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01885

Sigma-Aldrich

Docetaxel

purum, ≥97.0% (HPLC)

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Synonym(s):
Docetaxel anhydrous
Empirical Formula (Hill Notation):
C43H53NO14
CAS Number:
Molecular Weight:
807.88
MDL number:
PubChem Substance ID:
NACRES:
NA.25

grade

purum

Quality Level

assay

≥97.0% (HPLC)

form

powder or crystals

impurities

~6% water

mp

186-192 °C (dec.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](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)OC(C)(C)C)c6ccccc6

InChI

1S/C43H53NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,52)/t26-,27-,28+,30-,31+,32+,33-,35-,41+,42-,43+/m0/s1

InChI key

ZDZOTLJHXYCWBA-VCVYQWHSSA-N

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1 of 4

This Item
Y0001466PHR188328266
vibrant-m

01885

Docetaxel

vibrant-m

Y0001466

Anhydrous Docetaxel

vibrant-m

PHR1883

Docetaxel

vibrant-m

28266

Levofloxacin

form

powder or crystals

form

-

form

-

form

powder or crystals

Quality Level

200

Quality Level

-

Quality Level

300

Quality Level

200

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical

application(s)

-

grade

purum

grade

-

grade

-

grade

-

impurities

~6% water

impurities

-

impurities

-

impurities

-

General description

Docetaxel is a cytotoxic, semisynthetic, second-generation taxane derived from the needles of the European yew tree , with a baccatin ring , and is an anthracycline antibiotic. It is related to paclitaxel but structurally it differs from paclitaxel on the 3′ position of the side chain and 10′ position of the baccatin ring.

Application

Docetaxel has been used:
  • to test its effect on lysosomal autophagic flux in gastric cancer cells
  • in combination with stearidonic acid (SDA) to increase its efficacy and enhancing cell death in human prostate cancer cells
  • as a microtubule-stabilizing agent in prostate and cervical cancer cells
  • in combination with a γ-secretase inhibitor (GSI) in prostate cancer stem-like cells (PCSCs) to test its effect on the notch signaling pathway

Biochem/physiol Actions

Docetaxel (DOC) is an anti-microtubule agent , a standard anti-cancer drug used in first-line chemotherapy treatment in many types of cancer including prostate and breast cancer. It elicits a stronger effect of inhibiting angiogenesis in both in vitro and in vivo by acting on vascular endothelial growth factor (VEGF) associated with tumor cells. Being involved in many key cellular processes such as cell cycle, angiogenesis, and gene expression; docetaxel interacts with many signaling pathways, such as the epidermal growth factor receptor (EGFR) pathway, Ras pathway, etc.
Docetaxel is a taxane anti-cancer agent related to paclitaxel. It binds to and stabilizes the β−tubulin subunit of microtubules, preventing depolymerization of the mitotic spindle thus leading to cell cycle arrest and apoptosis.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation markHealth hazard

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Lact. - Muta. 2 - Repr. 1B - Skin Irrit. 2 - STOT RE 1

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Alberto Montero et al.
The Lancet. Oncology, 6(4), 229-239 (2005-04-07)
Docetaxel is a semisynthetic taxane, a class of anticancer agents that bind to beta tubulin, thereby stabilising microtubules and inducing cell-cycle arrest and apoptosis. Docetaxel was first approved for the treatment of anthracycline-refractory metastatic breast cancer in the mid-1990s. Since
Roy S Herbst et al.
Cancer treatment reviews, 29(5), 407-415 (2003-09-16)
Different tumors have different aberrations in signaling and growth stimulation pathways that drive cancer growth. An understanding of these processes is key to the development of new anticancer agents and to identifying optimal treatment strategies and patient populations suitable for
Hugo E R Ford et al.
The Lancet. Oncology, 15(1), 78-86 (2013-12-18)
Second-line chemotherapy for patients with oesophagogastric adenocarcinoma refractory to platinum and fluoropyrimidines has not shown benefits in health-related quality of life (HRQoL). We assessed whether the addition of docetaxel to active symptom control alone can improve survival and HRQoL for
Giuseppe Di Lorenzo et al.
European urology, 54(5), 1089-1094 (2008-02-16)
Although the taxanes represent the most active agents for the first-line treatment of metastatic hormone-refractory prostate cancer (HRPC), most patients eventually progress while receiving taxane-based treatments. No agents are approved for second-line therapy in HRPC, but common standard practice for
Lei Wang et al.
Stem cell research & therapy, 11(1), 258-258 (2020-06-27)
Prostate cancer stem-like cells (PCSCs) likely participate in tumor progression and recurrence and demonstrate resistance to chemotherapy. The Notch pathway plays a role in the maintenance of the stemness in PCSCs. This study aimed to investigate the efficacy of Notch

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