Maximum transepidermal flux for similar size phenolic compounds is enhanced by solvent uptake into the skin

Journal of Controlled Release

Volumn 154, Issue 1, 2011, Pages 50-57

  Zhang, Qian ^a   Li, Peng ^a   Roberts, Michael S ^a,b  

^a UNIVERSITY OF SOUTH AUSTRALIA   (Australia)

^b UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Diffusivity; Maximum flux; Solubility in the stratum corneum; Solvent uptake

Indexed keywords

ATR FTIR; ATTENUATED TOTAL REFLECTANCE FOURIER TRANSFORM INFRARED; BINARY SOLVENT SYSTEMS; COSOLVENTS; DIFFUSIVITIES; IN-VITRO; INTERCELLULAR LIPIDS; LIPOPHILICITY; MAXIMUM FLUX; MULTIPHOTON MICROSCOPY; PHENOLIC COMPOUNDS; PROPYLENE GLYCOLS; SKIN PENETRATION; SOLVENT UPTAKE; STRATUM CORNEUM;

FOURIER TRANSFORMS; GLYCOLS; HYDROGEN BONDS; PROPYLENE; SOLUBILITY; SOLVENTS; VEHICLES;

PHENOLS;

PHENOL DERIVATIVE; PROPYLENE GLYCOL;

ARTICLE; CONTROLLED STUDY; DRUG PENETRATION; DRUG SOLUBILITY; DRUG UPTAKE; HUMAN; HUMAN TISSUE; IN VITRO STUDY; INFRARED SPECTROSCOPY; LIPOPHILICITY; MOLECULAR WEIGHT; MULTIPHOTON MICROSCOPY; PARTICLE SIZE; PRIORITY JOURNAL; SKIN PENETRATION; STRATUM CORNEUM;

ADMINISTRATION, CUTANEOUS; BIOLOGICAL TRANSPORT; DIFFUSION CHAMBERS, CULTURE; EPIDERMIS; FEMALE; HUMANS; HYDROGEN BONDING; MICROSCOPY, FLUORESCENCE, MULTIPHOTON; MOLECULAR WEIGHT; NAPHTHOLS; PERMEABILITY; PHENOLS; PROPYLENE GLYCOL; SKIN ABSORPTION; SOLUBILITY; SOLVENTS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TISSUE DISTRIBUTION;

EID: 79960898776     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2011.04.018     Document Type: Article

References (59)

