Prediction of the corneal permeability of drug-like compounds

Pharmaceutical Research

Volumn 27, Issue 7, 2010, Pages 1398-1407

  Kidron, Heidi ^a   Vellonen, Kati Sisko ^a   Del Amo, Eva M ^a   Tissari, Anita ^a   Urtti, Arto ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Computational model; Multivariate analysis; Ocular absorption; Ophthalmic drugs; QSPR

Indexed keywords

ACETAZOLAMIDE; ALPRENOLOL; ATENOLOL; BENZOLAMIDE; BEVANTOLOL; BUFURALOL; BUSPIRONE; CINOXACIN; CIPROFLOXACIN; CLONIDINE; CORYNANTHINE; CYCLOPHOSPHAMIDE; ENOXACIN; ETHOXZOLAMIDE; GATIFLOXACIN; IBUFENAC; LABETALOL; METOPROLOL; MOXIFLOXACIN; NADOLOL; NALIDIXIC ACID; NORFLOXACIN; OFLOXACIN; OXPRENOLOL; PINDOLOL; PROPRANOLOL; SOTALOL; TIMOLOL; UNINDEXED DRUG; YOHIMBINE; DRUG;

ANIMAL TISSUE; AQUEOUS HUMOR; ARTICLE; COMPUTER MODEL; COMPUTER PREDICTION; CONTROLLED STUDY; CORNEA PERMEABILITY; DRUG DESIGN; DRUG PENETRATION; HYDROGEN BOND; MATHEMATICAL COMPUTING; NONHUMAN; PH; PRIORITY JOURNAL; PROCESS OPTIMIZATION; QUANTITATIVE STRUCTURE PROPERTY RELATION; STEADY STATE; CHEMISTRY; COMPUTER SIMULATION; CORNEA; METABOLISM; MULTIVARIATE ANALYSIS; PERMEABILITY; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

COMPUTER SIMULATION; CORNEA; MULTIVARIATE ANALYSIS; PERMEABILITY; PHARMACEUTICAL PREPARATIONS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77953608956     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-010-0132-8     Document Type: Article

References (38)

