Apremilast Cocrystals with Phenolic Coformers
Apremilast (APR) is an anti-inflammatory drug commonly used in the treatment of psoriasis. In efforts to enhance its solubility, several cocrystals with similar structural features have been developed. This study investigates the cocrystallization of APR with four phenolic-type coformers: phenol, ca...
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MDPI AG
2024-12-01
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| Online Access: | https://www.mdpi.com/1420-3049/29/24/6060 |
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| author | Yelizaveta Naumkina Bohumil Kratochvíl Elena Korotkova Jan Čejka |
| author_facet | Yelizaveta Naumkina Bohumil Kratochvíl Elena Korotkova Jan Čejka |
| author_sort | Yelizaveta Naumkina |
| collection | DOAJ |
| description | Apremilast (APR) is an anti-inflammatory drug commonly used in the treatment of psoriasis. In efforts to enhance its solubility, several cocrystals with similar structural features have been developed. This study investigates the cocrystallization of APR with four phenolic-type coformers: phenol, catechol, pyrogallol, and hydroxyquinol. These coformers differ in the number and position of their hydroxyl groups, with their melting points varying by as much as 100 °C. Four novel cocrystal forms were synthesized, purified, and characterized using X-Ray diffraction and thermal analysis techniques. Surprisingly, the resulting cocrystals exhibited minimal differences in their melting points. The molecular packing of APR appears to limit the network-forming potential of the hydroxyl groups, a conclusion supported by the solved crystal structures, Hirshfeld surface analysis, and differential scanning calorimetry (DSC) results. |
| format | Article |
| id | doaj-art-7d8471193f014bcc83cf020c784adf6d |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-7d8471193f014bcc83cf020c784adf6d2024-12-27T14:43:05ZengMDPI AGMolecules1420-30492024-12-012924606010.3390/molecules29246060Apremilast Cocrystals with Phenolic CoformersYelizaveta Naumkina0Bohumil Kratochvíl1Elena Korotkova2Jan Čejka3Department of Solid State Chemistry, University of Chemistry and Technology, Prague, Technicka 5, 16628 Prague, Czech RepublicDepartment of Solid State Chemistry, University of Chemistry and Technology, Prague, Technicka 5, 16628 Prague, Czech RepublicChemical Engineering Department, National Research Tomsk Polytechnic University, Lenin Avenue 30, 634050 Tomsk, RussiaDepartment of Solid State Chemistry, University of Chemistry and Technology, Prague, Technicka 5, 16628 Prague, Czech RepublicApremilast (APR) is an anti-inflammatory drug commonly used in the treatment of psoriasis. In efforts to enhance its solubility, several cocrystals with similar structural features have been developed. This study investigates the cocrystallization of APR with four phenolic-type coformers: phenol, catechol, pyrogallol, and hydroxyquinol. These coformers differ in the number and position of their hydroxyl groups, with their melting points varying by as much as 100 °C. Four novel cocrystal forms were synthesized, purified, and characterized using X-Ray diffraction and thermal analysis techniques. Surprisingly, the resulting cocrystals exhibited minimal differences in their melting points. The molecular packing of APR appears to limit the network-forming potential of the hydroxyl groups, a conclusion supported by the solved crystal structures, Hirshfeld surface analysis, and differential scanning calorimetry (DSC) results.https://www.mdpi.com/1420-3049/29/24/6060cocrystalsApremilastphenolic compoundsπ–π interactionshydrogen bonds |
| spellingShingle | Yelizaveta Naumkina Bohumil Kratochvíl Elena Korotkova Jan Čejka Apremilast Cocrystals with Phenolic Coformers Molecules cocrystals Apremilast phenolic compounds π–π interactions hydrogen bonds |
| title | Apremilast Cocrystals with Phenolic Coformers |
| title_full | Apremilast Cocrystals with Phenolic Coformers |
| title_fullStr | Apremilast Cocrystals with Phenolic Coformers |
| title_full_unstemmed | Apremilast Cocrystals with Phenolic Coformers |
| title_short | Apremilast Cocrystals with Phenolic Coformers |
| title_sort | apremilast cocrystals with phenolic coformers |
| topic | cocrystals Apremilast phenolic compounds π–π interactions hydrogen bonds |
| url | https://www.mdpi.com/1420-3049/29/24/6060 |
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