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Crystal Structure of Antiinflammatory Sulindac

  • Koo Chung Hoe (Department of Chemistry, College of Natural Sciences, Seoul National University) ;
  • Kim Sang Hern (Department of Chemistry, College of Natural Sciences, Seoul National University) ;
  • Shin Wanchul (Department of Chemistry, College of Natural Sciences, Seoul National University)
  • 구정회 (서울대학교 자연과학대화학과) ;
  • 김상헌 (서울대학교 자연과학대화학과) ;
  • 신완철 (서울대학교 자연과학대화학과)
  • Published : 1985.08.20

Abstract

The crystal structure of sulindac, $C_{20}H_{17}Fo_3S$, one of the nonsteroid antiinflammatory agents, has been determined by the X-ray diffraction techniques using diffractometer data obtained by the $\varpi-2{\theta}$ scan technique with Cu $$K_{\alpha}$$ radiation from a crystal with space group symmetry Pbca and unit cell parameters a = 8.166(1), b = 18.291(8), c = 23.245(10) ${\AA}.$ The structure was solved by direct methods and refined by full-matrix least-squares to a final R = 0.11 for the 1153 observed reflections. The carboxyl group is nearly perpendicular to the indenyl ring as observed in indomethacin. The dihedral angle between the indenyl and phenyl rings is $35^{\circ}while$ the corresponding angle in indomethacin is $67^{\circ}.$ Crystal packing consists of a hydrogen bond and partial ring stacking between the indenyl rings.

Keywords

References

  1. J. Med. Chem. v.24 T. Y. Shen
  2. Adv. Drug Res. v.12 T. Y. Shen;C. A. Winter
  3. Drugs v.16 R. N. Brogden;R. C. Heel;T. M. Speight;G. S. Avery
  4. J. Pharmacol. Exp. Ther. v.201 D. E. Duggan;K. F. Hooke;E. A. Risley;T. Y. Shen;C. G. Van Arman
  5. Nature (London), New Biol. v.231 J. R. Vane
  6. J. Biol. Chem. v.254 R. W. Egan;P. H. Gale;F. A. Kuehl, Jr.
  7. J. Med. Chem. v.20 P. Gund;T. Y. Shen
  8. Bull. Soc. Chim. Belg. v.86 G. Dive;C. L. Lapier;G. Leroy
  9. Quantitative Structure-Activity Relationships of Drugs P. Gund;N. P. Jensen;J. G. Topliss(ed.)
  10. Antiinflammatory Agents: Chemistry and Pharmacology v.1 R. A. Scherrer;R. A. Scherrer(ed.);M. W. Whitehouse(ed.)
  11. J. Am. Chem. Soc. v.94 T. J. Kistenmacher;R. E. Marsh
  12. SHELX. Program for crystal structure determination G. M. Sheldrick
  13. ORTEP. Report ORNL-3794 C. K. Johnson
  14. Acta Cryst. v.B31 A. Domenicano;A. Vaciago
  15. Acta Cryst. v.21 R. Thomas;C. B. Shoemaker;K. Eriks
  16. PLUTO. Program for plotting molecular and crystal structures W. D. S. Motherwell;W. Clegg
  17. Top. Med. Chem. v.1 T. Y. Shen
  18. Eur. J. Med. Chem. Chim. Ther. v.16 F. Salvetti;A. Buttinoni;R. Ceserani;C. Tosi
  19. Acta Cryst. v.17 I. L. Karle;K. Britts;P. Gum
  20. Acta Cryst. v.B30 S. C. Nyburgh

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  2. Layered double hydroxide and sulindac coiled and scrolled nanoassemblies for storage and drug release vol.6, pp.20, 1985, https://doi.org/10.1039/c5ra25814f
  3. Using Milling to Explore Physical States: The Amorphous and Polymorphic Forms of Sulindac vol.108, pp.8, 1985, https://doi.org/10.1016/j.xphs.2019.03.017