Investigating the solubilization effect of oxcarbazepine by forming cocrystals

Oxcarbazepine (OXCBZ) is a poorly soluble drug that can't form a salt. It has an amide functional group and a carbonyl group in its structure, which can be used to form cocrystals. Three cocrystals of OXCBZ were successfully synthesized through liquid-assisted grinding and reaction crystallizat...

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Published inCrystEngComm Vol. 21; no. 32; pp. 4718 - 4729
Main Authors Li, Xiangrong, Yu, Guojia, Chen, Xinjian, He, Lichao, Zhou, Zhiyong, Ren, Zhongqi
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 2019
Subjects
Carbonyl groups
Carbonyls
Crystallization
Differential scanning calorimetry
Dihydroxybenzoic acid
Fourier transforms
Functional groups
Hydrogen bonds
Infrared analysis
NMR
Nuclear magnetic resonance
Oxalic acid
Salicylic acid
Solubility
Solubilization
Spectrum analysis
Thermogravimetric analysis
X ray powder diffraction
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Abstract Oxcarbazepine (OXCBZ) is a poorly soluble drug that can't form a salt. It has an amide functional group and a carbonyl group in its structure, which can be used to form cocrystals. Three cocrystals of OXCBZ were successfully synthesized through liquid-assisted grinding and reaction crystallization. Since OXCBZ has an amide group and a keto group, oxalic acid (OA), 2,5-dihydroxybenzoic acid (2,5-DHBA), and salicylic acid (SA) were selected as coformers which can form a hydrogen bond with an amide group or a keto group. The formation of OXCBZ cocrystals was confirmed by characterization via powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, Fourier transform infrared spectroscopy, scanning electron microscopy, and solid state nuclear magnetic resonance spectroscopy. Effects of different conditions on the preparation of the cocrystal were investigated to optimize the cocrystal preparation process. The apparent solubility and dissolution rate of the cocrystals were investigated too. The apparent solubility of the OXCBZ-OA and OXCBZ-2,5-DHBA cocrystals increased approximately 2.6 and 4.7 times that of the pure drug. Oxcarbazepine (OXCBZ) is a poorly soluble drug that can't form a salt. The apparent solubilities of the OXCBZ-OA and OXCBZ-2,5-DHBA cocrystals increased approximately 2.6 and 4.7 times of that of OXCBZ.
AbstractList Oxcarbazepine (OXCBZ) is a poorly soluble drug that can't form a salt. It has an amide functional group and a carbonyl group in its structure, which can be used to form cocrystals. Three cocrystals of OXCBZ were successfully synthesized through liquid-assisted grinding and reaction crystallization. Since OXCBZ has an amide group and a keto group, oxalic acid (OA), 2,5-dihydroxybenzoic acid (2,5-DHBA), and salicylic acid (SA) were selected as coformers which can form a hydrogen bond with an amide group or a keto group. The formation of OXCBZ cocrystals was confirmed by characterization via powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, Fourier transform infrared spectroscopy, scanning electron microscopy, and solid state nuclear magnetic resonance spectroscopy. Effects of different conditions on the preparation of the cocrystal were investigated to optimize the cocrystal preparation process. The apparent solubility and dissolution rate of the cocrystals were investigated too. The apparent solubility of the OXCBZ-OA and OXCBZ-2,5-DHBA cocrystals increased approximately 2.6 and 4.7 times that of the pure drug. Oxcarbazepine (OXCBZ) is a poorly soluble drug that can't form a salt. The apparent solubilities of the OXCBZ-OA and OXCBZ-2,5-DHBA cocrystals increased approximately 2.6 and 4.7 times of that of OXCBZ.
Oxcarbazepine (OXCBZ) is a poorly soluble drug that can't form a salt. It has an amide functional group and a carbonyl group in its structure, which can be used to form cocrystals. Three cocrystals of OXCBZ were successfully synthesized through liquid-assisted grinding and reaction crystallization. Since OXCBZ has an amide group and a keto group, oxalic acid (OA), 2,5-dihydroxybenzoic acid (2,5-DHBA), and salicylic acid (SA) were selected as coformers which can form a hydrogen bond with an amide group or a keto group. The formation of OXCBZ cocrystals was confirmed by characterization via powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, Fourier transform infrared spectroscopy, scanning electron microscopy, and solid state nuclear magnetic resonance spectroscopy. Effects of different conditions on the preparation of the cocrystal were investigated to optimize the cocrystal preparation process. The apparent solubility and dissolution rate of the cocrystals were investigated too. The apparent solubility of the OXCBZ–OA and OXCBZ–2,5-DHBA cocrystals increased approximately 2.6 and 4.7 times that of the pure drug.
Oxcarbazepine (OXCBZ) is a poorly soluble drug that can't form a salt. It has an amide functional group and a carbonyl group in its structure, which can be used to form cocrystals. Three cocrystals of OXCBZ were successfully synthesized through liquid-assisted grinding and reaction crystallization. Since OXCBZ has an amide group and a keto group, oxalic acid (OA), 2,5-dihydroxybenzoic acid (2,5-DHBA), and salicylic acid (SA) were selected as coformers which can form a hydrogen bond with an amide group or a keto group. The formation of OXCBZ cocrystals was confirmed by characterization via powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, Fourier transform infrared spectroscopy, scanning electron microscopy, and solid state nuclear magnetic resonance spectroscopy. Effects of different conditions on the preparation of the cocrystal were investigated to optimize the cocrystal preparation process. The apparent solubility and dissolution rate of the cocrystals were investigated too. The apparent solubility of the OXCBZ–OA and OXCBZ–2,5-DHBA cocrystals increased approximately 2.6 and 4.7 times that of the pure drug.
Author He, Lichao
Ren, Zhongqi
Zhou, Zhiyong
Li, Xiangrong
Yu, Guojia
Chen, Xinjian
AuthorAffiliation College of Chemical Engineering
Beijing University of Chemical Technology
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Snippet Oxcarbazepine (OXCBZ) is a poorly soluble drug that can't form a salt. It has an amide functional group and a carbonyl group in its structure, which can be...
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StartPage 4718
SubjectTerms Carbonyl groups
Carbonyls
Crystallization
Differential scanning calorimetry
Dihydroxybenzoic acid
Fourier transforms
Functional groups
Hydrogen bonds
Infrared analysis
NMR
Nuclear magnetic resonance
Oxalic acid
Salicylic acid
Solubility
Solubilization
Spectrum analysis
Thermogravimetric analysis
X ray powder diffraction
Title Investigating the solubilization effect of oxcarbazepine by forming cocrystals
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