Hostname: page-component-848d4c4894-xm8r8 Total loading time: 0 Render date: 2024-07-01T21:23:58.610Z Has data issue: false hasContentIssue false
  • English
  • Français

Crystal morphology prediction and experimental verification of venlafaxine hydrochloride

Published online by Cambridge University Press:  30 August 2022

Chenjing Liang Open the ORCID record for Chenjing Liang [Opens in a new window] ,
Jianghai Zhuang ,
Chenghan Zhuang ,
Zhaoxia Zhang ,
Guanglie Lv  and
Guoqing Zhang
Chenjing Liang
Affiliation:
School of Materials Science and Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, China
Jianghai Zhuang
Affiliation:
Zhejiang Apeloa Jiayuan Pharmaceutical Co., Ltd., Dongyang 322118, China
Chenghan Zhuang
Affiliation:
Zhejiang Apeloa Jiayuan Pharmaceutical Co., Ltd., Dongyang 322118, China
Zhaoxia Zhang
Affiliation:
School of Materials Science and Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, China
Guanglie Lv
Affiliation:
Zhejiang University, Hangzhou 310018, China
Guoqing Zhang*
Affiliation:
School of Materials Science and Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, China
*
a)Author to whom correspondence should be addressed. Electronic mail: zgq@zstu.edu.cn
Get access Rights & Permissions [Opens in a new window]

Abstract

This paper aims to explore the influence of solvent effects on the crystal habit of venlafaxine hydrochloride using the modified attachment energy (MAE) model by molecular dynamics (MD) simulation. Solvent effects were investigated based on the different morphologies of venlafaxine hydrochloride acquired by simulation and experimental technology from the solvents of isopropanol, dimethyl sulfoxide, and acetonitrile. Firstly, morphologically dominant crystal faces were obtained through the prediction of crystal habit in vacuum by the attachment energy (AE) model. Subsequently, the MAEs were calculated by the MD simulation to modify the crystal shapes in a real solvent environment, and the simulation results were in agreement with the experimental ones. Meanwhile, in order to have a better understanding of the solvent effects, the surface structure was introduced to analyze the solvent adsorption behaviors. The results show that the crystal habits of venlafaxine hydrochloride are affected by the combination of the AE and surface structures. Finally, the flowability of the obtained crystal powders from different solvents was investigated by measurement and analysis of the angle of repose and compressibility. The above results verify that the physical properties are closely related to the morphologies of the crystals.

Keywords

crystal habitsolvent effectmolecular dynamics simulationsurface structureintermolecular interaction
Type
Technical Article
Information
Powder Diffraction , Volume 37 , Issue 3 , September 2022 , pp. 133 - 142
Check for updates
Copyright
Copyright © Zhejiang Sci-tech University, 2022. Published by Cambridge University Press on behalf of International Centre for Diffraction Data