1. Q. Zhang, J.E. Grice, P. Li, O.G. Jepps, G.J. Wang, M.S. Roberts, Skin solubility determines maximum transepidermal flux for similar size molecules, Pharm. Res. 26 (2009) 1974-1985.
2. T. Yano, A. Nakagawa, M. Tsuji, K. Noda, Skin permeability of various non-steroidal anti-inflammatory drugs in man, Life Sci. 39 (1986) 1043-1050. (Pubitemid 16032179)
3. R.S. Hinz, C.R. Lorence, C.D. Hodson, C. Hansch, L.L. Hall, R.H. Guy, Percutaneous penetration of para-substituted phenols in vitro, Fundam. Appl. Toxicol. 17 (1991) 575-583.
4. D. Bucks, H.I. Maibach, Occlusion dose not uniformly enhance penetration in vivo, in: R.L. Bronaugh, H.I. Maibach (Eds.), Percutaneous Absorption: Drugs, Cosmetics, Mechanisms, Methodology, Taylor & Francis, Boca Raton, 2005, pp. 65-83.
5. B.M. Magnusson, S.E. Cross, G. Winckle, M.S. Roberts, Percutaneous absorption of steroids: determination of in vitro permeability and tissue reservoir characteristics in human skin layers, Skin Pharmacol. Physiol. 19 (2006) 336-342.
6. M.S. Roberts, R.A. Anderson, J. Swarbrick, Permeability of human epidermis to phenolic compounds, J. Pharm. Pharmacol. 29 (1977) 677-683.
7. R.O. Potts, R.H. Guy, Predicting skin permeability, Pharm. Res. 9 (1992) 663-669.
8. S.E. Cross, W.J. Pugh, J. Hadgraft, M.S. Roberts, Probing the effect of vehicles on topical delivery: understanding the basic relationship between solvent and solute penetration using silicone membranes, Pharm. Res. 18 (2001) 999-1005.
9. T. Ghafourian, E.G. Samaras, J.D. Brooks, J.E. Riviere, Validated models for predicting skin penetration from different vehicles, Eur. J. Pharm. Sci. 41 (2010) 612-616.
10. http://en.wikipedia.org/wiki/Propylene-glycol.
11. L. Duracher, L. Blasco, J.C. Hubaud, L. Vian, G. Marti-Mestres, The influence of alcohol, propylene glycol and 1,2-pentanediol on the permeability of hydrophilic model drug through excised pig skin, Int. J. Pharm. 374 (2009) 39-45.
12. R.M. Watkinson, R.H. Guy, J. Hadgraft, M.E. Lane, Optimisation of cosolvent concentration for topical drug delivery-II: influence of propylene glycol on ibuprofen permeation, Skin Pharmacol. Physiol. 22 (2009) 225-230.
13. G. Winckle, Y.G. Anissimov, S.E. Cross, G. Wise, M.S. Roberts, An integrated pharmacokinetic and imaging evaluation of vehicle effects on solute human epidermal flux and, retention characteristics, Pharm. Res. 25 (2008) 158-166.
14. J. Ostrenga, C. Steinmetz, B. Poulsen, S. Yett, Significance of vehicle composition. II. Prediction of optimal vehicle composition, J. Pharm. Sci. 60 (1971) 1180-1183.
15. R. Panchagnula, P.S. Salve, N.S. Thomas, A.K. Jain, P. Ramarao, Transdermal delivery of naloxone: effect of water, propylene glycol, ethanol and their binary combinations on permeation through rat skin, Int. J. Pharm. 219 (2001) 95-105. (Pubitemid 32391369)
16. A.M. Kligman, E. Christophers, Preparation of isolated sheets of human stratum corneum, Arch. Dermatol. 88 (1963) 702-705.
17. M.S. Roberts, E.J. Triggs, R.A. Anderson, Permeability of solutes through biological membranes measured by a desorption technique, Nature 257 (1975) 225-227.
18. R.A. Anderson, E.J. Triggs, M.S. Roberts, The percutaneous absorption of phenolic compounds. 3. Evaluation of permeability through human stratum corneum using a desorption technique, Aust. J. Pharm. Sci. 5 (1976) 107-110.
19. A.S. Huq, N.F. Ho, N. Husari, G.L. Flynn, W.E. Jetzer, L. Condie Jr., Permeation of water contaminative phenols through hairless mouse skin, Arch. Environ. Contam. Toxicol. 15 (1986) 557-566. (Pubitemid 16048644)
20. H.F. Frasch, L.Y. Zang, A.M. Barbero, S.E. Anderson, In vitro dermal penetration of 4-chloro-3-methylphenol from commercial metal working fluid and aqueous vehicles, J. Toxicol. Environ. Health A 73 (2010) 1394-1405.
