Hydroxychloroquine

September 18, 2017
I first fought malaria; now on to Zika.
What molecule am I?
Image of Hydroxychloroquine 3D Image of Hydroxychloroquine

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鈥揥inthrop Research Institute (Rensselaer, NY) published a聽. 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聽聽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: September 18, 2017

Chlorpyrifos, a controversial thiophosphate insecticide, was the聽Molecule of the Week for November 8, 2010. In May of this year, its manufacturers pressured the US Environmental Protection Agency to聽. The controversy has now been exacerbated by EPA鈥檚 decision to聽.

Adenosine, the聽Molecule of the Week for July 5, 2010, is the root structure of the energy-tranfer coenzymes ATP and ADP. More recently, it has been used as a component of antiwrinkle skin creams. The Teresian Carmelites, a charitable religious group, first marketed adenosine-containing Easeamine products in 2009. Shortly thereafter, however, cosmetic giant L鈥橭r茅al began to sell similar products.聽聽for violating the patents that they licensed from the University of Massachusetts.

Hydroxychloroquine
fast facts

CAS Reg. No.118-42-3
Molar mass335.87 g/mol
FormulaC18H26ClN3O
AppearanceWhite crystals聽
Melting point90 潞C聽
Water solubility26 mg/L

MOTW update:聽
April 20, 2020

Hydroxychloroquine was originally developed as a malaria drug, in 2017 it was being explored as a treatment for patients suffering from the Zika virus.* During the current coronavirus pandemic, dozens of clinical trials are under way to evaluate its efficacy against the SARS-CoV-2 virus.

*The US Food and Drug Administration 聽as a vaccine or treatment for Zika virus.

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