TY - JOUR

T1 - A new solvate of furosemide with dimethylacetamide

AU - Beloborodova, Alina A.

AU - Minkov, Vasily S.

AU - Boldyreva, Elena V.

PY - 2016

Y1 - 2016

N2 - The loop diuretic furosemide is used widely in the treatment of congestive heart failure and edema, and is practically insoluble in water. The physicochemical and pharmacokinetic properties of drugs can be modified by preparing the drug in an appropriate solid-state form. A new solvate of furosemide with dimethylacetamide (DMA) {systematic name: 4-chloro-2-[(furan-2-yl)methylamino]-5-sulfamoylbenzoic acid N,N-dimethylacetamide disolvate}, C12H11ClN2O5S·2C4H9NO, (I), is reported. The channeled structure formed on slow crystallization contains DMA solvent molecules in its channels. This structure adds to the evidence of varied conformations observed across all known structures, so supporting the idea that this flexible molecule has conformational lability. The current structure also differs from those of other previously known furosemide solvates in the number of solvent molecules per furosemide molecule, viz. 2:1 instead of 1:1. Desolvation of (I) gives the most stable form of furosemide, i.e. Form I.

AB - The loop diuretic furosemide is used widely in the treatment of congestive heart failure and edema, and is practically insoluble in water. The physicochemical and pharmacokinetic properties of drugs can be modified by preparing the drug in an appropriate solid-state form. A new solvate of furosemide with dimethylacetamide (DMA) {systematic name: 4-chloro-2-[(furan-2-yl)methylamino]-5-sulfamoylbenzoic acid N,N-dimethylacetamide disolvate}, C12H11ClN2O5S·2C4H9NO, (I), is reported. The channeled structure formed on slow crystallization contains DMA solvent molecules in its channels. This structure adds to the evidence of varied conformations observed across all known structures, so supporting the idea that this flexible molecule has conformational lability. The current structure also differs from those of other previously known furosemide solvates in the number of solvent molecules per furosemide molecule, viz. 2:1 instead of 1:1. Desolvation of (I) gives the most stable form of furosemide, i.e. Form I.

KW - crystal packing

KW - crystal structure

KW - desolvation

KW - furosemide

KW - hydrogen bonds

KW - lasix

KW - loop diuretic

KW - solvates

UR - http://www.scopus.com/inward/record.url?scp=85003009917&partnerID=8YFLogxK

U2 - 10.1107/S2053229616018398

DO - 10.1107/S2053229616018398

M3 - Article

AN - SCOPUS:85003009917

VL - 72

SP - 997

EP - 1001

JO - Acta Crystallographica Section C: Structural Chemistry

JF - Acta Crystallographica Section C: Structural Chemistry

SN - 2053-2296

ER -