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Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph.

ABSTRACT: The title compound, C₂₂H₂₄N₂O₇S·0.5C₂H₅OH·0.5H₂O {systematic name: (S)-4-acetamido-2-[1-(3-eth-oxy-4-meth-oxy-phen-yl)-2-(methyl-sulfon-yl)eth-yl]iso-indo-line-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 mol-ecule of AP and disordered mol-ecules of ethanol and water, both with half occupancy. The dihedral angle between the planes of the phenyl ring and the iso-indole ring is 67.9?(2)°. Extensive intra- and inter-molecular hydrogen bonds help to stabilize the mol-ecular conformation and sustain the crystal packing.

SUBMITTER: Wu YD

PROVIDER: S-EPMC5458300 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Crystal structure of an apremilast ethanol hemisolvate hemihydrate solvatomorph.

Wu Yun-Deng YD Liu Xiao-Hong XH Xu Jian J Zhang Si-Han SH Shen Kun K Sun Ling L He Yong-Mei YM Ma Yan Y Zhang Ai-Hua AH

Acta crystallographica. Section E, Crystallographic communications 20170509 Pt 6

The title compound, C22H24N2O7S·0.5C2H5OH·0.5H2O {systematic name: (S)-4-acetamido-2-[1-(3-eth-oxy-4-meth-oxy-phen-yl)-2-(methyl-sulfon-yl)eth-yl]iso-indo-line-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 o ...[more]

PMID: 28638635

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