Indications and Usage Mechanisms of Action Pharmacokinetics Clinical Research Drug Interactions Adverse Reactions Contradictions Precautions
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Docetaxel

Indications and Usage Mechanisms of Action Pharmacokinetics Clinical Research Drug Interactions Adverse Reactions Contradictions Precautions
Product Name
Docetaxel
CAS No.
114977-28-5
Chemical Name
Docetaxel
Synonyms
TAXOTERE;rp56976;BIND-014;Decetaxel;Doxetaxel;Anhydrous Docetaxel;Docetere;Docetaxel;Docetaxet;NSC_628503
CBNumber
CB1163212
Molecular Formula
C43H53NO14
Formula Weight
807.88
MOL File
114977-28-5.mol
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Docetaxel Property

Melting point:
186-192 °C (dec.)
alpha 
-36 º (c=0.74,EtOH)
Boiling point:
900.5±65.0 °C(Predicted)
Density 
1.38
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
Practically insoluble in water, freely soluble in anhydrous ethanol, soluble in methylene chloride.
form 
Solid
pka
11.20±0.46(Predicted)
color 
White
Water Solubility 
Soluble in dimethyl sulfoxide and ethanol. Insoluble in water.
Merck 
14,3397
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChIKey
BEDLLNJKXXVTSX-LWWLJZAUSA-N
LogP
2.456 (est)
CAS DataBase Reference
114977-28-5(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38-61
Safety Statements 
26-36/37-53-45
RIDADR 
1544
WGK Germany 
3
RTECS 
DA4172750
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29322090
Hazardous Substances Data
114977-28-5(Hazardous Substances Data)
Toxicity
LD50 intravenous in dog: 2500ug/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H341Suspected of causing genetic defects

H362May cause harm to breast-fed children

H372Causes damage to organs through prolonged or repeated exposure

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P263Avoid contact during pregnancy/while nursing.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
01885
Product name
Docetaxel
Purity
purum, ≥97.0% (HPLC)
Packaging
5MG-F
Price
$269
Updated
2024/03/01
Sigma-Aldrich
Product number
01885
Product name
Docetaxel
Purity
purum, ≥97.0% (HPLC)
Packaging
25MG-F
Price
$926
Updated
2024/03/01
Sigma-Aldrich
Product number
01885
Product name
Docetaxel
Purity
purum, ≥97.0% (HPLC)
Packaging
5mg
Price
$259
Updated
2023/01/07
Sigma-Aldrich
Product number
01885
Product name
Docetaxel
Purity
purum, ≥97.0% (HPLC)
Packaging
25mg
Price
$890
Updated
2023/01/07
Alfa Aesar
Product number
J60174
Product name
Docetaxel, 99%
Packaging
100mg
Price
$185
Updated
2024/03/01
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Docetaxel Chemical Properties,Usage,Production

Indications and Usage

Docetaxel is a taxane, antineoplastic, and anticancer drug used to treat locally advanced or metastatic breast cancer, even after the failure of cisplatin therapy. Its anti-tumor efficacy has been proven in in vitro tests to be 1.3-12 times that of paclitaxel. Clinical studies have shown that it is more effective than paclitaxel against anthracycline resistant breast cancer. Docetaxel is currently the most effective for the second-line treatment of anthracycline resistant breast cancer. In single cell therapy and combined chemotherapy for non-small cell lung cancer, it is one of the most effective drugs. It can be used for cancer of the uterus, and to study antibiotics, cell biology, cell signaling, neuroscience, apoptosis, and cell cycles. It is also used to study hair loss caused by docetaxel chemotherapy, and to prevent and treat small-cell lung cancer in patients contraindicated for chemotherapy. It is also used to investigate the roles of hypoxia-inducible factors-1α and 2α in androgen-insensitive prostate cancer cells.

Mechanisms of Action

Docetaxel promotes microtubule stabilization by promoting the assembly of microtubule dimers into microtubules, and preventing depolymerization, thus blocking cells in the G2 and M stages, and inhibiting the mitosis and proliferation of cancer cells. Its pharmacological effects are stronger than those of paclitaxel, with 3 times the intracellular concentration and long retention time within the cell, and twice the microtubule affinity; As a microtubule stabilizer and assembly promoter, its activity is twice that of paclitaxel; as a microtubule depolymerization inhibitor, its activity is also twice that of paclitaxel.

