In silico models to predict dermal absorption from complex agrochemical formulations

SAR and QSAR in Environmental Research

Volumn 25, Issue 7, 2014, Pages 565-588

  Guth, K ^a,b   Riviere, J E ^b,c   Brooks, J D ^b   Dammann, M ^a   Fabian, E ^a   van Ravenzwaay, B ^a   Schafer Korting M ^d   Landsiedel, R ^a  

^a BASF SE   (Germany)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

^c KANSAS STATE UNIVERSITY   (United States)

^d FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

agrochemicals; dermal absorption; mixture; quantitative structure permeability relationship (QSPR); risk assessment

Indexed keywords

AGRICULTURAL CHEMICALS; ANIMALS; LINEAR REGRESSION;

ABSORPTION EXPERIMENTS; COMPLEX MIXTURE; DERMAL ABSORPTION; IN-SILICO; IN-SILICO MODELS; IN-VITRO; IN-VIVO; QUANTITATIVE STRUCTURE PERMEABILITY RELATIONSHIP; QUANTITATIVE STRUCTURES; RISKS ASSESSMENTS;

RISK ASSESSMENT;

ANIMALIA; RATTUS;

AGRICULTURAL CHEMICAL; DRUG MIXTURE;

ANIMAL; BIOLOGICAL MODEL; COMPUTER SIMULATION; DRUG MIXTURE; HUMAN; METABOLISM; PHARMACOKINETICS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; SKIN; SKIN ABSORPTION; STATISTICAL MODEL;

AGROCHEMICALS; ANIMALS; COMPLEX MIXTURES; COMPUTER SIMULATION; HUMANS; LINEAR MODELS; MODELS, BIOLOGICAL; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS; SKIN; SKIN ABSORPTION;

EID: 84904060502     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/1062936X.2014.919358     Document Type: Article

References (48)

