CN105395477A - Docetaxel injection and preparation method thereof - Google Patents
Docetaxel injection and preparation method thereof Download PDFInfo
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- CN105395477A CN105395477A CN201510847067.3A CN201510847067A CN105395477A CN 105395477 A CN105395477 A CN 105395477A CN 201510847067 A CN201510847067 A CN 201510847067A CN 105395477 A CN105395477 A CN 105395477A
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
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- A—HUMAN NECESSITIES
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- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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Abstract
The invention relates to a docetaxel injection. The docetaxel injection is prepared from docetaxel, lipoic acid, medicinal absolute ethyl alcohol and polyethylene glycol stearate. The lipoic acid is added into the docetaxel injection, and stability of double bonds in the docetaxel is facilitated. In addition, the lipoic acid has the anti-oxidation effect and can slow down product degradation. In the injection preparation process, compared with an existing technology, the medicinal absolute ethyl alcohol is not removed. During clinical use, the step of adding ethyl alcohol for dilution is omitted, and use is safer, more convenient and faster. The four components in the injection are compounded for use, the docetaxel injection meets the USP35 docetaxel injection standard within the two-year life time, and the clinical application is safer.
Description
Technical field
The present invention relates to injection technical field, particularly relate to a kind of docetaxel injection and preparation method thereof.
Background technology
Docetaxel injection is applicable to the late period of chemotherapy failure in advance or the treatment of metastatic breast cancer, and docetaxel injection is also applicable to late period of chemotherapy failure based on cisplatin or the treatment of Metastatic Nsclc.Docetaxel injection can only be used for intravenous drip.
The adjuvant that docetaxel injection commercially available prod uses is citric acid and Tween 80, and uses citric acid to regulate the pH value of docetaxel injection to be 3-4.5; The solvent of commercially available prod is anhydrous alcohol for medical use, and in the preparation process of docetaxel injection, adopts the method first removing dehydrated alcohol sterilizing again.
Tween 80 has stimulation to human body, easily causes untoward reaction, and clinical application is safe not; In addition, not containing dehydrated alcohol in commercially available finished product, during Clinical practice, need first to dilute medicament with ethanol solution, and then after adding glucose solution or normal saline, could infuse to human body, operate more loaded down with trivial details, and add the risk of drug contamination.In addition, commercially available prod all adopts filtration sterilization method, and this degerming mode risk is larger.
Summary of the invention
The present invention is directed to the defect and deficiency that exist in prior art, provide a kind of docetaxel injection, described docetaxel injection is prepared from by comprising following component: docetaxel, thioctic acid, anhydrous alcohol for medical use, polyglycol distearate.
Present inventor finds unexpectedly, and above-mentioned four kinds of composite uses of component, obtained docetaxel injection has better safety.
Thioctic acid is that one is present in mitochondrial coenzyme, similar vitamin, can eliminate accelerated ageing and the free radical caused a disease.Thioctic acid enters cell in vivo after intestinal absorption, has fat-soluble and water miscible characteristic concurrently, therefore can go everywhere without any hindrance here at whole body, arrive any one cell area, provides human body comprehensive usefulness, is the fat-soluble and water miscible universal antioxidant of tool.In docetaxel injection, add thioctic acid, be conducive to the stable of double bond in docetaxel, in addition, thioctic acid has antioxidation, can slow down the degraded of product.
Polyglycol distearate, being called for short HS-15, is a kind of solubilizing agent, adopts polyglycol distearate to replace existing Tween 80, can reduce the zest to human body of medicine, farthest ensure drug safety.
Preferably, the invention provides a kind of docetaxel injection, in 100mL injection, comprise 2-8g docetaxel, 0.25-1g thioctic acid.
Further preferably, the invention provides a kind of docetaxel injection, in 100mL injection, comprise 2g docetaxel, 0.25-1g thioctic acid.
Preferably, the invention provides a kind of docetaxel injection, in 100mL injection, comprise 2-8g docetaxel, 0.25-1g thioctic acid, 50mL anhydrous alcohol for medical use, 50mL polyglycol distearate.
Further preferably, the invention provides a kind of docetaxel injection, in 100mL injection, comprise 2g docetaxel, 0.5g thioctic acid, 50mL anhydrous alcohol for medical use, 50mL polyglycol distearate.
Adopt the docetaxel injection that any one formula above-mentioned prepares, its pH value is within the scope of the former pH value 3-4.5 grinding product (trade name: taxotere).
Invention also provides the preparation method of any one docetaxel injection above-mentioned, be specially: use anhydrous alcohol for medical use to be dissolved by thioctic acid, obtain thioctic acid alcoholic solution; Docetaxel is dissolved in described thioctic acid alcoholic solution, obtains pastille thioctic acid alcoholic solution, for subsequent use; By polyglycol distearate 50-60 DEG C of heating for dissolving, then joined in described pastille thioctic acid alcoholic solution, mix homogeneously, obtain mixture, 0.1%-0.3% (w/v) active carbon is added in described mixture, stirring and adsorbing 10-20min, filters decarburization and namely obtains intermediate; Described intermediate is poured in bottle, gland, then adopts excessive sterilization to carry out sterilizing, after sterilizing, namely obtain docetaxel injection.
Preferably, the addition of described active carbon is 0.1%.That is, every 100mL docetaxel injection adds 0.1g active carbon.
Preferably, the condition of described excessive sterilizing is: at 121 DEG C, sterilizing 12min.
Further preferably, described excessive sterilizing is carried out in water-bath cabinet, namely best, is placed by the docetaxel injection prepared with water-bath cabinet, under 121 DEG C of conditions, and sterilizing 12min.
The present invention is when preparing docetaxel injection, do not remove etoh solvent, inventor is through study on the stability, find with dehydrated alcohol to be solvent, and in dehydrated alcohol, add thioctic acid be conducive to the stable of double bond in docetaxel, in addition, thioctic acid also has the effect of non-oxidizability, effectively can slow down the degraded of product under the combined effect of thioctic acid and HS-15.Therefore, do not remove ethanol and not only simplify preparation process, in addition, the docetaxel injection be prepared into, when Clinical practice, directly can add the glucose solution of 5% or the normal saline solution of 0.9%, without the need to first with ethanol water dilution, uses more convenient.
The docetaxel injection adopting formula of the present invention and process to prepare product within 2 years effect phases meets the standard of USP35 docetaxel injection, and clinical practice is safer.
Detailed description of the invention
Following examples for illustration of the present invention, but are not used for limiting the scope of the invention.
Embodiment 1
A kind of docetaxel injection, described docetaxel injection is prepared from by following component: docetaxel 20g, thioctic acid 5g, anhydrous alcohol for medical use 500mL, polyglycol distearate 500mL.
Embodiment 2
A kind of docetaxel injection, described docetaxel injection is prepared from by following component: docetaxel 2g, thioctic acid 1g, anhydrous alcohol for medical use 50mL, polyglycol distearate 50mL.
Embodiment 3
A kind of docetaxel injection, described docetaxel injection is prepared from by following component: docetaxel 2g, thioctic acid 0.25g, anhydrous alcohol for medical use 50mL, polyglycol distearate 50mL.
Embodiment 4
A kind of docetaxel injection, described docetaxel injection is prepared from by following component: docetaxel 2g, thioctic acid 0.5g, anhydrous alcohol for medical use 50mL, polyglycol distearate 50mL.
Embodiment 5
A kind of docetaxel injection, described docetaxel injection is prepared from by following component: docetaxel 40g, thioctic acid 5g, anhydrous alcohol for medical use 500mL, polyglycol distearate 500mL.
Embodiment 6
A kind of docetaxel injection, described docetaxel injection is prepared from by following component: docetaxel 80g, thioctic acid 5g, anhydrous alcohol for medical use 500mL, polyglycol distearate 500mL.
