Synonyms
Aminoquinolones; Chloroquine; Hydroxychloroquine
Definition
Hydroxychloroquine and chloroquine are antimalarial drugs used in the treatment of rheumatoid arthritis, systemic lupus erythematosus (SLE), antiphospholipid syndrome, skin diseases, and in the treatment of chronic Q fever. Hydroxychloroquine is the more widely used.
Chemical Structures and Properties
See Fig. 1
Hydroxychloroquine showing the structures of the neutral base and the dication which is the major form at physiological pH values. The pKa values of the cation form are 8.11 and 10.11 at 37 °C (Ferrari and Cutler 1987). Hydroxychloroquine is an enantiomeric compound. The chiral centre is marked. It is available as the racemic mixture. Chloroquine does not have the hydroxyl on the side chain. Hydroxychloroquine is used as its sulfate salt (100 mg of sulfate is equivalent to 78 mg of base)
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References
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Pile, K.D., Graham, G.G., Katelaris, C.H., Day, R.O. (2016). Antimalarial Drugs. In: Parnham, M.J. (eds) Compendium of Inflammatory Diseases. Springer, Basel. https://doi.org/10.1007/978-3-7643-8550-7_9
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