01885

Docetaxel

purum, ≥97.0% (HPLC)

• Synonym(s): Docetaxel anhydrous
• Empirical Formula (Hill Notation): C₄₃H₅₃NO₁₄
• CAS Number: 114977-28-5
• Molecular Weight: 807.88
• NACRES: NA.25
• PubChem Substance ID: 329747367
• UNSPSC Code: 51101929
• MDL number: MFCD00800737

Properties

• grade: purum
• Quality Segment: 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)

Description

General description

Docetaxel is a cytotoxic, semisynthetic, second-generation taxane derived from the needles of the European yew tree [1], with a baccatin ring [2], and is an anthracycline antibiotic.[3] 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.[2]

Application

Docetaxel has been used:

• to test its effect on lysosomal autophagic flux in gastric cancer cells[4]
• in combination with stearidonic acid (SDA) to increase its efficacy and enhancing cell death in human prostate cancer cells[3]
• as a microtubule-stabilizing agent in prostate and cervical cancer cells[5]
• in combination with a γ-secretase inhibitor (GSI) in prostate cancer stem-like cells (PCSCs) to test its effect on the notch signaling pathway[6]

Biochem/physiol Actions

Docetaxel (DOC) is an anti-microtubule agent [1], a standard anti-cancer drug used in first-line chemotherapy treatment in many types of cancer including prostate and breast cancer.[4] 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.[1] 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.[1]

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.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H315,H319,H341,H360D,H362,H372
• pcodes: P202 - P260 - P263 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• 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: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)