • Nowak A; Department of Cosmetic and Pharmaceutical, ChemistryPomeranian Medical University in, Szczecin, Powstanców Wielkopolskich Ave, 72, PL-70111 Szczecin, Poland.
  • Duchnik W; Department of Cosmetic and Pharmaceutical, ChemistryPomeranian Medical University in, Szczecin, Powstanców Wielkopolskich Ave, 72, PL-70111 Szczecin, Poland.
  • Kucharski L; Department of Cosmetic and Pharmaceutical, ChemistryPomeranian Medical University in, Szczecin, Powstanców Wielkopolskich Ave, 72, PL-70111 Szczecin, Poland.
  • Adamiak-Giera U; Department of Pharmacokinetics and Therapeutic Drug MonitoringPomeranian Medical University in Szczecin, Powstanców Wielkopolskich Ave, 72, PL-70111 Szczecin, Poland.
  • Lendzion-Bielun Z; Faculty of Chemical Technology and Engineering, Department of Inorganic Chemical Technology and Environment Engineering, West Pomeranian University of Technology in Szczecin, Pulaskiego, 10, PL-70322 Szczecin, Poland.
Eur J Pharm Biopharm ; : 114505, 2024 Sep 19.
Article en En | MEDLINE | ID: mdl-39306198
ABSTRACT
In the study, the modification of naproxen (NAP) with esters of four amino acids (AAs) glycine (GlyOiPr), L-proline (ProOiPr), L-leucine (LeuOiPr), and L-serine (SerOiPr) isopropyl ester was performed to improve water solubility and enhance the permeation of the drug through the skin in comparison to the parent NAP. The NAP derivatives were prepared using the equimolar ratio of the components. In-depth NMR and FTIR analysis revealed that the salts formed with the proton transfer from the carboxylic group of NAP to the amine group of the appropriate AA ester. The NAP salts exhibited improved solubility in water and PBS solution (pH 7.4) when compared to parent NAP. The values of the partition coefficient (log PO/W) for prepared salts were lower than for NAP, however, the salts maintained hydrophobic character determined by the positive values of log P. The In vitro permeation through the pig skin performed in Franz diffusion cells showed that all NAP salts exhibited a higher cumulative mass of permeated NAP (Q24h) than the parent acid. The highest permeation value was noted for [ProOiPr][NAP], with a pseudo-steady state flux (Jss) 32.5 µg NAP cm-2h-1, and Q24h = 246.4 µg NAP cm-2, it was 2.5 % of the applied dose. Moreover, topical preparations with [ProOiPr][NAP] and NAP were prepared based on two vehicles - Celugel® and Pentravan®- approved in pharmacy recipes. The permeation experiments through the Strat-M® showed, that both the Jss and Q24h of permeated drug from preparations containing [ProOiPr][NAP], were statistically several times greater than from the respective preparations with the unmodified acid. Additionally, preparations with [ProOiPr][NAP] provided significantly improved permeation of NAP than two commercial preparations, one of which contained naproxen as the acid and the other - as the sodium salt.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Eur J Pharm Biopharm Asunto de la revista: FARMACIA / FARMACOLOGIA Año: 2024 Tipo del documento: Article Pais de publicación: Países Bajos
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Eur J Pharm Biopharm Asunto de la revista: FARMACIA / FARMACOLOGIA Año: 2024 Tipo del documento: Article Pais de publicación: Países Bajos