Novel cyclosporin derivatives featuring enhanced skin penetration despite increased molecular weight

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 9, 2005, Pages 3157-3167

  Billich, Andreas ^a   Vyplel, Hermann ^a   Grassberger, Maximilian ^a   Schmook, Fritz P ^a   Steck, Andrea ^a   Stuetz, Anton ^a  

^a Novartis Inst for Biomed Research   (Austria)

Author keywords

500 Da rule; Cyclosporins; Prodrugs; Skin penetration

Indexed keywords

AMINE; CYCLOSPORIN A; CYCLOSPORIN A [8 DEXTRO O (2 HYDROXYETHYL)SERINE]; CYCLOSPORIN DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; PHOSPHATE; PHOSPHORYLCHOLINE; SULFATE; UNCLASSIFIED DRUG; [2 (O SULFATE)ETHYL 8 DEXTRO SERINE]CYCLOSPORIN; [2 [O (11 TRIMETHYLAMMONIOUNDECANOYL)]ETHYL 8 DEXTRO SERINE]CYCLOSPORIN CHLORIDE; [2 [O (2 TRIMETHYLAMMONIOETHOXYCARBONYL)]ETHYL 8 DEXTRO SERINE]CYCLOSPORIN CHLORIDE; [2 [O (4 TRIMETHYLAMMONIOBUTOXYCARBAMOYL)]ETHYL 8 DEXTRO SERINE]CYCLOSPORIN CHLORIDE; [2 [O (PHOSPHATE ETHYL ESTER)]ETHYL 8 DEXTRO SERINE]CYCLOSPORIN; [2 [O (PHOSPHATE)]ETHYL 8 DEXTRO SERINE]CYCLOSPORIN; [2 [O (PHOSPHOCHOLINE ESTER)]ETHYL 8 DEXTRO SERINE]CYCLOSPORIN; [2 [O (SUCCINIC ACID 2 OXYETHYL ESTER)] 8 DEXTRO SERINE]CYCLOSPORIN;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG EFFECT; DRUG PENETRATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IN VITRO STUDY; MOLECULAR WEIGHT; NONHUMAN; PHYSICAL CHEMISTRY; RAT; SKIN CULTURE; SKIN PENETRATION; SKIN PERMEABILITY; STRUCTURE ANALYSIS;

EID: 16244388265     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.02.049     Document Type: Article

References (52)

