Solutions as solutions - Synthesis and use of a liquid polyester excipient to dissolve lipophilic drugs and formulate sustained-release parenterals

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 79, Issue 3, 2011, Pages 584-591

  Asmus, Lutz R ^a   Gurny, Robert ^a   Möller, Michael ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Green chemistry; Lipophilic drugs; Pharmaceutical excipients; Polycondensation; Polyesters; Sustained release

Indexed keywords

EXCIPIENT; HALOPERIDOL; IBUPROFEN; LIDOCAINE; LORATADINE; METOPROLOL; ORGANIC SOLVENT; PARACETAMOL; PLASTICIZER; POLYESTER; POLYLACTIC ACID; POLYMER; RISPERIDONE;

ARTICLE; CATALYST; DRUG FORMULATION; DRUG PURIFICATION; GLASS TRANSITION TEMPERATURE; GREEN CHEMISTRY; INSTRUMENT STERILIZATION; SOLUTION AND SOLUBILITY; SUSTAINED RELEASE FORMULATION; SYNTHESIS; VISCOSITY;

CALORIMETRY, DIFFERENTIAL SCANNING; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; DELAYED-ACTION PREPARATIONS; DRUG STABILITY; EXCIPIENTS; LIPIDS; LORATADINE; MOLECULAR WEIGHT; POLYESTERS; RHEOLOGY; SOLUBILITY; SOLUTIONS; STERILIZATION; TRANSITION TEMPERATURE; VISCOSITY;

EID: 80053932589     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2011.07.007     Document Type: Article

References (33)

