Effect of crystallization conditions on modafinil substance polymorphism
https://doi.org/10.29235/1561-8331-2022-58-4-360-368
Abstract
The effect of the crystallization conditions of modafinil from its methanol solutions on the polymorphic state of the resulting substance was studied using the X-ray powder diffraction method. It is shown that changes in the cooling rate and the concentration of saturated solutions have an effect on obtaining samples of the modafinil substance with differences in diffractometric characteristics. Moreover, the cooling rate practically does not affect the yield of the crystalline product, which depends on the degree of saturation of crystallization solutions. It was found that the I polymorphic form of modafinil can be obtained from modafinil solutions with a concentration in the range of 0.34–0.44 M with slow cooling of solutions, mainly with a temperature gradient of 5–10 °C/hour to a temperature of 5 ± 2 °C. An increase in the cooling rate of saturated solutions and their concentration >0.44 M leads to the production of mixed polymorphic forms of modafinil crystals.
About the Authors
E. G. Karankevich
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus
Belarus
Belarus
Karankevich Elena G. – Ph. D. (Chemistry), Head of the Laboratory.
13, Surganov str., 220072 Minsk
Z. I. Kuvaeva
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus
Belarus
Belarus
Kuvaeva Zoya I. – D. Sc. (Chemistry), Professor. Head of the Department.
13, Surganov str., 220072, Minsk
L. V. Kulbitskaya
Institute of General and Inorganic Chemistry, National Academy of Sciences of Belarus
Belarus
Belarus
Kulbitskaya Lyudmila V. – Researcher.
9/1, Surganov str., 220072, Minsk
A. S. Popov
Belarusian State Aviation Academy
Belarus
Belarus
Popov Anton S. – Senior Lecturer, Head of the medical service.
77, Uborevich str., 220096, Minsk
References
1. Leonidov N. B. History of development of the concept of polymorphism of chemicals (brief essay). Rossiiskii himicheskii zhurnal = Russian Journal of General Chemistry, 1997, vol. 41, no. 5, pp. 10–22 (in Russian).
2. Rychkov D. A., Arkhipov S. G., Boldyreva E. V. Simple and efficient modifications of well known techniques for reliable growth of high-quality crystals of small bioorganic molecules. Journal of Applied Crystallography, 2014, vol. 47, pp. 1435–1442. https://doi.org/10.1107/s1600576714011273
3. Datta S., Grant D. J. W. Crystal structures of drugs: Advances in determination, prediction and engineering. Natural Reviews Drug Discovery, 2004, vol. 3, no. 1, pp. 42–57. https://doi.org/10.1038/nrd1280
4. Dunitz J. D., Bernstein J. Disappearing Polymorphs. Accounts of Chemical Research, 1995, vol. 28, no. 4, pp. 193–200. https://doi.org/10.1021/ar00052a005
5. Gildeeva G. N. Polymorphism: the influence on the quality of drugs and actual methods of analysis. Kachestvennaya klinicheskaya praktika = Good Clinical Practice, 2017, no. 1, pp. 56–59 (in Russian).
6. Prado L. D., Rocha H. Solid State in the Pharmaceutical Industry: A Brief Review January 2015. Revista Virtual de Quimica, 2015, vol. 7(6), pp. 2080–2112. https://doi.org/10.5935/1984-6835.20150123
7. Smirnova I. G., Gildeeva G. N., Chistyakov V. V. Analysis of crystal and three dimensional structures of drug substances. Vestnik Moskovskogo Universiteta. Ser. 2. Himiya = Moscow University Chemistry Bulletin, 2012, vol. 53, no. 4, pp. 234–240 (in Russian).
8. Pauchet M., Gervais C., Courvoisier L., Coquerel G. Successful Application of the Derived Crystal Packing (DCP) Model in Resolving the Crystal Structure of a Metastable Polymorph of ((±)Modafinil. Crystal Growth and Design, 2004, vol. 4, no. 6, pp. 1143–1151. https://doi.org/10.1021/cg030069t
9. Lohani S., Grant D. J. W. Polymorphism: in the Pharmaceutical Industry. Chapter 2. Thermodynamics of Polymorphs. Weinheim, Wiley-VCH, 2006. https://doi.org/10.1002/3527607889.ch2
10. Gavezzotti A. Chapter 6. Crystal polymorphism: Conventional and real wisdom. Journal Theoretical and Computational Chemistry, 2021, vol. 20, pp. 143–168. https://doi.org/10.1016/B978-0-12-823747-2.00001-9
11. Mahieux J., Sanselme M., Coquerel G. Access to several polymorphic forms of (±)-modafinil by using various solvation−desolvation processes. Crystal Growth and Design, 2016, vol. 16, pp. 396−405. https://doi.org/10.1021/acs.cgd.5b01384
12. Mahieux J., Sanselme M., Coquerel G. Access to single crystals of (±)-form IV of modafinil by crystallization in gels. Comparisons between (±)-forms I, III, and IV and (−)-form I. Crystal Growth and Design, 2013, vol. 13, pp. 908–917. https:// doi.org/10.1021/cg301630d
13. Linol J., Morelli T., Petit M.-N., Coquerel G. Inversion of the Relative Stability between Two Polymorphic Forms of (±) Modafinil under Dry High-Energy Milling: Comparisons with Results Obtained under Wet High-Energy Milling. Crystal Growth and Design, 2007, vol. 7, no. 9, pp. 1608–1611. https://doi.org/10.1021/cg0700723
14. Klopotov A. A., Abzaev Yu. A., Potekaev A. I., Volokitin O. G., Klopotov V. D. Physical bases of X-ray study of crystalline materials. Tomsk, Tomsk University Publ. 2013. 276 p. (in Russian).
15. Kovba L. M., Trunov V. K. X-ray phase analysis. 2nd ed. Moscow, Moscow State University, 1976. 232 p. (in Russian).
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