Pharmacokinetics

In a pharmacokinetic study in which cancer patients took 20-115 mg/m2, when the dose was 75-115 mg/m2 over a 1-2 hour intravenous drip, AUC was correlated with dose. Its pharmacokinetic characteristics conform to a three-compartmental pharmacokinetic model, with α, β, and γ half-lives of 4, 36, and 11.1 hours respectively. The concentration of the initial phase decreased rapidly, indicating that the drug was distributed to the peripheral compartment. The latter phase is partly due to the relatively slow elimination of the drug from the compartment. Within an hour of intravenous infusion of 100 mg/m2 of paclitaxel, the average peak was 3.7 ug/ml, AUC was 4.6 ug/ml•h, and total clearance and steady-state distribution were 21 L/h/m2 and 113 L. In vitro studies have shown that it has a plasma protein binding rate of more than 94-97%, and dexamethasone does not affect its protein binding. Docetaxel and its metabolites are mainly excreted from feces. Fecal and urinary excretion accounted for 75% and 6% of the dose, and only a small part is excreted in original form. In vitro studies have shown that docetaxel is metabolized by CYP3A4 isoenzymes, which can be inhibited by CYP3A4 inhibitors.

Clinical Research

Genotoxicity: docetaxel induced fractures in CHO-K1 cellular chromosome aberration tests and mouse bone marrow micronucleus tests, but no mutagenicity was observed in Ames tests and CHO/HGPRT gene mutation tests. Reproductive toxicity: no damage to fertility upon intravenous injection 0.3 mg/kg in mice (calculated by body surface area, about 1/50 of the recommended clinical dosage), but could cause reduction in testicular weight. This result is correlated with the results of repeatedly administering it to rats and dogs for 10 cycles (administered once every 21 days, for 6 months); when the intravenous doses were 5 mg/kg and 0.375 mg/kg respectively (converted by surface area, 1/3 and 1/15 of the recommended clinical dose, respectively), testicular atrophy and degeneration were observed. Similar effects were also observed in rats when given low doses more frequently. When rats and rabbits were given ≥0.3 mg/kg/day and 0.03 mg/kg/day (converted from surface area, respectively equivalent to 1/50 and 1/300 of the clinically recommended dose) during organogenesis), embryonic and fetal toxicity was observed (manifesting as intrauterine death, absorbed fetus, and fetal weight loss and delayed ossification). The above dose may case maternal toxicity.

Drug Interactions

In vitro studies have found that CYP3A4 inhibitors may interfere with the metabolism of docetaxel, so it should be used with caution in combination with such drugs (such as ketoconazole, erythromycin, cyclosporine, etc.)

Adverse Reactions

1. Bone marrow suppression: neutropenia is the most common adverse reaction is usually severe (under 500/mm3). Reversible and does not accumulate. Fever and infection associated with neutropenia have been reported in the literature. Anemia can be seen in most cases, with rare severe thrombocytopenia. 2. Allergic reactions: some patients experience severe allergic reactions, characterized by hypotension and bronchospasm, requiring interruption of treatment. The patient can return to normal immediately after discontinuing treatment. Mild allergic reactions, such as blush (with or without itchy erythema), chest tightness, back pain, difficulty breathing, drug fever, or chills, occur in some patients. 3. Skin reactions are usually manifest as erythema, mainly local rashes on hands and feet, sometimes also on arms, face, and chest, sometimes accompanied by itching. Rashes usually occur within a week of infusion, but can return before the next infusion. Severe symptoms, such as peeling after skin rash, occur rarely. Fingernail (or toenail) lesions may occur, characterized by hyperpigmentation or thinning, and sometimes pain and nail loss. 4. Fluid retention: edema, and a few reported cases of pleural effusion, ascites, pericardial effusion, increased capillary permeability, and weight gain. Lower limb fluid retention after four cycles of treatment or cumulative dose of 400mg/m2 may develop into systemic edema, and weight gain of 3kg or more. After discontinuing treatment, fluid retention gradually disappears. Corticosteroids should be given to prophylactically reduce fluid retention. 5. Gastrointestinal reactions such as nausea, vomiting, or diarrhea may occur. 6. There have been reports of neurotoxicity in clinical trials. 7. Cardiovascular adverse reactions such as hypotension, sinus tachycardia, palpitations, pulmonary edema, and hypertension may occur. 8. Other adverse reactions may include: hair loss, weakness, mucositis, joint and muscle pain, hypotension, and reaction at injection site. 9. Patients with normal liver function have also experienced elevated transaminase during treatment. For those with elevated bilirubin, the relationship with docetaxel is still unclear.

Contradictions

1 Patients with a history of severe allergic sensitivity to docetaxel or polysorbate-80.
2 Patients with white blood cell count under 1500/mm3.
3 Patients with severe liver damage.

Precautions

At present there is still insufficient strictly controlled clinical data for pregnant women. Patient who are a pregnant woman or become pregnant while using docetaxel should be informed of potential damage to the fetus and risk of miscarriage. Women who may become pregnant during treatment should use birth control. It is not clear whether docetaxel is excreted from human milk. Given that many drugs may be excreted from human milk, and that docetaxel may have serious adverse reactions for breastfeeding infants, mothers should stop breastfeeding before treatment.
The efficacy and safety of docetaxel in children has not yet been determined.

Description

Docetaxel, a semi-synthetic product from the taxoid family, was launched in 1995 first in South Africa and subsequently in several other markets for the treatment of ovarian, breast and non-small cell lung cancers. Like the naturally occurring antitumor agent paclitaxel, the first marketed taxoid, docetaxel promotes both the rate and extent of tubulin assembly into stable microtubules and inhibits their depolymerization. It acts as a mitotic spindle poison and induces a mitotic block in proliferating cells. This mechanism of action for taxoids is unique from other classes of anticancer agents. Docetaxel was reported to be twice as potent as paclitaxel in several in vitro protocols and also exhibit higher cytotoxicity. Clinical trials are on going for docetaxel for other types of tumors including pancreatic, gastric, head and neck cancers and soft tissue sarcomas.

Chemical Properties

Off-white Cryst

Originator

Rhone-Poulenc Rorer (France)

Uses

antineoplastic;binds to microtubules

Uses

Docetaxel is a semisynthetic analog of taxol that inhibits microtubule disassembly (IC50 = 0.2 μM) and inhibits cell replication (IC50 = 0.13 μM). It has proven more effective than taxol in preventing the proliferation of cancer cells. Docetaxel has applications in breast cancer and hormone-refractory prostate cancer. This product is intended for research applications.

Uses

Docetaxel used to treat variety of cancers (Lung, Breast, Prostate). It is a second-generation cytotoxic antimicrotubule agent and is mostly used in the pharmaceutical industry.

Definition

ChEBI: A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.

Manufacturing Process

Taxol, a material occurring in nature, and extracted from Taxus brevifolia (i.e. the Pacific yew tree). It consists of the A, B and C variants. Taxol is not water soluble, thereby complicating its delivery in vivo for therapeutic purposes.
A sample of Taxol (14.7 g, 17 mmol) was dissolved in pyridine (150 mL) and chlorotriethylsilane (23.03 g, 147 mmol) was added. The reaction was stirred at 25°C under N2. After 20 hours the reaction appeared complete by TLC analysis (7% MeOH/CH2Cl2). The mixture was concentrated to remove the pyridine. The residue was dissolved in CH2Cl2 and washed with water, 10% CuSO4, NaHCO3 and brine successively. The organic layer was dried over MgSO4, and concentrated to yield 20.89 g of the crude 2,7'-bis(triethylsilyl) Taxol. A portion of crude 2',7-bis(triethylsilyl) Taxol (14.50 g, 13.4 mmol) was dissolved in dry THF (150 mL). Zirconocene chloride hydride (7.75 g, 30.2 mmol) was added. The reaction was stirred at 25°C under N2. After 20 hours the reaction appeared complete by TLC analysis. The mixture was poured intocold hexanes, and the resulting precipitated Zr complexes were filtered off. The solution was concentrated to yield 17 g of the crude 2,7'-bis(triethylsilyl) Taxol imine. A portion of crude 2',7-bis(triethylsilyl) Taxol imine (8.36 g) was dissolved in 1% HCl/EtOH (180 mL) and the reaction was stirred at 25°C for 20 hours. The reaction appeared complete by TLC analysis. The mixture was poured into 800 mL of water and washed with hexane (180 mL times 3). The aqueous layer was neutralized with NaHCO3 to pH=7.0. The product was extracted with CH2Cl2. The organic layer was removed and concentrated to a solid. Silica gel chromatography (5% MeOH/CH2Cl2) yielded Taxol primary amine (2.41 g, 52% overall yield based on 5 g of Taxol used). Melting point 160°C-162°C.
A sample of Taxol primary amine (100 mg, 0.13 mmol) was dissolved in CH2Cl2 (10 mL) and HCl (15 mM in Et2O; 10 ml, 150 mmol) was added. The reaction was stirred at 25°C for 2 minutes. The mixture was concentrated to remove the solvents. The residue was redissolved in CH2Cl2 and precipitated in hexane. Filtration yielded 85 mg of Taxol PA (PA-primary amine) HCl (83%). Melting point 65°C. A sample of Taxol PA HCl (50 mg, 0.064 mmol) was dissolved in 0.5 ml of water. It was neutralized to pH 7.0 by addition of saturated NaHCO3, followed by extraction with CH2Cl2. The organic layer was concentrated and chromatographed (3% MeOH/CH2Cl2was used as mobile phase) to yield 30 mg of Taxol primary amine (63% yield). The 1H NMR and LRMS data agree well with a standard sample of Taxol primary amine.
Trimethylsilyl- and trichlorethoxycarbonyl-protecting group can be used. A mixture of impure Taxol A, B, C can be converted Taxol primary amine, which then can be converted to Taxol A or docetaxel.

brand name

Taxotere (Sanofi Aventis).

