Hydroxychloroquine

September 18, 2017
I first fought malaria; now on to Zika.
What molecule am I?

Hydroxychloroquine is a drug that was used originally to treat malaria, especially in patients who could not tolerate the similar compound chloroquine. It also has been used to combat autoimmune diseases such as lupus erythematosus.

In 1950, chemists Alexander R. Surrey and Henry F. Hammer at the Sterling–Winthrop Research Institute (Rensselaer, NY) published a synthesis of hydroxychloroquine. The parent company, Sterling Drug, obtained a US patent on the compound and its method of preparation the same year.

Fast-forward to the era of the Zika virus: Observing that the virus does not affect pregnant mice engineered to suppress a key autophagy* gene, Indira U. Mysorekar and colleagues at the Washington University School of Medicine (St. Louis) treated normal Zika-infected mice with autophagy-inhibiting hydroxychloroquine. The treated mice had less placental and fetal damage than the control group. The researchers postulate that the drug prevents Zika from crossing the placental barrier.

*Autophagy is the mechanism by which the body destroys damaged cellular material. The Zika virus overexpresses autophagy in the placenta.

MOTW Updates

Chlorpyrifos, a controversial thiophosphate insecticide, was the Molecule of the Week for November 8, 2010. In May of this year, its manufacturers pressured the US Environmental Protection Agency to rescind damaging biological evaluations of the pesticide. The controversy has now been exacerbated by EPA’s decision to delay any decision to ban chlorpyrifos until 2022.

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Hydroxychloroquine fast facts

CAS Reg. No. 118-42-3
Molar mass 335.87 g/mol
Formula C18H26ClN3O
Appearance White crystals 
Melting point 90 ºC 
Water solubility 26 mg/L
Chemical Abstract Service - a division of ACS

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