Next Article in Journal
Metal–Metal Bond in the Light of Pauling’s Rules
Next Article in Special Issue
Diagnosis of Agglomeration and Crystallinity of Active Pharmaceutical Ingredients in Over the Counter Headache Medication by Electrospray Laser Desorption Ionization Mass Spectrometry Imaging
Previous Article in Journal
Differential Protein Expression in Exponential and Stationary Growth Phases of Mycobacterium avium subsp. hominissuis 104
Previous Article in Special Issue
Thermal Stability of Amorphous Solid Dispersions
Article

Investigation of Solubility Behavior of Canagliflozin Hydrate Crystals Combining Crystallographic and Hirshfeld Surface Calculations

1
Department of Chemistry, Zhejiang University, Hangzhou 310028, China
2
Hangzhou Huadong Medicine Group Pharmaceutical Research Institute Co., Ltd., Hangzhou 310011, China
3
School of Information Engineering, Huzhou University, Huzhou 313000, China
*
Author to whom correspondence should be addressed.
Academic Editor: Carlos Eduardo Sabino Bernardes
Molecules 2021, 26(2), 298; https://doi.org/10.3390/molecules26020298
Received: 11 December 2020 / Revised: 31 December 2020 / Accepted: 5 January 2021 / Published: 8 January 2021
(This article belongs to the Special Issue Solid-State of Organic Pharmaceutical Compounds)
Canagliflozin (CG) was a highly effective, selective and reversible inhibitor of sodium-dependent glucose co-transporter 2 developed for the treatment of type 2 diabetes mellitus. The crystal structure of CG monohydrate (CG-H2O) was reported for the first time while CG hemihydrate (CG-Hemi) had been reported in our previous research. Solubility and dissolution rate results showed that the solubility of CG-Hemi was 1.4 times higher than that of CG-H2O in water and hydrochloric acid solution, and the dissolution rates of CG-Hemi were more than 3 folds than CG-H2O in both solutions. Hirshfeld surface analysis showed that CG-H2O had stronger intermolecular forces than CG-Hemi, and water molecules in CG-H2O participated three hydrogen bonds, forming hydrogen bond networks. These crystal structure features might make it more difficult for solvent molecules to dissolve CG-H2O than CG-Hemi. All these analyses might explain why the dissolution performance of CG-Hemi was better than CG-H2O. This work provided an approach to predict the dissolution performance of the drug based on its crystal structure. View Full-Text
Keywords: canagliflozin; hemihydrate; monohydrate; crystal structure; solubility canagliflozin; hemihydrate; monohydrate; crystal structure; solubility
Show Figures

Figure 1

MDPI and ACS Style

Zhu, Y.; Kang, Y.; Zhu, L.; Yu, K.; Chen, S.; Tang, G.; Hu, X. Investigation of Solubility Behavior of Canagliflozin Hydrate Crystals Combining Crystallographic and Hirshfeld Surface Calculations. Molecules 2021, 26, 298. https://doi.org/10.3390/molecules26020298

AMA Style

Zhu Y, Kang Y, Zhu L, Yu K, Chen S, Tang G, Hu X. Investigation of Solubility Behavior of Canagliflozin Hydrate Crystals Combining Crystallographic and Hirshfeld Surface Calculations. Molecules. 2021; 26(2):298. https://doi.org/10.3390/molecules26020298

Chicago/Turabian Style

Zhu, Yefen, Yanlei Kang, Ling Zhu, Kaxi Yu, Shuai Chen, Guping Tang, and Xiurong Hu. 2021. "Investigation of Solubility Behavior of Canagliflozin Hydrate Crystals Combining Crystallographic and Hirshfeld Surface Calculations" Molecules 26, no. 2: 298. https://doi.org/10.3390/molecules26020298

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop