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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/08/19 13:50:05」(JST)

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Baccatin III (left) Paclitaxel (right)


10-Deacetylbaccatin (left) Docetaxel (right)

Taxanes are diterpenes produced by the plants of the genus Taxus (yews), and are widely used as chemotherapy agents.^[1] Taxane agents include paclitaxel (Taxol) and docetaxel (Taxotere).

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

Production[edit source | edit]

As their name suggests, taxanes were first derived from natural sources, but some have been synthesized artificially. 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 action[edit source | edit]

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 — a "frozen mitosis". Thus, in essence, taxanes are mitotic inhibitors. In contrast to the taxanes, the vinca alkaloids destroy mitotic spindles. 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[edit source | edit]

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.^[2]

Hongdoushan A

Hongdoushan B

Hongdoushan C

References[edit source | edit]

^ Hagiwara, H.; Sunada, Y. (2004). "Mechanism of taxane neurotoxicity". Breast cancer (Tokyo, Japan) 11 (1): 82–85. PMID 14718798. edit
^ 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. PMID 12444707.

External links[edit source | edit]

Media related to taxanes at Wikimedia Commons

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UpToDate Contents

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1. タキサン誘発性肺毒性 taxane induced pulmonary toxicity
2. 転移性乳癌の全身治療：単剤化学療法 systemic treatment for metastatic breast cancer single agent chemotherapy
3. 転移性乳癌の全身治療：併用化学療法 systemic treatment for metastatic breast cancer combination chemotherapy
4. 転移性乳癌の全身治療：化学療法レジメンの選択 systemic treatment for metastatic breast cancer selection of chemotherapy regimen
5. 全身化学療法に対する輸注反応 infusion reactions to systemic chemotherapy

English Journal

Cancerous ovarian stem cells: Obscure targets for therapy but relevant to chemoresistance.

Ahmed N, Abubaker K, Findlay J, Quinn M.SourceWomen's Cancer Research Centre, Royal Women's Hospital, Melbourne, Australia; Department of Obstetrics and Gynaecology, University of Melbourne, Melbourne, Australia; Department of Surgery, University of Melbourne, Melbourne, Australia and; Prince Henry's Institute of Medical Research, Melbourne, Australia. nuzhat.ahmed@thewomens.org.au.
Journal of cellular biochemistry.J Cell Biochem.2013 Jan;114(1):21-34. doi: 10.1002/jcb.24317.
Chemotherapy with platinum and taxanes is the first line of treatment for all epithelial ovarian cancer (EOC) patients after debulking surgery. Even though the treatment is initially effective in 80% of patients, recurrent cancer is inevitable in the vast majority of cases. Emerging evidence suggest
PMID 22887554

Maternal and fetal outcomes of taxane chemotherapy in breast and ovarian cancer during pregnancy: case series and review of the literature.

Cardonick E, Bhat A, Gilmandyar D, Somer R.SourceDivision of Maternal Fetal Medicine, Department of Obstetrics and Gynecology, Cooper Medical School at Rowan University, Camden.
Annals of oncology : official journal of the European Society for Medical Oncology / ESMO.Ann Oncol.2012 Dec;23(12):3016-23. doi: 10.1093/annonc/mds170. Epub 2012 Aug 8.
Background The purpose of this study was to evaluate the use of taxane chemotherapy during pregnancy and compare maternal and neonatal outcomes with those in women who did not receive taxanes during pregnancy, and review current existing data. Study design This is a retrospective cohort study in wh
PMID 22875836

Japanese Journal

タキサン系抗癌剤による神経痛,しびれ : 牛車腎気丸 (特集漢方を上手に使う : エビデンスに基づいた外科診療) -- (癌化学療法の副作用と漢方)

高島勉
臨床外科 = Journal of clinical surgery 68(12), 1324-1327, 2013-11
NAID 40019833730

〈Case Reports〉Effective combination chemotherapy of taxanes and platinum in advanced uterine cervica cancer: a case report

Obata Koshiro,Amano Yoko,Ikoma Naoko,Omura Gen,Mitsuhashi Yoji,Inoue Yoshiki
Acta Medica Kinki University 37(1), 53-56, 2012-06
… We report a patient with advanced uterine cervical cancer who responded to neoadjuvant combination chemotherapy with taxanes and platinum. …
NAID 120004226582

パクリタキセルによる末梢神経障害に対する温灸の効果に関する検討

堀口美穂,辻川真弓,梅岡京子,坂口美和,大西和子,Horiguchi Miho,Tsujikawa Mayumi,Umeoka Kyoko,Sakaguchi Miwa,Onishi Kazuko
三重看護学誌 14(1), 67-79, 2012-03-15
… 結果，NRSにおいて，介入1～2週目の「しびれ」，「感覚の低下」に有意な低下を認めた．以上より，パクリタキセルによる末梢神経障害に対して，温灸治療はしびれ出現早期に有効な可能性が示された．Peripheral neuropathy induced by taxanes is a common side effect and reduces patients quality of life. …
NAID 120004027295