| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
Docetaxel impurity; tubulin
Microtubule/Tubulin. 7-Epi-docetaxel binds reversibly to microtubules with high affinity in a 1:1 stoichiometric ratio, similar to its parent compound docetaxel. This binding stabilizes microtubule structure and inhibits depolymerization, preventing cell division and promoting cell death. However, the antitumor activity of 7-epi-docetaxel is significantly inferior to that of docetaxel, and it is considered a less active impurity rather than a therapeutic agent. The compound does not interact with dimeric tubulin but binds to polymerized microtubules. |
|---|---|
| ln Vitro |
In vitro studies have shown that 7-Epi-docetaxel exhibits cytotoxic effects against cancer cell lines, but its activity is significantly lower than that of docetaxel. Research has demonstrated that the compound has comparable anticancer effects to docetaxel in some in vitro assays, but its in vivo antitumor effectiveness is inferior. The compound has been reported to induce the formation of an incomplete metaphase plate of chromosomes and an arrangement of spindle microtubules, indicating its ability to disrupt normal mitotic progression. Its cytotoxic potency is reduced due to the altered stereochemistry at C-7.
|
| ln Vivo |
In vivo antitumor effectiveness of 7-Epi-docetaxel was found to be inferior to that of docetaxel. Studies conducted by Jiang et al. demonstrated that 7-epi-docetaxel does not elicit acute toxic effects either as an active pharmaceutical ingredient or in bulk formulations. The compound has been evaluated in preclinical models of breast cancer and prostate cancer, where it showed some anticancer activity but was less potent than docetaxel. The reduced in vivo efficacy is attributed to its lower microtubule-stabilizing activity and potential differences in pharmacokinetic properties.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for 7-Epi-docetaxel assess its affinity for microtubules. The compound's binding to polymerized tubulin is measured using standard microtubule polymerization assays. Purified tubulin is incubated with varying concentrations of the compound in polymerization buffer containing GTP. Microtubule formation is monitored spectrophotometrically by measuring absorbance at 340 nm. The compound's ability to stabilize microtubules against cold-induced or calcium-induced depolymerization is assessed. Binding stoichiometry and affinity constants are determined using sedimentation or fluorescence-based methods. Competition binding experiments with radiolabeled docetaxel can be used to compare relative binding affinities.
|
| Cell Assay |
In vitro cell-based assays for 7-Epi-docetaxel use human cancer cell lines such as breast cancer (MCF-7, MDA-MB-231) and prostate cancer (PC-3, DU145) cells. Cells are seeded in 96-well plates and treated with varying concentrations of the compound for 48-72 hours. Cell viability is measured using MTT, XTT, or CCK-8 assays. IC50 values are calculated from dose-response curves. Cell cycle analysis is performed by flow cytometry following propidium iodide staining to assess the compound's effects on mitotic arrest. Apoptosis is evaluated using Annexin V/PI staining or caspase-3/7 activity assays.
|
| Animal Protocol |
In vivo animal studies for 7-Epi-docetaxel are typically conducted in murine xenograft models of human cancers. Immunodeficient mice are implanted subcutaneously with cancer cells (e.g., breast or prostate cancer cells). When tumors reach a certain size, animals are randomized to receive vehicle control or the compound at various doses (typically 5-30 mg/kg) via intravenous or intraperitoneal administration on a weekly or bi-weekly schedule. Tumor volumes are measured with calipers every 2-3 days, and tumor growth inhibition is calculated. Body weight and clinical signs are monitored for toxicity assessment. At study termination, tumors are excised for histology and biomarker analysis.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 7-Epi-docetaxel are similar to those of docetaxel due to their structural similarity. With a molecular weight of 807.88 and high lipophilicity, the compound is poorly water-soluble and requires formulation with solubilizing agents (e.g., Tween 80, ethanol) for parenteral administration. The compound is metabolized primarily by cytochrome P450 3A4 (CYP3A4). Standard pharmacokinetic parameters (clearance, volume of distribution, half-life, bioavailability) can be determined in preclinical species following intravenous or oral administration. As an impurity, comprehensive pharmacokinetic data for 7-epi-docetaxel are less extensively documented than for docetaxel itself.
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| Toxicity/Toxicokinetics |
Toxicological data for 7-Epi-docetaxel indicate that it does not elicit acute toxic effects as an active pharmaceutical ingredient or in bulk formulations. However, as a taxane analog, it shares the potential for dose-limiting toxicities associated with this drug class, including myelosuppression, peripheral neuropathy, and hypersensitivity reactions. The compound is not intended for therapeutic use and is supplied only as a research reference standard for analytical purposes. Comprehensive genotoxicity, carcinogenicity, and chronic toxicity studies have not been conducted for this impurity compound.
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| Additional Infomation |
7-Epi-docetaxel is a research-grade reference standard and impurity of the anticancer drug docetaxel. It is classified as a microtubule/tubulin-targeting agent in the cell cycle/DNA damage pathway. The compound is used in the pharmaceutical industry for analytical method development, method validation, and quality control during commercial production of docetaxel. Its synonyms include 7-Epi-10-oxo-docetaxel and 7-Epitaxotere. The compound has a purity of ≥98% and is supplied as a solid for research use only. Storage at -20degC is recommended. Not approved for clinical use.
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| Molecular Formula |
C43H53NO14
|
|---|---|
| Molecular Weight |
807.87922
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| Exact Mass |
807.347
|
| CAS # |
153381-68-1
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| PubChem CID |
58510442
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| Appearance |
White to light yellow solid powder
|
| LogP |
3.464
|
| Hydrogen Bond Donor Count |
5
|
| Hydrogen Bond Acceptor Count |
14
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| Rotatable Bond Count |
13
|
| Heavy Atom Count |
58
|
| Complexity |
1660
|
| Defined Atom Stereocenter Count |
11
|
| SMILES |
CC1=C2[C@H](C(=O)[C@@]3([C@@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C)O
|
| InChi Key |
ZDZOTLJHXYCWBA-MQOKZWAMSA-N
|
| InChi Code |
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
|
| Chemical Name |
[(1S,2S,3R,4S,7R,9R,10S,12R,15S)-4-acetyloxy-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
|
| Synonyms |
7-EPI-DOCETAXEL; 153381-68-1; 4-Epidocetaxel; 7-Epidocetaxel; 7-Epi Docetaxel; 7-Epitaxotere; 4-epi-Docetaxel; Docetaxel Impurity C;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~123.78 mM)
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.2378 mL | 6.1890 mL | 12.3781 mL | |
| 5 mM | 0.2476 mL | 1.2378 mL | 2.4756 mL | |
| 10 mM | 0.1238 mL | 0.6189 mL | 1.2378 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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