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Docetaxel (Molecule of the Month for July 2011)

Taxotere



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.

Formal Chemical Name (IUPAC)
1,7β,10β-trihydroxy-9-oxo-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-{(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate}

References

http://en.wikipedia.org/wiki/Docetaxel

http://www.taxotere.com

Picture of Docetaxel 3D model

click on the picture of  Docetaxel above to interact
with the 3D model of the
Docetaxel structure
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Picture of Docetaxel

C43H53NO14



Update by Karl Harrison
(Molecule of the Month for July 2011 )

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