Salts of S-(+)-Ibuprofen Formed via Its Reaction with the Antifibrinolytic Agents Aminocaproic Acid and Tranexamic Acid: Synthesis and Characterization

dc.contributor.authorFrösler, Hannah M.
dc.contributor.authorRamulumo, Humbelani S.
dc.contributor.authorEdmonds-Smith, Cesarina
dc.contributor.authorCaira, Mino R.
dc.date.accessioned2023-09-19T09:36:56Z
dc.date.available2023-09-19T09:36:56Z
dc.date.issued2023-08-08
dc.date.updated2023-08-25T12:37:17Z
dc.description.abstractThe paucity of multi-component compounds containing the non-steroidal anti-inflammatory drug (NSAID) S-(+)-ibuprofen (S-IBU) in combination with other drugs prompted the present study, which describes 1:1 salts of this active pharmaceutical ingredient (API) with the two most widely used antifibrinolytic APIs, namely 6-aminohexanoic acid (aminocaproic acid, ACA) and tranexamic acid (TXA), which are zwitterions in the solid state. Since NSAIDs are known to cause adverse side effects such as gastrointestinal ulceration, the presence of ACA and TXA in the salts with S-(+)-ibuprofen might counter these effects via their ability to prevent excessive bleeding. The salts were prepared by both the liquid-assisted grinding method and co-precipitation and were characterized by X-ray powder diffraction and single-crystal X-ray diffraction, thermal analysis, Fourier transform infrared spectroscopy, and solubility measurements. The X-ray analyses revealed a high degree of isostructurality, both at the level of their respective asymmetric units and in their extended crystal structures, with charge-assisted hydrogen bonds of the type N-H...O and O-H.. O featuring prominently. The thermal analysis indicated that both salts had significantly higher thermal stability than S-(+)-ibuprofen. Solubility measurements in a simulated biological medium showed insignificant changes in the solubility of S-(+)-ibuprofen when tested in the form of the salts (S-IBU) (TXA).
dc.identifierdoi: 10.3390/cryst13081222
dc.identifier.apacitationFrösler, Hannah M., Ramulumo, Humbelani S., Edmonds-Smith, C., & Caira, Mino R. (2023). Salts of S-(+)-Ibuprofen Formed via Its Reaction with the Antifibrinolytic Agents Aminocaproic Acid and Tranexamic Acid: Synthesis and Characterization. <i>Crystals</i>, 13(8), 1222. http://hdl.handle.net/11427/38770en_ZA
dc.identifier.chicagocitationFrösler, Hannah M., Humbelani S. Ramulumo, Cesarina Edmonds-Smith, and Mino R. Caira "Salts of S-(+)-Ibuprofen Formed via Its Reaction with the Antifibrinolytic Agents Aminocaproic Acid and Tranexamic Acid: Synthesis and Characterization." <i>Crystals</i> 13, 8. (2023): 1222. http://hdl.handle.net/11427/38770en_ZA
dc.identifier.citationFrösler, Hannah M., Ramulumo, Humbelani S., Edmonds-Smith, C. & Caira, Mino R. 2023. Salts of S-(+)-Ibuprofen Formed via Its Reaction with the Antifibrinolytic Agents Aminocaproic Acid and Tranexamic Acid: Synthesis and Characterization. <i>Crystals.</i> 13(8):1222. http://hdl.handle.net/11427/38770en_ZA
dc.identifier.ris TY - Journal Article AU - Frösler, Hannah M. AU - Ramulumo, Humbelani S. AU - Edmonds-Smith, Cesarina AU - Caira, Mino R. AB - The paucity of multi-component compounds containing the non-steroidal anti-inflammatory drug (NSAID) S-(+)-ibuprofen (S-IBU) in combination with other drugs prompted the present study, which describes 1:1 salts of this active pharmaceutical ingredient (API) with the two most widely used antifibrinolytic APIs, namely 6-aminohexanoic acid (aminocaproic acid, ACA) and tranexamic acid (TXA), which are zwitterions in the solid state. Since NSAIDs are known to cause adverse side effects such as gastrointestinal ulceration, the presence of ACA and TXA in the salts with S-(+)-ibuprofen might counter these effects via their ability to prevent excessive bleeding. The salts were prepared by both the liquid-assisted grinding method and co-precipitation and were characterized by X-ray powder diffraction and single-crystal X-ray diffraction, thermal analysis, Fourier transform infrared spectroscopy, and solubility measurements. The X-ray analyses revealed a high degree of isostructurality, both at the level of their respective asymmetric units and in their extended crystal structures, with charge-assisted hydrogen bonds of the type N-H...O and O-H.. O featuring prominently. The thermal analysis indicated that both salts had significantly higher thermal stability than S-(+)-ibuprofen. Solubility measurements in a simulated biological medium showed insignificant changes in the solubility of S-(+)-ibuprofen when tested in the form of the salts (S-IBU) (TXA). DA - 2023-08-08 DB - OpenUCT DP - University of Cape Town IS - 8 J1 - Crystals LK - https://open.uct.ac.za PY - 2023 T1 - Salts of S-(+)-Ibuprofen Formed via Its Reaction with the Antifibrinolytic Agents Aminocaproic Acid and Tranexamic Acid: Synthesis and Characterization TI - Salts of S-(+)-Ibuprofen Formed via Its Reaction with the Antifibrinolytic Agents Aminocaproic Acid and Tranexamic Acid: Synthesis and Characterization UR - http://hdl.handle.net/11427/38770 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/38770
dc.identifier.vancouvercitationFrösler Hannah M, Ramulumo Humbelani S, Edmonds-Smith C, Caira Mino R. Salts of S-(+)-Ibuprofen Formed via Its Reaction with the Antifibrinolytic Agents Aminocaproic Acid and Tranexamic Acid: Synthesis and Characterization. Crystals. 2023;13(8):1222. http://hdl.handle.net/11427/38770.en_ZA
dc.publisherMultidisciplinary Digital Publishing Institute
dc.publisher.departmentChemistry
dc.publisher.facultyScience
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.sourceCrystals
dc.source.journalissue8
dc.source.journalvolume13
dc.source.pagination1222
dc.source.urihttps://www.mdpi.com/journal/crystals
dc.titleSalts of S-(+)-Ibuprofen Formed via Its Reaction with the Antifibrinolytic Agents Aminocaproic Acid and Tranexamic Acid: Synthesis and Characterization
dc.typeJournal Article
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