CN1994279A - Preparation process of irinotecan hydrochloride liposome for injection - Google Patents
Preparation process of irinotecan hydrochloride liposome for injection Download PDFInfo
- Publication number
- CN1994279A CN1994279A CN 200610105371 CN200610105371A CN1994279A CN 1994279 A CN1994279 A CN 1994279A CN 200610105371 CN200610105371 CN 200610105371 CN 200610105371 A CN200610105371 A CN 200610105371A CN 1994279 A CN1994279 A CN 1994279A
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- liposome
- hydrochloride
- solution
- preparation
- irinotecan
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Abstract
The invention relates to a method for producing injection alcaine liposome, wherein it comprises that: dissolving liposome mixture into organic solvent; mixing liposome solution with buffer solution; compressing it via panlite film into uniform diameter, filtering out the organic solvent, to obtain blank liposome, adding alcaine solution, using pH adjuster to adjust pH value to alkali, to prepare the carrier liposome; or dissolving phosphatide, cholestrin and alcaine into organic solvent; atomizing and drying, vacuum drying or other method to remove organic solvent, to film the liposome; adding hydrating solution with drug to form carrier liposome. The inventive liposome has 50-200nm diameter and more than 95% package rate, with stable property.
Description
Technical field
The present invention relates to a kind of preparation method of liposome, be specifically related to a kind of preparation method of hydrochloride for injection irinotecan liposome.
Background technology
Irinotecan hydrochloride is the semi-synthetic derivant of camptothecine.Camptothecine can combine with topoisomerase I specifically, and the latter induces the reversibility single-strand break, thereby the dna double chain structure is untwisted; Irinotecan metabolite SN-38 can combine with topoisomerase I-DNA complex, thereby stops the connection again of fracture strand.Existing research prompting, the cytotoxicity of irinotecan is owing in the DNA building-up process, and replicative enzyme and topoisomerase I-DNA one SN-38 three complex interact, thereby cause the dna double chain interruption.Mammalian cell can not be repaired this dna double chain interruption effectively.Reach the purpose of killing tumor cell thus.
Irinotecan can be water-soluble, but its metabolite irinotecan hydrochloride just is its active component, and in metabolic process, can produce serious adverse effects, such as: tardy property diarrhoea, feel sick, vomiting, and can cause neutrophilic granulocyte to reduce, dyspnea, muscle contraction, spasm and paraesthesia etc., these untoward reaction have seriously influenced clinical use.
Summary of the invention
The objective of the invention is for overcoming disadvantages of background technology, and a kind of preparation method that improves the irinotecan hydrochloride curative effect and reduce the hydrochloride for injection irinotecan liposome of its toxic and side effects is provided.
To achieve these goals, the technical solution used in the present invention is: a kind of preparation method of hydrochloride for injection irinotecan liposome, it is characterized in that this method is by being dissolved in lipid mixture in the organic solvent, to the solution clear, get lipid soln, lipid soln mixes in gradient pump according to 1: 1～8 volume ratios with buffer, mixed blank liposome is by the homogenizer homogenizing or be covered with the unified particle diameter of squeezer extruding of polycarbonate membrane, effusive liposome mixed solution is immediately by the ultrafilter ultrafiltration, remove organic solvent, the middle buffer that constantly replenishes, obtain blank liposome, add irinotecan hydrochloride solution, and regulate pH value to alkalescence, make drug-loaded liposome with the agent of liposome pH regulator; Perhaps lipid mixture and irinotecan hydrochloride are dissolved in the organic solvent, remove organic solvent, make the lipid film forming, form drug-loaded liposome by the hydration solution hydration that adds hydrochloric irinotecan by spray drying or vacuum drying.
Described irinotecan hydrochloride consumption and blank liposome mole ratio are: 0.001～1: 1; Described organic solvent is the single solvent in chloroform, methanol, ethanol, the tert-butyl alcohol, isopropyl alcohol and the n-butyl alcohol, or the mixed solvent made of two or more solvent wherein; Described buffer is the citrate buffer solution of pH value between 3.3～8, or the tartaric acid buffer of pH value between 3.3～13, or the organic acid buffer of other pH value between 2.5～10; The aperture of described polycarbonate membrane is 20～400nm, 1～10 layer of the number of plies; The raw material that contains following molar percentage in the described lipid mixture: phosphatidylcholine 20～80%; Sphingomyelins 0～30%; Cardiolipin 0～30%; Cholesterol 20～80%; Polyethyleneglycol derivative 0～10%; Described phosphatidylcholine is egg yolk lecithin phatidylcholine, S-PC or hydrogenated soya phosphatide phatidylcholine; Polyethyleneglycol derivative is HSPE-S-mPEG
2000Or DSPE-PEG
2000The agent of described liposome pH regulator is Na
2CO
3Solution, NaOH solution, NH
4Cl solution, NaHCO
3Solution or Ca (OH)
2Solution; Described adjusting pH value to the pH scope that alkalescence refers to is 7.5～3.5.
