Conformational polymorphism of tolbutamide: A structural, spectroscopic, and thermodynamic characterization of Burger's Forms I-IV

Journal of Pharmaceutical Sciences

Volumn 99, Issue 7, 2010, Pages 2975-2990

  Thirunahari, Satyanarayana ^a,b   Aitipamula, Srinivasulu ^b   Chow, Pui Shan ^b   Tan, Reginald B H ^a,b  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

Author keywords

Anisotropic lattice contraction; Crystal structure; Density rule; Energy temperature diagram; Lattice energy; Polymorphism; Stability; Thermal analysis; Tolbutamide; X ray powder diffractometry

Indexed keywords

TOLBUTAMIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; COLD EXPOSURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG CONFORMATION; DRUG STABILITY; ENERGY; ENVIRONMENTAL TEMPERATURE; FOURIER TRANSFORMATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; LOW TEMPERATURE; SCANNING ELECTRON MICROSCOPY; SOLID STATE; TEMPERATURE DEPENDENCE; THERMODYNAMICS; X RAY DIFFRACTION;

EID: 77953313238     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22061     Document Type: Article

References (45)

1. Patlak M. 2002. New weapons to combat an ancient disease: Treating diabetes. FASEB J 16:1853.
2. 2004. A special issue on pharmaceutical solid polymorphism in drug development and regulation (Ed. Raw AS, Yu LX). Adv Drug Deliv Rev 56:235-418.
3. Gardner CR, Walsh CT, Almarsson O. 2004. Drugs as materials: Valuing physical form in drug discovery. Nat Rev Drug Discov 3:926-934. (Pubitemid 39529930)
4. Huang LF, Tong WQ. 2004. Impact of solid state properties on developability assessment of drug candidates. Adv Drug Deliv Rev 56:321-334.
5. Variankaval N, Cote AS, Doherty MF. 2008. From form to function: Crystallization of active pharmaceutical ingredients. AIChE J 54:1682-1688. (Pubitemid 352006859)
6. Muller M, Meier U, Wieckhusen D, Beck R, Pfeffer-Hennig S, Schneeberger R. 2006. Process development strategy to ascertain reproducible API polymorph manufacture. Cryst Growth Des 6:946-954.
7. Reutzel-Edens SM. 2006. Achieving polymorph selectivity in the crystallization of pharmaceutical solids: Basic considerations and recent advances. Curr Opin Drug Discov Dev 9:806-815.
8. Chemburkar SR, Bauer J, Deming K, Spiwek H, Patel K, Morris J, Henry R, Spanton S, Dziki W, Porter W, Quick J, Bauer P, Donaubauer J, Narayanan BA, Soldani M, Riley D, McFarland K. 2000. Dealing with the impact of Ritonavir polymorphs on the late stages of bulk drug process development. Org Process Res Dev 4:413-417.
9. Rouhi AM. 2003. The right stuff. Chem Eng News 81:32-35.
10. Llinas A, Goodman JM. 2008. Polymorph control: Past, present and future. Drug Discov Today 13:198-210.
11. Dunitz JD, Bernstein J. 1995. Disappearing polymorphs. Acc Chem Res 28:193-200.
12. Vippagunta SR, Brittain HG, Grant DJW. 2001. Crystalline solids. Adv Drug Deliv Rev 48:3-26.
13. Bingham AL, Hughes DS, Hursthouse MB, Lancaster RW, Tavener S, Threlfall TL. 2001. Over one hundred solvates of sulfathiazole. Chem Commun 7: 603-604.
14. Kuhnert-Brandstätter M, Wunsch S. 1969. Polymorphism and mixed crystal formation in sulfonamides and related compounds. Mikrochim Acta (Wien) 6: 1297-1307.
15. Simmons DL, Ranz RJ, Gyanchandani ND, Picotte P. 1972. [Form III was prepared by dissolving TB in ethanol at 60°C, slowly adding warm water and allowing it to cool to room temperature] Polymorphism in pharmaceuticals II-Tolbutamide. Can J Pharm Sci 7: 121-123.
16. Burger A. 1975. Zur polymorphie oraler antidiabetika. Sci Pharm 43: 161-168.
17. Rowe EL, Anderson BD. 1984. Thermodynamic studies of Tolbutamide polymorphs. J Pharm Sci 73: 1673-1675.
18. Nirmala KA, Gowda DSS. 1981. Structure determination of Tolbutamide. Acta Crystallogr Sect B Struct Sci 37: 1597-1599. CSD Refcode: ZZZPUS01.
19. Donaldson JD, Leary JR, Ross SD, Thomas MJK, Smith CH. 1981. The structure of the orthorhombic form of Tolbutamide (1-N-Butyl-3-P- Toluenesulphonylurea). Acta Crystallogr Sect B Struct Sci 37: 2245-2248. CSD Refcode: ZZZPUS02.
20. Leary JR, Ross SD, Thomas MJK. 1981. On the characterization of the polymorphs of Tolbutamide. Pharm Weekblad Sci Ed 3:62-66.
21. Kimura K, Hirayama F, Uekama K. 1999. Characterization of Tolbutamide polymorphs (Burger's forms II and IV) and polymorphic transition behavior. J Pharm Sci 88:385-391.
22. Hasegawa G, Komasaka T, Bando R, Yoshihashi Y, Yonemochi E, Fujii K, Uekusa H, Terada K. 2009. Reevaluation of solubility of Tolbutamide and polymorphic transformation from Form I to unknown crystal form. Int J Pharm 369:12-18.
23. Accelrys Software Inc. Materials Studio Version 4.3. San Diego, CA, USA. Accelrys Software Inc.
24. Neumann MA. 2003. X-cell: A novel indexing algorithm for routine tasks and difficult cases. J Appl Crystallogr 36:356-365.
25. Engel GE, Wilke S, Konig O, Harris KDM, Leusen FJJ. 1999. PowderSolve - A complete package for crystal structure solution from powder diffraction patterns. J Appl Crystallogr 32:1169-1179.
26. Dollase WA. 1986. Correction of intensities for preferred orientation in powder diffractometry: Application of the March model. J Appl Crystallogr 19:267-272.
27. Bernstein J, Davey RJ, Henck JO. 1999. Concomitant polymorphs. Angew Chem Int Ed 38:3441-3461.
28. Hess's law of heat summation: The enthalpy change accompanying a transformation is the same whether the process occurs in one or many steps and total enthalpy change is the summation of all steps.
29. Giron D. 1995. Thermal analysis and calorimetric methods in the characterization of polymorphs and solvates. Thermochim Acta 248:1-59.
30. Kawakami K. 2007. Reversibility of enantiotropically related polymorphic transformations from a practical viewpoint: Thermal analysis of kinetically reversible/irreversible polymorphic transformations. J Pharm Sci 96:982-989.
31. Bernstein J. 2002. Polymorphism in molecular crystals, UK: Oxford Science Publications.
32. Nangia A. 2008. Conformational polymorphism in organic crystals. Acc Chem Res 41:595-604.
33. Kim BH, Ahn MK, Hwang GT. 1999. Hydrogen bonding patterns in sulfonyl ureas: Pattern dependence on the nature of amine substituent. Bull Korean Chem Soc 20:273-275.
34. 2Nsynthon and design of SHG active crystal N-4-iodophenyl-N′-4′-nitrophenylurea. Chem Commun 10: 1202-1203.
35. Stephenson GA. 2000. Structure determination from conventional powder diffraction data: Application to hydrates, hydrochloride salts, and metastable polymorphs. J Pharm Sci 89:958-966.
36. Harris KDM, Cheung EY. 2004. How to determine structures when single crystals cannot be grown: Opportunities for structure determination of molecular materials using powder diffraction data. Chem Soc Rev 33:526-538.
37. Stephenson GA. 2006. Anisotropic lattice contraction in pharmaceuticals: The influence of cryo-crystallography on calculated powder diffraction patterns. J Pharm Sci 95:821-827.
38. Cruickshank DW. 1956. The analysis of the anisotropic thermal motion of molecules in crystals. Acta Crystallogr 9:754.
39. 13C cross-polarization magic-angle-spinning NMR. J Chem Soc Chem Commun 12:786-788.
40. Threlfall T. 2003. Structural and thermodynamic explanations of Ostwald's rule. Org Process Res Dev 7:1017-1027
41. Bugay DE. 1993. Solid-state nuclear magnetic resonance magnetic resonance spectroscopy - Theory and pharmaceutical applications. Pharm Res 10:317-327.
42. Harris RK. 2006. NMR studies of organic polymorphs & solvates. Analyst 131:351-373.
43. Grunenberg A, Henck JO, Siesler HW. 1996. Theoretical derivation and practical application of energy temperature diagrams as an instrument in preformulation studies of polymorphic drug substances. Int J Pharm 129:147-158.
44. Burger A, Ramberger R. 1979. On the polymorphism of pharmaceuticals and other molecular crystals. I. Theory of thermodynamic rules. Mikrochim Acta 2:259-271.
45. Sun CC. 2007. Thermal expansion of organic crystals and precision of calculated crystal density: A survey of Cambridge crystal database. J Pharm Sci 96:1043-1052.