Ion pair formation as a possible mechanism for the enhancement effect of lauric acid on the transdermal permeation of ondansetron

Pharmaceutical Development and Technology

Volumn 9, Issue 3, 2004, Pages 311-320

  Dimas, Dimitrios A ^a   Dallas, Paraskevas P ^a   Rekkas, Dimitrios M ^a  

^a UNIVERSITY OF ATHENS   (Greece)

Author keywords

Ion pair; Ondansetron; Penetration enhancer; Transdermal

Indexed keywords

CARBON; CARBONYL DERIVATIVE; FATTY ACID; IMIDAZOLE DERIVATIVE; LAURIC ACID; NITROGEN; OCTANOL; OLEIC ACID; ONDANSETRON; PENETRATION ENHANCING AGENT; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; DIFFERENTIAL SCANNING CALORIMETRY; DISTRIBUTION COEFFICIENT; DRUG DELIVERY SYSTEM; DRUG DISTRIBUTION; DRUG MECHANISM; DRUG MIXTURE; DRUG PENETRATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION PAIR COMPLEX; ION PERMEABILITY; LIPOPHILICITY; MAGNETISM; MELTING POINT; PARTITION COEFFICIENT; PRIORITY JOURNAL; THERMAL ANALYSIS; THERMODYNAMICS;

ALGORITHMS; ANTIEMETICS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIFFERENTIAL THERMAL ANALYSIS; HYDROGEN-ION CONCENTRATION; IONS; LAURIC ACIDS; MAGNETIC RESONANCE SPECTROSCOPY; ONDANSETRON; SKIN ABSORPTION; SOLUBILITY; STIMULATION, CHEMICAL; THERMODYNAMICS;

EID: 4444233327     PISSN: 10837450     EISSN: None     Source Type: Journal    
DOI: 10.1081/PDT-200031449     Document Type: Article

References (34)