Embodiment 7
The present embodiment provides the preparation method of the docetaxel injection described in embodiment 1, is specially: take 5g thioctic acid, adds 500mL anhydrous alcohol for medical use stirring and dissolving, obtains thioctic acid alcoholic solution; In described thioctic acid alcoholic solution, add 20g docetaxel, abundant stirring and dissolving, obtain pastille thioctic acid alcoholic solution; The polyglycol distearate of 500mL50-60 DEG C of heating for dissolving is added in described pastille thioctic acid alcoholic solution, fully mix, add active carbon 1g wherein, stir 15min, use 0.45 μm of membrane filtration decarburization; Fill is in 3mL cillin bottle, and button plug, gland, at 121 DEG C of sterilizing 12min, to obtain final product, and the docetaxel injection prepared after testing its pH value is 3.2-3.5.
Embodiment 8
The present embodiment provides the preparation method of the docetaxel injection described in embodiment 2, comprises the steps: to take 1g thioctic acid, adds 50mL anhydrous alcohol for medical use stirring and dissolving, obtains thioctic acid alcoholic solution; In described thioctic acid alcoholic solution, add 2g docetaxel, abundant stirring and dissolving, obtain pastille thioctic acid alcoholic solution; The polyglycol distearate of 50mL50-60 DEG C of heating for dissolving is added in described pastille thioctic acid alcoholic solution, fully mix, add active carbon 0.1g wherein, stir 15min, use 0.45 μm of membrane filtration decarburization; Fill, button plug, gland, at 121 DEG C of sterilizing 12min, to obtain final product, and the docetaxel injection prepared after testing its pH value is 3.12.
Embodiment 9
The present embodiment provides the preparation method of the docetaxel injection described in embodiment 3, and its preparation method is with embodiment 7, and difference is only that the amount of the thioctic acid added is 0.25g, and the docetaxel injection prepared after testing its pH value is 4.11.
Embodiment 10
The present embodiment provides the preparation method of the docetaxel injection described in embodiment 4, and its preparation method is with embodiment 7, and difference is only that the amount of the thioctic acid added is 0.5g, and the docetaxel injection prepared after testing its pH value is 3.47.
Embodiment 11
The present embodiment provides the preparation method of the docetaxel injection described in embodiment 5, its preparation method is with embodiment 1, difference is only that the amount of the thioctic acid added is 5g, and the amount of the docetaxel added is 40g, and the docetaxel injection prepared after testing its pH value is 3.2-3.8.
Embodiment 12
The present embodiment provides the preparation method of the docetaxel injection described in embodiment 6, its preparation method is with embodiment 1, difference is only that the amount of the thioctic acid added is 5g, and the amount of the docetaxel added is 80g, and the docetaxel injection prepared after testing its pH value is 3.2-3.8.
Comparative example 1
Take 2.5g thioctic acid, add 250ml anhydrous alcohol for medical use stirring and dissolving.Add 10g docetaxel, abundant stirring and dissolving.Add the polyglycol distearate of 250ml50-60 DEG C of heating for dissolving, fully mix.Add active carbon 0.5g and stir 15min, 0.45 μm of membrane filtration decarburization.Fill, puts in freeze dryer and removes ethanol, button plug, gland.At 121 DEG C of sterilizing 12min, to obtain final product.
Comparative example 2
Take 2.5g citric acid, add 250ml anhydrous alcohol for medical use stirring and dissolving.Add 10g docetaxel, abundant stirring and dissolving.Add the polyglycol distearate of 250ml50-60 DEG C of heating for dissolving, fully mix.Add active carbon 0.5g and stir 15min, 0.45 μm of membrane filtration decarburization.Fill, button plug, gland.At 121 DEG C of sterilizing 12min, to obtain final product.
Comparative example 3
This comparative example provides the preparation method of the docetaxel injection of market product Sanofi-Aventis drugmaker, be specially: get 20g docetaxel, add absolute ethyl alcohol and stirring to dissolve, the needle-use activated carbon adding 0.1% adsorbs 10 minutes, 0.45 μm of membrane filtration decarburization.Add 540g Tween 80, mix homogeneously, add anhydrous citric acid adjust ph to 3.4-4.1, dehydrated alcohol is settled to 1000ml, stirs 10 minutes.Fill, puts in freeze dryer and removes ethanol, jumps a queue, gland.At 121 DEG C of sterilizing 12min, to obtain final product.
