Discriminant and quantitative PLS analysis of competitive CYP2C9 inhibitors versus non-inhibitors using alignment independent GRIND descriptors

Journal of Computer-Aided Molecular Design

Volumn 16, Issue 7, 2002, Pages 443-458

  Afzeliu, Lovisa ^a,b   Masimirembwa, Collen M ^b   Karlén, Anders ^a   Anderson, Tommy B ^b   Zamora, Ismael ^c  

^a UPPSALA UNIVERSITY   (Sweden)

^b ASTRAZENECA R AND D   (Sweden)

^c sl Francesc Cabanes i Alibau 1 3   (Spain)

Author keywords

3D QSAR; ALMOND; Computational modeling; CYP2C9 inhibitors; Cytochrome P450; Discriminant PLS; Enzyme inhibition; GRIND descriptors

Indexed keywords

ALIGNMENT; COMPUTATIONAL CHEMISTRY; DISCRIMINANT ANALYSIS; MOLECULAR GRAPHICS;

3D-QSAR; ALMOND; COMPUTATIONAL MODELLING; CYP2C9 INHIBITOR; CYTOCHROMES P450; DESCRIPTORS; DISCRIMINANT PLS; GRID INDEPENDENT DESCRIPTOR DESCRIPTOR; GRID-INDEPENDENT;

ENZYME INHIBITION;

ACEBUTOLOL; ALPRENOLOL; BISOPROLOL; CEFMETAZOLE; CEFOTAXIME; CEFTRIAXONE; CYTOCHROME P450 2C9; CYTOCHROME P450 INHIBITOR; DICOUMAROL; FLUINDOSTATIN; GUANOSINE; LABETALOL; MICONAZOLE; NADOLOL; OMEPRAZOLE SULFONE; PANTOPRAZOLE; PHENYLBUTAZONE; PHENYTOIN; PINDOLOL; PROGESTERONE; PYRIMETHAMINE; QUERCETIN; QUININE; RABEPRAZOLE; SULFAPHENAZOLE; TERBUTALINE; THIOBARBITURIC ACID; TIABENDAZOLE; UNINDEXED DRUG; WARFARIN;

CALCULATION; CLUSTER ANALYSIS; COMPETITIVE INHIBITION; COMPUTER PROGRAM; CONTROLLED STUDY; DISCRIMINANT ANALYSIS; DRUG COMPETITION; DRUG STRUCTURE; ENZYME INHIBITION; MOLECULAR MODEL; PREDICTION; PRIORITY JOURNAL; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REGRESSION ANALYSIS; REVIEW; STEREOSPECIFICITY; THREE DIMENSIONAL IMAGING; VALIDATION PROCESS;

EID: 12244310480     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1021281008423     Document Type: Review

References (38)

1. Stockman, B.J., et al., FEBS Lett., 283 (1991) 267-269.
2. Schaal, W., et al., J. Med. Chem., 44 (2001) 155-169.
3. Martin, Y.C., et al., J. Comput-Aided Mol. Design, 7 (1992) 83-102.
4. CATALYST, Molecular Simulations: San Diego, CA.
5. Ekins, S., et al., J. Pharmacol. Exp. Ther., 288 (1999) 21-29.
6. Ekins, S., M.J. de Groot, and J.P. Jones, Drug Metab. Dis., 29 (2001) 936-944.
7. Jones, J.P., et al., Drug Metab. Dis., 24 (1996) 1-6.
8. Afzelius, L., et al., Mol. Pharmacol., 59 (2001) 909-919.
9. Goodford, P.J., J. Med. Chem., 28 (1985) 849-857.
10. Cramer, R.D.r., D.E. Patterson, and J.D. Bunce, J. Am. Chem. Soc., 110 (1988) 5959-5967.
11. Pastor, M., et al., J. Med. Chem., 43 (2000) 3233-3243.
12. Riganelli, D., et al., Pharm. Pharmacol. Lett., 3 (1993) 5-8.
13. Smith, D.A., M.J. Ackland, and B.C. Jones, Drug Discovery Today, 2 (1997) 406-414.
14. Murray, M., Int. J. Mol. Med., 3 (1999) 227-238.
15. Rendic, S. and F.J. Di Carlo, Drug Metab. Rev., 29 (1997) 413-580.
16. Masimirembwa, C.M., et al., Meth. Enzymol., (2001) submitted.
17. Smith, D.A., M.J. Ackland, and B.C. Jones, Drug Discovery Today, 2 (1997) 479-485.
18. Sjöström, M., S. Wold, and B. Söderström. Proc. PARC in Practice, (1985) North-Holland.
19. Wold, S., et al., Chemometrics: Mathematics and Statistics in Chemistry, K.B. R, Editor. 1984, Reidel Publishing Company, Holland: Dordrecht.
20. Bardsley, W.G., et al., Comput. Chem., 19 (1995) 75-)84.
21. Masimirembwa, C.M., et al., Drug Metabol. Dis., 27 (1999) 1117-1122.
22. Wold, S., K. Esbensen, and P. Geladi, Chem. Intell. Lab. Syst., 2 (1987) 37-52.
23. Oprea, T.I. and J. Gottfries, J. Combin. Chem., 3 (2001) 157-166.
24. Olsson, T. and V. Shcherbukhin, Synthesis and Structure Administration (SaSA). 1997-2000, AstraZeneca, http://www.astrazeneca.com.
25. Cruciani, G., M. Pastor, and W. Guba, Eur. J. Pharmaceut. Sci., 11 (2000) S29-39.
26. Miners, J.O. and D.J. Birkett, B. J. Clin. Pharmacol., 45 (1998) 525-538.
27. Rao, S., et al., J. Med. Chem., 43 (2000) 2789-2796.
28. Cruciani, G. and K.A. Watson, J. Med. Chem., 37 (1994) 2589-2601.
29. Baroni, M., et al., Quantit. Struct. Act. Rel., 12 (1993) 225-231.
30. Fedorov, V.V., Theory of Optimal Experiments. 1972, New York: Academic Press.
31. Albano, C., et al., Anal. Chim. Acta, 103 (1978) 429-443.
32. Cruciani, G., et al., Predictive Ability of Regression Models. Part I: Standard Deviation of Predicion Errors (SDEP). Journal of Chemometrics, 1992. 6: p. 335-346.
33. Box, G.E.P., W.G. Hunter, and S.J. Hunter, Statistics for experimenters. 1978: John Wiley.
34. Baroni, M., et al., Quantit. Struct. Act. Rel., 12 (1993) 9-20.
35. Zamora, I., T.I. Oprea, and A.L. Ungell, J. Med. Chem., (2001) submitted.
36. Hansch, C., Drug Metab. Rev., 1 (1972) 1-14.
37. Baroni, M., et al., Quantit. Struct. Act. Rel., 12 (1993) 9-20.
38. Miners, J.O., et al., Biochem. Pharmacol., 37 (1988) 1137-1144.