Human skin permeation of neutral species and ionic species: Extended linear free-energy relationship analyses

Journal of Pharmaceutical Sciences

Volumn 101, Issue 6, 2012, Pages 2034-2044

  Zhang, Keda ^a   Chen, Ming ^a   Scriba, Gerhard K E ^a   Abraham, Michael H ^b   Fahr, Alfred ^a   Liu, Xiangli ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Diffusion; Ionic species; LFER; Linear free energy relationship; Partition; Permeability; Permeation; Physicochemical properties; QSPR; Skin; Transdermal drug delivery

Indexed keywords

2 BUTANONE; 2 ETHOXYETHANOL; 2 NAPHTHOL; 4 CHLOROPHENOL; ACID; ANILINE; BARBITAL; BASE; BENZALDEHYDE; BENZENE; BENZYL ALCOHOL; BUTANOL; CAFFEINE; DECANOL; HEPTANOL; HEXANOL; META CRESOL; METHANOL; NONANOL; OCTANOL; ORTHO CRESOL; PARA CRESOL; PENTANOL; PHENETHYL ALCOHOL; PHENOL; PROPANOL; RESORCINOL; SODIUM ION; TETRYLAMMONIUM; UNINDEXED DRUG;

ARTICLE; ARTIFICIAL MEMBRANE; DIFFUSION; HUMAN; HUMAN TISSUE; ION TRANSPORT; LINEAR FREE ENERGY RELATIONSHIP; SKIN PERMEABILITY; STRATUM CORNEUM;

EID: 84862818406     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23086     Document Type: Article

References (37)