Following table 1 lists impurity and the content situation that docetaxel injection that embodiment 1 and comparative example 1-3 prepare is placed 24 months.
The docetaxel injection of table 1 embodiment 1 and comparative example 1-3 places 24 months impurity situations
Known by upper table data, adding polyglycol distearate ratio, to add Tween 80 more stable, and adding thioctic acid ratio, to add citric acid sample impurity degradation less, and content is higher.And it is substantially suitable with content with the sample impurity not volatilizing ethanol to volatilize ethanol.
Wherein, the sample of above-mentioned comparative example and embodiment adopts the detection method of USP35 docetaxel injection standard to detect, and concrete detection method is as follows:
Be chromatographic column filler (4.6mm × 150mm, 3.5 μm) with octadecylsilane chemically bonded silica, being mobile phase A with water, take acetonitrile as Mobile phase B, and flow velocity is 1.2ml/min, and determined wavelength is 232nm, and column temperature 45 DEG C, carries out gradient elution by table 2.Get docetaxel reference substance, impurity A, impurity B, impurity C, impurity D, add acetonitrile-Acetic Acid-Water (100:0.1:100) dissolution with solvents and dilute the solution made containing 0.2mg docetaxel, 1 μ g impurity A, impurity B, impurity C, impurity D in every 1ml, as system suitability solution.Get 20 μ l injection liquid chromatographies, record chromatogram, the separating degree between docetaxel and impurity A should be not less than 3.5.
Table 2 gradient elution specifying information
| Time (minute) | Mobile phase A (%) | Mobile phase B (%) |
| 0 | 72 | 28 |
| 9.0 | 72 | 28 |
| 39.0 | 28 | 72 |
| 39.1 | 0 | 100 |
| 49.0 | 0 | 100 |
| 49.1 | 72 | 28 |
| 60 | 72 | 28 |
Wherein, impurity A in table 1, impurity B, impurity C, the molecular formula of impurity D is as follows: impurity A: 5 β, 20-epoxy-1,7 β, 10 β-trihydroxy-9-oxotax-11-ene-2 α, 4,13 α-triyl4-acetate13-[(2R, 3S)-3-[[(1,1-dimethylethoxy) carbonyl] amino]-2-hydroxy-3-phenylpropanoate] 2-[(2E)-2-methylbut-2-enoate] (2-O-desbenzoyl-2-O-tiglyldocetaxel)
Impurity B: 5 β, 20-epoxy-1,7 β-dihydroxy-9,10-dioxotax-11-ene-2 α, 4,13 α-triyl4-acetate2-benzoate13-[(2R, 3S)-3-[[(1,1-dimethylethoxy) carbonyl] amino]-2-hydroxy-3-phenylpropanoate] (10-deoxy-10-oxodocetaxel)
Impurity C:5 β, 20-epoxy-1,7 α, 10 β-trihydroxy-9-oxotax-11-ene-2 α, 4,13 α-triyl4-acetate2-benzoate13-[(2R, 3S)-3-[[(1,1-dimethylethoxy) carbonyl] amino]-2-hydroxy-3-phenylpropanoate] (7-epi-docetaxel)
Impurity D:
5β,20-epoxy-1,7α-dihydroxy-9,10-dioxotax-11-ene-2α,4,13α-triyl4-acetate2-benzoate13-[(2R,3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-3-phenylpropanoate](10deoxy-10-oxo-7-epi-docetaxel)
Although above with general explanation, detailed description of the invention and test, the present invention is described in detail, and on basis of the present invention, can make some modifications or improvements it, this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (8)
1. a docetaxel injection, is characterized in that, described docetaxel injection is prepared from by comprising following component: docetaxel, thioctic acid, anhydrous alcohol for medical use, polyglycol distearate.
