Novel pseudopolymorph of the active metabolite of perindopril

Acta Crystallogr C. 2012 Sep;68(Pt 9):o341-3. doi: 10.1107/S0108270112032349. Epub 2012 Aug 1.

Abstract

The dimethyl sulfoxide hemisolvate of perindoprilat [systematic name: (1S)-2-((S)-{1-[(2S,3aS,7aS)-2-carboxyoctahydro-1H-indol-1-yl]-1-oxopropan-2-yl}azaniumyl)pentanoate dimethyl sulfoxide hemisolvate], C(17)H(28)N(2)O(5)·0.5C(2)H(6)OS, an active metabolite of perindopril, has been synthesized, structurally characterized by single-crystal X-ray diffraction and compared with its ethanol disolvate analogue [Pascard et al. (1991). J. Med. Chem. 34, 663-669]. Both compounds crystallize in the orthorhombic P2(1)2(1)2(1) space group in the same zwitterionic form, with a protonated alanine N atom and an anionic carboxylate group at the n-alkyl chain. The three structural units present in the unit cell (two zwitterions and the solvent molecule) are held together by a rich system of O-H···O, N-H···O and C-H···O hydrogen-bond contacts.

MeSH terms

  • Anions / chemistry*
  • Crystallization
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Indoles / chemistry*
  • Molecular Structure
  • Solvents / chemistry
  • Stereoisomerism

Substances

  • Anions
  • Indoles
  • Solvents
  • perindoprilat