Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph

The title compound, C(22)H(24)N(2)O(7)S·0.5C(2)H(5)OH·0.5H(2)O {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 phosphodieste...

Descripción completa

Detalles Bibliográficos
Autores principales: Wu, Yun-Deng, Liu, Xiao-Hong, Xu, Jian, Zhang, Si-Han, Shen, Kun, Sun, Ling, He, Yong-Mei, Ma, Yan, Zhang, Ai-Hua
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
Research Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5458300/
https://www.ncbi.nlm.nih.gov/pubmed/28638635
http://dx.doi.org/10.1107/S2056989017006661
_version_ 1783241734694633472
author Wu, Yun-Deng
Liu, Xiao-Hong
Xu, Jian
Zhang, Si-Han
Shen, Kun
Sun, Ling
He, Yong-Mei
Ma, Yan
Zhang, Ai-Hua
author_facet Wu, Yun-Deng
Liu, Xiao-Hong
Xu, Jian
Zhang, Si-Han
Shen, Kun
Sun, Ling
He, Yong-Mei
Ma, Yan
Zhang, Ai-Hua
author_sort Wu, Yun-Deng
collection PubMed
description The title compound, C(22)H(24)N(2)O(7)S·0.5C(2)H(5)OH·0.5H(2)O {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.
format Online
Article
Text
id pubmed-5458300
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-54583002017-06-21 Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph Wu, Yun-Deng Liu, Xiao-Hong Xu, Jian Zhang, Si-Han Shen, Kun Sun, Ling He, Yong-Mei Ma, Yan Zhang, Ai-Hua Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(22)H(24)N(2)O(7)S·0.5C(2)H(5)OH·0.5H(2)O {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. International Union of Crystallography 2017-05-09 /pmc/articles/PMC5458300/ /pubmed/28638635 http://dx.doi.org/10.1107/S2056989017006661 Text en © Wu et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Wu, Yun-Deng
Liu, Xiao-Hong
Xu, Jian
Zhang, Si-Han
Shen, Kun
Sun, Ling
He, Yong-Mei
Ma, Yan
Zhang, Ai-Hua
Crystal structure of an apremilast ethanol hemisolvate hemihydrate 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 Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5458300/
https://www.ncbi.nlm.nih.gov/pubmed/28638635
http://dx.doi.org/10.1107/S2056989017006661
work_keys_str_mv AT wuyundeng crystalstructureofanapremilastethanolhemisolvatehemihydratesolvatomorph
AT liuxiaohong crystalstructureofanapremilastethanolhemisolvatehemihydratesolvatomorph
AT xujian crystalstructureofanapremilastethanolhemisolvatehemihydratesolvatomorph
AT zhangsihan crystalstructureofanapremilastethanolhemisolvatehemihydratesolvatomorph
AT shenkun crystalstructureofanapremilastethanolhemisolvatehemihydratesolvatomorph
AT sunling crystalstructureofanapremilastethanolhemisolvatehemihydratesolvatomorph
AT heyongmei crystalstructureofanapremilastethanolhemisolvatehemihydratesolvatomorph
AT mayan crystalstructureofanapremilastethanolhemisolvatehemihydratesolvatomorph
AT zhangaihua crystalstructureofanapremilastethanolhemisolvatehemihydratesolvatomorph

Ejemplares similares