1. Elias, P.M. Stratum corneum revisited. J. Dermatol. 1999, 23, 756-758.
2. Pfister, W.R.; Hsieh, D.S.T. Permeation enhancers compatible with transdermal drug delivery systems. Part I: selection and formulation considerations. Pharm. Technol. 1990, 14 (9), 132-139.
3. Llacer, J.M.; Gallardo, V.; Parera, A.; Ruiz, M.A. Formation of ondansetron polymorphs. Int. J. Pharm. 1999, 177, 221-229.
4. Roila, F.; Favero, D.A. Ondansetron clinical pharmacokinetics. Clin. Pharmacokinet. 1995, 29 (2), 95-109.
5. Simpson, K.H.; Hicks, F.M. Clinical pharmacokinetics of ondansetron. A review. J. Pharm. Pharmacol. 1996, 48, 774-781.
6. Cothhup, P.V.; Felgate, C.C.; Palmer, J.L.; Scully, N.L. Determination of ondansetron in plasma and its pharmacokinetics in the young and elderly. J. Pharm. Sci. 1991, 80 (9), 868-871.
7. Llacer, J.M.; Ruiz, M.A.; Parera, A.; Gallardo, V. Adsortion-desorption of ondansetron on latex particles. Drug Dev. Ind. Pharm. 2000, 26 (3), 237-242.
8. www.fda.gov/medwatch/safety/2000/dec00.htm (accessed July 2002)
9. Anderson, P.O.; Knoben, J.E.; Troutman, W.G. Handbook of Clinical Drug Data; Appleton & Lange: Connecticut, 1999; 519.
10. Dimas, D.A.; Dallas, P.P.; Rekkas, D.M. Use of an 8132 asymmetrical factorial design for the in vitro evaluation of ondansetron permeation through human epidermis. Pharm. Dev. Technol. in press.
11. Walters, K.A.; Hadgraft, J. Pharmaceutical Skin Penetration Enhancement; Marcel Dekker: New York, 1993.
12. Quintanar-Guerrero, D.; Allemann, E.; Fessi, H.; Doelker, E. Applications of the ion-pair concept to hydrophilic substances with special emphasis on peptides. Pharm. Res. 1997, 14 (2), 119-127.
13. Lee, S.J.; Kurihara-Bengstrom, T.; Kim, S.W. Ion-paired drug diffusion through polymer membranes. Int. J. Pharm. 1987, 47, 59-73.
14. The United States Pharmacopeia 24; United States Pharmacopeial Convention: Rockville, MD, 2000. 1218-1220, 2231-2232.
15. Takahashi, K.; Rytting, J.H. Approach to improve permeation of ondansetron across shed snake skin as a model membrane. J. Pharm. Pharmacol. 2001, 53, 789-794.
16. Stott, P.W.; Williams, A.C.; Brian, B.W. Mechanistic study into the enhanced transdermal permeation of a model b-blocker, propanolol, by fatty acids: a melting point depression effect. Int. J. Pharm. 2001, 219, 161-176.
17. Green, P.G.; Hadgraft, J. Facilitated transfer of cationic drugs across a lipoidal membrane by oleic acid and lauric acid. Int. J. Pharm. 1987, 37, 251-255.
18. Green, P.G.; Guy, R.H.; Hadgraft, J. In vitro and in vivo enhancement of skin permeation with oleic lauric acids. Int. J. Pharm. 1988, 48, 103-111.
19. Barker, N.; Hadgraft, J. Facilitated percutaneous absorption: a model system. Int. J. Pharm. 1981, 8, 193-202.
20. Hadgraft, J.; Walters, K.A.; Wotton, R.K. Facilitated percutaneous absorption: a comparison and evaluation of two in vitro models. Int. J. Pharm. 1986, 32, 257-263.
21. Green, P.G.; Hadgraft, J.; Wolff, M. Physicochemical aspects of the transdermal delivery of bupranolol. Int. J. Pharm. 1989, 55, 259-265.
22. Pardo, A.; Shin, Y.; Cohen, S. Kinetics of transdermal penetration of an organic ion pair: physostigmine salicylate. J. Pharm. Sci. 1992, 81, 990-995.
23. Valenta, C.; Siman, U.; Kratzel, M.; Hadgraft, J. The dermal delivery of lignocaine: influence of ion pairing. Int. J. Pharm. 2000, 197, 77-85.
24. Hatanaka, T.; Kamon, T.; Morigaki, S.; Katayama, K.; Koizumi, T. Ion pair skin transport of a zwitterionic drug, cephalexin. J. Control. Release 2000, 66, 63-71.
25. Neubert, R. Ion pair transport across membranes. Pharm. Res. 1989, 6 (9), 743-747.
26. Ogiso, T.; Shintani, M. Mechanism for the enhancement effect of fatty acids on the percutaneous absorption of propanolol. J. Pharm. Sci. 1990, 79 (12), 1065-1071.
27. Dollimore, D.; Lerdkanchanaporn, S. Thermal analysis. Anal. Chem. 1998, 70, 27R-35R.
28. Stott, P.W.; Williams, A.C.; Barry, B.W. Transdermal delivery from eutectic systems: enhanced permeation of a model drug, ibuprofen. J. Control. Release 1998, 50, 297-308.
29. 2 system. J. Alloys Compd. 2001, 325, 78-83.
30. Ford, J.A.; Timmins, P. Pharmaceutical Thermal Analysis; John Wiley & Sons, Inc.: New York, 1989; 25-68.
31. Touitou, E.; Chow, D.D.; Lawter, J.R. Chiral b-blockers for transdermal delivery. Int. J. Pharm. 1994, 104, 19-28.
32. Rai, U.S.; George, S. Thermochemical studies on the eutectics and addition compounds in the binary systems of benzidine with p-nitrophenol, m-aminophenol and resorcinol. Thermochim. Acta 1994, 243, 17-25.
33. Rai, U.S.; Shekhar, H. Some physicochemical studies on the binary organic eutectics. Thermochim. Acta 1991, 175, 215-227.
34. Rai, U.S.; George, S. Physicochemical studies on organic eutectics and the 1:1 addition compound: benzidine-α-napthol system. J. Mater. Sci. 1992, 27, 17-25.