Synthesis and in vitro evaluation of aminoacyloxyalkyl esters of 2-(6- methoxy-2-naphthyl)propionic acid as novel naproxen prodrugs for dermal drug delivery

Pharmaceutical Research

Volumn 16, Issue 8, 1999, Pages 1172-1178

  Rautio, Jarkko ^a   Nevalainen, Tapio ^a   Taipale, Hannu ^a   Vepsäläinen, Jouko ^a   Gynther, Jukka ^a   Pedersen, Tina ^b   Järvinen, Tomi ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Hydrolysis kinetics; Lipophilicity; Naproxen; Prodrugs; Skin permeation; Solubility

Indexed keywords

2 (GLYCYLOXY)ETHYL 2 (6 METHOXY 2 NAPHTHYL)PROPANOIC ACID; 2 (ISOLEUCYLOXY)ETHYL 2 (6 METHOXY 2 NAPHTHYL)PROPANOIC ACID; 2 (LEUCYLOXY)ETHYL 2 (6 METHOXY 2 NAPHTHYL)PROPANOIC ACID; 2 (PHENYLALANYLOXY)ETHYL 2 (6 METHOXY 2 NAPHTHYL)PROPANOIC ACID; NAPROXEN; PRODRUG; UNCLASSIFIED DRUG;

ARTICLE; DRUG DELIVERY SYSTEM; DRUG HYDROLYSIS; DRUG PENETRATION; DRUG SOLUBILITY; DRUG SYNTHESIS; HUMAN; HUMAN TISSUE; LIPOPHILICITY; PRIORITY JOURNAL;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DRUG DELIVERY SYSTEMS; DRUG STABILITY; ESTERS; EVALUATION STUDIES; HUMANS; HYDROLYSIS; NAPROXEN; PRODRUGS; SKIN ABSORPTION; SOLUBILITY; SOLUTIONS;

EID: 0032803081     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1018981010047     Document Type: Article

References (20)

1. 1. H. Suh, H. W. Jun, M. T. Dzimianski, and G. W. Lu. Pharmacokinetic and local tissue disposition studies of naproxen following topical and systemic administration in dogs and rats. Biopharm. Drug Disp. 18:623-633 (1997).
2. 2. S. C. McNeill, R. O. Potts, and M. L. Francoeur. Local enhanced topical delivery (LETD) of drugs: Does it truly exist? Pharm. Res. 9:1422-1427 (1992).
3. 3. P. Singh and M. S. Roberts. Skin permeability and local tissue concentrations of nonsteroidal anti-Inflammatory drugs after topical application. J. Pharmacol. Exp. Ther. 268:144-151 (1994).
4. 4. R. N. Brogden, R. C. Heel, T. M. Speight, and G. S. Avery. Naproxen up to date: A review ot its pharmacological properties and therapeutic efficacy and use in rheumatic diseases and pain states. Drugs 18:241-277 (1979).
5. 5. T. Yano, A. Nakagawa, M. Tsuji, and K. Noda. Skin permeability of various non-steroidal anti-Inflammatory drugs in man. Life Sci. 39:1043-1050 (1986).
6. 6. F. A. van den Ouweland, P. C. Eenhoorn, Y. Tan, and F. W. J. Gribnau. Transcutaneous absorption of naproxen gel. Eur. J. Clin. Pharmacol. 36:209-211 (1989).
7. 7. G. B. Kasting, R. L. Smith, and B. D. Anderson, Prodrugs for dermal delivery: Solubility, molecular size, and functional group effects. In K. B. Sloan (ed.), Prodrugs, Topical and Ocular Drug Delivery, Marcel Dekker, inc., New York, 1992, pp 117-161.
8. 8. L. G. Mueller. Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation. US Patent 4, 912, 248 (1990).
9. 9. H. Weber, K. Meyer-Trumpener, and B.C. Lippold. Ester des naproxens als potentielle prodrugs zur hautpenetration. 2. mitt.: Penetrationseigenschaften an exzidierter mäusehaut. Arch. Pharm. (Weinheim) 327:681-686 (1994).
10. 10. F. P. Bonina, L. Montenegro, and F. Guerrera. Naproxen l-alkylazacycloalkan-2-one esters as dermal prodrugs: In vitro evaluation. Int. J. Pharm. 100:99-105 (1993).
11. 11. J. Rautio, H. Taipale, J. Gynther, J. Vepsälüinen, T. Nevalainen, and T. Jarvinen. In vitro evaluation of acyloxyalkyl esters as dermal prodrugs of ketoprofen and naproxen. J. Pharm. Sci. 87:1622-1628 (1998).
12. 12. E. J. F. Franssen, J. Koiter, C. A. M. Kuipers, A. P. Bruins, F. Moolenaar, D. de Zeeuw, W. H. Kruizinga, R. M. Kellogg, and D. K. F. Meijer. 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. 35:1246-1259 (1992).
13. 13. T. Järvinen, M. Poikolainen, P. Suhonen, J. Vepsäläinen, S. Alaranta, and A. Urtti. Comparison of enzymatic hydrolysis of pilocarpine prodrugs in human plasma, rabbit cornea, and butyrylcholinesterase solutions. J. Pharm. Sci. 84:656-660 (1995).
14. 14. K. B. Sloan, J. J. Getz, H. D. Beall, and R. J. Prankerd. Transdermal delivery of 5-fluorouracil (5-FU) through hairless mouse skin by l-alkylaminocarbonyl-5-FU prodrugs: Physicochemical characterization of prodrugs and correlations with transdermal delivery. Int. J. Pharm. 93:27-36 (1993).
15. 15. F. P. Bonina, L. Montenegro, P. De Caprariis, F. Palagiano, G. Trapani, and G. Liso. In vitro and in vivo evaluation of polyoxyethylene indomethacin esters as dermal prodrugs. J. Contr. Rel. 34:223-232 (1995).
16. 16. S. Y. Chang, S. B. Park, J. H. Jung, S. I. Shon, and H. J. Yoon. Ibuprofen heterocyclic esters as dermal prodrugs in vitro evaluation. S. T. P. Pharma Sci. 7:315-319 (1997).
17. 17. H. Bundgaard, N. Mork, and A. Hoclgaard. Enhanced delivery of nalidixic acid through human skin via acyloxymethyl ester prodrugs. Int. J. Pharm. 55:91-97 (1989a).
18. 18. M. Johansen, B. Mollgaard, P. K. Wotton, C. Larsen, and A. Hoelgaard. In vitro evaluation of dermal prodrug delivery-transport and bioconversion of a series of aliphatic esters of metronidazole. Int. J. Pharm. 32:199-206 (1986).
19. 19. H. Bundgaard. The double prodrug concept and its applications. Adv. Drug Del. Rev. 3:39-65 (1989b).
20. 20. K. B. Sloan. Prodrugs for dermal delivery. Adv. Drug Del. Rev. 3:67-101 (1989).