Gradient pump is used to be mixed in proportion lipid soln and buffer preparation blank liposome, and squeezer is used to control the particle diameter of blank liposome, and ultrafilter is used for removing the organic solvent of blank liposome and liposome is concentrated to suitable concentration.
The present invention is by the hydrochloride for injection irinotecan liposome of modern liposome technology preparation, this liposome is the lipid complex that is formed by lipids such as phosphatidylcholine, sphingomyelins, cholesterol and polyethyleneglycol derivative and irinotecan hydrochloride, this complex can change irinotecan pharmacokinetics in vivo, thereby changes its action effect and toxic characteristic.
The present invention compared with prior art has the following advantages: the method applied in the present invention is encapsulated in irinotecan hydrochloride in the liposome folliculus, avoided irinotecan hydrochloride in metabolic process, to produce serious adverse effects, improved the curative effect of irinotecan hydrochloride and reduced its toxic and side effects; According to the hydrochloride for injection irinotecan liposome of this explained hereafter, particle diameter is between 50～200nm, and envelop rate reaches more than 95%, stable in properties, and determined curative effect, safe and reliable, be suitable for suitability for industrialized production.
The specific embodiment
The present invention is described in further detail below in conjunction with embodiment.
Embodiment 1: the laboratory lab scale
(1) membrane process prepares the irinotecan hydrochloride liposome
Prescription:
Egg yolk lecithin phatidylcholine 2.12g (2.789473684mmol)
Cardiolipin 12.00g (15mmol)
Cholesterol 5.88g (15.23316062mmol)
Chloroform 13.00mL
200mL
Preparation method: egg yolk lecithin phatidylcholine, cardiolipin, cholesterol and irinotecan hydrochloride are dissolved in the organic solvent chloroform to the solution clear, the Rotary Evaporators evacuation is removed the organic solvent chloroform and is made the lipid film forming, the sucrose solution 200mL hydration of irinotecan hydrochloride 1.5g, cross 400nm, 200nm respectively, the 100nm film is unified particle diameter, make drug-loaded liposome, lyophilizing is stored in 2～4 ℃.
The preparation of embodiment 2:pH gradient method
(1) preparation of blank liposome
Prescription:
Phosphatidylcholine 10.605g (13.95394737mmol)
Cholesterol 4.395g (11.38601036mmol)
Ethanol 24.75mL
Tert-butyl alcohol 24.75mL
Citrate buffer solution is an amount of
150mL
Preparation method: phosphatidylcholine and cholesterol are dissolved in the mixed solvent of the ethanol and the tert-butyl alcohol 1: 1 (v/v) to the solution clear.Lipid soln and citrate buffer solution are mixed with pro-liposome according to 1: 4 volume ratio in gradient pump.Gradient pump links to each other with squeezer, the polycarbonate membrane of 5 100nm of squeezer middle berth.Mixed pro-liposome is by the unified particle diameter of squeezer extruding, effusive liposome mixed solution is immediately by the ultrafilter ultrafiltration, middle citrate buffer solution (pH=4.0) 750mL that constantly replenishes concentrates liposome then to aimed concn (100mg film material/mL), promptly get blank liposome.
(2) preparation of alkali injection
Weighing sodium carbonate 10.5g adds injection water 225mL dissolving, and filtration sterilization promptly gets the alkali injection.
(3) medicine carrying
The 6g irinotecan hydrochloride is dissolved in the dilute hydrochloric acid that 300mL contains the water of 10% (Wt/Wt) sucrose or 0.01mol/L, adds in the blank liposome of (1) step preparation, add the aqueous slkali of (2) step preparation and pH value is transferred to 7.5, stirring and evenly mixing leaves standstill 20min, degerming, packing, promptly.
