Taxane

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title: "Taxane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["microtubule-inhibitors", "mitotic-inhibitors", "taxanes"] topic_path: "general/microtubule-inhibitors" source: "https://en.wikipedia.org/wiki/Taxane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| ImageFile = Taxane numbering.svg | ImageClass = skin-invert-image | ImageSize = 200px | IUPACName = Taxane | SystematicName = (4R,4aR,6S,9R,10S,12aS)-4,9,12a,13,13-Pentamethyltetradecahydro-6,10-methanobenzo[10]annulene | OtherNames = |Section1={{Chembox Identifiers | CASNo = 1605-68-1 | PubChem = 9548828 | ChemSpiderID = 7827751 | SMILES = C[C@@H]1CCC[C@@]2([C@@H]1C[C@@H]3CCC@HC)C | InChI = 1S/C20H36/c1-14-7-6-11-20(5)12-10-17-15(2)8-9-16(13-18(14)20)19(17,3)4/h14-18H,6-13H2,1-5H3/t14-,15-,16+,17+,18-,20+/m1/s1 | InChIKey = DKPFODGZWDEEBT-QFIAKTPHSA-N | StdInChI = 1S/C20H36/c1-14-7-6-11-20(5)12-10-17-15(2)8-9-16(13-18(14)20)19(17,3)4/h14-18H,6-13H2,1-5H3/t14-,15-,16+,17+,18-,20+/m1/s1 | StdInChIKey = DKPFODGZWDEEBT-QFIAKTPHSA-N |Section2={{Chembox Properties | C=20 | H=36 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

Taxanes are a class of diterpenes. They were originally identified from plants of the genus Taxus (yews), and feature a taxadiene core. Paclitaxel (Taxol) and docetaxel (Taxotere) are widely used as chemotherapy agents.{{Cite journal | last1 = Hagiwara | first1 = H. | last2 = Sunada | first2 = Y. | title = Mechanism of taxane neurotoxicity | journal = Breast Cancer (Tokyo, Japan) | volume = 11 | issue = 1 | pages = 82–85 | year = 2004 | doi = 10.1007/BF02968008 | pmid = 14718798 | s2cid = 22096988

Taxanes present difficulties in formulation as medicines because they are poorly soluble in water.

Production

As their name suggests, taxanes were first derived from natural sources, but some have been semisynthesized. Paclitaxel was originally derived from the Pacific yew tree. Taxanes are difficult to synthesize because of their numerous chiral centres—taxol has 11 of these.

Recently, the presence of taxanes in the shells and leaves of Corylus avellana (the common hazel plant) has been reported.

Mechanism of action

::figure[src="https://upload.wikimedia.org/wikipedia/commons/9/9a/Fphar-12-770663-g001-Photoroom.png" caption="Mechanism of action of taxanes"] ::

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 as depolymerization is prevented. Thus, in essence, taxanes are mitotic inhibitors. In contrast to the taxanes, the vinca alkaloids prevent mitotic spindle formation through inhibition of tubulin polymerization. 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.

Substances

Hongdoushans A–C are oxygenated taxane diterpenes, isolated from the wood of Taxus wallichiana. Hongdoushan A (C29H44O7), hongdoushan B (C27H40O7), and hongdoushan C (C27H42O6) are reported to have anticancer activity in vitro. Taxuspines A–D have been isolated from Taxus. | align = left | image1 = Baccatin III.svg | width1 = 115 | alt1 = | caption1 = | image2 = Taxol.svg | width2 = 138 | alt2 = | caption2 = | footer = Baccatin III (left) Paclitaxel (right) | align = left | image1 = Deacetylbaccatin.png | width1 = 115 | alt1 = | caption1 = | image2 = Docetaxel.svg | width2 = 138 | alt2 = | caption2 = | footer = 10-Deacetylbaccatin (left) Docetaxel (right) | align = left | image1 = Taxuspine A.svg | width1 = 150 | alt1 = | caption1 = Taxuspine A | image2 = Taxuspine B.svg | width2 = 150 | alt2 = | caption2 = Taxuspine B | image3 = hongdoushan A.svg | caption3 = Hongdoushan A | footer =

Names

Taxanes are usually treated as synonymous with taxoids. The name "taxol" began as a common noun (analogous with other terms in which a genus name root was suffixed with -ol or -in), but it was later capitalized as a trade name, and the international nonproprietary name of the compound is paclitaxel.

References

References

  1. [[International Union of Pure and Applied Chemistry]]. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". [[Royal Society of Chemistry.
  2. (February 1997). "The Development and Clinical Utility of the Taxane Class of Antimicrotubule Chemotherapy Agents". Annual Review of Medicine.
  3. (2009). "Pharmacology".
  4. (2014). "How Taxol/paclitaxel kills cancer cells". Molecular Biology of the Cell.
  5. (2008). "Taxanes from Shells and Leaves of Corylus avellana". Journal of Natural Products.
  6. (January 2009). "Paclitaxel and other taxanes in hazel". Journal of Functional Foods.
  7. (2002). "Three new C-14 oxygenated taxanes from the wood of Taxus yunnanensis.". J Nat Prod.
  8. {{PubChem. 10417482
  9. {{PubChem. 5321744
  10. {{PubChem. 100991639
  11. {{PubChem. 5321746

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microtubule-inhibitorsmitotic-inhibitorstaxanes