Abstract
Paclitaxel is a mitotic inhibitor used in cancer chemotherapy. It was discovered in the US National Cancer Institute program in 1967 when Monroe E. Wall and Mansukh C. Wani isolated it from the bark of the Pacific yew tree, Taxus brevifolia, and named it taxol. When it was developed commercially, the generic name was changed to paclitaxel.
Paclitaxel is now used to treat patients with ovarian, breast, and advanced forms of Kaposi’s sarcoma. Paclitaxel stabilizes microtubules and, as a result, interferes with the normal breakdown of microtubules during cell division. Together with docetaxel, it forms the drug category of the taxanes.
While offering substantial improvement in patient care, paclitaxel has been a relatively controversial drug. There was originally concern because of the environmental impact of its original sourcing, no longer used, from the Pacific yew. So in recent years, extensive research has been done to find a way to produce it from alternative resources including related compounds and also to lessen the side effects of paclitaxel.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Zubrod CG, Schepartz S, Leiter J, Endicott KM, Carrese LM, Baker CG (1996) The chemotherapy program of the National Cancer Institute: history, analysis, and plans. Cancer Chemother Rep 50:349–540
Wall ME, Wani MC (1967) Recent progress in plant anti-tumor agents. In: 153rd national meeting of the American Chemical Society, Miami Beach, FL, Abstr M006
Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT (1971) Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 93:2325–2327
Spjut W (2010) Overview of the genus Taxus (Taxaceae): the species, their classification, and female reproductive morphology. Submitted for poster. III international workshop, Ponferrada, León, Spain, Mar 25–26
Commission on Nomenclature of Organic Chemistry (1978) Revised section F: natural products and related compounds. Eur J Biochem 86:1–8
Bui-Khac T, Dupuis N (2002) Process for extraction and purification of paclitaxel from natural sources. US6452024
Benigni DA, Gougoutas JZ, DiMarco JD (2005) Paclitaxel solvates. US6858644
Sadeghi-aliabadi H, Asghari G, Mostafavi SA, Esmaeili S (2009) Solvent optimization on Taxol extraction from Taxus baccata L, using HPLC and LC-MS. Daru J Pharm Sci 17(3):192–198
Nicolaou KC, Dai WM, Kiplin R (1994) Chemistry and biology of Taxol. Angewandte Chemie 33(1):15–44
Witherup KM, Look SA, Stasko MW, McCloud TG, Issaq HJ, Muschik GM (1989) High performance liquid chromatographic separation of taxol and related compounds from Taxus brevifolia. J Liq Chromat 12:2117–2132
Xu LX, Liu AR (1989) Determination of taxol in the extract of Taxus chinensis by reversed phase HPLC. Yaoxue Xuebao 24:552–555
Cardellina JH (1991) HPLC separation of taxol and cephalomannine. J Liq Chromat 14:659–665
Rizzo J, Riley C, Von Hoff D, Kuhn J, Phillips J, Brown T (1990) Analysis of anticancer drugs in biological fluids: determination of taxol with application to clinical pharmacokinetics. J Pharm Biomed Anal 8:159–164
Guchelaar HJ, Ten Napel CHH, de Vries EGE, Mulder NH (1994) Clinical, toxicological and pharmaceutical aspects of the antineoplastic drug taxol: a review. Clin Oncol 6(1):40–48
Rohr J (1997) Biosynthesis of Taxol. Angew Chem 36(20):2190–2195
Witherup KM, Look SA, Stasko MW, Ghiorzi TJ, Muschik GM, Cragg GM (1990) Taxus spp. needles contain amounts of taxol comparable to the bark of Taxus brevifolia: analysis and isolation. J Nat Prod 53(5):1249–1255
Bissery MA, Guenard D, Gueritte-Voegelein F, Lavelle F (1991) Experimental antitumor activity of taxotere, a taxol analogue. Cancer Res 51:4845
Pazdur R, Kudelka AP, Kavenagh JJ, Cohen PR, Raber MN (1993) The taxoids: paclitaxel (Taxol) and docetaxel (Taxotere). Cancer Treat Rev 19:351
Wang YF, Shi QW, Dong M, Kiyota H, Gu YC, Cong B (2011) Natural taxanes: developments since 1828. Chem Rev 111(12):7652–7709
Baloglu E, Kingston DGI (1999) The taxane diterpenoids. J Nat Prod 62(10):1448–1472
Ojima I, Das M (2009) Recent advances in the chemistry and biology of new generation taxoids. J Nat Prod 72(3):554–565
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this entry
Cite this entry
Sadeghi-aliabadi, H., Yegdaneh, A. (2013). Taxol and Related Compounds. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_143
Download citation
DOI: https://doi.org/10.1007/978-3-642-22144-6_143
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-22143-9
Online ISBN: 978-3-642-22144-6
eBook Packages: Chemistry and Materials ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics