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Merck

5.08227

Paclitaxel

InSolution, ≥97%, 25 mM in DMSO, from Taxus sp.

Synonym(s):

InSolution Paclitaxel, Taxus sp., TAXOL® InSolution, Baccatin III N-benzyl-β-phenylisoserine Ester

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About This Item

Empirical Formula (Hill Notation):
C47H51NO14
CAS Number:
33069-62-4
Molecular Weight:
853.91
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00869953
Assay:
≥97% (HPLC)
Form:
liquid
Quality level:
100
Storage condition:
OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

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Product Name

Paclitaxel, Taxus sp., InSolution, ≥97%, 25 mM in DMSO

SMILES string

N([C@H]([C@@H](O)C(=O)O[C@H]3C[C@]4([C@H](C6[C@]7([C@H](OC7)C[C@@H]([C@]6(C(=O)[C@@H](C(=C3C)C4(C)C)OC(=O)C)C)O)OC(=O)C)OC(=O)c5ccccc5)O)c2ccccc2)C(=O)c1ccccc1

InChI

1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38?,40-,45+,46-,47+/m0/s1

InChI key

RCINICONZNJXQF-VAZQATRQSA-N

assay

≥97% (HPLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

storage temp.

−70°C

Quality Level

100

Related Categories

General description

Paclitaxel, a microtubule-stabilizing agent, is a tricyclic diterpenoid characterized by a “taxane” complex ring and an amide group, which sometimes leads to its classification as a pseudo alkaloid. Its mechanism of action involves selectively disrupting microtubule dynamics, resulting in mitotic arrest and subsequent cell death. Paclitaxel demonstrates antineoplastic properties with a wide range of antitumor activity. As a chemotherapeutic agent, it selectively binds to the β-subunit of tubulin proteins, facilitating their polymerization and assembly, which stabilizes microtubule formation. This stabilization creates a dysfunctional mitotic spindle, leading to significant mitotic arrest during the G2/M phase and ultimately causing cell death via an apoptosis pathway.

Application

Paclitaxel has been used to study fibronectin type III domain-containing protein 5 (FNDC5)-mediated paclitaxel sensitivity in non-small cell lung cancer (NSCLC) cells.

Biochem/physiol Actions

Cell permeable: yes
Reversible: yes

Packaging

Packaged under inert gas

Physical form

A 25 mM (10 mg/468 µL) sterile-filtered solution of Paclitaxel, Taxus sp. (Cat. No. 580555) in DMSO.

Other Notes

Derry, W.B., et al. 1995. Biochemistry34, 2203.
Milas, L., et al. 1995. Cancer Chemother. Pharmacol.35, 297.
Donaldson, K.L., et al. 1994. Int. J. Cancer57, 847.
Hornback, N.B., et al. 1994. In Vivo8, 819.
Manthey, C.L., et al. 1992. J. Immunol.149, 2459.
Rowinsky, E.K., et al. 1992. Semin. Oncol. 19, 646.
Ding, A.H., et al. 1990. Science248, 370.
Mogensen, M.M. and Tucker, J.B. 1990. J. Cell Sci.97, 101.
Slichenmeyer, W.J. and Von Hoff, D.D. 1990. J. Clin. Pharmacol.30, 770.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Taxol is a registered trademark of Bristol-Myers Squibb Co.

Disclaimer

Toxicity: Standard Handling (A)

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Muta. 2 - Repr. 1B - STOT RE 2

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 2

flash_point_f

188.6 °F

flash_point_c

87 °C

Certificates of Analysis (COA)

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