Improving the applicability of (Q)SARs for percutaneous penetration in regulatory risk assessment

Human and Experimental Toxicology

Volumn 27, Issue 4, 2008, Pages 269-276

  Bouwman, T ^a   Cronin, M T D ^b   Bessems, J G M ^a   Van De Sandt, J J M ^a  

^a TNO   (Netherlands)

^b LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

Author keywords

(Q)SAR; Dermal absorption; Quantitative structure activity relationships; REACH; Risk assessment

Indexed keywords

ALGORITHM; ARTICLE; ECONOMIC ASPECT; HUMAN; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RISK ASSESSMENT; SKIN ABSORPTION; SKIN PENETRATION; SKINFOLD THICKNESS; BIOLOGICAL MODEL; CHEMISTRY; DRUG EFFECT; EUROPEAN UNION; GOVERNMENT REGULATION; LEGAL ASPECT; PHYSIOLOGY; PREDICTION AND FORECASTING;

XENOBIOTIC AGENT;

EUROPEAN UNION; GOVERNMENT REGULATION; HUMANS; MODELS, BIOLOGICAL; PREDICTIVE VALUE OF TESTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RISK ASSESSMENT; SKIN ABSORPTION; XENOBIOTICS;

EID: 52649166144     PISSN: 09603271     EISSN: 14770903     Source Type: Journal    
DOI: 10.1177/0960327107085829     Document Type: Article

References (50)

