Paclitaxel

Specifications / Handling

More Information
Product Details
Synonyms	Taxol; BMS 181339-01; NSC 125973, PTX
Product Type	Chemical
Properties
Formula	C₄₇H₅₁NO₁₄
MW	853.9
Merck Index	14: 6982
CAS	33069-62-4
Source/Host Chemicals	Isolated from the bark of the pacific yew tree (Taxus brevifolia).
Purity Chemicals	≥99% (HPLC)
Appearance	White powder.
Solubility	Soluble in DMSO, ethanol or acetonitrile.
Identity	Determined by ¹H-NMR.
InChi Key	RCINICONZNJXQF-MZXODVADSA-N
Smiles	[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](OC(C)=O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)C5=CC=CC=C5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)C1=CC=CC=C1)C1=CC=CC=C1
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Anticancer compound [1, 11, 14].
Chemotherapeutic used in patients with cancer and advanced forms of Kaposi's sarcoma [11, 12].
Microtubule assembly stabilizer. Reversibly binds to polymerized tubulin [2, 3, 6, 13, 14].
Anti-mitotic. Mitotic spindle assembly, chromosome segregation and cell division inhibitor. Induces cell cycle arrest at the G2/M phase [4, 5, 10, 13].
Apoptosis inducer through aberrant activation of cyclin-dependent kinases (CKDs) and the c-Jun N-terminal kinase/stress activated protein kinase (JNK/SAPK) [7-9, 10].
Immunosuppressor. Immunostimulant [15].
Antiproliferative agent for the prevention of restenosis [16].
TRAIL sensitizer [17]

Product References

Cytotoxic studies of paclitaxel (Taxol®) in human tumour cell lines: J.E. Liebmann, et al.; Br. J. Cancer 68, 1104 (1993)
Taxol (paclitaxel): mechanisms of action: S.B. Horwitz; Ann. Oncol. 5, S3 (1994) (Review)
Taxol (paclitaxel): a novel anti-microtubule agent with remarkable anti-neoplastic activity: R. Foa, et al.; Int. J. Clin. Lab. Res. 24, 6 (1994) (Review)
Taxol-induced mitotic block triggers rapid onset of a p53-independent apoptotic pathway: C.M. Woods, et al.; Mol. Med. 1, 506 (1995)
Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle: A. Jordan, et al.; Med. Res. Rev. 18, 259 (1998)
How Taxol stabilises microtubule structure: L.A. Amos & J. Löwe; Chem. Biol. 6, R65 (1999) (Review)
Mechanisms of Taxol-induced cell death are concentration dependent: K. Torres & S.B. Horwitz; Cancer Res. 58, 3620 (1998)
Molecular effects of paclitaxel: myths and reality (a critical review): M.V. Blagosklonny & T. Fojo; Int. J. Cancer 83, 151 (1999)
Microtubule dysfunction induced by paclitaxel initiates apoptosis through both c-Jun N-terminal kinase (JNK) dependent and -independent pathways in ovarian cancer cells: T.H. Wang, et al.; J. Biol. Chem. 274, 8208 (1999)
Paclitaxel-induced cell death: where the cell cycle and apoptosis come together: T.H. Wang, et al.; Cancer 88, 2619 (2000)
Paclitaxel in cancer therapy: T.M. Mekhail & M. Markman; Expert Opin. Pharmacother. 3, 755 (2002)
Overcoming multidrug resistance in taxane chemotherapy: R. Geney, et al.; Clin. Chem. Lab. Med. 40, 918 (2002)
Taxanes: microtubule and centrosome targets, and cell cycle dependent mechanisms of action: M. Abal, et al.; Curr. Cancer Drug Targets 300, 193 (2003)
Microtubule-stabilizing natural products as promising cancer therapeutics: B.M. Gallagher Jr.; Curr. Med. Chem. 14, 2959 (2007)
Paclitaxel and immune system: A. Javeed, et al.; Eur. J. Pharm. Sci. 38, 283 (2009) (Review)
Anti-proliferative compounds for the prevention of restenosis: M.C. Lavigne; Curr. Pharm. Des. 16, 3989 (2010)
Novel HTS strategy identifies TRAIL-sensitizing compounds acting specifically through the Caspase-8 apoptotic axis: D. Finlay, et al.;PLoS One 5, e13375 (2010)
Eribulin induces micronuclei and enhances the nuclear localization of cGAS in triple-negative breast cancer cells: H. Yamada, et al.; Res. square ahead of print (2023)

Call	+41 61 926 6040
Fax	+41 61 926 6049