Therapeutic Function

Antitumor

Hazard

A poison. Human systemic effects.

Clinical Use

Antineoplastic agent:
Treatment of breast cancer, prostate cancer and non-small cell lung cancer unresponsive to alternative therapies, also gastric adenocarcinoma, squamous cell carcinoma of head and neck

Drug interactions

Potentially hazardous interactions with other drugs
Antibacterials: concentration possibly increased by clarithromycin - avoid or reduce docetaxel dose
Antifungals: concentration possibly increased by itraconazole and voriconazole - avoid or reduce docetaxel dose.
Antipsychotics: avoid with clozapine - increased risk of agranulocytosis.
Antivirals: concentration possibly increased by indinavir, ritonavir and saquinavir avoid or reduce docetaxel dose.
Ciclosporin: possibly inhibits metabolism of ciclosporin; bioavailability of docetaxel increased by ciclosporin.

Metabolism

A study of [14C]-docetaxel has been conducted in three cancer patients. Docetaxel was eliminated in both the urine and faeces following cytochrome P450 3A4-mediated oxidative metabolism of the tert-butyl ester group, within seven days, the urinary and faecal excretion accounted for about 6% and 75% of the administered radioactivity, respectively. About 80% of the radioactivity recovered in faeces is excreted during the first 48 hours as one major inactive metabolite and 3 minor inactive metabolites and very low amounts of unchanged medicinal product.

storage

Store at +4°C

References

1) Fabbri et al. (2008), Mitotic catastrophe and apoptosis induced by docetaxel in hormone-refractory prostate cancer cells; J. Cell Physiol, 217 494 2) Dosso and Berthold (2008), Docetaxel in the management of prostate cancer: current standard of care and future directions; Expert Opin. Pharmacother, 9 1969 3) Homma et al. (2008), RPN2 gene confers docetaxel resistance in breast cancer; Nat. Med., 14 939 4) Kars et al. (2008), Reversal of Multidrug Resistance by Synthetic and Natural Compounds in Drug-Resistant MCF-7 Cell Lines; Chemotherapy, 54 194 5) Wallin et al. (2012), GDC-0941, A Novel Class I Selective PI3K Inhibitor, Enhances the Efficacy of Docetaxel in Human Breast Cancer Models by Increasing Cell Death In vitro and In vivo; Clin Cancer Res.,?18 3901 6) Heinemann et al. (2011), Synergistic effects of oncolytic reovirus and docetaxel chemotherapy in prostate cancer; BMC Cancer, 11 221

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Docetaxel Suppliers

Wuxi Dexin Biomedical Technology Co., Ltd
Tel
13812081281 16789019998
Email
13812081281@163
Country
China
ProdList
5
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58
Wuhan Ying Yuan Bei Biological Limited
Tel
13349903920 13349903920
Email
1540154086@qq.com
Country
China
ProdList
2995
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58
Nanjing Digger Medical Technology Co. Ltd.
Tel
025-025-51191215 18013836722
Fax
025-51191215
Email
2399235533@qq.com
Country
China
ProdList
4933
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58
Tongchuang Pharma(Suzhou). Co., Ltd.
Tel
0512-63263366 18912765016
Fax
0512-6326 3366
Email
tongtf110@sina.com
Country
China
ProdList
971
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62
Nanjing jingzhu bio-technology Co.,Ltd
Tel
025-52794219 13140719234
Email
2498234449@qq.com
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China
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74
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58
Jinan Good Medical &Technology Ltd Co.,
Tel
+86-0086-531-55562571,18953105926 +86-13553167512
Email
935170726@qq.com
Country
China
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73
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Cangzhou Enke Pharma-tech Co., Ltd.
Tel
0317-5296180 15533709196
Fax
0317-5106596
Email
sale@enkepharma.com
Country
China
ProdList
1898
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55
Minglong (Xianning) Pharmaceutical Co., LTD
Tel
155-7155-6913 15571556913
Email
354024111@qq.com
Country
China
ProdList
2596
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Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
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55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
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View Lastest Price from Docetaxel manufacturers

BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Docetaxel Anhydrous 114977-28-5
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-10-11
Hangzhou Hyper Chemicals Limited
Product
Docetaxel 114977-28-5
Price
US $0.00-0.00/Gram
Min. Order
10Gram
Purity
EP
Supply Ability
2kg
Release date
2024-04-25
Hangzhou Hyper Chemicals Limited
Product
Docetaxel 114977-28-5
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
USP, BP, EP
Supply Ability
5,000KG
Release date
2024-06-28

114977-28-5, DocetaxelRelated Search:


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