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 in | CrystEngComm Vol. 21; no. 32; pp. 4718 - 4729 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
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Royal Society of Chemistry
2019
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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
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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. |
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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 |
AuthorAffiliation_xml | – name: College of Chemical Engineering – name: Beijing University of Chemical Technology |
Author_xml | – sequence: 1 givenname: Xiangrong surname: Li fullname: Li, Xiangrong – sequence: 2 givenname: Guojia surname: Yu fullname: Yu, Guojia – sequence: 3 givenname: Xinjian surname: Chen fullname: Chen, Xinjian – sequence: 4 givenname: Lichao surname: He fullname: He, Lichao – sequence: 5 givenname: Zhiyong surname: Zhou fullname: Zhou, Zhiyong – sequence: 6 givenname: Zhongqi surname: Ren fullname: Ren, Zhongqi |
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CitedBy_id | crossref_primary_10_1016_j_molstruc_2022_134079 crossref_primary_10_1134_S002247662006013X crossref_primary_10_1208_s12249_022_02451_1 crossref_primary_10_1089_adt_2020_1052 crossref_primary_10_3390_pharmaceutics13060790 crossref_primary_10_1002_cjce_24662 crossref_primary_10_1016_j_molliq_2023_121929 crossref_primary_10_1039_D1CE00551K |
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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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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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