Ketoprofen 1-alkylazacycloalkan-2-one esters as dermal prodrugs: In vivo and in vitro evaluations

Drug Development and Industrial Pharmacy

Volumn 29, Issue 2, 2003, Pages 181-190

  Bonina, Francesco ^a   Santagati, Natale Alfredo ^a   Puglia, Carmelo ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

Controlled release; Dermal prodrug; Ketoprofen; N Alkyllactams; Skin permeation

Indexed keywords

ESTER DERIVATIVE; KETOPROFEN; KETOPROFEN DERIVATIVE; KETOPROFEN ESTER; NONSTEROID ANTIINFLAMMATORY AGENT; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED DRUG RELEASE; DERIVATIZATION; DRUG ABSORPTION; DRUG PENETRATION; DRUG SCREENING; ENZYME STABILITY; HUMAN; HUMAN TISSUE; HYDROLYSIS; LIPOPHILICITY; SKIN PERMEABILITY; SYNTHESIS;

ADULT; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; AREA UNDER CURVE; AZA COMPOUNDS; ERYTHEMA; ESTERS; FEMALE; GELS; HUMANS; KETOPROFEN; MALE; PRODRUGS; SKIN; SKIN ABSORPTION; TIME FACTORS; WATER;

EID: 0037221753     PISSN: 03639045     EISSN: None     Source Type: Journal    
DOI: 10.1081/DDC-120016726     Document Type: Article

References (31)

1. Evans, J.M.; McMahon, A.; McGilchrist, M.M.; White, G.; Murray, F.E.; McDevitt, D.G.; MacDonald, T.M. Topical non-steroidal antiinflammatory drugs and admission to hospital for upper gastrointestinal bleeding and perforation: a record linkage case-control study. Br. Med. J. 1995, 311, 22-26.
2. Berner, G.; Engels, B.; Vögtle-Junkert, U. Percutaneous ibuprofen therapy with traumadolgit gel: bioequivalence studies. Drugs Exp. Clin. Res. 1989, 15, 559-564.
3. Stuttgen, G. The present status of anti-inflammatory agents in dermatology. Drugs 1988, 36, 43-48.
4. Heyneman, C.A.; Lawless-Liday, C.; Wall, G.C. Oral versus topical NSAIDs in rheumatic disease: a comparison. Drugs 2000, 60, 555-574.
5. Stella, V.J.; Charman, W.N.A.; Naringrekar, V.H. Prodrugs: Do they have advantages in clinical practice? Drugs 1985, 29, 455-473.
6. Valenta, C.; Wanka, M.; Heidlas, J. Evaluation of novel soya-lecithin formulations for dermal use containing ketoprofen as model drug. J. Contr. Rel. 2000, 63, 165-173.
7. Finnin, B.C.; Morgan, T.M. Transdermal penetration enhancers: applications, limitations, and potential. J. Pharm. Sci. 1999, 88, 955-958.
8. Godwin, D.A.; Michniak, B.B. Influence of drug lipophilicity on terpenes as transdermal penetration enhancers. Drug Dev. Ind. Pharm. 1999, 25, 905-915.
9. Sasaki, H.; Kojima, M.; Nakamura, J.; Shibasaki, J. Acute toxicity and skin irritation of pyrrolidone derivatives as transdermal penetration enhancer. Chem. Pharm. Bull. (Tokyo) 1990, 38, 2308-2310.
10. Bonina, F.P.; Puglia, C.; Barbuzzi, T.; de Caprariis, P.; Palagiano, F.; Rimoli, M.G.; Saija, A. In vitro and in vivo evaluation of polyoxyethylene esters as dermal prodrugs of ketoprofen, naproxen and diclofenac. Eur. J. Pharm. Sci. 2001, 14, 123-134.
11. Bonina, F.P.; Montenegro, L.; Guerrera, F. Naproxen 1-alkylazacycloalkan-2-one esters as dermal prodrugs: in vitro evaluation. Int. J. Pharm. 1993, 100, 99-105.
12. Bonina, F.P.; Montenegro, L.; Trapani, G.; Franco, M.; Liso, G. In vitro evaluation of N-acyllactam esters of indomethacin as dermal prodrugs. Int. J. Pharm. 1995, 124, 45-51.
13. Bonina, F.P.; Montenegro, L.; de Caprariis, P.; Palagiano, F.; Trapani, G.; Liso, G. In vitro and in vivo evaluation of polyoxyethylene indomethacin esters as dermal prodrugs. J. Contr. Rel. 1995, 34, 223-232.
14. Palagiano, F.; Arenare, L.; Barbato, F.; La Rotonda, M.I.; Quaglia, F.; Bonina, F.P.; Montenegro, L.; de Caprariis, P. In vitro and in vivo evaluation of terpenoid esters of indomethacin as dermal prodrugs. Int. J. Pharm. 1997, 149, 171-182.
15. Quan, D.; Higuchi, R.I.; Takayama, K.; Higashiyama, K.; Nagai, T. Enhancing effect of piperidone derivatives on the percutaneous absorption of indomethacin. Drug Design. Del. 1990, 6, 61-71.
16. Sidel 'Kovskaya, F.P.; Kolodkin, F.L.; Shiroyan, F.R. Synthesis of N-β-hydroxyethillactams and their reaction with thionil chloride. Izv. Akad. Nauk. SSSR. Ser. Khim. 1965, 2, 374-376.
17. Celerier, J.P.; Haddad, M.; Saliou, C.; Lhommet, G. B-enhammino-esters bicycliques: sinthese et reduction stereospecifiques acces a l'isoretronecanal, la trachelanthamide, la lupinine et l'epilupinine. Tetrahedron 1989, 45, 6161-6170.
18. Nielsen, N.M.; Bundgaard, H. Glycolamide esters as biolabile prodrugs of carboxylic acid agents: synthesis, stability, bioconversion and physicochemical properties. Int. J. Sci. 1988, 77, 285-297.
19. Lambert, W.J. Modelling oil-water partioning and membrane permeation using reversedphase chromatography. J. Chromatogr. A 1993, 656, 469-484.
20. Kligman, A.M.; Christophers, E. Preparation of isolated sheets of human skin. Arch. Dermatol. 1963, 88, 702-705.
21. Swarbrick, J.; Lee, G.; Brom, J.; Gensmantel, N.P. Drug permeation through human skin I: effect of storage conditions of skin. J. Invest. Dermatol. 1982, 78, 63-66.
22. Toitou, E.; Fabin, B. Altered skin permeation of a highly lipophilic molecule: tetrahydrocannabinol. Int. J. Pharm. 1988, 43, 17-22.
23. Wong, O.; Tsuzuki, N.; Nghiem, B.; Kuehnhoff, J.; Itoh, T.; Masaki, K.; Huntington, J.; Konishi, R.; Rytting, J.H.; Higuchi, T. Unsaturated cyclic ureas as new non-toxic biodegradable transdermal penetration enhancers: II. Evaluation study. Int. J. Pharm. 1989, 52, 191-202.
24. Guy, R.H.; Hadgraft, J. Percutaneous penetration enhancement: physicochemical consideration and implications for prodrug design. In Prodrugs: Topical and Ocular Drug Delivery; Sloan, K.B., Ed.; Marcel Dekker: New York, 1992; 1-16.
25. Bronaugh, R.L.; Stewart, R.F. Methods for in vitro percutaneous absorption studies. III. Hydrophobic compounds. J. Pharm. Sci. 1984, 73, 1255-1258.
26. Bouclier, M.; Chatelus, A.; Hensby, C.N. In vivo animal models for the evaluation of anti-inflammatory drug action in the skin. In Nonsteroidal Anti-inflammatory Drugs; Lowe, N.J., Hensby, C.N., Eds.; Karger: Basel, 1989; 118-132.
27. Chan, S.Y.; Li Wan Po, A. Quantitative assessment of nonsteroidal anti-inflammatory topical products in nicotinate-induced erythema using tristimulus colour analysis. Int. J. Pharm. 1992, 83, 73-86.
28. Westerhof, W.; Van Hasselt, B.A.A.M.; Kammeijer, A. Quantification of UV-induced erythema with a portable computer chromameter. Photodermatology 1986, 3, 310-314.
29. Muizzuidin, N.; Marenus, K.; Maes, D.; Smith, W.P. Use of chromameter in assessing the efficacy of anti-irritans and tanning accelerators. J. Soc. Cosm. Chem. 1990, 41, 369-378.
30. Braue, E.H., Jr.; Mershon, M.M.; Wade, J.V.; Litchfield, M.R. In vivo assessment of vescicant skin injury using Minolta Chroma Meter. J. Soc. Cosm. Chem. 1990, 41, 259-265.
31. Anderson, R.R.; Parrish, J.A. The optics of human skin. J. Invest. Dermatol. 1981, 77, 13-19.