Citation: Hong-Mei Yu, Bao-Xi Zhang, Wen-Hui Xing, Mei-Ju Liu, Feng-Feng Wang, Ning-Bo Gong, Li Zhang, Yang Lu, Guan-Hua Du. Investigation into the structures and physicochemical properties of multi-component crystals of voriconazole[J]. Chinese Chemical Letters, ;2023, 34(6): 107668. doi: 10.1016/j.cclet.2022.07.011 shu

Investigation into the structures and physicochemical properties of multi-component crystals of voriconazole

Hong-Mei Yu ^a ,
Bao-Xi Zhang ^a ,
Wen-Hui Xing ^a ,
Mei-Ju Liu ^a ,
Feng-Feng Wang ^b ,
Ning-Bo Gong ^{a, *,} ,
Li Zhang ^{a, *,} ,
Yang Lu ^{a, *,} ,
Guan-Hua Du ^c

a.
Beijing Key Laboratory of Polymorphic Drugs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
b.
National Institutes for Food and Drug Control, Beijing 102629, China
c.
Beijing City Key Laboratory of Drug Target Identification and Drug Screening, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

gnb@imm.ac.cn

zhangl@imm.ac.cn

luy@imm.ac.cn

Received Date: 19 May 2022
Revised Date: 12 June 2022
Accepted Date: 6 July 2022
Available Online: 14 July 2022

Figures(7)

Voriconazole (VZL) is a second-generation and broad-spectrum triazole against fungal infections. Being a BCS (biopharmaceutics classification system) class Ⅱ compound, the poor aqueous solubility has limited its bioavailability and clinical efficacy. Aims to overcome this disadvantage, a cocrystallization strategy based on crystal engineering principles has resulted in five new multi-component crystals of VZL with maleic acid, L-tartaric, protocatechuic, gallic, and 3,5-dinitrobenzoic acids. Structure analysis revealed that the hydroxyl/carboxylic acid···triazole N₃ hydrogen bonding interaction appears as a main supramolecular heterosynthon in the VZL multi-component crystals with organic acids. And VZL molecule has a flexible conformation in each of the five multi-component structures. The newly synthesized multi-component crystals showed impressive solubility improvement compared to that of the raw material of VZL. Molecular electrostatic potential surfaces (MEPS) analysis based on density functional (DFT) calculations revealed that hydrogen bond interactions in cocrystals mainly involved pairwise interactions in the global maxima and minima sites, but this rule is not always followed. This study indicates the potential of cocrystals to improve the solubility and dissolution rate of VZL
- Multi-component crystal,
- Voriconazole,
- Solubility,
- Dissolution,
- Stability
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