EXPLORING STRUCTURAL ASPECTS OF NATEGLINIDE POLYMORPHS USING POWDER X-RAY DIFFRACTION
Objective: The present manuscript highlights the structural aspects of some polymorphic forms of nateglinide using powder x-ray diffraction (PXRD) pattern.
Methods: All the polymorphic forms were isolated as microcrystalline powder, therefore, powder diffraction patterns was used as a tool to determine the crystal structure. For this, Reflux Plus module of BIOVIA Material Studio software was used. Polymorph prediction (PP) and crystal morphology analysis were performed to estimate the global minimum in lattice energy landscape and morphologically important (M. I.) facets, respectively. Besides this, to investigate the behavior of polymorphs in solution phase, in vitro studies (enthalpy of solution, solubility, intrinsic dissolution rate) were also performed.
Results: A new form MS was prepared and characterized. The Form H, B, MS and S were found to exist in space group P-1, C2, P-4 and P-42C, respectively. These crystal structures were found to lie on local minima in crystal energy landscape. The stability ranking of nateglinide polymorphs follows the order: Form MS<Form B<Form H<Form S.
Conclusion: This research work demonstrates that PXRD is a valuable alternative for determining the structure of microcrystalline powders.
2. Butterhof C, BÃ¤rwinkel K, Senker J, Breu J. Polymorphism in co-crystals: a metastable form of the ionic co-crystal 2 Hbzâ€¢1 nabz crystallised by flash evaporation. CrystEngComm 2012;14:6744-9.
3. Harris KDM, Tremayne M, Kariuki BM. Contemporary advances in the use of powder x-ray diffraction for structure determination. Angew Chem Int 2001;40:1626.
4. Harris KDM. New opportunities for structure determination of molecular materials directly from powder diffraction data. Cryst Growth Des 2003;3:887-95.
5. Harris KDM. Crystal structure determination from powder diffraction data. Chem Mater 1996;8:2554-70.
6. Gopi G, Kannan K. Fabrication and in vitro evaluation of nateglinide-loaded ethyl cellulose nanoparticles. Asian J Pharm Clin Res 2015;8:93-6.
7. Tessler L, Goldberg I. Bis(nateglinide) hydronium chloride, and its unique self-assembly into extended polymeric arrays via O-Hâ€¦O, N-Hâ€¦Cl and O-Hâ€¦Cl hydrogen bonds. Acta Crystallogr 2005;61:738-40.
8. Sumikawa M, Koguchi Y, Ohgane T, Irie Y, Takahashi SY. Crystals of n (trans-4-isopropylcyclohexlycarbonyl)-d phenylalanine and methods for preparing them. US Patent No. 5,463,116; 1995.
9. Ronit Y, Shapiro E, Dolitzky B, Gozlan Y, Gome B. Polymorphic forms of nateglinide. Patent No. 7,148,376 B2; 2006.
10. Gang Li, Qun WX, Xiang YM, Jia YC, Guo QS. Study on stability of nateglinide polymorphism. Chin Chem Lett 2003;14:730-3.
11. Bruni G, Berbennia V, Milanesea C, Girella A, Cardinib A, ViganÃ²b E, et al. Thermodynamic relationships between nateglinide polymorphs. J Pharm Biomed Anal 2009;50:764-70.
12. Brunia G, Berbennia V, Milanesea C, Girella A, Cardinib A, Lanfranconib S, et al. New solid modifications of nateglinide. J Pharm Biomed Anal 2010;51:1054-9.
13. Brunia G, Berbennia V, Milanesea C, Girella A, Cardinib A, Lanfranconib S, et al. Determination of the nateglinide polymorphic purity through DSC. J Pharm Biomed Anal 2011;54:1196-9.
14. Upadhyay P, Dantuluri AK, Kumar L, Bansal AK. Estimating relative stability of polymorphs by generation of configurational free energy phase diagram. J Pharm Sci 2012;101:1843-51.
15. Pasha SW, Madhu MVV, Satyanarayana B, Paladugu ND, Rajeev KM, Arief MD, et al. Evaluation of crystal forms of nateglinide. Int J Res Pharm Sci 2013;4:427-37.
16. Gang Li, Jiaying C, Guanglie LU, Qunwei Xu. Determination of the nateglinide polymorphism structure and reduction in the blood glucose level. J Nanjing Normal University 2005;28:65-8.
17. Jain V, Dhaked DK, Kasetti Y, Bharatam PV. Computational study on the conformational preferences in Nateglinide. J Phys Org Chem 2011;25:649-57.
18. Beyer T, Lewis T, Price SL. Which organic crystal structures are predictable by lattice energy minimisation? CrystEngComm 2001;3:178-212.
19. Price SL. From crystal structure prediction to polymorph prediction: interpreting the crystal energy landscape. Phys Chem Chem Phys 2008;10:1996-2009.
20. Moreno-Calvo E, Calvet T, Cuevas-Diarte MA, Aquilano D. Relationship between the crystal structure and morphology of carboxylic acid polymorphs. Predicted and Experimental Morphologies. Cryst Growth Des 2010;10:4262-71.
21. Singh MR, Ramkrishna DA. Comprehensive approach to predicting crystal morphology distributions with population balances. Cryst Growth Des 2013;13:1397-411.
22. Graeme MD. Current approaches to predicting molecular organic crystal structure. Crystallogr Rev 2011;17:3-52.
23. Birva AA, Zarna RD, Ronak RD, Vijayendra Swamy SM, Chetana BP. Stability indicating HPLC method for determination of vilazodone hydrochloride. Int J Curr Pharm Res 2017;9:123-9.
24. Neumann M. X-Cell: a novel indexing algorithm for routine tasks and difficult cases. J Appl Crystallogr 2003;36:356-65.
25. Coombes DS, Catlow CRA, Gale JD, Rohl AL, Price SL. Calculation of attachment energies and relative volume growth rates as an aid to polymorph prediction. Cryst Growth Des 2005;5:879-85.
26. Prywer J. Morphological importance of crystal faces in connection with growth rates and crystallographic structure of crystal. Cryst Growth Des 2002;2:281-6.
27. Prywer J. Effect of crystal geometry on disappearance of slow-growing faces. J Cryst Growth 2001;224:134-44.
28. Chadha R, Bhandari S, Arora P, Chhikara R. Characterization, quantification and stability of differently prepared amorphous forms of some oral hypoglycaemic agents. Pharm Dev Tech 2013;18:504-14.
29. Sumikawa M, Makoto M, MIYaZakL K, Shigehro N, Matsuzawa Y. Methods for producing nateglinide B-type crystals. US Patent No. 7,544,834 B2; 2009.
30. Beyer T, Day GM, Price SL. The prediction, morphology, and mechanical properties of the polymorphs of paracetamol. J Am Chem Soc 2001;123:5086-94.
31. Anghel AT, Day GM, Price SL. A study of the known and hypothetical crystal structures of pyridine: why are there four molecules in the asymmetric unit cell? CrystEngComm 2002;4:348-55.
32. Lewis TC, Tocher DA, Day GM, Price SL. A computational and experimental search for polymorphs of parabanic acid-a salutary tale leading to the crystal structure of oxo-ureido-acetic acid methyl ester. CrystEngComm 2003;5:3-9.
33. Gang Li, Qun-Weib LI XU, Cheng R, Huang Yong-Ke, Chang-Gao. Polymorphism and solubility of nateglinide. Acta Chim Sin 2007;65:2817-20.