ISSN:
0887-624X
Keywords:
ibuprofen
;
ketoprofen
;
naproxen
;
copolymer reactivity
;
thermal stability
;
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Three nonsteroidal antiinflammatory drugs, 2-(4-isobutylphenyl)-propionic acid (ibuprofen), 2-(3-benzoylphenyl)-propionic acid (ketoprofen), and 2-(6-methoxy-2-naphthyl)-propionic acid (naproxen), were covalently linked with 2-hydroxyethyl methacrylate (HEMA). The drug-linked HEMA (M1) (ibuprofen-linked HEMA abbreviated as HI; ketoprofen-linked HEMA as HK, and naproxen-linked HEMA as HN), were respectively copolymerized with methacrylic acid (M2), MA, to obtain macromolecular prodrugs. The compositions of the copolymers were determined by means of a 1H-NMR spectroscopy and monomer reactivity ratios were estimated using the Kelen-Tüdös linear differential equation. The reactivity ratios are: r1 = 0.101 ± 0.012, r2 = 1.071 ± 0.065 for HI-MA; r1 = 0.344 ± 0.066, r2 = 0.966 ± 0.032 for HN-MA, and r1 = 0.650 ± 0.182, r2 = 1.032 ± 0.106 for HK-MA, respectively. The monomer reactivity toward to MA radical estimated from 1/r2 values is almost same for all three monomers (1/r2 ∼ 1). The glass transition temperatures of three drug-linked homopolymers go hand in hand with the steric hindrance of three drugs, i.e., ketoprofen 〉 naproxen ≫ ibuprofen calculated the minimum energy by computer molecular modeling. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 1481-1490, 1998
Additional Material:
8 Ill.
Type of Medium:
Electronic Resource
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