Preparation and characterization of new salts of tioconazole. Comparison of their dissolution performance

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dc.citation.titleInternational Journal of Pharmaceutics
dc.citation.volume652
dc.creatorMoroni, Aldana Beatriz
dc.creatorPérez Mayoral, Elena
dc.creatorLionello, Diego Fernando
dc.creatorVega, Daniel Roberto
dc.creatorKaufman, Teodoro Saúl
dc.creatorCalvo, Natalia Lorena
dc.date.accessioned2024-09-30T14:40:59Z
dc.date.available2024-09-30T14:40:59Z
dc.date.issued2024-01-23
dc.description.abstractTioconazole is an effective antifungal agent with very low solubility in aqueous media, which limits its bioavailability and efficacy. Aiming to overcome the drug limitations by improving the solubility of this active pharmaceutical ingredient, solution precipitation techniques were employed to prepare four new crystalline salts, namely the mesylate, tosylate, maleate (1:1), and fumarate (1:1) hemihydrate. The thermal stabilities, dissolution properties, and structural characteristics of the solids were determined, and the study was extended to compare their properties with the already-known oxalate salt. The structural characterization of the new phases was carried out using a multi-method approach, which included thermal (differential scanning calorimetry and thermogravimetry), diffractometric (powder X-ray diffraction), and spectroscopic (near-infrared and mid-infrared) methodologies. The determination of the melting point of the salts confirmed the findings made by thermal methods. Functional characteristics of the salts, involving their intrinsic dissolution rates were also determined. It was found that the salts exhibited improved thermal stability and that the nature of the counterion modulated their dissolution characteristics. The salts displayed better intrinsic dissolution rates than the free base, to the point of being “highly soluble” according to the Biopharmaceutical Classification System. At pH 4.3, the sulfonic acid derivatives exhibited better dissolution rates than their carboxylic acid-derived counterparts, greatly improved regarding bare tioconazole. The results suggest that the salts have great potential to be used as replacements for the free base; in principle, careful salt selection may help to fulfill each solubility need for the different scenarios where the drug may be used.
dc.description.filFil: Moroni, Aldana Beatriz. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET). Área de Análisis de Medicamentos; Argentina.
dc.description.filFil: Pérez Mayoral, Elena. Universidad Nacional de Educación a Distancia. Departamento de Química Inorgánica y Química Técnica; España.
dc.description.filFil: Lionello, Diego Fernando. Universidad Nacional General San Martín. Instituto de Tecnología Sabato (CNEA); Argentina.
dc.description.filFil: Lionello, Diego Fernando. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes. Departamento de Física de la Materia Condensada (CONICET/UNSaM); Argentina.
dc.description.filFil: Vega, Daniel Roberto. Universidad Nacional General San Martín. Escuela de Ciencia y Tecnologia (CNEA); Argentina.
dc.description.filFil: Vega, Daniel Roberto. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes. Departamento de Física de la Materia Condensada (CONICET/UNSaM); Argentina.
dc.description.filFil: Kaufman, Teodoro Saúl. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET). Área de Análisis de Medicamentos; Argentina.
dc.description.filFil: Calvo, Natalia Lorena. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET). Área de Análisis de Medicamentos; Argentina.
dc.description.sponsorshipConsejo Nacional de Investigaciones Científicas y Técnicas (CONICET): PIP 2021-0765
dc.description.sponsorshipAgencia Nacional de Promoción de la Investigación, el Desarrollo Tecnológico y la Innovación (Agencia I+D+i): PICT 2019-1155
dc.description.sponsorshipAgencia Santafesina de Ciencia Tecnología e Innovación (ASaCTeI): IO2019-302, BMG-N-2021-134
dc.description.sponsorshipFundación Carolina
dc.description.versionpeerreviewed
dc.format.extent1-9
dc.identifier.citationMoroni, A. B., Pérez Mayoral, E., Lionello, D. F., Vega, D. R., Kaufman, T. S. and Calvo, N. L. (2023). Preparation and characterization of new salts of tioconazole. Comparison of their dissolution performance. International Journal of Pharmaceutics, 652. https://doi.org/10.1016/j.ijpharm.2024.123855
dc.identifier.e-issn1873-3476
dc.identifier.issn0378-5173
dc.identifier.urihttps://hdl.handle.net/2133/27899
dc.language.isoen
dc.publisherElsevier
dc.relation.publisherversionhttps://doi.org/10.1016/j.ijpharm.2024.123855
dc.relation.publisherversionhttps://www.sciencedirect.com/science/article/abs/pii/S0378517324000899?via%3Dihub
dc.rightsembargoedAccess
dc.rights.holderMoroni, Aldana Beatriz
dc.rights.holderPérez Mayoral, Elena
dc.rights.holderLionello, Diego Fernando
dc.rights.holderVega, Daniel Roberto
dc.rights.holderKaufman, Teodoro Saúl
dc.rights.holderCalvo, Natalia Lorena
dc.rights.holderUniversidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas
dc.rights.holderElsevier
dc.rights.textAttribution-NonCommercial-NoDerivatives 4.0 Internationalen
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectTioconazole
dc.subjectSalt formation
dc.subjectSolid-state characterization
dc.subjectPowder dissolution
dc.subjectPowder X-ray diffractometry
dc.subjectThermal methods
dc.subjectVibrational spectroscopy
dc.titlePreparation and characterization of new salts of tioconazole. Comparison of their dissolution performance
dc.typearticulo
dc.type.versionacceptedVersion

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