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Merck

Y0000739

Paclitaxel semi-synthetic for system suitability

European Pharmacopoeia (EP) Reference Standard

Sinónimos:

Paclitaxel

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About This Item

Fórmula empírica (notación de Hill):
C47H51NO14
Número de CAS:
Peso molecular:
853.91
Beilstein:
1420457
Número MDL:
Código UNSPSC:
41116107
ID de la sustancia en PubChem:
NACRES:
NA.24

grado

pharmaceutical primary standard

familia API

paclitaxel

fabricante / nombre comercial

EDQM

mp

213 °C (dec.) (lit.)

aplicaciones

pharmaceutical (small molecule)

formato

neat

temp. de almacenamiento

2-8°C

cadena SMILES

[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

Clave InChI

RCINICONZNJXQF-MZXODVADSA-N

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Descripción general

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Aplicación

Paclitaxel semi-synthetic for system suitability EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Acciones bioquímicas o fisiológicas

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).

Envase

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Precaución

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

Otras notas

Sales restrictions may apply.

Producto relacionado

Referencia del producto
Descripción
Precios

Pictogramas

Health hazard

Palabra de señalización

Danger

Frases de peligro

Clasificaciones de peligro

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

Órganos de actuación

Central nervous system,Bone marrow,Cardio-vascular system

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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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)
Stěpán Koudelka et al.
Journal of controlled release : official journal of the Controlled Release Society, 163(3), 322-334 (2012-09-20)
Over the past three decades, taxanes represent one of the most important new classes of drugs approved in oncology. Paclitaxel (PTX), the prototype of this class, is an anti-cancer drug approved for the treatment of breast and ovarian cancer. However
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
Denise A Yardley
Journal of controlled release : official journal of the Controlled Release Society, 170(3), 365-372 (2013-06-19)
Taxanes are a key chemotherapy component for several malignancies, including metastatic breast cancer (MBC), ovarian cancer, and advanced non-small cell lung cancer (NSCLC). Despite the clinical benefit achieved with solvent-based (sb) taxanes, these agents can be associated with significant and
Taroh Satoh et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 32(19), 2039-2049 (2014-05-29)
In Asian countries, paclitaxel once per week is used as second-line treatment in advanced gastric cancer, including human epidermal growth factor receptor 2 (HER2) -positive tumors. The role of anti-HER2 agents, including lapatinib, in this setting and population is unclear.

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