Defining optimum lipophilicity and molecular weight ranges for drug candidates-Molecular weight dependent lower log D limits based on permeability

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 10, 2009, Pages 2844-2851

  Waring, Michael J ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Caco 2; Lipophilicity; Molecular weight; Permeability

Indexed keywords

ARTICLE; CELL STRAIN CACO 2; DRUG BIOAVAILABILITY; DRUG PENETRATION; DRUG TRANSPORT; IONIZATION; LIPOPHILICITY; MOLECULAR WEIGHT; STATISTICAL ANALYSIS;

ALGORITHMS; CACO-2 CELLS; CELL MEMBRANE PERMEABILITY; DRUG DESIGN; HUMANS; HYDROPHOBICITY; MOLECULAR WEIGHT; PHARMACEUTICAL PREPARATIONS;

EID: 65449179589     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.03.109     Document Type: Article

References (36)

1. Lipnski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Delivery Rev. 23 (1997) 3
2. Navia M.A., and Chaturverdi P.R. Drug Discovery Today 1 (1996) 179-189
3. Wenlock M.C., Austin R.P., Barton P., Davis A.M., and Leeson P.D. J. Med. Chem. 46 (2003) 1250-1256
4. Leeson P.D., and Springthorpe B. Nat. Rev. Drug Disc. 6 (2007) 881-890
5. Hughes J.D., Blagg J., Price D.A., Bailey S., DeCrescenzo G.A., Devraj R.V., Ellsworth E., Fobian Y.M., Gibbs M.E., Gilles R.W., Greene N., Huang E., Krieger-Burke T., Loesel J., Wager T., Whiteley L., and Zhang Y. Bioorg. Med. Chem. Lett. 18 (2008) 4872-4875
6. Waring M.J., and Johnstone C. Bioorg. Med. Chem. Lett. 17 (2007) 1759-1764
7. Gleeson M.P. J. Med. Chem. 51 (2008) 817-834
8. Egan W.J., Merz K.M., and Baldwin J.J. J. Med. Chem. 43 (2000) 3867-3877
9. Ghose A.K., Viswanadhan V.N., and Wendoloski J.J. J. Phys. Chem. A 102 (1998) 3762-3772
10. Veber D.F., Johnson S.R., Cheng H.-Y., Smith B.R., Ward K.W., and Kopple K.D. J. Med. Chem. 45 (2002) 2615-2623
11. Martin Y.C. J. Med. Chem. 48 (2005) 3164-3170
12. Yoshida F., and Topliss J.G. J. Med. Chem. 43 (2000) 2575-2585
13. Camenisch G., Folkers G., and van de Waterbeemd H. Eur. J. Pharm. Sci. 6 (1998) 321-329
14. Camenisch G., Alsenz J., van de Waterbeemd H., and Folkers G. Eur. J. Pharm. Sci. 6 (1998) 313-319
15. Didziapetris R., Japertas P., Avdeef A., and Petrauskas A. J. Drug Targeting 11 (2003) 391-406
16. Artursson P., and Karlsson J. Biochem. Biophys. Res. Commun. 175 (1991) 880-885
17. Mandagere A.K., Thompson T.N., and Hwang K.K. J. Med. Chem. 45 (2002) 304-311
18. Maubon N., Le Vee M., Fossati L., Audry M., Le Ferrec E., Bolze S., and Fardel O. Fund. Clin. Pharmacol. 21 (2007) 659-663
19. Bruneau P., and McElroy N.R. J. Chem. Inf. Model. 46 (2006) 1379-1387
20. http://www.daylight.com.
21. SAS Institute. jmp Statistical Software. http://www.jmp.com/software.
22. http://www.acdlabs.com.
23. Ho N.F.H., Park J.Y., Morozowich W., and Higuchi W.I. In: Roche E.B. (Ed). Design of Bioparmaceutical Properties through Prodrugs and Analogs (1977), APhA/APS, Washington, DC 136-227
24. Ho N.F.H., Park J.Y., Ni P.F., and Higuchi W.I. In: Crouthamel W.G., and Sarapu A. (Eds). Animal Models for Oral Drug Delivery in Man: In Situ and In Vivo Approaches (1983), APhA/APS, Washington, DC 27-106
25. http://www.fda.gov/cder/OPS/BCS_guidance.htm
26. Martin A., Bustamante P., and Chun A. Physical Pharmacy: Physical Chemical Principles in the Pharmaceutical Sciences (1993), Lea and Febiger, Philadelphia
27. Kakemi K., Arita T., Hori R., and Konishi R. Chem. Pharm. Bull. 17 (1967) 1534-1539
28. Wagner J.G., and Sedman A.J. J. Pharmacokinet. Biopharm. 1 (1973) 23-50
29. Garringues T.M., Pérez-Varona A.T., Climent E., Bermejo M.V., martin-Villdore A., and Plá-Delfina J.M. Int. J. Pharm. 64 (1990) 127-138
30. Lee A.J., King J.R., and Barrett D.A. J. Control. Release 45 (1997) 141-151
31. Adson A., Burton P.S., Raub Th.J., Barshun C.L., Audus K.L., and Ho N.F.H. J. Pharm. Sci 84 (1995) 1197-1204
32. Camenisch G., Alsenz J., van de Waterbeemd H., and Folkers G. Eur. J. Pharm. Sci. 6 (1998) 313-319
33. Hansch C. Acc. Chem. Res. 2 (1969) 232-239
34. Kubinyi H. Arzneim. Forsch. (Drug Res.) 26 (1976) 1991-1997
35. Hosmer D.W., and Lemeshow S. Applied Logistic Regression. 2nd Ed. (2000), Wiley, New York, Chichester
36. Kansy M., Senner F., and Gurbenator K. J. Med. Chem. 41 (1998) 1007-1010