Intermolecular Interactions in Crystalline Hydroxychloroquine Sulfate in Comparison with Those in Selected Antimalarial Drugs

Abstract The crystal structure of hydroxychloroquine sulfate (OHClQ) was determined in order to compare its conformation and intermolecular interactions to those in the crystalline chloroquine phosphate (ClQP) and quinine salicylate (QSal) monohydrate. The crystals of OHClQ are monoclinic with the space group P2₁/c and unit-cell dimensions: a = 10.4966(1) ?, b = 8.8056(1) ?, c = 21.8603(3) ?, β = 101.074(1)°. The quinoline antimalarial drugs may interact with their putative receptors by formation of characteristic hydrogen-bonded rings. The protonated nitrogen atoms and/or hydroxyl groups of the drug cation are proton donors, while the oxygen atoms of anions are proton acceptors. Water molecules may intermediate in these interactions. Graphical Abstract Hydroxychloroquine sulfate is a drug used in the treatment of malaria and rheumatic diseases. The X-ray structure analysis shows an important role of intermolecular hydrogen bonds in the crystal architecture. Comparison with chloroquine phosphate and quinine salicylate indicates that the organization of the drug cations is determined by the anions.