1. Maurice DM, Mishima S. In: Sears ML, editor. Ocular pharmacokinetics. Berlin-Heidelberg: Springer Verlag; 1984. p. 16-119.
2. RD Schoenwald RL Ward 1978 Relationship between steroid permeability across excised rabbit cornea and octanol-water partition coefficients J Pharm Sci. 67 786 788 10.1002/jps.2600670614 1:CAS:528:DyaE1cXkslWhtb0%3D 660456
3. A Urtti L Salminen 1993 Minimizing systemic absorption of topically administered ophthalmic drugs Surv Ophthalmol. 37 435 456 10.1016/0039-6257(93) 90141-S 1:STN:280:DyaK3s3ps1Oluw%3D%3D 8100087 (Pubitemid 23144013)
4. HS Huang RD Schoenwald JL Lach 1983 Corneal penetration behavior of beta-blocking agents II: assessment of barrier contributions J Pharm Sci. 72 1272 1279 10.1002/jps.2600721109 1:CAS:528:DyaL2cXhvFM%3D 6139472
5. E Toropainen VP Ranta A Talvitie P Suhonen A Urtti 2001 Culture model of human corneal epithelium for prediction of ocular drug absorption Invest Ophthalmol Vis Sci. 42 2942 2948 1:STN:280:DC%2BD3MnjvFSktg%3D%3D 11687540
6. E Toropainen VP Ranta KS Vellonen J Palmgren A Talvitie M Laavola, et al. 2003 Paracellular and passive transcellular permeability in immortalized human corneal epithelial cell culture model Eur J Pharm Sci. 20 99 106 10.1016/S0928-0987(03)00173-8 1:CAS:528:DC%2BD3sXnt1Gls74%3D 13678798 (Pubitemid 37103237)
7. J Linnankoski VP Ranta M Yliperttula A Urtti 2008 Passive oral drug absorption can be predicted more reliably by experimental than computational models-fact or myth Eur J Pharm Sci. 34 129 139 10.1016/j.ejps.2008.03.001 1:CAS:528:DC%2BD1cXms1Whu7c%3D 18455374
8. J Linnankoski JM Makela VP Ranta A Urtti M Yliperttula 2006 Computational prediction of oral drug absorption based on absorption rate constants in humans J Med Chem. 49 3674 3681 10.1021/jm051231p 1:CAS:528:DC%2BD28XksFKks74%3D 16759110 (Pubitemid 43902473)
9. S Winiwarter NM Bonham F Ax A Hallberg H Lennernas A Karlen 1998 Correlation of human jejunal permeability (in vivo) of drugs with experimentally and theoretically derived parameters. A multivariate data analysis approach J Med Chem. 41 4939 4949 10.1021/jm9810102 1:CAS:528:DyaK1cXntFKltLw%3D 9836611 (Pubitemid 28555452)
10. GP Moss JC Dearden H Patel MT Cronin 2002 Quantitative structure-permeability relationships (QSPRs) for percutaneous absorption Toxicol In Vitro 16 299 317 10.1016/S0887-2333(02)00003-6 1:CAS:528: DC%2BD38XjvVehtbo%3D 12020604 (Pubitemid 34521704)
11. F Yoshida JG Topliss 1996 Unified model for the corneal permeability of related and diverse compounds with respect to their physicochemical properties J Pharm Sci. 85 819 823 10.1021/js960076m 1:CAS:528:DyaK28XktFOrsLo%3D 8863270 (Pubitemid 26269475)
12. XC Fu WQ Liang 2002 A simple model for the prediction of corneal permeability Int J Pharm. 232 193 197 10.1016/S0378-5173(01)00902-4 1:CAS:528:DC%2BD38XjvFCjtQ%3D%3D 11790503 (Pubitemid 34076765)
13. RD Schoenwald HS Huang 1983 Corneal penetration behavior of beta-blocking agents I: physiochemical factors J Pharm Sci. 72 1266 1272 10.1002/jps. 2600721108 1:CAS:528:DyaL2cXhvFI%3D 6139471
14. Y Li J Liu D Pan AJ Hopfinger 2005 A study of the relationship between cornea permeability and eye irritation using membrane-interaction QSAR analysis Toxicol Sci. 88 434 446 10.1093/toxsci/kfi319 1:CAS:528:DC%2BD2MXht1Wis7rI 16162848 (Pubitemid 41672151)
15. A Edwards MR Prausnitz 2001 Predicted permeability of the cornea to topical drugs Pharm Res. 18 1497 1508 10.1023/A:1013061926851 1:CAS:528:DC%2BD3MXos1aqu78%3D (Pubitemid 33022403)
16. MW Duffel IS Ing TM Segarra JA Dixson CF Barfknecht RD Schoenwald 1986 N-Substituted sulfonamide carbonic anhydrase inhibitors with topical effects on intraocular pressure J Med Chem. 29 1488 1494 10.1021/jm00158a028 1:CAS:528:DyaL28Xks1SmtLc%3D 3735316
17. TH Maren L Jankowska G Sanyal HF Edelhauser 1983 The transcorneal permeability of sulfonamide carbonic anhydrase inhibitors and their effect on aqueous humor secretion Exp Eye Res. 36 457 479 10.1016/0014-4835(83)90041-6 1:CAS:528:DyaL3sXksVOmtro%3D 6852128
