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Merck

T7191

Paclitaxel

semisynthetic, ≥98%, Apoptosis inducer

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About This Item

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

Key Documents

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Product Name

Paclitaxel, from semisynthetic, ≥98%

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

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 key

RCINICONZNJXQF-MZXODVADSA-N

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

Quality Level

100

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.
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.

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.

Disclaimer

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

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

target_organs

Central nervous system,Bone marrow,Cardio-vascular system

Storage Class

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

T7191-1MG-PW: + T7191-25MG-PW: + T7191-VAR: + T7191-5MG-PW: + T7191-5MG: + T7191-1MG: + T7191-25MG: + T7191-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000492906
0000492906
0000431274
0000431274
0000398623

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Antisense Elements (Genetics) Research Focus, 181-181 (2007)
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
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
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
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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