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Taxane

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The chemical structure of paclitaxel.

The taxanes are diterpenes produced by the plants of the genus Taxus (yews). As their name suggests, they were first derived from natural sources, but some have been synthesized artificially. Taxanes include paclitaxel (Taxol) and docetaxel (Taxotere). Paclitaxel was originally derived from the Pacific yew tree.

Taxanes have been used to produce various chemotherapy drugs.[1] The principal mechanism of action of the taxane class of drugs is the disruption of microtubule function. Microtubules are essential to cell division, and taxanes stabilize GDP-bound tubulin in the microtubule, thereby inhibiting the process of cell division — a "frozen mitosis". Thus, in essence, taxanes are mitotic inhibitors. In contrast to the taxanes, the vinca alkaloids destroy mitotic spindles. Both taxanes and vinca alkaloids are, therefore, named spindle poisons or mitosis poisons, but they act in different ways. Taxanes are also thought to be radiosensitizing.

Taxanes are difficult to synthesize because of their numerous chiral centres — Taxol has 11 of these. Taxanes present difficulties in formulation as medicines because they are poorly soluble in water.


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