Febuxostat–p-Toluenesulfonic Acid Multi-Component Crystal: Characterization, Crystal Growth and Elucidation of the Salt/Co-Crystal Nature

The multi-component solid form of febuxostat (FEB) with p-toluenesulfonic acid was synthesized by solvent-drop grinding and cooling-evaporative crystallization and characterized by powder X-ray diffraction (XRPD), thermogravimetry (TGA), differential scanning calorimetry (DSC), and infrared spectros...

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Vydané v:Crystals (Basel) Ročník 13; číslo 5; s. 836
Hlavní autori: Ungur, Doriana T., Santiso-Quinones, Gustavo, Pop, Mihaela M., Tamas, Tudor L., Guguta, Carmen, Stam, Danny, Mija, Alice, Iordache, Coca A.
Médium: Journal Article
Jazyk:English
Vydavateľské údaje: Basel MDPI AG 18.05.2023
Predmet:
Aging
Basicity
Bioavailability
Cooling
Crystal growth
Crystal structure
Crystallization
Crystals
Dissolution
Evaporative cooling
febuxostat
Fourier transforms
FT-IR
High temperature
Infrared spectroscopy
p-toluenesulfonic acid
Pharmaceutical industry
Pharmacokinetics
Relative humidity
Rheumatism
salt/co-crystal
SC-XRD
Solvents
Thermogravimetry
Uric acid
X ray powder diffraction
ISSN:2073-4352, 2073-4352
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Abstract The multi-component solid form of febuxostat (FEB) with p-toluenesulfonic acid was synthesized by solvent-drop grinding and cooling-evaporative crystallization and characterized by powder X-ray diffraction (XRPD), thermogravimetry (TGA), differential scanning calorimetry (DSC), and infrared spectroscopy (FT-IR). The multi-component form was stable after exposure at elevated temperature and relative humidity and powder dissolution measurements revealed five-fold aqueous solubility improvement relative to FEB. Additionally, the decrease in pH after dissolution suggests a potential for enhancing the drug absorption in the lower stomach. In the context of the regulatory requirements, the salt/co-crystal nature of the form was elucidated by a combination of crystallization process development and crystal growth, followed by SC-XRD and FT-IR. Despite the very weak basicity of the drug, crystal structure determination combined with spectroscopy analysis revealed salt formation by the transfer of the acidic proton from p-toluenesulfonic acid to FEB. Our study emphasizes the importance of the crystal structure knowledge in understanding the type of interactions present in multi-component crystals as well as complying with the specific regulatory requirements.
AbstractList The multi-component solid form of febuxostat (FEB) with p-toluenesulfonic acid was synthesized by solvent-drop grinding and cooling-evaporative crystallization and characterized by powder X-ray diffraction (XRPD), thermogravimetry (TGA), differential scanning calorimetry (DSC), and infrared spectroscopy (FT-IR). The multi-component form was stable after exposure at elevated temperature and relative humidity and powder dissolution measurements revealed five-fold aqueous solubility improvement relative to FEB. Additionally, the decrease in pH after dissolution suggests a potential for enhancing the drug absorption in the lower stomach. In the context of the regulatory requirements, the salt/co-crystal nature of the form was elucidated by a combination of crystallization process development and crystal growth, followed by SC-XRD and FT-IR. Despite the very weak basicity of the drug, crystal structure determination combined with spectroscopy analysis revealed salt formation by the transfer of the acidic proton from p-toluenesulfonic acid to FEB. Our study emphasizes the importance of the crystal structure knowledge in understanding the type of interactions present in multi-component crystals as well as complying with the specific regulatory requirements.
Author Santiso-Quinones, Gustavo
Ungur, Doriana T.
Pop, Mihaela M.
Guguta, Carmen
Mija, Alice
Tamas, Tudor L.
Iordache, Coca A.
Stam, Danny
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  surname: Iordache
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CitedBy_id crossref_primary_10_1016_j_molstruc_2023_136596
crossref_primary_10_3390_molecules29235631
crossref_primary_10_1016_j_jelechem_2025_119281
crossref_primary_10_1016_j_molstruc_2025_143294
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ContentType Journal Article
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Snippet The multi-component solid form of febuxostat (FEB) with p-toluenesulfonic acid was synthesized by solvent-drop grinding and cooling-evaporative crystallization...
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StartPage 836
SubjectTerms Aging
Basicity
Bioavailability
Cooling
Crystal growth
Crystal structure
Crystallization
Crystals
Dissolution
Evaporative cooling
febuxostat
Fourier transforms
FT-IR
High temperature
Infrared spectroscopy
p-toluenesulfonic acid
Pharmaceutical industry
Pharmacokinetics
Relative humidity
Rheumatism
salt/co-crystal
SC-XRD
Solvents
Thermogravimetry
Uric acid
X ray powder diffraction
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