1. G.L. Capella, O.D. Casa-Alberighi, and A.F. Finzi Int. J. Dermatol. 40 2001 551
2. A.B. Kauvar, and M.J. Stiller Int. J. Dermatol. 33 1994 86
3. D.S. Groisser, C.E. Griffiths, C.N. Ellis, and J. Voorhees J. Dermatol. Clin. 9 1991 817
4. H. Zachariae, and T. Steen Olsen Clin. Nephrol. 43 1995 154
5. J.M. Naeyaert, J.M. Lachapelle, H. Degreef, M. de la Brassinne, M. Heenen, and J. Lambert Dermatology 198 1999 145
6. E.M. Higgins, J. McLelland, P.S. Friedmann, J.N. Matthews, and S. Shuster J. Dermatol. Sci. 2 1991 79
7. G.W. Cole, S. Shimomaye, and M. Goodman Contact Dermatitis 19 1988 129
8. Y. De Prost, C. Bodemer, and D. Teillac Arch. Dermatol. 125 1989 570
9. T. Bunse, H.J. Schulze, and G. Mahrle Z. Hautkr. 65 1990 541
10. J.I. Duncan, S.N. Payne, A.J. Winfield, A.D. Ormerod, and A. Thomson Br. J. Dermatol. 123 1990 631
11. H.J. Schulze, G. Mahrle, and G.K. Steigleder Br. J. Dermatol. 122 1990 113
12. M.A. De Rie, M.M. Meinardi, and J.D. Bos Acta Derm. Venereol. 71 1991 452
13. C. Surber, P. Itin, S. Buchner, and H.I. Maibach Contact Dermatitis 26 1992 116
14. J.I. Duncan, R.A. Wakeel, A.J. Winfield, A.D. Ormerod, and A.W. Thomson Acta Derm. Venereol. 73 1993 84
15. M. Mizoguchi, K. Kawaguchi, Y. Ohsuga, Y. Ikari, A. Yanagawa, and Y. Mizushima Lancet 339 1992 1120
16. A.V. Powles, B.S. Baker, J. McFadden, A.J. Rutman, C.E. Griffiths, L. Fry, and H. Valdimarsson Lancet 1 1988 537
17. M.K. Burns, C.N. Ellis, D. Eisen, E. Duell, C.E. Griffiths, T.M. Annesley, T.A. Hamilton, J.E. Birnbaum, and J. Voorhees J. Arch. Dermatol. 128 1992 786
18. R.C. Hermann, R.S. Taylor, C.N. Ellis, N.A. Williams, N.D. Weiner, G.L. Flynn, T.M. Annesley, and J. Voorhees J. Skin Pharmacol. 1 1988 246
19. U. Mrowietz Acta Derm. Venereol. 72 1992 321
20. J.D. Bos, and M.M. Meinardi Exp. Dermatol. 9 2000 165
21. G.L. Flynn T.R. Gerity C.J. Henry Principles of Route to Route Extrapolation for Risk Assessment 1990 Elsevier New York 93 127
22. R.O. Potts, and R.H. Guy Pharm. Res. 9 1992 663
23. W.J. Pugh, and J. Hadgraft Int. J. Pharm. 103 1994 163
24. M.H. Abraham, H.S. Chadha, and R.C. Mitchell J. Pharm. Pharmacol. 47 1995 8
25. B.D. Gute, G.D. Grunwald, and S.C. Basak SAR QSAR Environ. Res. 10 1999 1
26. T. Degim, J. Hadgraft, S. Ilbasmis, and Y. Ozkan J. Pharm. Sci. 92 2003 656
27. F.P. Schmook, A. Stuetz, and J. Reinhardt Skin pharmacol. 6 1993 116
28. A. Stuetz, J.G. Meingassner, F. Schatz, and F. Schmook J. Dermatol. Treatment 5 1994 S19
29. Morrison, M. A.; Meucci, V. P.; Lunetta, S. E.; Zajac, M. B.; Simpson, E. A. Eur. Pat. Appl. EP 473961 A2 920311, 1992
30. P.C. Hiestand, M. Graeber, U. Hurtenbach, P. Herrmann, S. Cammisuli, B.P. Richardson, M.K. Eberle, and J.F. Borel Transplant. Proc. 24 1992 31
31. M.K. Eberle, P. Hiestand, A.-M. Jutzi-Eme, F. Nuninger, and H.R. Zihlmann J. Med. Chem. 38 1995 1853
32. M. Yoshikawa, T. Kato, and T. Takenishi Bull. Chem. Soc. Jpn. 42 1969 3505
33. H. Pajouhesh, and A.J. Hancock J. Lipid Res. 25 1984 294
34. N.T. Thuong, and P. Chabrier Bull. Soc. Chim. Fr. 1974 667
35. R. Traber, H. Hofmann, and H. Kobel J. Antibiot. 42 1989 591
36. T.J. Franz Kinetics of Cutaneous Drug Penetration Int. J. Dermatol. 22 1983 499
37. R.M. Wenger Pharm. Rev. 41 1989 243
38. F.P. Schmook, J.G. Meingassner, and A. Billich Int. J. Pharm. 215 2001 51
39. J. Kao, F.K. Patterson, and J. Hall Toxicol. Appl. Pharmacol. 81 1985 502
40. B. van Ravenzwaay, and E. Leibold Hum. Exp. Toxicol. 23 2004 421
41. A. Billich, H. Aschauer, A. Aszódi, and A. Stuetz Int. J. Pharm. 269 2004 29
42. J.B. Rothbard, S. Garlington, Q. Lin, T. Kirschberg, E. Kreider, P.L. McGrane, P.A. Wender, and P.A. Khavari Nat. Med. 6 2000 1253
43. J.D. Bos Eur. J. Dermatol. 13 2003 455
44. K. Wolff, and A. Stuetz Expert Opin. Pharmacother. 5 2004 643
45. K. Thestrup-Pedersen Curr. Opin. Allergy Clin. Immunol. 3 2003 359
46. K. Wolff Dermatol Clin. 22 2004 461
47. W. Montagna, and V.R. Formisano J. Anat. 89 1955 425
48. A.W. Kopf AMA Arch. Derm. 75 1957 1
49. G. Moretti, and H. Mescon J. Histochem. Cytochem. 4 1956 247
50. G. Parenti, G. Meroni, and A. Ballabio Curr. Opin. Genet. Dev. 7 1997 386
51. Y.A. Hannun, C. Luberto, and K.M. Argraves Biochemistry 40 2001 4893
52. S. Berger, and S. Braun 200 and More NMR Experiments: A Practical Course 2004 Wiley-VCH Weinheim