Synthesis and pharmacokinetic behaviour of ester derivatives of 4-isobutylphenyl-2-propionic acid (Ibuprofen) with end-hydroxylated poly(N-vinyl pyrrolidinone) and poly(N-acryloyl morpholine) oligomers

J Biomater Sci Polym Ed. 1997;8(10):741-54. doi: 10.1163/156856297x00281.

Abstract

Four derivatives of 4-isobutylphenyl-2-propionic acid (Ibuprofen), in which the drug was bound by ester linkages to poly(ethylene glycols) (PEG 2000-I), monomethoxy poly(ethylene glycols) (PEG 1900-I), poly(N-vinyl pyrrolidinone) (PVP-I) and poly(N-acryloyl morpholine) (PACM-I), all having approximatively the same number average molecular weight (Mn congruent equal to 2000), were prepared and tested for their pharmacokinetic properties after oral administration. It was found that the two end-hydroxylated amphiphilic oligomers of polyvinylic structure, PACM and PVP, whose physico-chemical properties are comparable to those of PEGs especially as regards solvent affinity, have in principle a similar potential as promoieties for preparing oligomeric prodrugs.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylic Resins
  • Administration, Oral
  • Animals
  • Binding Sites
  • Biocompatible Materials / chemistry*
  • Chromatography, Gel
  • Chromatography, High Pressure Liquid
  • Esters / chemical synthesis
  • Esters / pharmacokinetics
  • Hydroxylation
  • Ibuprofen / administration & dosage
  • Ibuprofen / blood
  • Ibuprofen / chemical synthesis*
  • Ibuprofen / pharmacokinetics*
  • Molecular Weight
  • Polyethylene Glycols / chemistry*
  • Polymers
  • Prodrugs
  • Pyrrolidinones / chemistry*
  • Rats
  • Rats, Sprague-Dawley
  • Solvents / metabolism
  • Structure-Activity Relationship

Substances

  • Acrylic Resins
  • Biocompatible Materials
  • Esters
  • Polymers
  • Prodrugs
  • Pyrrolidinones
  • Solvents
  • poly(acryloylmorpholine)
  • Polyethylene Glycols
  • N-vinyl-2-pyrrolidinone
  • Ibuprofen