Piperazinylalkyl prodrugs of naproxen improve in vitro skin permeation

European Journal of Pharmaceutical Sciences - Tập 11 - Trang 157-163 - 2000
Jarkko Rautio1, Tapio Nevalainen1, Hannu Taipale1, Jouko Vepsäläinen2, Jukka Gynther1, Krista Laine1, Tomi Järvinen1
1Department of Pharmaceutical Chemistry, University of Kuopio, P.O. Box 1627, FIN-70211 Kuopio, Finland
2Department of Chemistry, University of Kuopio, P.O. Box 1627, FIN-70211 Kuopio, Finland

Tài liệu tham khảo

Bonina, 1993, Naproxen 1-alkylazacycloalkan-2-one esters as dermal prodrugs: in vitro evaluation, Int. J. Pharm., 100, 99, 10.1016/0378-5173(93)90080-Y Bundgaard, 1989, Enhanced delivery of nalidixic acid through human skin via acyloxymethyl ester prodrugs, Int. J. Pharm., 55, 91, 10.1016/0378-5173(89)90028-8 Chan, 1989, Prodrugs for dermal delivery, Int. J. Pharm., 55, 1, 10.1016/0378-5173(89)90270-6 Chang, 1997, Ibuprofen heterocyclic esters as dermal prodrugs in vitro evaluation, STP Pharm. Sci., 7, 315 Franssen, 1992, Low molecular weight proteins as carriers for renal drug targeting. Preparation of drug-protein conjugates and drug-spacer derivatives and their catabolism on renal cortex homogenates and lysosomal lysates, J. Med. Chem., 35, 1246, 10.1021/jm00085a012 Goosen, 1998, Correlation between physicochemical characteristics, pharmacokinetic properties and transdermal absorption of NSAID’s, Int. J. Pharm., 163, 203, 10.1016/S0378-5173(97)00359-1 Guy, 1983, Drug delivery to local subcutaneous structures following topical administration, J. Pharm. Sci., 72, 1375, 10.1002/jps.2600721203 Kasting, 1992, Prodrugs for dermal delivery: solubility, molecular size, and functional group effects, 117 Kerr, 1998, 7-Alkylcarbonyloxymethyl prodrugs of theophylline: topical delivery of theophylline, Int. J. Pharm., 167, 37, 10.1016/S0378-5173(98)00043-X McNeill, 1992, Local enhanced topical delivery (LETD) of drugs: does it truly exist?, Pharm. Res., 9, 1422, 10.1023/A:1015854728278 Mikulak, 1998, Transdermal delivery and accumulation of indomethacin in subcutaneous tissues in rats, J. Pharm. Pharmacol., 50, 153, 10.1111/j.2042-7158.1998.tb06170.x Milosovich, 1989, The utilization of prodrugs to enhance transdermal absorption of testosterone, deoxycorticosterone and indomethacin, Prog. Clin. Biol. Res., 292, 273 Mueller, L.G., 1990. Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation. US Patent 4, 912, 248. Pop, 1996, Derivatives of dexanabinol. II. Salts of amino acid esters containing tertiary and quaternary heterocyclic nitrogen with increased water-solubility, Pharm. Res., 13, 469, 10.1023/A:1016017331353 Rautio, 1998, In vitro evaluation of acyloxyalkyl esters as dermal prodrugs of ketoprofen and naproxen, J. Pharm. Sci., 87, 1622, 10.1021/js970465w Rautio, 1999, Synthesis and in vitro evaluation of aminoacyloxyalkyl esters of 2-(6-methoxy-2-naphthyl)propionic acid as novel naproxen prodrugs for dermal drug delivery, Pharm. Res., 16, 1172, 10.1023/A:1018981010047 Roy, 1994, Permeability of ketorolac acid and its ester analogs (prodrug) through human cadaver skin, J. Pharm. Sci., 83, 1548, 10.1002/jps.2600831106 Singh, 1994, Skin permeability and local tissue concentrations of nonsteroidal anti-inflammatory drugs after topical application, J. Pharmacol. Exp. Ther., 268, 144 Sloan, 1989, Prodrugs for dermal delivery, Adv. Drug. Deliv. Rev., 3, 67, 10.1016/0169-409X(89)90005-7 Sloan, 1992, Functional group considerations in the development of prodrug approaches to solving topical delivery problems, 17 Suh, 1997, Pharmacokinetic and local tissue disposition studies of naproxen following topical and systemic administration in dogs and rats, Biopharm. Drug. Disp., 18, 623, 10.1002/(SICI)1099-081X(199710)18:7<623::AID-BDD46>3.0.CO;2-V Tammara, 1993, Synthesis and evaluation of morpholinoalkyl ester prodrugs of indomethacin and naproxen, Pharm. Res., 10, 1191, 10.1023/A:1018976520391 Tammara, 1994, Morpholinoalkyl ester prodrugs of diclofenac: synthesis, in vitro and in vivo evaluation, J. Pharm. Sci., 83, 644, 10.1002/jps.2600830510 Taylor, 1998, 1-Alkylcarbonyloxymethyl prodrugs of 5-fluorouracil (5-FU): synthesis, physicochemical properties, and topical delivery of 5-FU, J. Pharm. Sci., 87, 15, 10.1021/js9702574 Todd, 1990, Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states, Drugs., 40, 91, 10.2165/00003495-199040010-00006 van den Ouweland, 1989, Transcutaneous absorption of naproxen gel, Eur. J. Clin. Pharmacol., 36, 209, 10.1007/BF00609198 Weber, 1994, Ester des naproxens als potentielle prodrugs zur hautpenetration, 2. Mitt.: Penetrationseigenschaften an exzidierter mäusehaut, Arch. Pharm. (Weinheim), 327, 681, 10.1002/ardp.19943271102 Yano, 1986, Skin permeability of various non-steroidal anti-inflammatory drugs in man, Life. Sci., 39, 1043, 10.1016/0024-3205(86)90195-5