21. M.S. Roberts, Y.G. Anissimov, Mathematical models in percutaneous absorption, in: R.L. Bronaugh, H.I. Maibach (Eds.), Percutaneous Absorption: Drugs, Cosmetics, Mechanisms, Methodology, Taylor & Francis, Boca Raton, 2005, pp. 1-44.
22. P.V. Raykar, M.C. Fung, B.D. Anderson, The role of protein and lipid domains in the uptake of solutes by human stratum corneum, Pharm. Res. 5 (1988) 140-150.
23. G.M. Golden, D.B. Guzek, R.R. Harris, J.E. McKie, R.O. Potts, Lipid thermotropic transitions in human stratum corneum, J. Invest. Dermatol. 86 (1986) 255-259.
24. M.L. Francoeur, G.M. Golden, R.O. Potts, Oleic acid: its effects on stratum corneum in relation to (trans)dermal drug delivery, Pharm. Res. 7 (1990) 621-627.
25. G.M. Golden, D.B. Guzek, A.H. Kennedy, J.E. McKie, R.O. Potts, Stratum corneum lipid phase transitions and water barrier properties, Biochemistry 26 (1987) 2382-2388. (Pubitemid 17080985)
26. K. Babita, V. Kumar, V. Rana, S. Jain, A.K. Tiwary, Thermotropic and spectroscopic behavior of skin: relationship with percutaneous permeation enhancement, Curr. Drug Deliv. 3 (2006) 95-113.
27. W. He, X. Guo, M. Zhang, Transdermal permeation enhancement of N-trimethyl chitosan for testosterone, Int. J. Pharm. 356 (2008) 82-87.
28. S. Nicoli, A.L. Bunge, M.B. Delgado-Charro, R.H. Guy, Dermatopharmacokinetics: factors influencing drug clearance from the stratum corneum, Pharm. Res. 26 (2009) 865-871.
29. H. Tori, M. Tasumi, Theoretical analyses of the amide I infrared bands of globular proteins, in: H.H. Mantsch, D. Chapman (Eds.), Infrared Spectroscopy of Biomolecules, Wiley-Liss, New York, 1996, pp. 1-18.
30. C.A. Rice-Evans, A.T. Diplock, M.C.R. Symons, Techniques in free radical research, in: R.H. Burdon, P.H. van Knippenberg (Eds.), Laboratory Techniques in Biochemistry and Molecular Biology, Elsevier, New York, 1999, pp. 207-218.
31. H.K. Vaddi, P.C. Ho, Y.W. Chan, S.Y. Chan, Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum, Biol. Pharm. Bull. 26 (2003) 220-228. (Pubitemid 41699669)
32. K.S. Bhatia, S. Gao, J. Singh, Effect of penetration enhancers and iontophoresis on the FT-IR spectroscopy and LHRH permeability through porcine skin, J. Control. Release 47 (1997) 81-89. (Pubitemid 27154403)
33. A.K. Levang, K. Zhao, J. Singh, Effect of ethanol/propylene glycol on the in vitro percutaneous absorption of aspirin, biophysical changes and macroscopic barrier properties of the skin, Int. J. Pharm. 181 (1999) 255-263. (Pubitemid 29229812)
34. Y.S. Krishnaiah, V. Satyanarayana, R.S. Karthikeyan, Effect of the solvent system on the in vitro permeability of nicardipine hydrochloride through excised rat epidermis, J. Pharm. Pharm. Sci. 5 (2002) 123-130.
35. T. Ghafourian, E.G. Samaras, J.D. Brooks, J.E. Riviere, Modelling the effect of mixture components on permeation through skin, Int. J. Pharm. 398 (2010) 28-32.
36. J.E. Riviere, J.D. Brooks, Predicting skin permeability from complex chemical mixtures: dependency of quantitative structure permeation relationships on biology of skin model used, Toxicol. Sci. 119 (2010) 224-232.
37. K.J. Fanning, Y.G. Anissimov, M.S. Roberts, Sulphonylurea physicochemical-pharmacokinetic relationships in the pancreas and liver, J. Pharm. Sci. 98 (2009) 2807-2821.
38. C. Hansch, J.M. Clayton, Lipophilic character and biological activity of drugs. II. The parabolic case, J. Pharm. Sci. 62 (1973) 1-21.
39. B.M. Magnusson, Y.G. Anissimov, S.E. Cross, M.S. Roberts, Molecular size as the main determinant of solute maximum flux across the skin, J. Invest. Dermatol. 122 (2004) 993-999.
40. W.J. Roberts, K.B. Sloan, Correlation of aqueous and lipid solubilities with flux for prodrugs of 5-fluorouracil, theophylline, and 6-mercaptopurine: a Potts-Guy approach, J. Pharm. Sci. 88 (1999) 515-522. (Pubitemid 29220977)
