In-vitro and in-vivo evaluation of oligoethylene esters as dermal prodrugs of 18β-glycyrrhetic acid

Journal of Pharmacy and Pharmacology

Volumn 58, Issue 3, 2006, Pages 311-319

  Puglia, Carmelo ^a   Ostacolo, Carmine ^b   Sacchi, Antonia ^b   Laneri, Sonia ^b   Bonina, Francesco ^a  

^a UNIVERSITY OF CATANIA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; ETHYLENE GLYCOL DERIVATIVE; GLYCYRRHETINIC ACID; NICOTINIC ACID METHYL ESTER; POLYOXYETHYLENE; PRODRUG; WATER;

ADULT; ANTIINFLAMMATORY ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIFFUSION; DRUG PENETRATION; DRUG SYNTHESIS; EPIDERMIS; ERYTHEMA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN EXPERIMENT; HUMAN TISSUE; HYDROLYSIS; IN VITRO STUDY; IN VIVO STUDY; LIPOPHILICITY; MASS SPECTROMETRY; PARTITION COEFFICIENT; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SKIN ABSORPTION; STRATUM CORNEUM;

ADMINISTRATION, CUTANEOUS; ADULT; ANTI-INFLAMMATORY AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DERMATOLOGIC AGENTS; DRUG STABILITY; ERYTHEMA; ESTERS; FEMALE; GELS; GLYCYRRHETINIC ACID; HUMANS; HYDROLYSIS; MALE; NICOTINIC ACIDS; PERMEABILITY; POLYETHYLENE GLYCOLS; PRODRUGS; SKIN; SKIN ABSORPTION;

EID: 33644752713     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.58.3.0004     Document Type: Article

References (30)

1. Arase, Y., Ikeda, K., Murashima, N., Chayama, K., Tsubota, A., Koida, I., Suzuki, Y., Saitoh, S., Kobayashi, M., Kumada, H. (1997) The long term efficacy of glycyrrhizin in chronic hepatitis C patients. Cancer 79: 1494-1500
2. Bonina, F. P., Montenegro, L., Trapani, G., Franco, M., Liso, G. (1995) In vitro evaluation of N-acyllactam esters of indomethacin as dermal prodrugs. Int. J. Pharm. 124: 45-51
3. Bonina, F. P., Puglia, C., Barbuzzi, T., de Caprariis, P., Palagiano, F., Rimoli, M. G., Saija, A. (2001) In vitro and in vivo evaluation of polyoxyethylene esters as dermal prodrugs of ketoprofen, naproxen and diclofenac. Eur. J. Pharm. Sci. 14: 123-134
4. Bonina, F. P., Rimoli, M. G., Avallone, L., Barbato, F., Amato, M., Puglia, C., Ricci, M., de Caprariis, P. (2002) New oligoethylene ester derivatives of 5-iodo-2′-deoxyuridine as dermal prodrugs: synthesis, physicochemical properties, and skin permeation studies. J. Pharm. Sci. 91: 171-179
5. Bonina, F., Santagati, N. A., Puglia, C. (2003) Ketoprofen 1-alkylazacycloalkan-2-one esters as dermal prodrugs: in vivo and in vitro evaluations. Drug. Dev. Ind. Pharm. 29: 181-190
6. Capella, G. L., Finzi, A. F. (2003) Complementary therapy for psoriasis. Dermatol. Ther. 16: 164-174
7. El-Kattan, A. F., Asbill, C. S., Kim, N., Michniak, B. B. (2001) The effects of terpene enhancers on the percutaneous permeation of drugs with different lipophilicities. Int. J. Pharm. 215: 229-240
8. Farina, C., Pinza, M., Pifferi, G. (1998) Synthesis and anti-ulcer activity of new derivatives of glycyrrhetic, oleanolic and ursolic acids. Farmaco 53: 22-32
9. Guy, R. H., Hadgraft, J. (1992) Percutaneous penetration enhancement: physicochemical considerations and implications for prodrug design. In: Sloan, K. B. (ed.) Prodrugs: topical and ocular drug delivery. Marcel Dekker, New York, pp 1-16
10. Inoue, H., Mori, T., Shibata, S., Koshihara, Y. (1989) Modulation by glycyrrhetinic acid derivatives of TPA-induced mouse ear edema. Br. J. Pharmacol. 96: 204-210
11. Kearney, A. S. (1996) Prodrugs and targeted drug delivery. Adv. Drug Deliv. Rev. 19: 225-239
12. Lambert, W. J. (1993) Modeling oil-water partitioning and membrane permeation using reversed-phase chromatography. J. Chromatogr. A. 656: 469-484
13. Lien, E. J., Gao, H. (1995) QSAR analysis of skin permeability of various drugs in man as compared to in vivo and in vitro studies in rodents. Pharm. Res. 12: 583-587
14. Magnusson, B. M., Pugh, W. J., Roberts, M. S. (2004a) Simple rules defining the potential of compounds for transdermal delivery or toxicity. Pharm. Res. 21: 1047-1054
15. Magnusson, B. M., Anissimov, Y. G., Cross, S. E., Roberts, M. S. (2004b) Molecular size as the main determinant of solute maximum flux across the skin. J. Invest. Dermatol. 122: 993-999
16. Monene, L. M., Goosen, C., Breytenbach, J. C., Hadgraft, J., du Plessis, J. (2005) Percutaneous absorption of cyclizine and its alkyl analogues. Eur. J. Pharm. Sci. 24: 239-244
17. Puglia, C., Tropea, S., Rizza, L., Santagati, N. A., Bonina, F. (2005) In vitro percutaneous absorption studies and in vivo evaluation of anti-inflammatory activity of essential fatty acids (EFA) from fish oil extracts. Int. J. Pharm. 299: 41-48
18. Ricci, M., Puglia, C., Bonina, F., Di Giovanni, C., Giovagnoli, S., Rossi, C. (2005) Evaluation of indomethacin percutaneous absorption from nanostructured lipid carriers (NLC): in vitro and in vivo studies. J. Pharm. Sci. 94: 1149-1159
19. Rossi, T., Castelli, M., Zandomeneghi, G., Ruberto, A., Benassi, L., Magnoni, C., Santachiara, S., Baggio, G. (2003) Selectivity of action of glycyrrhizin derivatives on the growth of MCF-7 and HEP-2 cells. Anticancer Res. 23: 3813-3818
20. Salakhutdinov, B. A., Dalimov, D. N., Aripov, T. F., Tukfatullina, I. I., Ziyatdinova, R. K., Dzhuraev, A. Z., Kamaev, F. G., Izotova, L., Yu., Ibragimov, B. T., Mavridis, I., Giastas, P. (2002) Synthesis, structure, and membrane activity of new glycyrrhetic acid derivatives. Chem. Nat. Compd. 38: 249-256
21. Shin, S. C., Kim, H. J., Oh, I. J., Cho, C. W., Yang, K. H. (2005) Development of tretinoin gels for enhanced transdermal delivery. Eur. J. Pharm. Biopharm. 60: 67-71
22. Siewert, M., Dressman, J., Brown, C. K., Shah, V. P. (2003) FIP/AAPS Guidelines to dissolution/in vitro release testing of novel/special dosage forms. AAPS Pharm. Sci. Tech. 4: E7
23. Sloan, K. B. (ed.) (1992) Prodrugs: topical and ocular drug delivery. Marcel Dekker, New York
24. Sloan, K. B., Wasdo, S. (2003) Designing for topical delivery: prodrugs can make the difference. Med. Res. Rev. 23: 763-793
25. Takahashi, H., Onishi, H., Machida, Y. (2004) Glycyrrhetic acid-loaded microparticles: liver-specific delivery and therapeutic potential against carbon tetrachloride-induced hepatitis. J. Pharm. Pharmacol. 56: 437-444
26. Teelucksingh, S., Mackie, A. D., Burt, D., McIntyre, M. A., Brett, L., Edwards, C. R. (1990) Potentiation of hydrocortisone activity in skin by glycyrrhetinic acid. Lancet 335: 1060-1063
27. Touitou, E., Fabin, B. (1988) Altered skin permeation of a highly lipophilic molecule: tetrahydrocannabinol. Int. J. Pharm. 43: 17-22
28. Um, S. J., Park, M. S., Park, S. H., Han, H. S., Kwon, Y. J., Sin, H. S. (2003) Synthesis of new glycyrrhetinic acid (GA) derivatives and their effects on tyrosinase activity. Bioorg. Med. Chem. 11: 5345-5352
29. Yalkowsky, S. H., Valvani, S. C. (1980) Solubility and partitioning I: solubility of nonelectrolytes in water. J. Pharm. Sci. 69: 912-922
30. Yalkowsky, S. H., Valvani, S. C., Roseman, T. J. (1983) Solubility and partitioning VI: octanol solubility and octanol-water partition coefficients. J. Pharm. Sci. 72: 866-870