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T7191

Sigma-Aldrich

Paclitaxel

from semisynthetic, ≥98%

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Empirical Formula (Hill Notation):
C47H51NO14
CAS Number:
Molecular Weight:
853.91
Beilstein/REAXYS Number:
1420457
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

semisynthetic

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

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1 of 4

This Item
T7402PHR1803Y0000700
vibrant-m

T7191

Paclitaxel

vibrant-m

T7402

Paclitaxel

vibrant-m

PHR1803

Paclitaxel

Quality Level

100

Quality Level

200

Quality Level

300

Quality Level

-

solubility

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

solubility

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

solubility

-

solubility

-

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

originator

Bristol-Myers Squibb

originator

Bristol-Myers Squibb

originator

-

originator

-

biological source

semisynthetic

biological source

Taxus brevifolia

biological source

-

biological source

-

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

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


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Antisense Elements (Genetics) Research Focus, 181-181 (2007)
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
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
M Onrubia et al.
Current medicinal chemistry, 20(7), 880-891 (2012-12-06)
Taxol (paclitaxel) and its derivatives are microtubule-stabilizing drugs widely used in the treatment of several types of cancer, including mammary, prostate, ovarian and non-small-cell lung carcinoma, as well as AIDS-associated Kaposi's sarcoma and other types of tumor. Taxanes stabilize microtubules

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