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

CAS Number

* 1605-68-1

3D model (JSmol)

* Interactive image

ChemSpider |

* 7827751

PubChem CID

* 9548828

InChI

* 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

SMILES

* C[C@@H]1CCC[C@@]2([C@@H]1C[C@@H]3CC[C@H]([C@@H](C3(C)C)CC2)C)C

Properties

Chemical formula

| 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).

Infobox references

Tracking categories (test):

* SizeSet

Baccatin III (left) Paclitaxel (right)

10-Deacetylbaccatin (left) Docetaxel (right)

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.

## Contents

* 1 Production
* 2 Mechanism of action
* 3 Substances
* 4 Names
* 5 See also
* 6 References
* 7 External links

## 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.[4][5] 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.[6][7]

## Mechanism of action

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

Chemical structure of hongdoushan A

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]

Taxuspine A

Taxuspine B

## 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

* Abeotaxane
* Docetaxel
* Taxine
* Taxuyunnanine

## References

1. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. pp. 1540. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
2. ↑ Hagiwara, H.; Sunada, Y. (2004). "Mechanism of taxane neurotoxicity". Breast Cancer (Tokyo, Japan) 11 (1): 82–85. doi:10.1007/BF02968008. PMID 14718798.
3. ↑ 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.
4. ↑ Hacker, Miles (2009). "Adverse Drug Reactions". Pharmacology. pp. 327–352. doi:10.1016/B978-0-12-369521-5.00013-0. ISBN 9780123695215.
5. ↑ 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. PMID 25213191.
6. ↑ 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.
7. ↑ 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.
8. ↑ "Three new C-14 oxygenated taxanes from the wood of Taxus yunnanensis.". J Nat Prod 65 (11): 1700–2. 2002. doi:10.1021/np020235j. PMID 12444707.
9. ↑ CID 10417482 from PubChem
10. ↑ CID 5321744 from PubChem
11. ↑ CID 100991639 from PubChem
12. ↑ CID 5321746 from PubChem

## External links

* v
* t
* e

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)|

| Block microtubule assembly|

* Vinca alkaloids (Vinblastine#
* Vincristine#
* Vinflunine§
* Vindesine
* Vinorelbine#)

|

Block microtubule disassembly|

* Taxanes (Cabazitaxel
* Docetaxel#
* Larotaxel
* Ortataxel†
* Paclitaxel#
* Tesetaxel)
* Epothilones (Ixabepilone)

DNA replication
inhibitor|

| DNA precursors/
antimetabolites
(S phase)|

| Folic acid|

* Dihydrofolate reductase inhibitor (Aminopterin
* Methotrexate#
* Pemetrexed
* Pralatrexate)
* Thymidylate synthase inhibitor (Raltitrexed
* Pemetrexed)

|

Purine|

* Adenosine deaminase inhibitor (Pentostatin)

* Halogenated/ribonucleotide reductase inhibitors (Cladribine
* Clofarabine
* Fludarabine)
* Nelarabine

* Thiopurine (Tioguanine#
* Mercaptopurine#)

Pyrimidine|

* Thymidylate synthase inhibitor (Fluorouracil#
* Capecitabine#
* Doxifluridine
* Tegafur (+gimeracil/oteracil)
* Carmofur
* Floxuridine)

* DNA polymerase inhibitor (Cytarabine#)

* Ribonucleotide reductase inhibitor (Gemcitabine#)

* Hypomethylating agent (Azacitidine
* Decitabine)

Deoxyribonucleotide|

* Ribonucleotide reductase inhibitor (Hydroxycarbamide#)

Topoisomerase inhibitors
(S phase)|

| I|

* Camptotheca (Camptothecin
* Cositecan†
* Belotecan
* Gimatecan
* Exatecan
* Irinotecan#
* Lurtotecan‡
* Silatecan§
* Topotecan
* Rubitecan‡)

|

II|

* Podophyllum (Etoposide#
* Teniposide)

II+Intercalation|

* Anthracyclines (Aclarubicin
* Daunorubicin#
* Doxorubicin#
* Epirubicin
* Idarubicin
* Amrubicin†
* Pirarubicin
* Valrubicin
* Zorubicin)
* Anthracenediones (Mitoxantrone
* Pixantrone)

Crosslinking of DNA
(CCNS)|

| Alkylating|

* Nitrogen mustards: Chlormethine
* Cyclophosphamide# (Ifosfamide#
* Trofosfamide)
* Chlorambucil# (Melphalan
* Prednimustine)
* Bendamustine#
* Uramustine

* Nitrosoureas: Carmustine
* Lomustine (Semustine)
* Fotemustine
* Nimustine
* Ranimustine
* Streptozocin

* Alkyl sulfonates: Busulfan (Mannosulfan
* Treosulfan)

* Aziridines: Carboquone
* Thiotepa
* Triaziquone
* Triethylenemelamine

|

Platinum-based|

* Carboplatin#
* Cisplatin#
* Dicycloplatin
* Nedaplatin
* Oxaliplatin#
* Satraplatin

Nonclassical|

* Hydrazines (Procarbazine#)
* Triazenes (Dacarbazine#
* Temozolomide)
* Altretamine
* Mitobronitol
* Pipobroman

Intercalation|

* Streptomyces (Actinomycin#
* Bleomycin#
* Mitomycins
* Plicamycin)

Photosensitizers/PDT|

* Aminolevulinic acid / Methyl aminolevulinate
* Efaproxiral
* Porphyrin derivatives (Porfimer sodium
* Talaporfin
* Temoporfin
* Verteporfin)

Other|

| Enzyme inhibitors|

* FI (Tipifarnib§)
* CDK inhibitors (Abemaciclib
* Alvocidib†
* Palbociclib
* Ribociclib
* Seliciclib†)
* PrI
* Bortezomib
* Carfilzomib
* Ixazomib
* PhI (Anagrelide)
* IMPDI (Tiazofurin§)
* LI (Masoprocol)
* PARP inhibitor (Niraparib
* Olaparib
* Rucaparib)
* HDAC (Belinostat
* Panobinostat
* Romidepsin
* Vorinostat)
* PIKI (Idelalisib)

|

Receptor antagonists|

* ERA (Atrasentan)
* Retinoid X receptor (Bexarotene)
* Sex steroid (Testolactone)

Other/ungrouped|

* Amsacrine
* Trabectedin
* Retinoids (Alitretinoin
* Tretinoin#)
* Arsenic trioxide
* Asparagine depleters (Asparaginase#/Pegaspargase)
* Celecoxib
* Demecolcine
* Elesclomol§
* Elsamitrucin
* Estramustine phosphate
* Etoglucid
* Lonidamine
* Lucanthone
* Mitoguazone
* Mitotane
* Oblimersen†
* Omacetaxine mepesuccinate
* Eribulin

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

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