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: September 18, 2017
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.
Adenosine, the 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’Oréal began to sell similar products. The Teresians have sued L’Oréal for violating the patents that they licensed from the University of Massachusetts.
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 |
MOTW update:
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 has not approved hydroxychloroquine as a vaccine or treatment for Zika virus.
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