5.08227

Paclitaxel

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

• Synonym(e): InSolution Paclitaxel, Taxus sp., TAXOL^® InSolution, Baccatin III N-benzyl-β-phenylisoserine Ester
• Empirische Formel (Hill-System): C₄₇H₅₁NO₁₄
• CAS-Nummer: 33069-62-4
• Molekulargewicht: 853.91
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00869953
• Assay: ≥97% (HPLC)
• Form: liquid
• Storage condition: OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

Eigenschaften

• Produktname: Paclitaxel, Taxus sp., InSolution, ≥97%, 25 mM in DMSO
• Quality Segment: 100
• 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
• 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

Beschreibung

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.[1]

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)

Sicherheitshinweise

• pictograms: GHS08
• signalword: Danger
• pcodes: P202 - P260 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Muta. 2 - Repr. 1B - STOT RE 2
• wgk: WGK 2
• flash_point_f: 188.6 °F
• flash_point_c: 87 °C
• target_organs: Central nervous system,Bone marrow,Cardio-vascular system
• hcodes: H341,H360FD,H373
• Lagerklasse: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects