Design of improved permeation enhancers for transdermal drug delivery

Journal of Pharmaceutical Sciences

Volumn 98, Issue 11, 2009, Pages 4085-4099

  Godavarthy, Srinivas S ^a   Yerramsetty, Krishna M ^a   Rachakonda, Vijay K ^a   Neely, Brian J ^a   Madihally, Sundararajan V ^a   Robinson Jr , Robert L ^a   Gasem, Khaled A M ^a  

^a Oklahoma State University   (United States)

Author keywords

Cell culture; Molecular modeling; Morphology; Permeation enhancers; QSPR; Skin; Transdermal drug delivery

Indexed keywords

1 (1 ADAMANTYL) 2 PYRROLIDINONE; 1 (4 NITROPHENYL)PYRROLIDINE 2,5 DIONE; 1 DODECYL 2 PYRROLIDINONE; 1 METHYL 2 PYRROLIDINONE; 2 PYRROLIDONE DERIVATIVE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 3 AMINO 1 HYDROXY 2 PYRROLIDINONE; 3 METHYL 2 OXAZOLIDINONE; DECANOL; LAURIC ACID; MELATONIN; NONANOL; OLEIC ACID; OXAZOLIDINONE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; ARTIFICIAL NEURAL NETWORK; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG PENETRATION; FIBROBLAST; GENETIC ALGORITHM; HISTOLOGY; NONHUMAN; QUANTITATIVE STRUCTURE PROPERTY RELATION; SKIN PERMEABILITY; STAINING;

EID: 70349647154     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21940     Document Type: Article

References (47)