1. OECD. OECD, Test No. 427: Skin Absorption: In Vivo Method, OECD Guidelines for the Testing of Chemicals, Section 4, OECD Publishing, 2004. Available at http://dx.doi.org/10.1787/9789264071063-en.
2. OECD. OECD, Test No. 428: Skin Absorption: In Vitro Method, OECD Guidelines for the Testing of Chemicals, Section 4, OECD Publishing, 2004. Available at http://dx.doi.org/10.1787/9789264071087-en.
3. EFSA Panel on Plant Protection Products and their Residues (PPR), Guidance on dermal absorption, EFSA J. 10 (2012), pp. 1-30.
4. The European Parliament and the Council of the European Union, Regulation (EC) No 1907/2006 of the European Parliament and of the Council of 18 December 2006 concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH), establishing a European Chemicals Agency, amending Directive 1999/45/EC and repealing Council Regulation (EEC) No 793/93 and Commission Regulation (EC) No 1488/94 as well as Council Directive 76/769/EEC and Commission Directives 91/155/EEC, 93/67/EEC, 93/105/EC and 2000/21/EC, Official Journal of the European Union L396(2006) (December 2006), pp. 1-849.
5. European Chemicals Agency (ECHA), Guidance in information requirements and chemical safety assessment, Chaper R.7c: Endpoint specific guidance, ECHA, 2008.
6. R.O. Potts and R.H. Guy, Predicting skin permeability, Pharm. Res. 9 (1992), pp. 663-669.
7. W.J. Pugh, Relationship between H-bonding of penetrants to stratum corneum lipids and diffusion, J. Toxicol. Cutan. Ocul. Toxicol. 20 (2001), pp. 303-317.
8. M.H. Abraham and F. Martins, Human skin permeation and partition: General linear free-energy relationship analyses, J. Pharm. Sci. 93 (2004), pp. 1508-1523.
9. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Deliv. Rev. 23 (1997), pp. 3-25.
10. D. Fitzpatrick, J. Corish, and B. Hayes, Modelling skin permeability in risk assessment - the future, Chemosphere 55 (2004), pp. 1309-1314.
11. S. Mitragotri, Y.G. Anissimov, A.L. Bunge, H.F. Frasch, R.H. Guy, J. Hadgraft, G.B. Kasting, M.E. Lane, and M.S. Roberts, Mathematical models of skin permeability: An overview, Int. J. Pharm. 418 (2011), pp. 115-129.
12. A. Wilschut, W.F. ten Berge, P.J. Robinson, and T.E. Mckone, Estimating skin permeation. The validation of five mathematical skin permeation models, Chemosphere 30 (1995), pp. 1275-1296.
13. J. Kielhorn, S. Melching-Kollmuss, and I. Mangelsdorf, Dermal Absorption, Environmental Health Criteria 235, World Health Organization, 2006.
14. B. van Ravenzwaay and E. Leibold, A comparison between in vitro rat and human and in vivo rat skin absorption studies, Hum. Exp. Toxicol. 23 (2004), pp. 421-430.
15. A. Henning, D. Neumann, K.H. Kostka, C.M. Lehr, and U.F. Schaefer, Influence of human skin specimens consisting of different skin layers on the result of in vitro permeation experiments, Skin Pharmacol. Physiol. 21 (2008), pp. 81-88.
16. D. Karadzovska, J.D. Brooks, and J.E. Riviere, Modeling the effect of experimental variables on the in vitro permeation of six model compounds across porcine skin, Int. J. Pharm. 443 (2013), pp. 58-67.
17. E.G. Samaras, J.E. Riviere, and T. Ghafourian, The effect of formulations and experimental conditions on in vitro human skin permeation-Data from updated EDETOX database, Int. J. Pharm. 434 (2012), pp. 280-291.
18. J.J. Hostynek and P.S. Magee, Modelling in vivo human skin absorption, Quant. Struct-Act. Relat. 16 (1997), pp. 473-479.
19. H.F. Frasch, L.Y. Zang, A.M. Barbero, and S.E. Anderson, In vitro dermal penetration of 4-chloro-3-methylphenol from commercial metal working fluid and aqueous vehicles, J. Toxicol. Environ. Health 73 (2010), pp. 1394-1405.
20. J.E. Riviere and J.D. Brooks, Predicting skin permeability from complex chemical mixtures, Toxicol. Appl. Pharmacol. 208 (2005), pp. 99-110.
21. J.E. Riviere and J.D. Brooks, Prediction of dermal absorption from complex chemical mixtures: Incorporation of vehicle effects and interactions into a QSPR framework, SAR QSAR Environ. Res. 18 (2007), pp. 31-44.
22. S. Geinoz, R.H. Guy, B. Testa, and P.A. Carrupt, Quantitative structure-permeation relationships (QSPeRs) to predict skin permeation: A critical evaluation, Pharm. Res. 21 (2004), pp. 83-92.
23. H.-D. Belitz, W. Grosch, and P. Schieberle, Lehrbuch der Lebensmittelchemie, Springer Verlag, Berlin, Heidelberg, 2008.
24. OECD, Guidance document on the validation of (quantitative) structure-activity relationships [(Q)SAR] models, Organisation for Economic Co-operation and Development, 2007.
25. P. Gramatica, Principles of QSAR models validation: Internal and external, QSAR Comb. Sci. 26 (2007), pp. 694-701.
