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Y0000739

Paclitaxel semi-synthetic for system suitability

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

Paclitaxel

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About This Item

Empirical Formula (Hill Notation):
C47H51NO14
CAS Number:
33069-62-4
Molecular Weight:
853.91
Beilstein:
1420457
MDL number:
MFCD00869953
UNSPSC Code:
41116107
PubChem Substance ID:
329831125
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

paclitaxel

manufacturer/tradename

EDQM

mp

213 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

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

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

InChI key

RCINICONZNJXQF-MZXODVADSA-N

Gene Information

human ... 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

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.

Application

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

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. 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).

Packaging

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

Caution

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

Other Notes

Sales restrictions may apply.

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Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H341,H360FD,H372

Hazard Classifications

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

Target Organs

Central nervous system,Bone marrow,Cardio-vascular system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Miguel A Ojeda-Lopez et al.
Nature materials, 13(2), 195-203 (2014-01-21)
Bundles of taxol-stabilized microtubules (MTs)--hollow tubules comprised of assembled αβ-tubulin heterodimers--spontaneously assemble above a critical concentration of tetravalent spermine and are stable over long times at room temperature. Here we report that at concentrations of spermine several-fold higher the MT
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.
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
Bradley J Monk et al.
The Lancet. Oncology, 15(8), 799-808 (2014-06-22)
Angiogenesis is a valid target in the treatment of epithelial ovarian cancer. Trebananib inhibits the binding of angiopoietins 1 and 2 to the Tie2 receptor, and thereby inhibits angiogenesis. We aimed to assess whether the addition of trebananib to single-agent
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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