Embodiment 3: amplify production technology
(1) preparation of blank liposome
Prescription:
Cardiolipin 211.8g (278.6842105mmol)
Cholesterol 88.2g (228.4974093mmol)
Ethanol 495mL
Tert-butyl alcohol 495mL
Citrate buffer solution 3000mL
3000mL
Preparation method: cardiolipin and cholesterol are dissolved in the mixed solvent of the ethanol and the tert-butyl alcohol 1: 1 (v/v) to the solution clear.Lipid soln and citrate buffer solution are mixed with pro-liposome according to 1: 4 volume ratio in gradient pump.Gradient pump links to each other with squeezer, the polycarbonate membrane of 5 100nm of squeezer middle berth.Mixed pro-liposome is by the unified particle diameter of squeezer extruding, effusive liposome mixed solution is immediately by the ultrafilter ultrafiltration, middle citrate buffer solution (pH=4.0) 15L that constantly replenishes concentrates liposome then to aimed concn (100mg film material/mL), promptly get blank liposome.
(2) preparation of alkali injection
Weighing sodium carbonate 84g adds injection water 1800mL dissolving, and filtration sterilization promptly gets the alkali injection.
(3) medicine carrying
The 24g irinotecan hydrochloride is dissolved in the dilute hydrochloric acid that 1200mL contains the water of 10% (Wt/Wt) sucrose or 0.01mol/L, add in the blank liposome of (1) step preparation, the aqueous slkali that adds the preparation of (2) step transfers to 7.5 with pH value, stirring and evenly mixing leaves standstill 20min, degerming, with proppant sucrose, packing, lyophilizing, promptly.
Embodiment 4:pH gradient method prepares long circulating liposomes
(1) preparation of blank liposome
Prescription:
Phosphatidylcholine 8.773g (11.543421.5mmol)
Cholesterol 3.232g (8.373056995mmol)
HSPE-S-mPEG
2000 2.995g(1.047202797mmol)
Ethanol 24.75mL
Tert-butyl alcohol 24.75mL
0.1mol/L NaOH solution an amount of
150mL
Preparation method: with phosphatidylcholine, cholesterol and HSPE-S-mPEG
2000Be dissolved in the mixed solvent of the ethanol and the tert-butyl alcohol 1: 1 (v/v) to the solution clear.Lipid soln and citrate buffer solution are mixed with pro-liposome according to 1: 4 volume ratio in gradient pump.Gradient pump links to each other with squeezer, the polycarbonate membrane of 5 100nm of squeezer middle berth.Mixed pro-liposome is by the unified particle diameter of squeezer extruding, effusive liposome mixed solution is immediately by the ultrafilter ultrafiltration, the middle citrate buffer solution 750mL that constantly replenishes concentrates liposome then to aimed concn (100mg film material/mL), promptly get blank liposome.
(2) preparation of alkali injection
Weighing sodium carbonate 10.5g adds injection water 225mL dissolving, and filtration sterilization promptly gets the alkali injection.
(3) medicine carrying
The 6g irinotecan hydrochloride is dissolved in the dilute hydrochloric acid that 600mL contains the water of 10% (Wt/Wt) sucrose or 0.01mol/L, adds in the blank liposome of (1) step preparation, the aqueous slkali that adds the preparation of (2) step transfers to 7.5 with pH value, stirring and evenly mixing leaves standstill 20min, degerming, packing, promptly.
Embodiment 5:pH gradient method prepares long circulating liposomes
(1) preparation of blank liposome
Prescription:
Phosphatidylcholine 10.605g (13.95394737mmol)
Cholesterol 3.232g (8.373056995mmol)
DSPE-PEG
2000 2.995g(1.047202797mmol)
Ethanol 24.75mL
Tert-butyl alcohol 24.75mL
0.1mol/L MaOH solution an amount of
150mL
Preparation method: with phosphatidylcholine, cholesterol and DSPE-PEG
2000Be dissolved in the mixed solvent of the ethanol and the tert-butyl alcohol 1: 1 (v/v) to the solution clear.Lipid soln and citrate buffer solution are mixed with pro-liposome according to 1: 4 volume ratio in gradient pump.Gradient pump links to each other with squeezer, the polycarbonate membrane of 5 100nm of squeezer middle berth.Mixed pro-liposome is by the unified particle diameter of squeezer extruding, effusive liposome mixed solution is immediately by the ultrafilter ultrafiltration, the middle citrate buffer solution 750mL that constantly replenishes concentrates liposome then to aimed concn (100mg film material/mL), promptly get blank liposome.
