Docetaxel (Molecule of the Month for July 2011)
Docetaxel is a clinically well-established anti-mitotic chemotherapy medication (that is, it interferes with cell division). It is used mainly for the treatment of breast, ovarian, prostate, and non-small cell lung cancer. Docetaxel has an FDA approved claim for treatment of patients who have locally advanced, or metastatic breast or non small-cell lung cancer who have undergone anthracycline-based chemotherapy and failed to stop cancer progression or relapsed and a European approval for use in hormone-refractory prostate cancer.
Docetaxel is marketed worldwide under the name Taxotere by Sanofi-Aventis. Annual sales in 2010 were Euro 2.122 billion ($US 3.1 billion). Docetaxel is of the chemotherapy drug class; taxane, and is a semi-synthetic analogue of paclitaxel (Taxol), an extract from the bark of the rare Pacific yew tree Taxus brevifolia. Due to scarcity of paclitaxel, extensive research was carried out leading to the formulation of docetaxel – an esterified product of 10-deacetyl baccatin III, which is extracted from the renewable and readily available European yew tree.
Docetaxel differs from paclitaxel at two positions in its chemical structure. It has a hydroxyl functional group on carbon 10, whereas paclitaxel has an acetate ester, and a tert-butyl carbamate ester exists on the phenylpropionate side chain instead of the benzyl amide in paclitaxel. The carbon 10 functional group change causes docetaxel to be more water soluble than paclitaxel.
Update by Karl Harrison
(Molecule of the Month for July 2011 )
All the images on this web site are are made available with a Creative Commons Attribution license and so can be used as long as the attribution © Karl Harrison 3DChem.com is written with the image. High resolution images and illustrations are available on request.