Vismodegib

November 27, 2017
I’m a drug that may eventually stamp out several cancers.
What molecule am I?
Image of Vismodegib 3D Image of Vismodegib

Vismodegib is a drug that the US Food and Drug Administration approved in 2012 for treating basal-cell carcinoma, a sometimes difficult-to-eradicate skin cancer. It is marketed by Genentech (South San Francisco, CA) under the trade name Erivedge.

Vismodegib is the first drug to be approved by FDA that targets the hedgehog* (Hh) signaling pathway. The Hhpathway is vital for the formation of organs in the body, and abnormal Hh signaling is associated with the development of cancer cells.

This past October, the Genentech research team received one of six ACS 2017 Heroes of Chemistry awards for developing products that improve people’s lives.

Genentech has more plans for vismodegib. It is in clinical trials for other cancers, including pancreatic, stomach, and lung.

*Why hedgehog? It’s the name of a signaling molecule that is encoded by the Hh gene. The absence of the gene makes fruit fly larvae look like the bristly animal of the same name.

Vismodegib fast facts

CAS Reg. No. 879085-55-9
Molar mass 421.30 g/mol 
Formula C19H14Cl2N2O3S
Appearance White crystals 
Melting point 186–188 ºC*
Water solubility ≈1 g/L (pH 7)

MOTW update

Glyphosate was the Molecule of the Week for October 5, 2009. For decades, glyphosate has been a widely used herbicide, but in recent years pesticide applicators have claimed that exposure to it caused non-Hodgkins lymphoma. This past week, however, the results of a study on 54,000 workers showed that there is no significant association between glyphosate exposure and cancer—with the possible exception of multiple myeloma, which may the the focus of future studies.

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