26. B.E. Vecchia and A.L. Bunge, Animal models: A comparison of permeability coefficients for excised skin from humans and animals, in Dermal Absorption Models in Toxicology and Pharmacology, J.E. Riviere, ed., CRC Press, Boca Raton, 2006, pp. 305-333.
27. K. Safferling, Dermale Permeation in vitro: Einfluss von unterschiedlichen Parametern an Ratten- und Schweinehautmodellen, Diploma thesis, Hochschule Darmstadt, 2008.
28. L.A. Kirchner, R.P. Moody, E. Doyle, R. Bose, J. Jeffery, and I. Chu, The prediction of skin permeability by using physicochemical data, ATLA 25 (1997), pp. 359-370.
29. A.P. Worth and M.T.D. Cronin, The use of discriminant analysis, logistic regression and classification tree analysis in the development of classification models for human health effects, J. Mol. Struc. -Theochem 622 (2003), pp. 97-111.
30. F.N. Marzulli, D.W.C. Brown, and H.I. Maibach, Techniques for studying skin penetration, Toxicol. Appl. Pharmacol. 3 (1969), pp. 76-83.
31. H. Kubinyi, Statistical methods, in QSAR: Hansch Analysis and Related Approaches, R. Mannhold, P. Krogsgaard-Larsen, and H. Timmerman, eds., VCH Verlagsgesellschaft, Weinheim, 1993, pp. 91-107.
32. European Centre for Ecotoxicology and Toxicology of Chemicals (ECETOC), Category approaches, Read-across, (Q)SAR - Technical Report No. 116, 2012.
33. R. Todeschini and V. Consonni, Molecular Descriptors for Chemoinformatics. Volume 1: Alphabetical Listing, Wiley-VCH, Weinheim, 2009.
34. J.E. Grice, Q. Zhang, and M.S. Roberts, Chemical structure - Skin transport relationships, in Toxicology of the Skin, N.A. Monteiro-Riviere, ed., Informa Healthcare, New York, 2010, pp. 55-68.
35. R.L. Bronaugh and T.J. Franz, Vehicle effects on percutaneous absorption: In vivo and in vitro comparisons with human skin, Br. J. Dermatol. 115 (1986), pp. 1-11.
36. R.E. Baynes, J.D. Brooks, B.M. Barlow, and J.E. Riviere, Physicochemical determinants of linear alkylbenzene sulfonate (LAS) disposition in skin exposed to aqueous cutting fluid mixtures, Toxicol. Ind. Health 18 (2002), pp. 237-248.
37. P.H. Dugard and R.C. Scott, A method of predicting percutaneous absorption rates from vehicle to vehicle: An experimental assessment, Int. J. Pharm. 28 (1986), pp. 219-227.
38. J.E. Riviere, Principles of drug movement in the body, in Comparative Pharmacokinetics - Principles, Techniques and Applications, J.E. Riviere, ed., Wiley-Blackwell, 2011, pp. 13-25.
39. B.W. Barry, Vehicle effect: What is an enhancer?, in Topical Drug Bioavailability, Bioequivalence and Penetration, P.V. Shah and H. Maibach, eds., Plenum Press, New York, 1993, pp. 261-276.
40. G.K. Menon, S.H. Lee, and M.S. Roberts, Ultrastructural effects of some solvents and vehicles on the stratum corneum and other skin components: Evidence for an "Extended mosaic-partitioning model of the skin barrier", in Dermal Absorption and Toxicity, M.S. Roberts and K.A. Walters, eds., Marcel Dekker, New York - Basel - Hong Kong 1998, pp. 727-751.
41. M.S. Roberts and S.E. Cross, Skin transport, in Dermatological and Transdermal Formulations, K.A. Walters, ed., Marcel Dekker Inc, New York, 2002, pp. 89-195.
42. H.E. Bodde, J. Verhoeven, and L.M.J. Vandriel, The skin compliance of transdermal drug delivery systems, Crit. Rev. Ther. Drug Carrier Syst. 6 (1989), pp. 87-115.
43. H. Baker, The skin as a barrier, in Textbook of Dermatology, A. Rock, ed., Blackwell Scientific Publications, Oxford, 1986, pp. 355-365.
44. Y. Dancik, M.A. Miller, J. Jaworska, and G.B. Kasting, Design and performance of a spreadsheet-based model for estimating bioavailability of chemicals from dermal exposure, Adv. Drug Deliv. Rev. 65 (2013), pp. 221-236.
45. S. Hansen, A. Henning, A. Naegel, M. Heisig, G. Wittum, D. Neumann, K.H. Kostka, J. Zbytovska, C.M. Lehr, and U.F. Schaefer, In-silico model of skin penetration based on experimentally determined input parameters. Part I: Experimental determination of partition and diffusion coefficients, Eur. J. Pharmaceut. Biopharmaceut. 68 (2008), pp. 352-367.
46. J.M. Nitsche and H. Frasch, Dynamics of diffusion with reversible binding in microscopically heterogeneous membranes: General theory and applications to dermal penetration, Chem. Eng. Sci. 66 (2011), pp. 2019-2041.
47. N.A. Monteiro-Riviere, J.P. van Miller, G. Simon, R.L. Joiner, J.D. Brooks, and J.E. Riviere, Comparative in vitro percutaneous absorption of nonylphenol and nonylphenol ethoxylates (NPE-4 and NPE-9) through human, porcine and rat skin, Toxicol. Ind. Health 16 (2000), pp. 49-57.
48. R.C. Scott, M. Walker, and P.H. Dugard, A comparison of the in vitro permeability properties of human and some laboratory-animal skins, Int. J. Cosmetic Sci. 8 (1986), pp. 189-194.