41. G.L. Flynn, S.H. Yalkowsky, Correlation and prediction of mass transport across membranes. I. Influence of alkyl chain length on flux-determining properties of barrier and diffusant, J. Pharm. Sci. 61 (1972) 838-852.
42. A.L. Bunge, R.L. Cleek, A new method for estimating dermal absorption from chemical exposure: 2. Effect of molecular weight and octanol-water partitioning, Pharm. Res. 12 (1995) 88-95.
43. B. Bendas, U. Schmalfuß, R. Neubert, Influence of propylene glycol as cosolvent on mechanisms of drug transport from hydrogels, Int. J. Pharm. 116 (1995) 19-30.
44. I.M. Schneider, B. Dobner, R. Neubert, W. Wohlrab, Evaluation of drug penetration into human skin ex vivo using branched fatty acids and propylene glycol, Int. J. Pharm. 145 (1996) 187-196.
45. L. Trottet, C. Merly, M. Mirza, J. Hadgraft, A.F. Davis, Effect of finite doses of propylene glycol on enhancement of in vitro percutaneous permeation of loperamide hydrochloride, Int. J. Pharm. 274 (2004) 213-219.
46. C. Herkenne, A. Naik, Y.N. Kalia, J. Hadgraft, R.H. Guy, Effect of propylene glycol on ibuprofen absorption into human skin in vivo, J. Pharm. Sci. 97 (2008) 185-197.
47. R.O. Potts, R.H. Guy, A predictive algorithm for skin permeability: the effects of molecular size and hydrogen bond activity, Pharm. Res. 12 (1995) 1628-1633.
48. W.J. Pugh, M.S. Roberts, J. Hadgraft, Epidermal permeability-penetrant structure relationships: 3. The effect of hydrogen bonding interactions and molecular size on diffusion across the stratum corneum, Int. J. Pharm. 138 (1996) 149-165.
49. J. du Plessis, W.J. Pugh, A. Judefeind, J. Hadgraft, Physico-chemical determinants of dermal drug delivery: effects of the number and substitution pattern of polar groups, Eur. J. Pharm. Sci. 16 (2002) 107-112.
50. M.S. Roberts, R.A. Anderson, J. Swarbrick, D.E. Moore, The percutaneous absorption of phenolic compounds: the mechanism of diffusion across the stratum corneum, J. Pharm. Pharmacol. 30 (1978) 486-490.
51. M.S. Roberts, R.A. Anderson, D.E. Moore, J. Swarbrick, The distribution of non-electrolytes between human stratum corneum and water, Aust. J. Pharm. Sci. 6 (1977) 77-82.
52. P. Santos, A.C. Watkinson, J. Hadgraft, M.E. Lane, Oxybutynin permeation in skin: the influence of drug and solvent activity, Int. J. Pharm. 384 (2010) 67-72.
53. A. Hoelgaard, B. Møllgaard, Dermal drug delivery-improvement by choice of vehicle or drug derivative, J. Control. Release 2 (1985) 111-120. (Pubitemid 16195931)
54. J.E. Grice, S. Ciotti, N. Weiner, P. Lockwood, S.E. Cross, M.S. Roberts, Relative uptake of minoxidil into appendages and stratum corneum and permeation through human skin in vitro, J. Pharm. Sci. 99 (2010) 712-718.
55. K.B. Sloan, S.A.M. Koch, K.G. Siver, Mannich base derivatives of theophylline and 5-fluorouracil: syntheses, properties and topical delivery characteristics, Int. J. Pharm. 21 (1984) 251-264. (Pubitemid 14017177)
56. S. Majumdar, J. Thomas, S. Wasdo, K.B. Sloan, The effect of water solubility of solutes on their flux through human skin in vitro, Int. J. Pharm. 329 (2007) 25-36.
57. J. Juntunen, S. Majumdar, K.B. Sloan, The effect of water solubility of solutes on their flux through human skin in vitro: a prodrug database integrated into the extended Flynn database, Int. J. Pharm. 351 (2008) 92-103.
58. J.E. Riviere, J.D. Brooks, Predicting skin permeability from complex chemical mixtures, Toxicol. Appl. Pharmacol. 208 (2005) 99-110. (Pubitemid 41377125)
59. M.S. Roberts, K.A. Walters, The relationship between structure and barrier function of skin, in: M.S. Roberts, K.A. Walters (Eds.), Dermal Absorption and Toxicity Assessment, Marcel Dekker, New York, 1998, pp. 1-42.