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Merck

T1912

Paclitaxel

From Taxus yannanensis, Apoptosis inducer, powder

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Fórmula empírica (notación de Hill):
C47H51NO14
Número CAS:
33069-62-4
Peso molecular:
853.91
NACRES:
NA.77
PubChem Substance ID:
24899998
UNSPSC Code:
12161501
MDL number:
MFCD00869953
Beilstein/REAXYS Number:
1420457

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Nombre del producto

Paclitaxel, from Taxus yannanensis, powder

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

Taxus yannanensis

form

powder

color

white

mp

213 °C (dec.) (lit.)

solubility

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

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes

originator

Bristol-Myers Squibb

storage temp.

2-8°C

Quality Level

200

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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Application

Paclitaxel has been used to study PREP2-tubulin interactions using coimmunoprecipitation assays on NIH3T3 cell extracts. This drug has also been used to stabilize tubulin obtained from pig brain.

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).

Disclaimer

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

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.

General description

Chemical structure: taxoide

Preparation Note

Paclitaxel is soluble in DMSO at 50 mg/ml and can be stored frozen for several months. It is also soluble in methanol (undergoes transesterification), acetonitrile and ethanol. Paclitaxel is rapidly destroyed in weakly alkaline, methanolic solutions and in strongly acidic methanolic solutions (1:1 of methanol:concentrated HCl). It is also soluble in a mixture of 50% Cremophor EL and 50% anhydrous ethanol.

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

Clase de almacenamiento

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

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Certificados de análisis (COA)

Lot/Batch Number
0000431492
0000431491
0000431490
0000431490
0000431492

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Akane Furuta et al.
The Journal of biological chemistry, 284(9), 5927-5935 (2009-01-07)
Outer arm dynein (OAD) of cilia and flagella contains two or three distinct heavy chains, each having a motor function. To elucidate their functional difference, we compared the in vitro motile properties of Chlamydomonas wild-type OAD containing the alpha, beta
Makoto Iimori et al.
Nature communications, 7, 11117-11117 (2016-04-01)
Temporal regulation of microtubule dynamics is essential for proper progression of mitosis and control of microtubule plus-end tracking proteins by phosphorylation is an essential component of this regulation. Here we show that Aurora B and CDK1 phosphorylate microtubule end-binding protein
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
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)
Zhiping Zhang et al.
Expert opinion on drug delivery, 10(3), 325-340 (2013-01-08)
Paclitaxel (PTX) is one of the most effective broad-spectrum chemotherapeutic agents in the treatment of cancers. However, its clinical application has been limited due to its poor water solubility. Its current clinical administration uses the adjuvant of serious side effects
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