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Nilutamide.

Niraj S Trasi, Phillip E Fanwick, Lynne S Taylor

    Acta Crystallographica. Section E, Structure Reports Online
    |March 14, 2012
    PubMed
    Summary

    The crystal structure of nilutamide, an antiandrogen drug, was determined at 150 K. This study reveals its molecular arrangement and intermolecular hydrogen bonding, forming chains parallel to the c axis.

    Area of Science:

    • Crystallography
    • Medicinal Chemistry

    Background:

    • Nilutamide is a non-steroidal antiandrogen used in treating prostate cancer.
    • Understanding its crystal structure is crucial for drug formulation and development.

    Purpose of the Study:

    • To elucidate the crystal structure of nilutamide at a low temperature (150 K).
    • To analyze the molecular geometry, including the dihedral angle between the imidazoline and benzene rings.
    • To identify intermolecular interactions and their role in crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction at 150 K.
    • Analysis of crystallographic data to determine atomic positions and bond lengths/angles.
    • Identification of hydrogen bonding networks.

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    Main Results:

    • The crystal structure of nilutamide (C(12)H(10)F(3)N(3)O(4)) was successfully determined.
    • A dihedral angle of 51.49° was observed between the imidazoline and benzene ring planes.
    • Intermolecular hydrogen bonding (N-H⋯O) was identified, leading to the formation of chains along the c-axis.

    Conclusions:

    • The determined crystal structure provides detailed insights into nilutamide's solid-state properties.
    • The observed hydrogen bonding pattern influences the molecular arrangement and crystal packing.
    • This structural information can aid in the design of improved nilutamide formulations or related compounds.