View source for Taxane

{{Chembox
| ImageFile = Taxane numbering.svg
| ImageSize = 200px
| IUPACName = Taxane<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=1540 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| SystematicName = (4''R'',4a''R'',6''S'',9''R'',10''S'',12a''S'')-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]3CC[C@H]([C@@H](C3(C)C)CC2)C)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
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| Density = 
| MeltingPt = 
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|Section3={{Chembox Hazards
| MainHazards = 
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}}

'''Taxanes''' are a class of [[diterpene]]s. 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.<ref>{{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 
}}</ref><ref>{{cite journal|last1=Rowinsky, MD|first1=Eric K.|title=The Development and Clinical Utility of the Taxane Class of Antimicrotubule Chemotherapy Agents|journal=Annual Review of Medicine|date=February 1997|volume=48|issue=1|pages=353–374|doi=10.1146/annurev.med.48.1.353|pmid=9046968}}</ref> [[Cabazitaxel]] was FDA approved to treat hormone-refractory [[prostate cancer]]. 

Taxanes present difficulties in [[Pharmaceutical formulation|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 [[semisynthesis|semisynthesized]]. Paclitaxel was originally derived from the [[Pacific yew]] tree.<ref name="Hacker2009">{{cite book|last1=Hacker|first1=Miles|title=Pharmacology|chapter=Adverse Drug Reactions|year=2009|pages=327–352|doi=10.1016/B978-0-12-369521-5.00013-0|isbn=9780123695215}}</ref><ref name="WeaverBement2014">{{cite journal|last1=Weaver|first1=Beth A.|last2=Bement|first2=William|title=How Taxol/paclitaxel kills cancer cells|journal=Molecular Biology of the Cell|volume=25|issue=18|year=2014|pages=2677–2681|issn=1059-1524|doi=10.1091/mbc.e14-04-0916|pmid=25213191|pmc=4161504|doi-access=free}}</ref> 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.<ref>{{cite journal |doi=10.1021/np0704046 |title=Taxanes from Shells and Leaves of Corylus avellana |year=2008 |last1=Ottaggio |first1=Laura |last2=Bestoso |first2=Federica |last3=Armirotti |first3=Andrea |last4=Balbi |first4=Alessandro |last5=Damonte |first5=Gianluca |last6=Mazzei |first6=Mauro |last7=Sancandi |first7=Monica |last8=Miele |first8=Mariangela |journal=Journal of Natural Products |volume=71 |pages=58–60 |pmid=18163585 |issue=1 }}</ref><ref>{{cite journal |doi=10.1016/j.jff.2008.09.004 |title=Paclitaxel and other taxanes in hazel |date=January 2009 |last1=Hoffman |first1=Angela M |last2=Shahidi |first2=Fereidoon |journal=Journal of Functional Foods |volume=1 |pages=33–37 |issue=1 |doi-access=free }}</ref>

== Mechanism of action ==
[[File:Fphar-12-770663-g001-Photoroom.png|thumb|right|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 [[Guanosine diphosphate|GDP]]-bound [[tubulin]] in the microtubule, thereby inhibiting the process of cell division as ''depolymerization'' is prevented. Thus, in essence, taxanes are [[mitotic inhibitor]]s. 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 poison]]s or mitosis poisons, but they act in different ways. Taxanes are also thought to be [[Radiosensitivity|radiosensitizing]].

== Substances ==
Hongdoushans A–C are oxygenated taxane diterpenes, isolated from the wood of ''[[Taxus wallichiana]]''. Hongdoushan A (C<sub>29</sub>H<sub>44</sub>O<sub>7</sub>), hongdoushan B (C<sub>27</sub>H<sub>40</sub>O<sub>7</sub>), and hongdoushan C (C<sub>27</sub>H<sub>42</sub>O<sub>6</sub>) are reported to have anticancer activity ''in vitro''.<ref name="pmid12444707">{{cite journal|vauthors=Banskota AH, Usia T, Tezuka Y, Kouda K, Nguyen NT, Kadota S | title=Three new C-14 oxygenated taxanes from the wood of Taxus yunnanensis. | journal=J Nat Prod | year= 2002 | volume= 65 | issue= 11 | pages= 1700–2 | pmid=12444707 | doi= 10.1021/np020235j}}</ref> [[Taxuspines]] A–D have been isolated from ''Taxus''.<ref>{{PubChem|10417482}}</ref><ref>{{PubChem|5321744}}</ref><ref>{{PubChem|100991639}}</ref><ref>{{PubChem|5321746}}</ref>
{{multiple image
| align = left
| image1 = Baccatin III.svg
| width1 = 115
| alt1 = 
| caption1 = 
| image2 = Taxol.svg
| width2 = 138
| alt2 = 
| caption2 = 
| footer = [[Baccatin III]] (left) [[Paclitaxel]] (right)
}}{{clear-left}}
{{multiple image
| align = left
| image1 = Deacetylbaccatin.png
| width1 = 115
| alt1 = 
| caption1 = 
| image2 = Docetaxel.svg
| width2 = 138
| alt2 = 
| caption2 = 
| footer = [[10-Deacetylbaccatin]] (left) [[Docetaxel]] (right)
}}{{clear-left}}
{{multiple image
| 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 = 
}}{{clear-left}}

==Names==
Taxanes are usually treated as [[synonym]]ous with [[taxoid]]s. The name "taxol" began as a common noun (analogous with other terms in which a genus name root was [[suffix]]ed with ''[[wikt:-ol#Etymology 2|-ol]]'' or ''[[wikt:-in#Suffix|-in]]''), but it was later capitalized as a trade name, and the [[international nonproprietary name]] of the compound is paclitaxel.

== See also ==
* [[Abeotaxane]]
* [[Docetaxel]]
* [[Taxine]]
* [[Taxuyunnanine]]

== References ==
{{reflist}}

==External links==
* {{commons category inline|Taxanes|lcfirst=yes}}

{{Chemotherapeutic agents}}

[[Category:Microtubule inhibitors]]
[[Category:Mitotic inhibitors]]
[[Category:Taxanes| ]]