(2) preparation of alkali injection
Weighing sodium carbonate 10.5g adds injection water 225mL dissolving, and filtration sterilization promptly gets the alkali injection.
(3) medicine carrying
The 6g irinotecan hydrochloride is dissolved in the dilute hydrochloric acid that 600mL contains the water of 10% (Wt/Wt) sucrose or 0.01mol/L, adds in the blank liposome of (1) step preparation, the aqueous slkali that adds the preparation of (2) step transfers to 7.5 with pH value, stirring and evenly mixing leaves standstill 20min, degerming, packing, promptly.
The supplementary material proportioning of the foregoing description, organic solvent kind and ratio, technical process etc. are not enumerated one by one, and through facts have proved of applicant: the processing technology that is provided, supplementary material and proportioning thereof, organic solvent selection and proportioning, buffer are selected and proportioning etc. all comprises in the claims.
According to the irinotecan hydrochloride liposome of this explained hereafter, envelop rate reaches more than 95%, stable in properties, and determined curative effect, safe and reliable, be suitable for suitability for industrialized production.
Explanation of nouns: HSPE-PEG
2000Represent that its mean molecule quantity is Polyethylene Glycol-hydrogenated soya phosphatide acyl ethanolamine of 2000; DSPE-PEG
2000Represent that its mean molecule quantity is Polyethylene Glycol-distearyl acyl group PHOSPHATIDYL ETHANOLAMINE of 2000.
Claims (10)
1, a kind of preparation method of hydrochloride for injection irinotecan liposome, it is characterized in that this method is by being dissolved in lipid mixture in the organic solvent, to the solution clear, get lipid soln, lipid soln mixes in gradient pump according to 1: 1～8 volume ratios with buffer, mixed blank liposome is by the homogenizer homogenizing or be covered with the unified particle diameter of squeezer extruding of polycarbonate membrane, effusive liposome mixed solution is immediately by the ultrafilter ultrafiltration, remove organic solvent, the middle buffer that constantly replenishes obtains blank liposome, adds irinotecan hydrochloride solution, and it is extremely alkaline to regulate pH value with the agent of liposome pH regulator, makes drug-loaded liposome; Perhaps lipid mixture and irinotecan hydrochloride are dissolved in the organic solvent, remove organic solvent, make the lipid film forming, form drug-loaded liposome by the hydration solution hydration that adds hydrochloric irinotecan by spray drying or vacuum drying.
2, the preparation method of hydrochloride for injection irinotecan liposome according to claim 1 is characterized in that described irinotecan hydrochloride consumption and blank liposome mole ratio are: 0.001～1: 1.
3, the preparation method of hydrochloride for injection irinotecan liposome according to claim 1, it is characterized in that described organic solvent is the single solvent in chloroform, methanol, ethanol, the tert-butyl alcohol, isopropyl alcohol and the n-butyl alcohol, or the mixed solvent made of two or more solvent wherein.
4, the preparation method of hydrochloride for injection irinotecan liposome according to claim 1, it is characterized in that described buffer is the citrate buffer solution of pH value between 3.3～8, or the tartaric acid buffer of pH value between 3.3～13, or the organic acid buffer of other pH value between 2.5～10.
5, the preparation method of hydrochloride for injection irinotecan liposome according to claim 1, the aperture that it is characterized in that described polycarbonate membrane is 20～400nm, 1～10 layer of the number of plies.
6, the preparation method of hydrochloride for injection irinotecan liposome according to claim 1 is characterized in that containing in the described lipid mixture raw material of following molar percentage: phosphatidylcholine 20～80%; Sphingomyelins 0～30%; Cardiolipin 0～60%; Cholesterol 20～80%; Polyethyleneglycol derivative 0～10%.
7, the preparation method of hydrochloride for injection irinotecan liposome according to claim 6 is characterized in that described polyethyleneglycol derivative is HSPE-S-mPEG
2000Or DSPE-PEG
2000
8, the preparation method of hydrochloride for injection irinotecan liposome according to claim 6 is characterized in that described phosphatidylcholine is egg yolk lecithin phatidylcholine, S-PC or hydrogenated soya phosphatide phatidylcholine.