1. Chong S, Fung HL. 1989. Transdermal drug delivery systems: Pharmacokinetics, clinical efficacy, and tolerance development. In: Hadgraft J, Guy RH, editors. Transdermal drug delivery: Developmental issues and research initiatives. 1st edition. New York: Marcel Dekker. pp. 135-154.
2. Monteiro-Riviere NA. 1991. Comparative anatomy, physiology, and biochemistry of mammalian skin. In: Hobson DW, editor. Dermal and ocular toxicology: Fundamentals and methods. 1st edition. Boca Raton, FL: CRC Press. pp. 3-73.
3. Monteiro-Riviere NA. 1996. Anatomical factors affecting barrier function. In: Marzulli FN, Maibach HI, editors. Dermatotoxicology. 1st edition. Washington, DC: Taylor & Francis. pp. 43-70.
4. Chang SK, Riviere JE. 1993. Effect of humidity and occlusion on the percutaneous absorption of parathion in vitro. Pharm Res 10:152-155. (Pubitemid 23020854)
5. Elias PM. 1983. Epidermal lipids, barrier function, and desquamation. J Invest Dermatol 80:44-49.
6. Barry BW. 2001. Novel mechanisms and devices to enable successful transdermal drug delivery. Eur J Pharm Sci 14:101-114.
7. Kadir R, Stempler D, Liron Z, Cohen S. 1987. Delivery of theophylline into excised human skin from alkanoic acid solutions: A "push-pull" mechanism. J Pharm Sci 76:774-779.
8. Karande P, Jain A, Mitragotri S. 2004. Discovery of transdermal penetration enhancers by high-throughput screening. Nat Biotechnol 22:192-197. (Pubitemid 38160534)
9. Williams AC, Barry BW. 2004. Penetration enhancers. Adv Drug Deliv Rev 56:603-618.
10. Barry BW, Williams AC. 1995. Permeation enhancement through skin. In: Swarbrick J, Boylan JC, editors. Encyclopedia of pharmaceutical technology. 1st edition. New York: Marcel Dekker, Inc. pp. 449-493.
11. Goates CY, Knutson K. 1994. Enhanced permeation of polar compounds through human epidermis. I. Permeability and membrane structural changes in the presence of short chain alcohols. Biochim Biophys Acta 1195:169-179.
12. Kanikkannan N, Kandimalla K, Lamba SS, Singh M. 1999. Structure-activity relationship of chemical penetration enhancers in transdermal drug delivery. Curr Med Chem 6:593-608.
13. Neely BJ, Madihally SV, Robinson RL, Jr., Gasem KAM. 2008. Non-linear quantitative structure-property relationship modeling of skin permeation coefficient. J Pharm Sci DOI: 10.1002/jps.21678.
14. Golla S, Madihally SV, Robinson RL, Jr., Gasem KAM. 2008. Quantitative structure-property relationship modeling of skin sensitization: A quantitative prediction. Toxicol In Vitro (in press).
15. Godavarthy SS, Robinson RL, Jr., Gasem KAM. 2006. QSPR approach for melting-point prediction. Ind Eng Chem Res 45:12.
16. Godavarthy SS. 2004. Design of improved solvents for extractive distillation. Stillwater, Oklahoma: School of Chemical Engineering, Oklahoma State University.
17. Andega S, Kanikkannan N, Singh M. 2001. Comparison of the effect of fatty alcohols on the permeation of melatonin between porcine and human skin. J Control Release 77:17-25. (Pubitemid 33022612)
18. Kandimalla K, Kanikkannan N, Andega S, Singh M. 1999. Effect of fatty acids on the permeation of melatonin across rat and pig skin in-vitro and on the transepidermal water loss in rats in-vivo. J Pharm Pharmacol 51:783-790. (Pubitemid 29377949)
19. Potts RO, Guy RH. 1992. Predicting skin permeability. Pharm Res 9:663-669.
20. Baert B, Deconinck E, Van Gele M, Slodicka M, Stoppie P, Bode S, Slegers G, Vander Heyden Y, Lambert J, Beetens J, De Spiegeleer B. 2007. Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds. Bioorg Med Chem 15:6943-6955. (Pubitemid 47451795)
21. Schmook FP, Meingassner JG, Billich A. 2001. Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption. Int J Pharm 215:51-56. (Pubitemid 32206603)
22. Vallet V, Cruz C, Josse D, Bazire A, Lallement G, Boudry I. 2007. In vitro percutaneous penetration of organophosphorus compounds using full-thickness and split-thickness pig and human skin. Toxicol In Vitro 21:1182-1190.
23. Venkatasubramanian V, Chan K, Caruthers JM. 1994. Computer-aided molecular design using genetic algorithms. Comput Chem Eng 18:833-844.
24. Venkatasubramanian V, Chan K, Caruthers JM. 1994. Proceedings of the Fifth International Symposium on Process Systems Engineering, (PSE 94), Kyongu, South Korea, 1994.
25. Venkatasubramanian V, Sundaram A. 1998. Genetic algorithms: Introduction and applications. 1st edition. New York: Wiley.
26. Venkatasubramanian V, Sundaram A, Chan K, Caruthers JM. 1996. Computer-aided molecular design using neural networks and genetic algorithms. In: Devillers J, editor. Genetic algorithms in molecular modeling. 1st edition. New York: Academic Press. pp. 271-302.
27. Sundaram A, Ghosh P, Venkatasubramanian V, Caruthers JM, Daly DT. 1999. Proceedings of the International Conference on Foundations of Computer Aided Process Design, Snowmass, CO, 1999, pp. 478-481.
28. Sundaram A, Venkatasubramanian V. 1998. Parametric sensitivity and search-space characterization studies of genetic algorithms for computer-aided polymer design. J Chem Info Comput Sci 38:1177-1191. (Pubitemid 128591284)
29. Gani R, Brignole EA. 1983. Molecular design of solvents for liquid extraction based on UNIFAC. Fluid Phase Equilibria 13:331-340. (Pubitemid 14599958)
30. Gani R, Nielsen B, Fredenslund A. 1991. A group contribution approach to computer-aided molecular design. AIChE J 37:1318-1332. (Pubitemid 21693455)
31. Joback KG, Stephanopoulos G. 1989. Proceedings FOCAPD, Snowmass Village, Colorado, 1989, pp. 363-387.
32. Macchietto S, Odele O, Omatsone O. 1990. Design of optimal solvents for liquid-liquid extraction and gas absorption processes. Chem Eng Res Des 68:429-433. (Pubitemid 21670764)
33. Vaidyanathan R, El-Halwagi M. 1994. Computer-aided design of high performance polymers. J Elastomers Plast 25:277-293.
34. Maranas CD. 1996. Optimal computer-aided molecular design: A polymer design case study. Ind Eng Chem Res 35:3403-3414. (Pubitemid 126474867)
35. Morley C. 2006. OpenBabelGUI. 2.0.2 edition.
36. Osborne DW, Henke JJ. 1997. Skin penetration enhancers cited in the technical literature. Pharm Technol 21:58-66.
37. Mosmann T. 1983. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J Immunol Methods 65:55-63. (Pubitemid 14203433)
38. Rachakonda VK, Yerramsetty KM, Madihally SV, Robinson RL, Gasem KAM. 2008. Screening of chemical penetration enhancers for transdermal drug delivery using electrical resistance of skin. Pharm Res 25:2697-2704.
39. Andega S, Kanikkannan N, Singh M. 2001. Comparison of the effect of fatty alcohols on the permeation of melatonin between porcine and human skin. J Control Release 77:17-25. (Pubitemid 33022612)
40. Zhao K, Singh S, Singh J. 2001. Effect of menthone on the in vitro percutaneous absorption of tamoxifen and skin reversibility. Int J Pharm 219:177-181. (Pubitemid 32391376)
41. Godwin DA, Michniak BB, Creek KE. 1997. Evaluation of transdermal penetration enhancers using a novel skin alternative. J Pharm Sci 86:1001-1005. (Pubitemid 27382900)
42. Solomon GM, Morse EP, Garbo MJ, Milton DK. 1996. Stillbirth after occupational exposure to nmethyl-2-pyrrolidone: A case report and review of the literature. J Occup Environ Med 38:705.
43. Kojima H, Sato A, Hanamura A, Katada T, Konishi H. 1998. Evaluation of skin irritation in a reconstituted human dermal model(3-D model) using water insoluble fatty acids, fatty alcohols and hydrocarbons. Altern Anim Test Exp 5:201-210.
44. Yerramsetty KM, Rachakonda VK, Madihally SV, Robert L, Robinson J, Gasem KAM. 2008. Influence of enhancer characteristics and drug hydrophobicity on permeation enhancement. J Control Release (in preparation).
45. ChemAxon. Marvin and Calculator Plugin Demo. Budapest, Hungary: ChemAxon.
46. Karelson M, Perkson A. 1999. The correlation and prediction of densities of organic liquids. Comput Chem 23:49-59. (Pubitemid 129662868)
47. Moser K, Kriwet K, Naik A, Kalia YN, Guy RH. 2001. Passive skin penetration enhancement and its quantification in vitro. Eur J Pharm Biopharm 52:103-112. (Pubitemid 32755887)