T7191

Paclitaxel

Name: Paclitaxel
Brand: SIGMA

semisynthetic, ≥98%, Apoptosis inducer

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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:

24900422

UNSPSC Code:

12161501

MDL number:

MFCD00869953

Beilstein/REAXYS Number:

1420457

Nom du produit

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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Catégories apparentées

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).

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.

Disclaimer

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

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.

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 methanol at 50 mg/ml and yields a clear, colorless solution. It is also soluble in ethanol, water and DMSO.

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

0000492906

0000431274

0000398623

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

Laulimalide induces dose-dependent modulation of microtubule behaviour in the C. elegans embryo.

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

High sensitivity assays for docetaxel and paclitaxel in plasma using solid-phase extraction and high-performance liquid chromatography with UV detection.

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

nab-Paclitaxel potentiates gemcitabine activity by reducing cytidine deaminase levels in a mouse model of pancreatic cancer.

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

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

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