Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph
The title compound, C22H24N2O7S·0.5C2H5OH·0.5H2O {systematic name: (S)-4-acetamido-2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]isoindoline-1,3-dione ethanol hemisolvate hemihydrate}, is a novel solvatomorph of apremilast (AP), which is an inhibitor of phosphodiesterase 4 (PDE4) and is in...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2017-06-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989017006661 |
| _version_ | 1819294132156235776 |
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| author | Yun-Deng Wu Xiao-Hong Liu Jian Xu Si-Han Zhang Kun Shen Ling Sun Yong-Mei He Yan Ma Ai-Hua Zhang |
| author_facet | Yun-Deng Wu Xiao-Hong Liu Jian Xu Si-Han Zhang Kun Shen Ling Sun Yong-Mei He Yan Ma Ai-Hua Zhang |
| author_sort | Yun-Deng Wu |
| collection | DOAJ |
| description | The title compound, C22H24N2O7S·0.5C2H5OH·0.5H2O {systematic name: (S)-4-acetamido-2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]isoindoline-1,3-dione ethanol hemisolvate hemihydrate}, is a novel solvatomorph of apremilast (AP), which is an inhibitor of phosphodiesterase 4 (PDE4) and is indicated for the treatment of adult patients with active psoriatic arthritis. The asymmetric unit contains one molecule of AP and disordered molecules of ethanol and water, both with half occupancy. The dihedral angle between the planes of the phenyl ring and the isoindole ring is 67.9 (2)°. Extensive intra- and intermolecular hydrogen bonds help to stabilize the molecular conformation and sustain the crystal packing. |
| first_indexed | 2024-12-24T04:21:27Z |
| format | Article |
| id | doaj.art-02feeca27d734257917455580faa287e |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-24T04:21:27Z |
| publishDate | 2017-06-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-02feeca27d734257917455580faa287e2022-12-21T17:15:47ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902017-06-0173682182410.1107/S2056989017006661wm5386Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorphYun-Deng Wu0Xiao-Hong Liu1Jian Xu2Si-Han Zhang3Kun Shen4Ling Sun5Yong-Mei He6Yan Ma7Ai-Hua Zhang8SpringPharma Tech Co. Ltd, Weidi Road 9, 210046 Nanjing, People's Republic of ChinaSpringPharma Tech Co. Ltd, Weidi Road 9, 210046 Nanjing, People's Republic of ChinaSpringPharma Tech Co. Ltd, Weidi Road 9, 210046 Nanjing, People's Republic of ChinaSpringPharma Tech Co. Ltd, Weidi Road 9, 210046 Nanjing, People's Republic of ChinaSpringPharma Tech Co. Ltd, Weidi Road 9, 210046 Nanjing, People's Republic of ChinaJiangSu Center for Safety Evaluation of Drugs, Majia Street 26, 210009 Nanjing, People's Republic of ChinaSpringPharma Tech Co. Ltd, Weidi Road 9, 210046 Nanjing, People's Republic of ChinaSpringPharma Tech Co. Ltd, Weidi Road 9, 210046 Nanjing, People's Republic of ChinaSpringPharma Tech Co. Ltd, Weidi Road 9, 210046 Nanjing, People's Republic of ChinaThe title compound, C22H24N2O7S·0.5C2H5OH·0.5H2O {systematic name: (S)-4-acetamido-2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]isoindoline-1,3-dione ethanol hemisolvate hemihydrate}, is a novel solvatomorph of apremilast (AP), which is an inhibitor of phosphodiesterase 4 (PDE4) and is indicated for the treatment of adult patients with active psoriatic arthritis. The asymmetric unit contains one molecule of AP and disordered molecules of ethanol and water, both with half occupancy. The dihedral angle between the planes of the phenyl ring and the isoindole ring is 67.9 (2)°. Extensive intra- and intermolecular hydrogen bonds help to stabilize the molecular conformation and sustain the crystal packing.http://scripts.iucr.org/cgi-bin/paper?S2056989017006661apremilastPDE4psoriatic arthritiscrystal structurehydrogen bondingsolvatomorph |
| spellingShingle | Yun-Deng Wu Xiao-Hong Liu Jian Xu Si-Han Zhang Kun Shen Ling Sun Yong-Mei He Yan Ma Ai-Hua Zhang Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph Acta Crystallographica Section E: Crystallographic Communications apremilast PDE4 psoriatic arthritis crystal structure hydrogen bonding solvatomorph |
| title | Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph |
| title_full | Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph |
| title_fullStr | Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph |
| title_full_unstemmed | Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph |
| title_short | Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph |
| title_sort | crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph |
| topic | apremilast PDE4 psoriatic arthritis crystal structure hydrogen bonding solvatomorph |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989017006661 |
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