1. T. Maharana, B. Mohanty, and Y.S. Negi Melt-solid polycondensation of lactic acid and its biodegradability Prog. Polym. Sci. 34 2009 99 124
2. A. Sodergard, and M. Stolt Properties of lactic acid based polymers and their correlation with composition Prog. Polym. Sci. 27 2002 1123 1163 (Pubitemid 34614061)
3. R.E. Drumright, P.R. Gruber, and D.E. Henton Polylactic acid technology Adv. Mater. 12 2000 1841 1846 (Pubitemid 32090435)
4. B. Gupta, N. Revagade, and J. Hilborn Poly(lactic acid) fiber: an overview Prog. Polym. Sci. 32 2007 455 482 (Pubitemid 46441434)
5. S.G. Wang, W.J. Cui, and J.Z. Bei Bulk and surface modifications of polylactide Anal. Bioanal. Chem. 381 2005 547 556
6. J.C. Middleton, and A.J. Tipton Synthetic biodegradable polymers as orthopedic devices Biomaterials 21 2000 2335 2346
7. Y. Ikada, and H. Tsuji Biodegradable polyesters for medical and ecological applications Macromol. Rapid Commun. 21 2000 117 132
8. T. Trimaille, R. Gurny, and M. Moller Synthesis and properties of novel poly(hexyl-substituted lactides) for pharmaceutical applications Chimia 59 2005 348 352 (Pubitemid 40935282)
9. W.P. Cheng and A.J. Tipton, Composition, US Patent 0029,544, 2010.
10. T. Trimaille, R. Gurny, and M. Moller Poly(hexyl-substituted lactides): novel injectable hydrophobic drug delivery systems J. Biomed. Mater. Res. A 80A 2007 55 65 (Pubitemid 44913333)
11. M.E. Kraeling, and R.L. Bronaugh In vitro percutaneous absorption of alpha hydroxy acids in human skin J. Soc. Cosmet. Chem. 48 1997 187 197
12. US Food and Drug Administration, Alpha Hydroxy Acids in Cosmetics. http://www.fda.gov/Cosmetics/ProductandIngredientSafety/ SelectedCosmeticIngredients/ucm107940.htm (page last updated 07/06/2009, page accessed 06/27/2011).
13. T. Trimaille, M. Moller, and R. Gurny Synthesis and ring-opening polymerization of new monoalkyl-substituted lactides J. Polym. Sci. Polym. Chem. 42 2004 4379 4391
14. S.H. Hyon, K. Jamshidi, and Y. Ikada Effects of residual monomer on the degradation of dl-lactide polymer Polym. Int. 46 1998 196 202 (Pubitemid 128494632)
15. B. Bittner, M. Morlock, H. Koll, G. Winter, and T. Kissel Recombinant human erythropoietin (rhEPO) loaded poly(lactide-co-glycolide) microspheres: influence of the encapsulation technique and polymer purity on microsphere characteristics Eur. J. Pharm. Biopharm. 45 1998 295 305 (Pubitemid 28270818)
16. A. Rothen-Weinhold, N. Oudry, K. Schwach-Abdellaoui, S. Frutiger-Hughes, G.J. Hughes, D. Jeannerat, U. Burger, K. Besseghir, and R. Gurny Formation of peptide impurities in polyester matrices during implant manufacturing Eur. J. Pharm. Biopharm. 49 2000 253 257 (Pubitemid 30229874)
17. A. Stjerndahl, A. Finne-Wistrand, A.C. Albertsson, C.M. Backesjo, and U. Lindgren Minimization of residual tin in the controlled Sn(II)octoate-catalyzed polymerization of epsilon-caprolactone J. Biomed. Mater. Res. A 87 2008 1086 1091
18. H.R. Kricheldorf, and H. Hachmann-Thiessen Copolymerization of epsilon-caprolactone and glycolide - a comparison of bismuth(III) hexanoate and tin(II) octanoate as initiators J. Polym. Sci. Polym. Chem. 43 2005 3268 3277 (Pubitemid 41343540)
19. K. Hiltunen, J.V. Seppala, and M. Harkonen Effect of catalyst and polymerization conditions on the preparation of low molecular weight lactic acid polymers Macromolecules 30 1997 373 379 (Pubitemid 127567622)
20. N. Cohen-Arazi, J. Katzhendler, M. Kolitz, and A.I. Domb Preparation of new alpha-hydroxy acids derived from amino acids and their corresponding polyesters Macromolecules 41 2008 7259 7263
21. L.R. Asmus, R. Gurny, and M. Moller Solutions for lipophilic drugs - a biodegradable polymer acting as solvent, matrix, and carrier to "solve" drug delivery issues Int. J. Artif. Organs 34 2011 238 242
22. G. Popovic, M. Cakar, and D. Agbaba Acid-base equilibria and solubility of loratadine and desloratadine in water and micellar media J. Pharmaceut. Biomed. 49 2009 42 47
23. O. Wachsen, K. Platkowski, and K.H. Reichert Thermal degradation of poly-l-lactide - studies on kinetics, modelling and melt stabilisation Polym. Degrad. Stabil. 57 1997 87 94 (Pubitemid 127416174)
24. U. Gbureck, J.E. Barralet, K. Spatz, L.M. Grover, and R. Thull Ionic modification of calcium phosphate cement viscosity. Part I: Hypodermic injection and strength improvement of apatite cement Biomaterials 25 2004 2187 2195 (Pubitemid 38102418)
25. W. Rungseevijitprapa, and R. Bodmeier Injectability of biodegradable in situ forming microparticle systems (ISM) Eur. J. Pharm. Sci. 36 2009 524 531
26. O. Martin, and L. Averous Poly(lactic acid): plasticization and properties of biodegradable multiphase systems Polymer 42 2001 6209 6219 (Pubitemid 32323229)
27. N. Ljungberg, and B. Wesslen The effects of plasticizers on the dynamic mechanical and thermal properties of poly(lactic acid) J. Appl. Polym. Sci. 86 2002 1227 1234 (Pubitemid 35011732)
28. P. Blasi, A. Schoubben, S. Giovagnoli, L. Perioli, M. Ricci, and C. Rossi Ketoprofen poly(lactide-co-glycolide) physical interaction AAPS PharmSciTech 8 2007
29. R. Dunn Application of the ATRIGEL® implant drug delivery technology for patient-friendly, cost-effective product development Drug Deliv. Technol. 3 2003
30. B.M. Prenner, D. Capano, and A.G. Harris Efficacy and tolerability of loratadine versus fexofenadine in the treatment of seasonal allergic rhinitis: a double-blind comparison with crossover treatment of nonresponders Clin. Ther. 22 2000 760 769 (Pubitemid 30452000)
31. G.J. Wang, I.G. Tucker, M.S. Roberts, and L.W. Hirst In vitro and in vivo evaluation in rabbits of a controlled release 5-fluorouracil subconjunctival implant based on poly(d,l-lactide-co-glycolide) Pharm. Res. 13 1996 1059 1064 (Pubitemid 26259007)
32. H.W. Chu, C.M. Lloyd, W. Karmaus, P. Maestrelli, P. Mason, G. Salcedo, J. Thaikoottathil, and A.J. Wardlaw Developments in the field of allergy in 2009 through the eyes of clinical and experimental allergy Clin. Exp. Allergy 40 2010 1611 1631
33. I.I. Salem, N.M. Najib, N.M. Idkaidek, and A. Retrospective Open-label analysis of the population pharmacokinetics of a single 10-mg dose of loratadine in healthy white Jordanian male volunteers Clin. Ther. 32 2010 391 395