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Crystallography Reports

, Volume 63, Issue 6, pp 930–936 | Cite as

Crystal Structures and Thermodynamic Properties of New Atypical Antipsychotic Cariprazine and Its Hydrochloride

  • Jiali Ye
  • Kaihang Liu
  • Xinbo Zhou
  • Jianming Gu
  • Xiurong Hu
STRUCTURE OF ORGANIC COMPOUNDS
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Abstract

A cariprazine, an oral atypical antipsychotic acting as a D2 and D3 receptor partial agonist, has been crystallized as a free base, trans-N-{4-[2-[4-(2,3-dichlorophenyl)piperazine-1-yl]ethyl]cyclohexyl}-N',N'-dimethylurea, C21H32Cl2N4O (I), and as a chloride salt, trans-N-{4-[2-[4-(2,3-dichlorophenyl)piperazine-1-yl]ethyl]cyclohexyl}-N',N'-dimethylurea hydrochloride, C21H33Cl2N4O+Cl (II). In both structures, the cariperazine molecule is in an extended conformation. The dimethylurea group exhibits a syn conformation of the O atoms in the I, whereas an almost anti orientation is present in the II. Two terminal groups, dimethylurea and dichlorophenyl ring, are oriented differently in the I and II. The cariprazine molecules in the I are linked into an infinite zigzag chains by N–H···O hydrogen bonds, where the neighboring cariprazine molecules form an L-shape configuration. In the II, the molecules of cariprazine are connected with the chloride anion by N–H···Cl charge-assisted hydrogen bonds, which are further stabilized by weak intermolecular interactions, forming horizontal molecular chain along the b axis. This study reveals the variations in the solid-state conformation of cariprazine molecule in different crystalline environments.

Notes

ACKNOWLEDGMENTS

This work would not have been possible without the effort and encouragement of several individuals of my colleagues. The authors thank Prof. Linshen Chen from Department of Chemistry of Zhejiang University for his kindly help on the DSC analysis.

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Copyright information

© Pleiades Publishing, Inc. 2018

Authors and Affiliations

  • Jiali Ye
    • 1
    • 2
  • Kaihang Liu
    • 1
  • Xinbo Zhou
    • 3
  • Jianming Gu
    • 1
  • Xiurong Hu
    • 1
  1. 1.Chemistry Department, Zhejiang UniversityHangzhouPeople’s Republic of China
  2. 2.College of Pharmaceutical Science, Zhejiang Chinese Medical UniversityHangzhouPeople’s Republic of China
  3. 3.Zhejiang Jingxin Pharmaceutical Co., Ltd.XinchangPeople’s Republic of China

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