2. docetaxel injection according to claim 1, is characterized in that: in 100mL injection, comprises 2-8g docetaxel, 0.25-1g thioctic acid.
3. docetaxel injection according to claim 1 and 2, is characterized in that: in 100mL injection, comprises 2g docetaxel, 0.25-1g thioctic acid.
4. docetaxel injection according to claim 1, is characterized in that: in 100mL injection, comprises 2-8g docetaxel, 0.25-1g thioctic acid, 50mL anhydrous alcohol for medical use, 50mL polyglycol distearate.
5. docetaxel injection according to claim 4, is characterized in that: in 100mL injection, comprises 2g docetaxel, 0.5g thioctic acid, 50mL anhydrous alcohol for medical use, 50mL polyglycol distearate.
6. prepare the method for the arbitrary described docetaxel injection of claim 1-5, it is characterized in that: use anhydrous alcohol for medical use to be dissolved by thioctic acid, obtain thioctic acid alcoholic solution; Docetaxel is dissolved in described thioctic acid alcoholic solution, obtains pastille thioctic acid alcoholic solution, for subsequent use; By polyglycol distearate 50-60 DEG C of heating for dissolving, then joined in described pastille thioctic acid alcoholic solution, mix homogeneously, obtain mixture, 0.1%-0.3% (w/v) active carbon is added in described mixture, stirring and adsorbing 10-20min, filters decarburization and namely obtains intermediate; Described intermediate is poured in bottle, gland, then adopts excessive sterilization to carry out sterilizing, after sterilizing, namely obtain docetaxel injection.
7. preparation method according to claim 6, is characterized in that: the addition of described active carbon is 0.1%.
8. preparation method according to claim 6, is characterized in that: the condition of described excessive sterilization is: at 121 DEG C, sterilizing 12min.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366052A (en) * | 2016-08-16 | 2017-02-01 | 江苏红豆杉药业有限公司 | Separating and purifying method for impurities in semi-synthesized docetaxel |
| CN107970210A (en) * | 2017-12-05 | 2018-05-01 | 湖北九州通中加医药有限公司 | A kind of non-pre- dissolubility docetaxel injection |
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| WO2011049650A1 (en) * | 2009-10-19 | 2011-04-28 | Scidose Llc | Docetaxel formulations with lipoic acid |
| CN102988285A (en) * | 2012-12-13 | 2013-03-27 | 哈药集团技术中心 | Docetaxel injection composition and preparation method thereof |
| CN103893111A (en) * | 2012-12-30 | 2014-07-02 | 天津万亚通科技有限公司 | Quickly dissolvable injection pharmaceutical preparation |
| CN104606135A (en) * | 2015-01-22 | 2015-05-13 | 李宏 | Docetaxel-containing composition and preparation method thereof |
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2015
- 2015-11-26 CN CN201510847067.3A patent/CN105395477A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011049650A1 (en) * | 2009-10-19 | 2011-04-28 | Scidose Llc | Docetaxel formulations with lipoic acid |
| CN102988285A (en) * | 2012-12-13 | 2013-03-27 | 哈药集团技术中心 | Docetaxel injection composition and preparation method thereof |
| CN103893111A (en) * | 2012-12-30 | 2014-07-02 | 天津万亚通科技有限公司 | Quickly dissolvable injection pharmaceutical preparation |
| CN104606135A (en) * | 2015-01-22 | 2015-05-13 | 李宏 | Docetaxel-containing composition and preparation method thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366052A (en) * | 2016-08-16 | 2017-02-01 | 江苏红豆杉药业有限公司 | Separating and purifying method for impurities in semi-synthesized docetaxel |
| CN106366052B (en) * | 2016-08-16 | 2019-04-23 | 江苏红豆杉药业有限公司 | The isolation and purification method of impurity in a kind of semi-synthetic Docetaxel |
| CN107970210A (en) * | 2017-12-05 | 2018-05-01 | 湖北九州通中加医药有限公司 | A kind of non-pre- dissolubility docetaxel injection |
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Application publication date: 20160316 |