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Related Experiment Videos

Two absorption furosemide prodrugs.

A W Mombrú1, R A Mariezcurrena, L Suescun

  • 1Laboratorio de Cristalografía y Química del Estado Sólido, Facultad de Química, Universidad de la República, Montevideo, Uruguay.

Acta Crystallographica. Section C, Crystal Structure Communications
|April 30, 1999
PubMed
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This study details the crystal structures of two furosemide prodrugs, revealing similar molecular conformations but distinct crystal packing. Hydrogen bonding networks stabilize both structures, offering insights into drug design.

Area of Science:

  • Crystallography
  • Medicinal Chemistry
  • Drug Discovery

Background:

  • Furosemide is a widely used diuretic.
  • Prodrugs are designed to improve drug delivery and efficacy.
  • Understanding the solid-state structure of prodrugs is crucial for formulation and stability.

Purpose of the Study:

  • To elucidate the crystal structures of two novel furosemide prodrugs.
  • To compare their molecular conformations and crystal packing with existing furosemide prodrugs.
  • To investigate the role of hydrogen bonding in their structural stabilization.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the structures.
  • Comparison of crystallographic data (space group, unit cell parameters).

Related Experiment Videos

  • Analysis of molecular conformation and intermolecular interactions (hydrogen bonding).

    • Main Results:

    • The crystal structures of hexanoyloxymethyl 4-chloro-N-furfuryl-5-sulfamoyl-anthranilate (I) and benzoyloxymethyl 4-chloro-N-furfuryl-5-sulfamoylanthranilate (II) were determined.
    • Compound (I) crystallized in the trigonal space group R3, while compound (II) crystallized in the monoclinic space group P2(1)/n.
    • Both prodrugs exhibited similar molecular conformations to other known furosemide prodrugs, with differences primarily in crystal packing and system.
    • A three-dimensional hydrogen-bond network was observed in the packing of both structures.

    Conclusions:

    • The crystallographic analysis provides detailed structural insights into these furosemide prodrugs.
    • Differences in crystal packing, despite similar conformations, may influence physicochemical properties.
    • The identified hydrogen-bond networks are key to the stability of these prodrug structures.