RS, S (+) - and R (−)-ibuprofen cocrystal polymorphs: Vibrational spectra, XRD measurement and DFT calculation studies
In this paper, cocrystal polymorphs of RS-ibuprofen (RS-IBU), S (+)-ibuprofen (S(+)-IBU), R (−)-ibuprofen (R(−)-IBU) with nicotinamide (NIC) were synthesized by different methods. RS-IBU is a chiral drug with only one chiral center in the molecule, which has two enantiomers (S (+)-IBU and R (−)-IBU)...
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Elsevier
2025-02-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844025003664 |
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| author | Yaqi Jing Qiuhui Zhao Jiale Zhang Jiadan Xue Jianjun Liu Jianyuan Qin Zhi Hong Yong Du |
| author_facet | Yaqi Jing Qiuhui Zhao Jiale Zhang Jiadan Xue Jianjun Liu Jianyuan Qin Zhi Hong Yong Du |
| author_sort | Yaqi Jing |
| collection | DOAJ |
| description | In this paper, cocrystal polymorphs of RS-ibuprofen (RS-IBU), S (+)-ibuprofen (S(+)-IBU), R (−)-ibuprofen (R(−)-IBU) with nicotinamide (NIC) were synthesized by different methods. RS-IBU is a chiral drug with only one chiral center in the molecule, which has two enantiomers (S (+)-IBU and R (−)-IBU). Due to the low solubility and bioavailability of IBU, its application is limited. The pharmaceutical cocrystal technology can improve the physicochemical properties of the drug. In this paper, we characterized RS-IBU, S (+)-IBU, R (−)-IBU, NIC, physical mixtures and cocrystal polymorphs by terahertz (THz), Raman and X-ray Diffraction (XRD), respectively. By observing the experimental results, we could clearly distinguish the cocrystal polymorphs. We found that the melt recrystallization method can generate cocrystal form A, while the solvent drop grinding method and solution evaporation method can generate cocrystal form B. In addition, in order to verify the successful preparation of them, we used density functional theory (DFT) to optimize and simulate the theoretical structures of the RS-IBU: NIC cocrystal polymorphs, and compared the simulated results with the experimental results. These research results provide a reference for the analysis and preparation of pharmaceutical cocrystal polymorphs and help to distinguish the cocrystal polymorphs. |
| format | Article |
| id | doaj-art-f815c63b84064e77b881b5aad7db8ff8 |
| institution | Kabale University |
| issn | 2405-8440 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj-art-f815c63b84064e77b881b5aad7db8ff82025-01-25T04:11:22ZengElsevierHeliyon2405-84402025-02-01113e41986RS, S (+) - and R (−)-ibuprofen cocrystal polymorphs: Vibrational spectra, XRD measurement and DFT calculation studiesYaqi Jing0Qiuhui Zhao1Jiale Zhang2Jiadan Xue3Jianjun Liu4Jianyuan Qin5Zhi Hong6Yong Du7Centre for THz Research, China Jiliang University, Hangzhou, 310018, ChinaCentre for THz Research, China Jiliang University, Hangzhou, 310018, ChinaCentre for THz Research, China Jiliang University, Hangzhou, 310018, ChinaDepartment of Chemistry, Zhejiang Sci-Tech University, Hangzhou, 310018, ChinaCentre for THz Research, China Jiliang University, Hangzhou, 310018, ChinaCentre for THz Research, China Jiliang University, Hangzhou, 310018, ChinaCentre for THz Research, China Jiliang University, Hangzhou, 310018, ChinaCentre for THz Research, China Jiliang University, Hangzhou, 310018, China; Corresponding author.In this paper, cocrystal polymorphs of RS-ibuprofen (RS-IBU), S (+)-ibuprofen (S(+)-IBU), R (−)-ibuprofen (R(−)-IBU) with nicotinamide (NIC) were synthesized by different methods. RS-IBU is a chiral drug with only one chiral center in the molecule, which has two enantiomers (S (+)-IBU and R (−)-IBU). Due to the low solubility and bioavailability of IBU, its application is limited. The pharmaceutical cocrystal technology can improve the physicochemical properties of the drug. In this paper, we characterized RS-IBU, S (+)-IBU, R (−)-IBU, NIC, physical mixtures and cocrystal polymorphs by terahertz (THz), Raman and X-ray Diffraction (XRD), respectively. By observing the experimental results, we could clearly distinguish the cocrystal polymorphs. We found that the melt recrystallization method can generate cocrystal form A, while the solvent drop grinding method and solution evaporation method can generate cocrystal form B. In addition, in order to verify the successful preparation of them, we used density functional theory (DFT) to optimize and simulate the theoretical structures of the RS-IBU: NIC cocrystal polymorphs, and compared the simulated results with the experimental results. These research results provide a reference for the analysis and preparation of pharmaceutical cocrystal polymorphs and help to distinguish the cocrystal polymorphs.http://www.sciencedirect.com/science/article/pii/S2405844025003664Chiral structure of ibuprofenNicotinamideCocrystal polymorphismVibrational spectraXRD measurementStructural optimization |
| spellingShingle | Yaqi Jing Qiuhui Zhao Jiale Zhang Jiadan Xue Jianjun Liu Jianyuan Qin Zhi Hong Yong Du RS, S (+) - and R (−)-ibuprofen cocrystal polymorphs: Vibrational spectra, XRD measurement and DFT calculation studies Heliyon Chiral structure of ibuprofen Nicotinamide Cocrystal polymorphism Vibrational spectra XRD measurement Structural optimization |
| title | RS, S (+) - and R (−)-ibuprofen cocrystal polymorphs: Vibrational spectra, XRD measurement and DFT calculation studies |
| title_full | RS, S (+) - and R (−)-ibuprofen cocrystal polymorphs: Vibrational spectra, XRD measurement and DFT calculation studies |
| title_fullStr | RS, S (+) - and R (−)-ibuprofen cocrystal polymorphs: Vibrational spectra, XRD measurement and DFT calculation studies |
| title_full_unstemmed | RS, S (+) - and R (−)-ibuprofen cocrystal polymorphs: Vibrational spectra, XRD measurement and DFT calculation studies |
| title_short | RS, S (+) - and R (−)-ibuprofen cocrystal polymorphs: Vibrational spectra, XRD measurement and DFT calculation studies |
| title_sort | rs s and r ibuprofen cocrystal polymorphs vibrational spectra xrd measurement and dft calculation studies |
| topic | Chiral structure of ibuprofen Nicotinamide Cocrystal polymorphism Vibrational spectra XRD measurement Structural optimization |
| url | http://www.sciencedirect.com/science/article/pii/S2405844025003664 |
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