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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:
114977-28-5
Molecular Weight:
807.88
MDL number:
MFCD00800737
UNSPSC Code:
51101929
PubChem Substance ID:
329747367
NACRES:
NA.25

grade

purum

Quality Level

200

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

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

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

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is the solubility of Docetaxel, Product O1885?

    This product is practically insoluble in water and soluble in ethanol, methanol, and chloroform.  The solubility in TWEEN 80 is >45 mg/mL.

  4. What is the stability of Docetaxel, Product O1885, in solution?

    When 2 mL of a 45 mg/mL solution of this product in TWEEN 80 is mixed with 6 mL of a 15.25:84.75 (v/v) solution of absolute ethanol and water, the resulting solution should be physically stable. No precipitation should be observed for at least 12 hours of storage of the resulting solution at room temperature.

  5. Is Docetaxel, Product O1885, suitable for drug use?

    No. This product is not USP grade and is therefore unsuitable for drug use. It is sold for Research & Development use only.

  6. How do I reconstitute Docetaxel, Product O1885, for use in cell culture?

    Docetaxel is soluble in ethanol, and ethanol can be tolerated as long as the dose of added ethanol is low enough.  DMSO would also work as a solvent; the authors of one paper (see link below) prepared a 10 mM stock solution and used it within 7 days (final DMSO concentration was no higher than 0.2%).

  7. What are the storage conditions for Docetaxel, Product O1885?

    The product should be stored at room temperature (15°C to 25°C) and protected from light. Refrigerating and freezing does not adversely affect the product. If refrigerated, vials should be allowed to warm to room temperature before opening them.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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
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
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
Jasdeep K Saggar et al.
International journal of cancer, 134(11), 2726-2734 (2013-12-18)
Many chemotherapy drugs have poor therapeutic activity in regions distant from tumor blood vessels because of poor tissue penetration and low cytotoxic activity against slowly-proliferating cells. The hypoxia-activated pro-drug TH-302 may have selective toxicity for hypoxic and neighboring cells in
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