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Andrews, J. M., Ninan, P. T., and Nemeroff, C. B. (1996). “Venlafaxine: a novel antidepressant that has a DUAL mechanism of action,” J. Depression 4, 48–56.3.0.CO;2-B>CrossRefGoogle Scholar
Chen, F., Zhou, T., and Wang, M. (2020). “Spheroidal crystal morphology of RDX in mixed solvent systems predicted by molecular dynamics,” J. Phys. Chem. Solids 136, 109196.CrossRefGoogle Scholar
Dzade, N. Y., Roldan, A., and de Leeuw, N. H. (2016). “Surface and shape modification of mackinawite (FeS) nanocrystals by cysteine adsorption: a first-principles DFT-D2 study,” Phys. Chem. Chem. Phys. 18, 32007–32020.CrossRefGoogle ScholarPubMed
Graaf, J., Filion, L., Marechal, M., Roij, R., and Dijkstra, M. (2012). “Crystal-structure prediction via the floppy-box Monte Carlo algorithm: method and application to hard (non)convex particles,” Chem. Phys. 137, 214101.Google ScholarPubMed
Hartman, P. and Bennema, P. (1980). “The attachment energy as a habit controlling factor I. Theoretical considerations,” J. Cryst. Growth 49, 145–156.CrossRefGoogle Scholar
Jiang, Y., Xu, J., and Zhang, H. (2013). “Research progress on HMX crystallization morphology,” J. Mater. Renew. 27, 11–17.Google Scholar
Khoshkhoo, S. and Anwar, J. (1996). “Study of the effect of solvent on the morphology of crystals using molecular simulation: application to α-resorcinol and N-n-octyl-D-gluconamide,” J. Chem. Soc. Faraday Trans. 92, 1023–1025.CrossRefGoogle Scholar
Kitamura, M. and Ishizu, T. (2000). “Growth kinetics and morphological change of polymorphs of L-glutamic acid,” J. Cryst. Growth 209, 138–145.CrossRefGoogle Scholar
Lecrubier, Y., Bourin, M., Moon, C. A. L., Schifano, F., Blanchard, C., Danjou, P., and Hackett, D. (1997). “Efficacy of venlafaxine in depressive illness in general practice,” Acta Psychiatr. Scand. 95, 485–493.CrossRefGoogle ScholarPubMed
Li, J., Jin, S., Lan, G., Xu, Z., Wu, N., Chen, S., and Li, L. (2019). “The effect of solution conditions on the crystal morphology of β-HMX by molecular dynamics simulations,” J. Cryst. Growth 507, 38–45.CrossRefGoogle Scholar
Liu, Y. (2021). “Crystal morphology prediction method of energetic materials: attachment energy model and Its development,” J. Chinese J. Explosives & Propellants 44, 578–588.Google Scholar
Liu, J., Chang, Z., He, Y., Yang, M., and Dang, J. (2007). “Solvent effects on the crystallization of avermectin B1a,” J. Cryst. Growth 307, 131–136.CrossRefGoogle Scholar
MacLeod, C. S., and Muller, F. L. (2012). “On the fracture of pharmaceutical needle-shaped crystals during pressure filtration: case studies and mechanistic understanding,” J. Org. Process Res. Dev. 16, 425–434.CrossRefGoogle Scholar
Mckinnon, J. J., Jayatilaka, D., and Spackman, M. A. (2007). “Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces,” J. Chem. Commun. 37, 3814–3816.CrossRefGoogle Scholar
Miroslav, V., Peter, S., Jan, L., and Eva, V. (2012). “Crystal habit modifications of imatinib mesylate under various precipitation conditions,” J. Monatsh Chem. 143, 65–71.Google Scholar
Olver, J. S., Burrows, G. D., and Norman, T. R. (2001). “Third-generation antidepressants,” J. CNS Drugs 15, 941–954.CrossRefGoogle ScholarPubMed
Parmar, M. M., Khan, O., Seton, L., and Ford, J. L. (2007). “Polymorph selection with morphology control using solvents,” J. Cryst. Growth Des. 7, 1635–1642.CrossRefGoogle Scholar
Salvalaglio, M., Vetter, T., Giberti, F., Mazzotti, M., and Parrinello, M. (2012). “Uncovering molecular details of urea crystal growth in the presence of additives,” J. Am. Chem. Soc. 134, 17221–17233.CrossRefGoogle ScholarPubMed
Sivalakshmidevi, A., Vyas, K., Mahender, R., and Reddyb, G. (2002). “A monoclinic polymorph of venlafaxine hydrochloride,” J. Acta Cryst. 58, 1072–1074.Google Scholar
Spackman, M. A., and Jayatilaka, D. (2009). “Hirshfeld surface analysis,” J. Cryst. Eng. Comm. 11, 19–32.CrossRefGoogle Scholar
Spackman, M. A., and Mckinnon, J. J. (2002). “Fingerprinting intermolecular interactions in molecular crystals,” J. Cryst. Eng. Comm. 4, 378–392.CrossRefGoogle Scholar
Ter Horst, J. H., Kramer, H. J. M., Rosmalen, G. M., and Jansens, P. J. (2002). “Molecular modelling of the crystallization of polymorphs. Part I: the morphology of HMX polymorphs,” J. Cryst. Growth 237, 2215–2220.CrossRefGoogle Scholar
Urbelis, J. H., and Swift, J. A. (2014). “Solvent effects on the growth morphology and phase purity of CL-20,” J. Cryst. Growth Des. 14, 1642–1649.CrossRefGoogle Scholar
Weissbuch, I., Addadi, L., Lahav, M., and Leiserowitz, L. (1991). “Molecular recognition at crystal interfaces,” J. Sci. 253, 637–645.Google ScholarPubMed
Xu, T., and Wang, Y. (2017). “Quantitative determination of venlafaxine hydrochloride polymorphs using X-ray powder diffractometry,” Chinese J. New Drugs 26, 2614–2619.Google Scholar
Xu, G., Lu, P., Li, M., Liang, C., Xu, P., Liu, D., and Chen, X. (2018). “Investigation on characterization of powder flowability using different testing methods,” Exp. Therm. Fluid Sci. 92, 390–401.CrossRefGoogle Scholar
Zatloukal, Z., and Šklubalová, Z. (2008). “Drained angle of free-flowable powders,” Part. Sci. Technol. 26, 595–607.CrossRefGoogle Scholar
Zhang, W., Chen, C., and Zhang, S. (2013). “Equilibrium crystal shape of Ni from first principles,” J. Phys. Chem. C 117, 21274–21280.CrossRefGoogle Scholar
Zhang, M., Liang, Z., Wu, F., and Chen, J. (2017). “Crystal engineering of ibuprofen compounds: from molecule to crystal structure to morphology prediction by computational simulation and experimental study,” J. Cryst. Growth 467, 47–53.CrossRefGoogle Scholar
Zhao, Q., Liu, N., Wang, B., and Wang, W. (2016). “A study of solvent selectivity on the crystal morphology of FOX-7 via a modified attachment energy model,” J. RSC Adv. 6, 59784–59793.CrossRefGoogle Scholar
Zhu, D., Zhang, S., Cui, P., Wang, C., Dai, J., Zhou, L., et al. (2020). “Solvent effects on catechol crystal habits and aspect ratios: a combination of experiments and molecular dynamics simulation study,” J. Crystals 10, 316–332.CrossRefGoogle Scholar