The application of molecular structural predictors of intestinal absorption to screening of compounds for transdermal penetration

Journal of Pharmacy and Pharmacology

Volumn 62, Issue 6, 2010, Pages 750-755

  Grice, Jeffrey E ^a   Cross, Sheree E ^a   Brownlie, Craig ^a   Roberts, Michael S ^a,b  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b UNIVERSITY OF SOUTH AUSTRALIA   (Australia)

Author keywords

Maximum absorbable dose; Maximum flux; Membrane transport; Polar surface area; Rotatable bonds

Indexed keywords

ARTICLE; CELL STRAIN CACO 2; CHEMICAL BOND; DRUG ABSORPTION; DRUG DIFFUSION; DRUG DOSE; DRUG TRANSPORT; EPIDERMIS; INTESTINE; JEJUNUM; LIPOPHILICITY; MAXIMUM ABSORBABLE DOSE; MOLECULAR WEIGHT; PARTITION COEFFICIENT; QUANTITATIVE STRUCTURE ACTIVITY RELATION; CACO 2 CELL LINE; CHEMISTRY; FORECASTING; HUMAN; INTESTINE ABSORPTION; INTRADERMAL DRUG ADMINISTRATION; METABOLISM; REGRESSION ANALYSIS; SKIN ABSORPTION; TRANSPORT AT THE CELLULAR LEVEL;

DRUG;

ADMINISTRATION, CUTANEOUS; BIOLOGICAL TRANSPORT; CACO-2 CELLS; FORECASTING; HUMANS; INTESTINAL ABSORPTION; MOLECULAR WEIGHT; PHARMACEUTICAL PREPARATIONS; REGRESSION ANALYSIS; SKIN ABSORPTION;

EID: 77953562371     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.62.06.0011     Document Type: Article

References (35)

1. Artursson P et al. Caco-2 monolayers in experimental and theoretical predictions of drug transport. Adv Drug Deliv Rev 2001 46: 27 43. (Pubitemid 33653412)
2. Kansy M et al. Physicochemical high throughput screening: parallel artificial membrane permeation assay in the description of passive absorption processes. J Med Chem 1998 41: 1007 1010.
3. Fujii M et al. Evaluation of Yucatan micropig skin for use as an in vitro model for skin permeation study. Biol Pharm Bull 1997 20: 249 254.
4. Yanagimoto et al. Skin disposition of drugs after topical application in hairless rats. Chem Pharm Bull (Tokyo) 1999 47: 749 754.
5. Scheuplein RJ, Blank IH. Permeability of the skin. Physiol Rev 1971 51: 702 747.
6. Fitzpatrick D et al. Modelling skin permeability in risk assessment-the future. Chemosphere 2004 55: 1309 1314.
7. Pugh WJ et al. 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.
8. Stenberg P et al. Virtual screening of intestinal drug permeability. J Control Release 2000 65: 231 243.
9. Lipinski CA et al. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 2001 46: 3 26.
10. Palm K et al. Evaluation of dynamic polar molecular surface area as predictor of drug absorption: comparison with other computational and experimental predictors. J Med Chem 1998 41: 5382 5392.
11. Veber DF et al. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 2002 45: 2615 2623.
12. Winiwarter S et al. Correlation of human jejunal permeability (in vivo) of drugs with experimentally and theoretically derived parameters. A multivariate data analysis approach. J Med Chem 1998 41: 4939 4949.
13. Osterberg T, Norinder U. Prediction of polar surface area and drug transport processes using simple parameters and PLS statistics. J Chem Inf Comput Sci 2000 40: 1408 1411.
14. Kotecha J et al. Prediction of oral absorption in humans by experimental immobilized artificial membrane chromatography indices and physicochemical descriptors. Int J Pharm 2008 360: 96 106.
15. Ertl P et al. Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 2000 43: 3714 3717.
16. Palm K et al. Correlation of drug absorption with molecular surface properties. J Pharm Sci 1996 85: 32 39.
17. Stenberg P et al. Experimental and computational screening models for the prediction of intestinal drug absorption. J Med Chem 2001 44: 1927 1937.
18. Winiwarter S et al. Hydrogen bonding descriptors in the prediction of human in vivo intestinal permeability. J Mol Graph Model 2003 21: 273 287.
19. Clark DE. Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 2. Prediction of blood-brain barrier penetration. J Pharm Sci 1999 88: 815 821.
20. Fu XC et al. Predicting blood-brain barrier penetration of drugs by polar molecular surface area and molecular volume. Acta Pharmacol Sin 2001 22: 663 668.
21. Kelder J et al. Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs. Pharm Res 1999 16: 1514 1519.
22. Iyer M et al. Prediction and mechanistic interpretation of human oral drug absorption using MI-QSAR analysis. Mol Pharm 2007 4: 218 231.
23. Barry BW. Novel mechanisms and devices to enable successful transdermal drug delivery. Eur J Pharm Sci 2001 14: 101 114.
24. Prausnitz MR, Langer R. Transdermal drug delivery. Nat Biotechnol 2008 26: 1261 1268.
25. Potts RO, Guy RH. Predicting skin permeability. Pharm Res 1992 9: 663 669.
26. Magnusson BM et al. Molecular size as the main determinant of solute maximum flux across the skin. J Invest Dermatol 2004 122: 993 999.
27. Pugh WJ, Hadgraft J. Ab initio prediction of hunman skin permeability coefficients. Int J Pharm 1994 103: 163 178.
28. du Plessis J et al. Physico-chemical determinants of dermal drug delivery: effects of the number and substitution pattern of polar groups. Eur J Pharm Sci 2002 16: 107 112.
29. Hilgers AR et al. Predicting oral absorption of drugs: a case study with a novel class of antimicrobial agents. Pharm Res 2003 20: 1149 1155.
30. Zhang Q et al. Skin solubility determines maximum transepidermal flux for similar size molecules. Pharm Res 2009 26: 1974 1985.
31. Magnusson BM et al. Percutaneous absorption of steroids: determination of in vitro permeability and tissue reservoir characteristics in human skin layers. Skin Pharmacol Physiol 2006 19: 336 342.
32. Tronde A et al. Pulmonary absorption rate and bioavailability of drugs in vivo in rats: structure-absorption relationships and physicochemical profiling of inhaled drugs. J Pharm Sci 2003 92: 1216 1233.
33. Fanning KJ et al. Sulphonylurea physicochemical-pharmacokinetic relationships in the pancreas and liver. J Pharm Sci 2009 98: 2807 2821.
34. Zhu C et al. A comparative study of artificial membrane permeability assay for high throughput profiling of drug absorption potential. Eur J Med Chem 2002 37: 399 407.
35. Sun D et al. In vitro testing of drug absorption for drug 'developability' assessment: forming an interface between in vitro preclinical data and clinical outcome. Curr Opin Drug Discov Devel 2004 7: 75 85.