Abstract
Aromatic diaminidines such as pentamidine, stilbamidine, and propamides are anti-protozoal agents. Pentamidine diisethionate is used in the treatment of African sleeping sickness and Indian kala-azar caused by the protozoa Trypanosoma rhodesiense, T. gambiense and Leishmania donovani. Crystals of pentamidine diisethionate dihydrate obtained from an aqueous ethanol–propanol mixture, are triclinic, space group P¯1 with cell dimensions a = 8.794(1), b = 13.979(2), c = 14.821(1)Å, α = 61.89(1), β = 79.30(1), γ = 90.00(1)°, V = 1571.1(6)Å3, D m = 1.33 Mg/m3, D x = 1.333 Mg/m3, and Z = 2. The central pentanediol chain is planar and the dihedral angle between this group and the two benzoyl groups are ± 5.8(5)° and ± 6.0(5)°, respectively. The dihedral angle between the imidamido group and the benzoyl groups are ±28.3(4) and ±151.7(4)°, respectively. The crystal structure is stabilized by a number of hydrogen bonds involving the pentamidine, the two isethionate anions and the water molecules. The conformation of this dihydrate form is slightly different than the trihydrate form studied by Lowe and coworkers but the overall conformational features are similar.
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Srikrishnan, T., De, N.C., Alam, A.S. et al. Crystal and molecular structure of pentamidine diisethionate: an anti-protozoal drug used in AIDS related pneumonia. J Chem Crystallogr 34, 813–818 (2004). https://doi.org/10.1007/s10870-004-7658-8
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DOI: https://doi.org/10.1007/s10870-004-7658-8