18. W Wang H Sasaki DS Chien VH Lee 1991 Lipophilicity influence on conjunctival drug penetration in the pigmented rabbit: a comparison with corneal penetration Curr Eye Res. 10 571 579 10.3109/02713689109001766 1:STN:280:DyaK3MzntFyrtw%3D%3D 1680041
19. CH Chiang RD Schoenwald 1986 Ocular pharmacokinetic models of clonidine-3H hydrochloride J Pharmacokin Biopharm. 14 175 211 10.1007/BF01065260 1:CAS:528:DyaL28XkvFSkt7w%3D
20. CH Chiang RD Schoenwald HS Huang 1986 Corneal permeability of adrenergic agents potentially useful in glaucoma J Taiwan Pharmaceut Assoc. 38 67 84 1:CAS:528:DyaL1cXht1M%3D
21. RD Schoenwald JA Houseman 1982 Disposition of cyclo-phosphamide in the rabbit and human cornea Biopharm Drug Dispos. 3 231 241 10.1002/bdd.2510030306 1:CAS:528:DyaL38XmtVOltLg%3D 7139064 (Pubitemid 12068888)
22. MG Eller RD Schoenwald JA Dixson T Segarra CF Barfknecht 1985 Topical carbonic anhydrase inhibitors. III: optimization model for corneal penetration of ethoxzolamide analogues J Pharm Sci. 74 155 160 10.1002/jps.2600740210 1:CAS:528:DyaL2MXhvFOmsLo%3D 3989684 (Pubitemid 15135801)
23. NC Wu CH Chiang AR Lee 1993 Studies of carbonic anhydrase inhibitors: physicochemical properties and bioactivities of new thiadiazole derivatives J Ocul Pharmacol. 9 97 108 10.1089/jop.1993.9.97 8345292
24. L Jankowska A Bar-Ilan TH Maren 1986 The relations between ionic and nonionic diffusion of sulfonamides across the rabbit cornea Invest Ophthal Vis Sci. 27 29 37 1:CAS:528:DyaL28Xht1amsLk%3D 3941035
25. Advanced Chemistry Developement, Toronto, Canada.
26. EE Bolton Y Wang PA Thiessen SH Bryant 2008 PubChem: integrated platform of small molecules and biological activities Annu Rep Comput Chem 4 217 241 10.1016/S1574-1400(08)00012-1 1:CAS:528:DC%2BD1MXpsFWqsA%3D%3D
27. Umetrics AB, Box 7960, SE-90719 Umeå, Sweden. Simca-P. 10.5.
28. Wold S. In: van de Waterbeemd H, editor. PLS for multivariate linear modeling. Weinheim: VCH; 1995. p. 195-218.
29. CS Rao RD Schoenwald CF Barfknecht SL Laban 1992 Biopharmaceutical evaluation of ibufenac, ibuprofen, and their hydroxyethoxy analogs in the rabbit eye J Pharmacokinet Biopharm. 20 357 388 10.1007/BF01062463 1:CAS:528:DyaK3sXntlehug%3D%3D 1479559 (Pubitemid 23034404)
30. RD Schoenwald DS Chien 1988 Ocular absorption and disposition of phenylephrine and phenylephrine oxazolidine Biopharm Drug Dispos. 9 527 538 10.1002/bod.2510090603 1:CAS:528:DyaL1MXhvVSlug%3D%3D 3228574
31. Rusinko A, Hellberg MR, May JA, Owen GR. Use of MDCK cell line to predict corneal penetration of drugs. 2007;11114649.
32. AP Worth MTD Cronin 2000 Structure-permeability relationship for transcorneal penetration ATLA 28 403 413
33. U Norinder P Sjoberg T Osterberg 1998 Theoretical calculation and prediction of brain-blood partitioning of organic solutes using MolSurf parametrization and PLS statistics J Pharm Sci. 87 952 959 10.1021/js970439y 1:CAS:528:DyaK1cXkvVGksb4%3D 9687339 (Pubitemid 28381252)
34. A Malkia L Murtomaki A Urtti K Kontturi 2004 Drug permeation in biomembranes: in vitro and in silico prediction and influence of physicochemical properties Eur J Pharm Sci. 23 13 47 10.1016/j.ejps.2004.05.009 1:CAS:528:DC%2BD2cXmvFCru7c%3D 15324921 (Pubitemid 39485996)
35. AM Tonjum 1977 Movement of horseradish peroxidase in the cornea, sclera and the anterior uvea Acta Ophthalmol (Copenh) 55 771 780 10.1111/j.1755-3768. 1977.tb08275.x 1:STN:280:DyaE1c%2Fhs1Ogsw%3D%3D
36. A Urtti 2006 Challenges and obstacles of ocular pharmacokinetics and drug delivery Adv Drug Deliv Rev. 58 1131 1135 10.1016/j.addr.2006.07.027 1:CAS:528:DC%2BD28Xht1CnsL3M 17097758
37. I Ahmed TF Patton 1985 Importance of the noncorneal absorption route in topical ophthalmic drug delivery Invest Ophthalmol Vis Sci. 26 584 587 1:CAS:528:DyaL2MXktFKgt7g%3D 3884542
38. Kawazu K, Oshita A, Nakamura T, Nakashima M, Ichikawa N, Sasaki H. Transport of acebutolol through rabbit corneal epithelium. 2006;29:846-9.