1. http://ecb.jrc.it/reach/reach-legislation/
2. http://echa.europa.eu/reach-en.html/
3. http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2007:136:0281: 0282:EN:PDF
4. http://ihcp.jrc.ec.europa.eu/docs/20051107its.pdf
5. http://www.oecd.orgl/dataoecd/55/35/38130292.pdf
6. Potts RO Guy RH. Predicting skin permeability. Pharm Res 1992 ; 9: 663-669.
7. Barratt MD. Quantitative structure-activity relationships for skin permeability. Toxicol In Vitro 1995 ; 9: 27-37.
8. Potts RO Guy RH. A predictive algorithm for skin permeability: the effects of molecular size and hydrogen bond activity. Pharm Res 1995 ; 12: 1628-1633.
9. Pugh WJ Degim IT Hadgraft J. Epidermal permeability-penetrant structure relationships: 4, QSAR of permeant diffusion across human stratum corneum in terms of molecular weight, H-bonding and electronic charge. Int J Pharm 2000 ; 197: 203-211.
10. Abraham MH Martins F Mitchell RC. The factors that influence skin penetration of solutes. J Pharm Pharmacol 1995 ; 47: 8-16.
11. Pugh WJ Hadgraft J. Ab initio prediction of human skin permeability coeefficients. Int J Pharm 1994 ; 103: 163-178.
12. Cronin MTD Dearden JC Moss GP Murray-Dickson G. Investigation of the mechanism of flux across human skin in vitro by quantitative structure-permeability relationships. Eur J Pharm Sci 1999 ; 7: 325-330.
13. Cronin MTD. The prediction of skin permeability using quantitative structure-activity relationships (QSARs). In: J Riviere, (ed), Dermal absorption models in toxicology and pharmacology. Boca Raton (Florida, USA): CRC Press ; 2005.
14. Degim T. New tools and approaches for predicting skin permeability. Drug Discov Today 2006 ; 11: 517-523.
15. http://www.who.int/ipcs/publications/ehc/ehc235.pdf
16. Moss GP Dearden JC Patel H Cronin MTD. Quantitative structure- permeability relationships (QSPRs) for percutaneous absorption. Toxicol In Vitro 2002 ; 16: 299-317.
17. Walker JD Whittaker C McDougal JN. Role of the TSCA Interagency Testing Committee in meeting the U.S. Governments data needs: designating chemicals for percutaneus absorption testing. In: F Marzulli H Maibach, (eds), Dermatotoxicology. Washington (District of Columbia, USA): Taylor & Francis ; 1996.
18. Geinoz S Guy RH Testa B Carrupt PA. Quantitative structure-permeation relationships (QSPeRs) to predict skin permeation: a critical evaluation. Pharm Res 2004 ; 21: 83-92.
19. http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
20. http://home.wxs.nl/∼wtberge/qsarperm.html
21. Abraham MH Martins F. Human skin permeation and partition: general linear free-energy relationship analyses. J Pharm Sci 2004 ; 93: 1508-1523.
22. Buchwald P Bodor N. A simple, predictive, structure-based skin permeability model. J Pharm Pharmacol 2001 ; 53: 1087-1098.
23. Lim CW Fujiwara S Yamashita F Hashida M. Prediction of human skin permeability using a combination of molecular orbital calculations and artificial neural network. Biol Pharm Bull 2002 ; 25: 361-366.
24. Magnusson BM Anissimov YG Cross SE Roberts MS. Molecular size as the main determinant of solute maximum flux across the skin. J Invest Dermatol 2004 ; 122: 993-999.
25. Raevsky OA Schaper K-J. Quantitative estimation of hydrogen bond contribution to permeability and absorption processes of some chemicals and drugs. Eur J Med Chem 1998 ; 33: 799-807.
26. Lien EJ Gao H. QSAR analysis of skin permeability of various drugs in man as compared to in vivo and in vitro studies in rodents. Pharm Res 1995 ; 12: 583-587.
27. Roy TA. SAR models for estimating the percutaneous absorption of polynuclear aromatic hydrocarbons. SAR and QSAR Environ Res 1998 ; 9: 171-185.
28. Abraham MH Martins F Mitchell RC. Algorithms for skin permeability using hydrogen bond descriptors: the problem of steroids. J Pharm Pharmacol 1997 ; 49: 858-865.
29. Brown SL Rossi JE. A simple method for estimating termal absorption of chemicals in water. Chemospere 1989 ; 19: 1989-2001.
30. Cronin MT Dearden JC Moss GP Murray-Dickson G. Investigation of the mechanism of flux across human skin in vitro by quantitative structure-permeability relationships. Eur J Pharm Sci 1999 ; 7: 325-330.
31. Dearden JC Cronin MTD Patel H Raevsky OA. QSAR prediction of human skin permeability coefficient. J Pharm Pharmacol 2000 ; 52 (Suppl.): 221.
32. el Tayar N. Partitioning of solutes in different solvent systems: the contribution of hydrogen-bonding capacity and polarity. J Pharm Sci 1991 ; 80: 590-598.
33. el Tayar N. Percutaneous penetration of drugs: a quantitative structure-permeability relationship study. J Pharm Sci 1991 ; 80: 744-749.
34. Frasch HF. A random walk model of skin permeation. Risk Anal 2002 ; 22: 265-276.
35. Fujiwara S Yamashita F Hashida M. QSAR analysis of interstudy variable skin permeability based on the "latent membrane permeability concept. J Pharm Sci 2003 ; 92: 1939-1946.
36. Gute BD Grunwald GD Basak SC. Prediction of the dermal penetration of polycyclic aromatic hydrocarbons (PAHs): a hierarchical QSAR approach. SAR QSAR Environ Res 1999 ; 10: 1-15.
37. Guy RH Potts RO. Structure-permeability relationships in percutaneous penetration. J Pharm Sci 1992 ; 81: 603-604.
38. Hostynek JJ Magee PS. Modelling in vivo human skin absorption. Quant Struct-Act Rel 1997 ; 16: 473-479.
39. Kitagawa S Li H Sato S. Skin permeation of parabens in excised guinea pig dorsal skin, its modification by penetration enhancers and their relationship with n-octanol/water partition coefficients. Chem Pharm Bull 1997 ; 45: 1354-1357.
40. Lee CK Uchida T Kitagawa K Yagi A Kim NS Goto S. Skin permeability of various drugs with different lipophilicity. J Pharm Sci 1994 ; 83: 562-565.
41. Lipnick RL. Outliers: their origin and use in the classification of molecular mechanisms of toxicity. Sci Total Environ 1991 ; 109-110: 131-353.
42. Martinez-Pla JJ Martin-Biosca Y Sagrado S Villanueva-Camanas RM Medina-Hernandez MJ. Biopartitioning micellar chromatography to predict skin permeability. Biomed Chromatogr 2003 ; 17: 530-537.
43. McKone TE Howd RA. Estimating dermal uptake of nonionic organic chemicals from water and soil: I. Unified fugacity-based models for risk assessments. Risk Anal 1992 ; 12: 543-557.
44. Moody RP MacPherson H. Determination of dermal absorption QSAR/QSPRs by brute force regression: multiparameter model development with Molsuite 2000. J Toxicol Environ Health Part A 2003 ; 66: 1927-1942.
45. Moss GP Cronin MT. Quantitative structure-permeability relationships for percutaneous absorption: re-analysis of steroid data. Int J Pharm 2002 ; 238: 105-109.
46. Patel H ten Berge W Cronin MT. Quantitative structure-activity relationships (QSARs) for the prediction of skin permeation of exogenous chemicals. Chemosphere 2002 ; 48: 603-613.
47. Sartorelli P. Prediction of percutaneous absorption from physicochemical data: a model based on data of in vitro experiments. Ann Occup Hyg 1998 ; 42: 267-276.
48. Flynn GL. Physicochemical determinants of skin absorption. In: TR Gerrity CJ Henry, (eds), Principles of route-to-route extrapolation for risk assessment. New York: Elsevier ; 1990.
49. http://edetox.ncl.ac.uk/index.html.
50. http://toxsci.oxfordjournals.org/cgi/reprint/kfj071v1