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T7402

Sigma-Aldrich

Paclitaxel

from Taxus brevifolia, ≥95% (HPLC), powder

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About This Item

Empirical Formula (Hill Notation):
C47H51NO14
CAS Number:
33069-62-4
Molecular Weight:
853.91
Beilstein:
1420457
MDL number:
MFCD00869953
UNSPSC Code:
12161501
PubChem Substance ID:
24277878
NACRES:
NA.77

biological source

Taxus brevifolia

Quality Level

200

Assay

≥95% (HPLC)

form

powder

color

white

mp

213 °C (dec.) (lit.)

solubility

DMSO: 50 mg/mL (can be stored frozen for several months)
methanol: soluble 50 mg/mL, clear, colorless (undergoes transesterification)
ethanol: soluble

antibiotic activity spectrum

viruses

Mode of action

DNA synthesis | interferes

originator

Bristol-Myers Squibb

storage temp.

2-8°C

SMILES string

[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)c5ccccc5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)c6ccccc6)c7ccccc7

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-MZXODVADSA-N

Gene Information

human ... BCL2(596) , TUBA1A(7846) , TUBA1B(10376) , TUBA1C(84790) , TUBA3C(7278) , TUBA3E(112714) , TUBA4A(7277) , TUBB(203068) , TUBB1(81027) , TUBB2A(7280) , TUBB2B(347733) , TUBB3(10381) , TUBB4A(10382) , TUBB4B(10383) , TUBB6(84617) , TUBB8(347688)

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General description

Chemical structure: taxoide

Application

Paclitaxel has been used as a component of the dechorionation buffer for Gryllus bimaculatus eggs. Paclitaxel has also been used for studying its effect on the movement of all-trans retinoic acid (ATRA) differentiated NB4 cells.

Biochem/physiol Actions

Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Caution

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

Preparation Note

Paclitaxel is soluble in methanol at 50 mg/ml and yields a clear, colorless solution. It is also soluble in DMSO (50 mg/ml) and ethanol.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H341,H360FD,H371,H372

Hazard Classifications

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

Target Organs

Central nervous system,Bone marrow,Cardio-vascular system, Eyes,Central nervous system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

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Barbara T McGrogan et al.
Biochimica et biophysica acta, 1785(2), 96-132 (2007-12-11)
The taxanes, paclitaxel and docetaxel are microtubule-stabilizing agents that function primarily by interfering with spindle microtubule dynamics causing cell cycle arrest and apoptosis. However, the mechanisms underlying their action have yet to be fully elucidated. These agents have become widely
Karl-Heinz Altmann et al.
Natural product reports, 24(2), 327-357 (2007-03-29)
This review article provides an overview on the current state of research in the area of microtubule-stabilizing agents from natural sources, with a primary focus on the biochemistry, biology, and pharmacology associated with these compounds. A variety of natural products
Isao Sarashina et al.
Development, growth & differentiation, 47(2), 99-108 (2005-03-18)
Early embryogenesis of the two-spotted cricket Gryllus bimaculatus was examined by scanning electron microscopy and several fluorescence staining methods, with special reference to these four issues: (i) the location of micropyles; (ii) the transfer of the female pronucleus following meiosis;
Joakim da Silva et al.
Biomaterials, 31(8), 2201-2208 (2009-12-18)
Whilst rigid, planar surfaces are often used to study cell migration, a physiological scenario requires three-dimensional (3D) scaffolds with tissue-like stiffness. This paper presents a method for fabricating periodic hydrogel scaffolds with a 3D honeycomb-like structure from colloidal crystal templates.
Yoo-Joung Ko et al.
The Lancet. Oncology, 14(8), 769-776 (2013-05-28)
No standard treatment exists for patients with platinum-refractory urothelial cancer. Taxanes and vinflunine are commonly used, but response is less than 20% with no survival benefit. In this phase 2 study, we assessed efficacy and tolerability of nanoparticle albumin-bound (nab)
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