T1912

Paclitaxel

Name: Paclitaxel
Brand: SIGMA

From Taxus yannanensis, Apoptosis inducer, powder

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About This Item

Formule empirique (notation de Hill) :

C₄₇H₅₁NO₁₄

Numéro CAS:

33069-62-4

Poids moléculaire :

853.91

NACRES:

NA.77

PubChem Substance ID:

24899998

UNSPSC Code:

12161501

MDL number:

MFCD00869953

Beilstein/REAXYS Number:

1420457

Nom du produit

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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Catégories apparentées

Inhibiteurs bioactifs à base de petites molécules

Petites molécules bioactives

Biochem/physiol Actions

Le paclitaxel est un puissant médicament antinéoplasique et antimitotique à squelette taxane qui se fixe à l'extrémité N-terminale de la β-tubuline et qui stabilise les microtubules en bloquant le cycle cellulaire à la phase G2/M. L'altération des microtubules induit l'apoptose, d'abord par une voie dépendante de la JNK, puis par une voie indépendante de la JNK, probablement en lien avec l'activation de la protéine kinase A (PKA) ou de la kinase Raf-1, entraînant la phosphorylation de la protéine Bcl-2. Un métabolite important de l'action du cytochrome CYP2CB est l'hydroxypaclitaxel 6α (6α-OHP).

Disclaimer

Le paclitaxel subit une transestérification dans le méthanol et une hydrolyse en solution aqueuse.

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.

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

GHS08

signalword

Danger

hcodes

H341,H360FD,H372

pcodes

P202 - P260 - P264 - P280 - P308 + P313 - P405

Hazard Classifications

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

target_organs

Central nervous system,Bone marrow,Cardio-vascular system

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Systematic comparison of in vitro motile properties between Chlamydomonas wild-type and mutant outer arm dyneins each lacking one of the three heavy chains.

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

Phosphorylation of EB2 by Aurora B and CDK1 ensures mitotic progression and genome stability.

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

Bioprocessing of plant in vitro systems for the mass production of pharmaceutically important metabolites: paclitaxel and its derivatives.

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

Nanoparticle albumin-bound paclitaxel for second-line treatment of metastatic urothelial carcinoma: a single group, multicentre, phase 2 study.

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)

Bevacizumab combined with chemotherapy for platinum-resistant recurrent ovarian cancer: The AURELIA open-label randomized phase III trial.

Eric Pujade-Lauraine et al.

Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 32(13), 1302-1308 (2014-03-19)

In platinum-resistant ovarian cancer (OC), single-agent chemotherapy is standard. Bevacizumab is active alone and in combination. AURELIA is the first randomized phase III trial to our knowledge combining bevacizumab with chemotherapy in platinum-resistant OC. Eligible patients had measurable/assessable OC that

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Product Information Sheet - T1912

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