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. Cabazitaxel was FDA approved to treat hormone-refractory prostate cancer.
|Systematic IUPAC name
3D model (JSmol)
|Molar mass||276.508 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Taxanes present difficulties in formulation as medicines because they are poorly soluble in water.
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.
Mechanism of actionEdit
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.
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.
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.
- Hagiwara, H.; Sunada, Y. (2004). "Mechanism of taxane neurotoxicity". Breast Cancer (Tokyo, Japan). 11 (1): 82–85. PMID 14718798.
- Rowinsky, MD, Eric K. (February 1997). "THE DEVELOPMENT AND CLINICAL UTILITY OF THE TAXANE CLASS OF ANTIMICROTUBULE CHEMOTHERAPY AGENTS". Annual Review of Medicine. 48 (1): 353–374. doi:10.1146/annurev.med.48.1.353. PMID 9046968.
- Hacker, Miles (2009). "Adverse Drug Reactions": 327–352. doi:10.1016/B978-0-12-369521-5.00013-0. Cite journal requires
- Weaver, Beth A.; Bement, William (2014). "How Taxol/paclitaxel kills cancer cells". Molecular Biology of the Cell. 25 (18): 2677–2681. doi:10.1091/mbc.e14-04-0916. ISSN 1059-1524.
- Ottaggio, Laura; Bestoso, Federica; Armirotti, Andrea; Balbi, Alessandro; Damonte, Gianluca; Mazzei, Mauro; Sancandi, Monica; Miele, Mariangela (2008). "Taxanes from Shells and Leaves of Corylus avellana". Journal of Natural Products. 71 (1): 58–60. doi:10.1021/np0704046. PMID 18163585.
- Hoffman, Angela M; Shahidi, Fereidoon (January 2009). "Paclitaxel and other taxanes in hazel". Journal of Functional Foods. 1 (1): 33–37. doi:10.1016/j.jff.2008.09.004.
- Banskota AH, Usia T, Tezuka Y, Kouda K, Nguyen NT, Kadota S (2002). "Three new C-14 oxygenated taxanes from the wood of Taxus yunnanensis". J Nat Prod. 65 (11): 1700–2. doi:10.1021/np020235j. PMID 12444707.
- Media related to taxanes at Wikimedia Commons