1. Geinoz S, Guy RH, Testa B, Carrupt PA. 2004. Quantitative structure-permeation relationships (QSPeRs) to predict skin permeation: A critical evaluation. Pharm Res 21(1):83-92.
2. Abraham MH, Acree WE Jr. 2010. The transfer of neutral molecules, ions and ionic species from water to wet octanol. Phys Chem Chem Phys 12(40):13182-13188.
3. Abraham MH, Zhao YH. 2005. Characterisation of the water/o-nitrophenyl octyl ether system in terms of the partition of nonelectrolytes and of ions. Phys Chem Chem Phys 7(12):2418-2422.
4. Abraham MH. 2003. The determination of air/water partition coefficients for alkyl carboxylic acids by a new indirect method. J Environ Monit 5(5):747-752.
5. Abraham MH, Acree WE Jr. 2005. Characterisation of the water-isopropyl myristate system. Int J Pharm 294(1-2):121-128.
6. Sprunger L, Blake-Taylor BH, Wairegi A, Acree WE Jr., Abraham MH. 2007. Characterization of the retention behavior of organic and pharmaceutical drug molecules on an immobilized artificial membrane column with the Abraham model. J Chromatogr A 1160(1-2):235-245.
7. Wang Y, Sun J, Liu H, Liu J, Zhang L, Liu K, He Z. 2009. Predicting skin permeability using liposome electrokinetic chromatography. Analyst 134(2):267-272.
8. Gil-Agusti M, Esteve-Romero J, Abraham MH. 2006. Solute-solvent interactions in micellar liquid chromatography: Characterization of hybrid micellar systems of sodium dodecyl sulfate-pentanol. J Chromatogr A 1117(1):47-55.
9. Burns ST, Agbodjan AA, Khaledi MG. 2002. Characterization of solvation properties of lipid bilayer membranes in liposome electrokinetic chromatography. J Chromatogr A 973(1-2):167-176.
10. Zhao YH, Le J, Abraham MH, Hersey A, Eddershaw PJ, Luscombe CN, Butina D, Beck G, Sherborne B, Cooper I, Platts JA. 2001. Evaluation of human intestinal absorption data and subsequent derivation of a quantitative structure-activity relationship (QSAR) with the Abraham descriptors. J Pharm Sci 90(6):749-784.
11. Abraham MH, Martins F. 2004. Human skin permeation and partition: General linear free-energy relationship analyses. J Pharm Sci 93(6):1508-1523.
12. Zhao YH, Abraham MH, Hersey A, Luscombe CN. 2003. Quantitative relationship between rat intestinal absorption and Abraham descriptors. Eur J Med Chem 38(11-12):939-947.
13. Abraham MH, Acree WE Jr. 2010. Equations for the transfer of neutral molecules and ionic species from water to organic phases. J Org Chem 75(4):1006-1015.
14. Abraham MH. 2011. The permeation of neutral molecules, ions, and ionic species through membranes: Brain permeation as an example. J Pharm Sci 100(5):1690-1701.
15. Abraham MH, Acree WE Jr. 2010. The transfer of neutral molecules, ions and ionic species from water to ethylene glycol and to propylene carbonate; descriptors for pyridinium cations. New J Chem 34(10):2298-2305.
16. Zhang K, Chen M, Scriba GK, Abraham MH, Fahr A, Liu X. 2011. Linear free energy relationship analysis of retention factors in cerasome electrokinetic chromatography intended for predicting drug skin permeation. J Pharm Sci 100(8):3105-3113.
17. Meindl WR, Von Angerer E, Schoenenberger H, Ruckdeschel G. 1984. Benzylamines: Synthesis and evaluation of antimycobacterial properties. J Med Chem 27(9):1111-1118.
18. Singh P, Roberts MS. 1994. Skin permeability and local tissue concentrations of nonsteroidal anti-inflammatory drugs after topical application. J Pharmacol Exp Ther 268(1):144-151.
19. Hirvonen J, Rytting JH, Paronen P, Urtti A. 1991. Dodecyl N, N-dimethylamino acetate and azone enhance drug penetration across human, snake, and rabbit skin. Pharm Res 8(7):933-937.
20. Roberts MS, Anderson RA, Swarbrick J. 1977. Permeability of human epidermis to phenolic compounds. J Pharm Pharmacol 29(11):677-683.
21. Bronaugh RL, Congdon ER. 1984. Percutaneous absorption of hair dyes: Correlation with partition coefficients. J Invest Dermatol 83(2):124-127.
22. Gwak HS, Choi JS, Choi HK. 2005. Enhanced bioavailability of piroxicam via salt formation with ethanolamines. Int J Pharm 297(1-2):156-161.
23. Roy SD, Flynn GL. 1990. Transdermal delivery of narcotic analgesics: pH, anatomical, and subject influences on cutaneous permeability of fentanyl and sufentanil. Pharm Res 7(8):842-847.
24. Kasting GB, Bowman LA. 1990. DC electrical properties of frozen, excised human skin. Pharm Res 7(2):134-143.
25. Peck KD, Ghanem AH, Higuchi WI. 1995. The effect of temperature upon the permeation of polar and ionic solutes through human epidermal membrane. J Pharm Sci 84(8):975-982.
26. Cruciani G, Baroni M, Clementi S, Costantino G, Riganelli D, Skagerberg B. 1992. Predictive ability of regression-models.1. Standard-deviation of prediction errors (Sdep). J Chemometr 6(6):335-346.
27. Hawkins DM. 2004. The problem of overfitting. J Chem Inf Comput Sci 44(1):1-12.
28. Johnson ME, Blankschtein D, Langer R. 1997. Evaluation of solute permeation through the stratum corneum: Lateral bilayer diffusion as the primary transport mechanism. J Pharm Sci-Us 86(10):1162-1172.
29. Burns ST, Khaledi MG. 2002. Rapid determination of liposome-water partition coefficients (K-lw) using liposome electrokinetic chromatography (LEKC). J Pharm Sci 91(7):1601-1612.
30. Wang TF, Kasting GB, Nitsche JM. 2006. A multiphase microscopic diffusion model for stratum corneum permeability. I. Formulation, solution, and illustrative results for representative compounds. J Pharm Sci 95(3):620-648.
31. Hills EE, Abraham MH, Hersey A, Bevan CD. 2011. Diffusion coefficients in ethanol and in water at 298 K: Linear free energy relationships. Fluid Phase Equilibr 303(1):45-55.
32. Mitragotri S. 2003. Modeling skin permeability to hydrophilic and hydrophobic solutes based on four permeation pathways. J Control Release 86(1):69-92.
33. Mitragotri S, Johnson ME, Blankschtein D, Langer R. 1999. An analysis of the size selectivity of solute partitioning, diffusion, and permeation across lipid bilayers. Biophys J 77(3):1268-1283.
34. Abraham MH, Acree WE Jr. Equations for the partition of neutral molecules, ions and ionic species from water to water-ethanol mixtures. J Soln Chem (in press).
35. Michniak BB, Meidan V, Al-Khalili M, Wertz PW. 2005. Skin: Physiology and penetration pathways. In Delivery system handbook for personal care and cosmetic products: Technology, applications, and formulations; Rosen MR, Ed. Norwich: William Andrew, pp 78-95.
36. Buchwald P, Bodor N. 2001. A simple, predictive, structure-based skin permeability model. J Pharm Pharmacol 53(8):1087-1098.
37. Abraham MH, Chadha HS, Whiting GS, Mitchell RC. 1994. Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the delta log P parameter of Seiler. J Pharm Sci 83(8):1085-1100.