Home > Docetaxel (Molecule of the Month for February 2007 )
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C43 H53 N O14
Docetaxel is an anti-neoplastic medication used mainly for the treatment of breast, ovarian, and non-small cell lung cancer. Docetaxel is marketed under the name Taxotere Injection Concentrate by Sanofi-Aventis. Docetaxel is administered as a one-hour infusion every three weeks generally over a ten cycle course
Docetaxel is of the chemotherapy drug class; taxane, and is a semi-synthetic analogue of Taxol (paclitaxel), an extract from the rare Western yew tree Taxus brevifolia. Due to scarcity of Taxol, 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 Taxol at two positions in its chemical structure. It has a hydroxyl functional group on carbon 10, whereas Taxol has an acetate ester and a tert-butyl substitution exists on the phenylpropionate side chain. The carbon 10 functional group change causes docetaxel to be more lipid soluble than Taxol.
The anti-cancer activity of docetaxel is due to promoting and stabilising microtubule assembly, while preventing physiological microtubule depolymerisation/disassembly in the absence of GTP. This leads to a significant decrease in free tubulin, needed for microtubule formation and results in inhibition of mitotic cell division between metaphase and anaphase, preventing further cancer cell division and growth.
Formal Chemical Name (IUPAC)
(2R,3S)-N-carboxy-3-phenylisoserine, N-tert-butyl ester, 13-ester with 5, 20-epoxy-1, 2, 4, 7, 10, 13-hexahydroxytax-11-en-9-one 4-acetate 2-benzoate, trihydrate
Update by Karl Harrison
(Molecule of the Month for February 2007 )