9, the preparation method of hydrochloride for injection irinotecan liposome according to claim 1 is characterized in that the agent of described liposome pH regulator is Na
2CO
3Solution, NaOH solution, NH
4Cl solution, NaHCO
3Solution or Ca (OH)
2Solution.
10, the preparation method of hydrochloride for injection irinotecan liposome according to claim 1 is characterized in that described adjusting pH value to the pH scope that alkalescence refers to is 7.5～3.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610105371 CN1994279A (en) | 2006-12-31 | 2006-12-31 | Preparation process of irinotecan hydrochloride liposome for injection |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610105371 CN1994279A (en) | 2006-12-31 | 2006-12-31 | Preparation process of irinotecan hydrochloride liposome for injection |
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| Publication Number | Publication Date |
|---|---|
| CN1994279A true CN1994279A (en) | 2007-07-11 |
Family
ID=38249538
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|---|---|---|---|
| CN 200610105371 Pending CN1994279A (en) | 2006-12-31 | 2006-12-31 | Preparation process of irinotecan hydrochloride liposome for injection |
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| CN101953792A (en) * | 2010-09-06 | 2011-01-26 | 中华人民共和国卫生部肝胆肠外科研究中心 | Irinotecan nano circulating liposome and preparation method thereof |
| WO2011066684A1 (en) * | 2009-12-03 | 2011-06-09 | 江苏恒瑞医药股份有限公司 | Liposome of irinotecan or its hydrochloride and preparation method thereof |
| CN102697720A (en) * | 2012-06-29 | 2012-10-03 | 海南灵康制药有限公司 | Irinotecan hydrochloride lipid nanoparticles injection |
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| CN104906586A (en) * | 2014-03-10 | 2015-09-16 | 中国科学院上海药物研究所 | Irinotecan hydrochloride composite phospholipid composition, preparation method and applications thereof |
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2006
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| CN103120645B (en) * | 2009-12-03 | 2015-03-11 | 江苏恒瑞医药股份有限公司 | Irinotecan or irinotecan hydrochloride lipidosome and preparation method thereof |
| WO2011066684A1 (en) * | 2009-12-03 | 2011-06-09 | 江苏恒瑞医药股份有限公司 | Liposome of irinotecan or its hydrochloride and preparation method thereof |
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| JP2013512262A (en) * | 2009-12-03 | 2013-04-11 | ジエンス ヘンルイ メデイシンカンパニー リミテッド | Irinotecan or its hydrochloride liposome and method for producing the same |
| CN102271659B (en) * | 2009-12-03 | 2013-09-18 | 江苏恒瑞医药股份有限公司 | Liposome of irinotecan or its hydrochloride and preparation method thereof |
| EP2508170A4 (en) * | 2009-12-03 | 2014-01-15 | Jiangsu Hengrui Medicine Co | Liposome of irinotecan or its hydrochloride and preparation method thereof |
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| CN101953792B (en) * | 2010-09-06 | 2011-12-28 | 中华人民共和国卫生部肝胆肠外科研究中心 | Irinotecan nano circulating liposome and preparation method thereof |
| CN101953792A (en) * | 2010-09-06 | 2011-01-26 | 中华人民共和国卫生部肝胆肠外科研究中心 | Irinotecan nano circulating liposome and preparation method thereof |
| CN109549925A (en) * | 2012-06-14 | 2019-04-02 | 伯尔尼大学 | For treating the customization liposome of bacterium infection |
| CN109549925B (en) * | 2012-06-14 | 2022-06-17 | 伯尔尼大学 | Customized liposomes for treating bacterial infections |
| CN102697720A (en) * | 2012-06-29 | 2012-10-03 | 海南灵康制药有限公司 | Irinotecan hydrochloride lipid nanoparticles injection |
| CN104906586A (en) * | 2014-03-10 | 2015-09-16 | 中国科学院上海药物研究所 | Irinotecan hydrochloride composite phospholipid composition, preparation method and applications thereof |
| CN105982857B (en) * | 2015-02-09 | 2019-03-08 | 湖南科伦药物研究有限公司 | A kind of irinotecan hydrochloride lipidosome composition and preparation method thereof |
| CN105982857A (en) * | 2015-02-09 | 2016-10-05 | 四川科伦药物研究院有限公司 | Irinotecan hydrochloride lipidosome composition and preparation method thereof |
| CN109937046A (en) * | 2016-09-09 | 2019-06-25 | 艾利西斯股份有限公司 | Liposome anti-cancer composition |
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