Conformational analysis of Ibuprofen by crystallographic database searching and potential energy calculation

International Journal of Pharmaceutics

Volumn 165, Issue 1, 1998, Pages 107-116

  Shankland, Norman ^a   Florence, Alastair J ^a   Cox, Philip J ^b   Wilson, Chick C ^c   Shankland, Kenneth ^c  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b ROBERT GORDON UNIVERSITY   (United Kingdom)

^c RUTHERFORD APPLETON LABORATORY   (United Kingdom)

Author keywords

Cambridge Structural Database; Conformational analysis; Ibuprofen; MOPAC

Indexed keywords

IBUPROFEN;

ARTICLE; CALCULATION; COMPUTER PROGRAM; CRYSTALLOGRAPHY; DATA BASE; DRUG CONFORMATION; ENERGY; PRIORITY JOURNAL;

EID: 0032550315     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(98)00010-6     Document Type: Article

References (19)

1. Allen, F.H., Kennard, O., 1993. 3D search and research using the Cambridge Structural Database. Chem. Des. Autom. News 8, 1, 31-37.
2. Allen, F.H., 1996. Knowledge acquisition from crystallographic databases: applications in molecular modelling, crystal engineering and structural chemistry. In: Gans, W., Amann, A., Boeyens, J.C.A. (Eds.), Fundamental Principles of Molecular Modeling. Plenum, New York, pp. 105-118.
3. Bürgi H.-B., Dunitz J.D. From crystal statics to chemical dynamics. Acc. Chem. Res. 16:1983;153-161.
4. Bürgi, H.-B., Dunitz, J.D., 1994a. Structure correlation; the chemical point of view. In: Bürgi, H.-B., Dunitz, J.D. (Eds.), Structure Correlation, vol. 1. VCH, Weinheim, pp. 163-204.
5. Bürgi, H.-B., Dunitz, J.D., 1994b. Symmetry aspects of structure correlation. In: Bürgi, H.-B., Dunitz, J.D. (Eds.), Structure Correlation, vol. 1. VCH, Weinheim, pp. 23-70.
6. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. AM1: A new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107:1985;3902-3909.
7. Doucet, J.-P., Weber, J., 1997a. Access to experimental geometrical parameters. In: Computer-Aided Molecular Design: Theory and Applications. Academic Press, London, pp. 81-123.
8. Doucet, J.-P., Weber, J., 1997b. Exploring the conformational space: distance geometry and model builders. In: Computer-Aided Molecular Design: Theory and Applications. Academic Press, London, pp. 197-238.
9. Hofmann D.W.M., Lengauer T. A discrete algorithm for crystal structure prediction of organic molecules. Acta Crystallogr. A53:1997;225-235.
10. Johnson, C.K., 1971. ORTEPII, Report 3794, revised. Oak Ridge National Laboratory, Tennessee, USA, 1971.
11. Kitaigorodsky, A.I., 1973. The effect of the crystalline field on the shape of a molecule. In: Molecular Crystals and Molecules. Academic Press, New York, pp. 186-192.
12. Leach, A.R., 1996. Conformational analysis. In: Molecular Modelling: Principles and Applications. Addison-Wesley, Harlow, pp. 413-480.
13. McConnell J.F. 2-(4-Isobutylphenyl) Propionic acid. Cryst. Struct. Commun. 3:1974;73-75.
14. Murray-Rust P., Bürgi H.-B., Dunitz J.D. Chemical reaction paths. V. The SN1 reaction of tetrahedral molecules. J. Am. Chem. Soc. 97:1975;921-922.
15. Murray-Rust, P., 1982. How useful are X-ray studies of conformation? In: Griffin, J.F., Duax, W.L. (Eds.), Molecular Structure and Biological Activity. Elsevier, New York, pp. 117-133.
16. Schweizer, W.B., 1994. Conformational analysis. In: Bürgi, H.-B., Dunitz, J.D. (Eds.), Structure Correlation, vol. 1. VCH, Weinheim, pp. 369-404.
17. Shankland, K., David, W.I.F., Csoka, T., McBride, L., 1998. Structure solution of Ibuprofen from powder diffraction data by the application of a genetic algorithm combined with prior conformational analysis. Int. J. Pharm. 165, 117-126.
18. Shankland N., Wilson C.C., Florence A.J., Cox P.J. Refinement of the Ibuprofen crystal structure at 100 K by single-crystal pulsed neutron diffraction. Acta Crystallogr. C53:1997;951-954.
19. Stewart J.J.P. MOPAC: A semi-empirical molecular orbital program. J. Comput.-Aided Mol. Des. 4:1990;1-105.