Taxane

Source: Wikipedia, the free encyclopedia.
(Redirected from
Taxanes
)
Taxane
Names
IUPAC name
Taxane[1]
Systematic IUPAC name
(4R,4aR,6S,9R,10S,12aS)-4,9,12a,13,13-Pentamethyltetradecahydro-6,10-methanobenzo[10]annulene
Identifiers
3D model (
JSmol
)
ChemSpider
  • 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
    Key: DKPFODGZWDEEBT-QFIAKTPHSA-N
  • 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
    Key: DKPFODGZWDEEBT-QFIAKTPHSA-N
  • C[C@@H]1CCC[C@@]2([C@@H]1C[C@@H]3CC[C@H]([C@@H](C3(C)C)CC2)C)C
Properties
C20H36
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 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.[2][3] Cabazitaxel was FDA approved to treat hormone-refractory prostate cancer.

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

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.[6][7]

Mechanism of action

Mechanism of action of taxanes

The principal mechanism of action of the taxane class of drugs is the disruption of

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.[8] Taxuspines A–D have been isolated from Taxus.[9][10][11][12]

Baccatin III (left) Paclitaxel (right)
10-Deacetylbaccatin (left) Docetaxel (right)
Taxuspine A
Taxuspine B
Hongdoushan A

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.

See also

References

  1. ISBN 978-0-85404-182-4
    .
  2. S2CID 22096988
    .
  3. PMID 9046968
    .
  4. ISBN 9780123695215
    .
  5. PMID 25213191
    .
  6. PMID 18163585
    .
  7. doi:10.1016/j.jff.2008.09.004
    .
  8. PMID 12444707
    .
  9. ^ CID 10417482 from PubChem
  10. ^ CID 5321744 from PubChem
  11. ^ CID 100991639 from PubChem
  12. ^ CID 5321746 from PubChem

External links

  • Media related to taxanes at Wikimedia Commons
Retrieved from "https://en.wikipedia.org/w/index.php?title=Taxane&oldid=1220549324"