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T7191

Sigma-Aldrich

Paclitaxel

from semisynthetic, ≥98%

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About This Item

Empirical Formula (Hill Notation):
C47H51NO14
CAS Number:
33069-62-4
Molecular Weight:
853.91
Beilstein/REAXYS Number:
1420457
MDL number:
MFCD00869953
UNSPSC Code:
12161501
PubChem Substance ID:
24900422
NACRES:
NA.77

biological source

semisynthetic

Quality Level

100

assay

≥98%

impurities

natural taxane impurities, none detected (except ≤0.5% paclitaxel degradation products.)

mp

213 °C (dec.) (lit.)

solubility

DMSO: soluble 50 mg/mL
methanol: soluble 50 mg/mL, clear, colorless
H2O: soluble (hydrolyzes)
ethanol: soluble

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes

originator

Bristol-Myers Squibb

storage temp.

−20°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 to study its effects on tumor regression in mouse models of pancreatic ductal adenocarcinoma. Paclitaxel has also been used as an internal standard for chromatographic assays of docetaxel. Furthermore, paclitaxel has been used to analyze its effects on Caenorhabditis elegans embryos.

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).
Paclitaxel is highly lipophilic. It serves as a substrate for p-glycoprotein, a multi-drug resistance protein. Paclitaxel is thus, less localized to the brain. Apart from its cytocidal action, paclitaxel is known to stimulate tumor invasion process.

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.

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 ethanol, water and DMSO.

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Megha Bajaj et al.
PloS one, 8(8), e71889-e71889 (2013-08-13)
Laulimalide is a microtubule-binding drug that was originally isolated from marine sponges. High concentrations of laulimalide stabilize microtubules and inhibit cell division similarly to paclitaxel; however, there are important differences with respect to the nature of the specific cellular defects
Anders Andersen et al.
BMC clinical pharmacology, 6, 2-2 (2006-01-18)
The taxanes paclitaxel and docetaxel have traditionally been used in high doses every third week in the treatment of cancer. Lately there has been a trend towards giving weekly low doses to improve the therapeutic index. This article describes the
Antisense Elements (Genetics) Research Focus, 181-181 (2007)
Kristopher K Frese et al.
Cancer discovery, 2(3), 260-269 (2012-05-16)
Nanoparticle albumin-bound (nab)-paclitaxel, an albumin-stabilized paclitaxel formulation, demonstrates clinical activity when administered in combination with gemcitabine in patients with metastatic pancreatic ductal adenocarcinoma (PDA). The limited availability of patient tissue and exquisite sensitivity of xenografts to chemotherapeutics have limited our
Moutushy Mitra et al.
Investigative ophthalmology & visual science, 52(8), 5441-5448 (2011-05-07)
To explore the possibility of stathmin as an effective therapeutic target and to evaluate the synergistic combination of stathmin RNAi and the antimicrotubule agents paclitaxel and vincristine to retinoblastoma Y79 cells. RNAi-mediated specific inhibition of stathmin expression in Y79 cells
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