CN1526407A - Antitumor protopanoxadiol injection and its prepn process - Google Patents
Antitumor protopanoxadiol injection and its prepn process Download PDFInfo
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- CN1526407A CN1526407A CNA2004100021095A CN200410002109A CN1526407A CN 1526407 A CN1526407 A CN 1526407A CN A2004100021095 A CNA2004100021095 A CN A2004100021095A CN 200410002109 A CN200410002109 A CN 200410002109A CN 1526407 A CN1526407 A CN 1526407A
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Abstract
The present invention discloses one kind of antitumor protopanoxadiol injection and its preparation process. The injection contains rare ginsenoside, injection solvent and assistant, and has high curative effect, high bioavailability and stable quality.
Description
Technical field
The present invention relates to a kind of antineoplastic rare ginsenoside injection and preparation method thereof, further relate to protopanoxadiol injection, lyophilized powder, infusion preparation.
Background technology
The early existing report of the antitumor action that Radix Ginseng has along with the further investigation to Radix Ginseng, to gradually clear and definite of constituent of ginseng, is found some ginsenosides, has extraordinary antitumor action as protopanoxadiol.
Ginsenoside's preparation both can be used as the direct killing cancerous cell clinically, but also combined with chemotherapy, radiotherapy kills and wounds the effect of cancerous cell with raising, and alleviated its detrimental effect to body.The ginsenoside also is used for the recovery of tumor post-operation body, is used for the patient with advanced cancer mitigation symptoms, improves patient's general state and the effect that prolongs life.
At present, clinical practice antineoplastic rare ginsenoside all mostly is oral Preparation, because the content of rare ginsenoside in Radix Ginseng is lower, and the rare ginsenoside that has prepares by existing ginsenoside is advanced manual method, and the oral administration bioavailability is very low, causes the great wasting of resources; Disclosed the injection of some rare ginsenosides in the existing patent documentation, as, CN1182433, ginsenoside's saponins by human intestinal bacteria metabolite and anticancer preparation thereof, but there is not one piece of document specifically to disclose the technical scheme of its used for intravenous injection preparation.
The injection of rare ginsenoside is intravenous formulations especially, medicinal liquid directly injects tissue or blood vessel, have absorb fast, onset rapidly, reliable effect, the characteristics that bioavailability is high, and the ginsenoside is along with the reduction of sugared aglucon number, and ginsenoside's water solublity worse and worse; Because the unusual indissoluble of rare ginsenoside, and unstable in solution, therefore rare ginsenoside is made injection, intravenous injection especially, its slightly solubility has become the technology barrier that is difficult to cross over.
Summary of the invention
The present invention is directed to above-mentioned technological deficiency a kind of antineoplastic protopanoxadiol intravenous injection is provided.
Protopanoxadiol injection of the present invention contains protopanoxadiol, injection solvent and additives, protopanoxadiol can be for extracting from panax ginseng plant, also can be synthetic by manual method, as chemical synthesis, bacterial metabolism method etc., wherein among the present invention protopanoxadiol be 20 (R)-protopanoxadiols, 20 (S)-protopanoxadiols or 20 (R, S)-protopanoxadiol; Its protopanoxadiol is 0.1-50% (w/v) at injection content, its preferred content is 0.2-20% (w/v), and wherein the preferred protopanoxadiol monomer of the present invention can adopt extracting method or synthetic and the acquisition of bacterial metabolism method that the prior art document discloses.
Injection solvent is a kind of, two or more the combination in water for injection, ethanol, propylene glycol, glycerol, isopropyl alcohol, isobutanol and the Polyethylene Glycol among the present invention; Additives are a kind of, two or more the combination in pH regulator agent, stabilizing agent, isoosmotic adjusting agent and the proppant.Wherein injection solvent is preferably two or more combination of the water for injection that accounts for injection 0.5%～99.9% (volume ratio), ethanol, propylene glycol, glycerol, isopropyl alcohol, isobutanol, Polyethylene Glycol, more preferably a kind of, two or more combination in water for injection, ethanol, glycerol and the Polyethylene Glycol of injection solvent among the present invention.
Additives are a kind of, two or more the combination in pH regulator agent, stabilizing agent, isoosmotic adjusting agent, the proppant among the present invention.
PH regulator agent among the present invention in the additives can be one or more in the following material: phosphoric acid and salt thereof, sodium hydroxide, hydrochloric acid, organic amine, potassium hydroxide, calcium hydroxide, tartaric acid and salt thereof, carbonic acid and salt thereof, borate family, citric acid and salt thereof, lactic acid and salt thereof; Stabilizing agent can be one or more sodium sulfite, sodium sulfite, sodium pyrosulfite, ascorbic acid, EDTA and salt thereof, glycine, cysteine, citric acid and salt thereof, tartaric acid and salt thereof, the methionine in the following material; Isoosmotic adjusting agent can be one or more sorbitol, fructose, sodium chloride, calcium chloride, potassium chloride, magnesium chloride, ammonium sulfate, glucose, Chile saltpeter, potassium nitrate, Borax, boric acid, the glycerol in the following material; Proppant is glycine, mannitol, lactose, dextran, dextran, sucrose or sodium chloride.
Protopanoxadiol injection of the present invention can also contain solubilizing agent, wherein solubilizing agent is polyglycol distearate, Tweens, poloxamer or polyoxyethylene castor oil, polyoxyethylene castor oil or moor husky nurse (poloxamer) more preferably, wherein the content of solubilizing agent is 0.1～30% (w/v) that accounts for the injection volume.
Effective active composition dissolving of the present invention can adopt water for injection to add the method for solubilizing agent; The method that also can adopt the composite injection solvent method or adopt the composite injection solvent to add solubilizing agent is dissolved.
The protopanoxadiol injection is an injection among the present invention.Injection of the present invention contains protopanoxadiol, injection solvent and PH regulator, wherein protopanoxadiol be 20 (R)-protopanoxadiols, 20 (S)-protopanoxadiols or 20 (R, S)-protopanoxadiol; Injection solvent of the present invention is a kind of, two or more combination in water for injection, ethanol, glycerol, propylene glycol and the Polyethylene Glycol; Be preferably double solvents for PEG-alcohol-water, PEG-water or glycerol-alcohol-water, alcohol-water; More preferably PEG accounts for the 20-50% (volume) of double solvents volume, and ethanol accounts for the 20-50% (volume) of double solvents volume, and all the other are the PEG-alcohol-water double solvents of water for injection; The PH regulator is phosphoric acid and salt buffer solution phosphate, tartrate, borate or dilute sodium hydroxide, is preferably phosphoric acid and salt buffer solution thereof.
The pH scope of injection solution of the present invention is 4～9, and preferred PH scope is 6-8.
The protopanoxadiol injection solution can also contain solubilizing agent among the present invention, and wherein solubilizing agent is polyoxyethylene castor oil or poloxamer (poloxamer).
Protopanoxadiol injection among the present invention can also further can also contain stabilizing agent, and wherein stabilizing agent is EDTA-2Na, tartaric acid or sodium sulfite; The best is EDTA-2Na, and wherein the content of stabilizing agent is 0.002～0.02% (w/v) that accounts for the injection total amount.
The preparation method preparation of the conventional injection in this area that the protopanoxadiol injection preparation can adopt among the present invention.
Among the present invention, the protopanoxadiol injection can be the frozen powder for injection pin.When being the frozen powder for injection pin, it contains protopanoxadiol, injection solvent and proppant, wherein protopanoxadiol be 20 (R)-protopanoxadiols, 20 (S)-protopanoxadiols or 20 (R, S)-protopanoxadiol; Injection solvent be water, ethanol, propylene glycol, glycerol, isopropyl alcohol, isobutanol and Polyethylene Glycol any, two or more combination; A kind of, two or more combination of water for injection, ethanol, glycerol, Polyethylene Glycol; Proppant is glycine, mannitol, lactose, dextran, dextran, sucrose or sodium chloride, more preferably mannitol or glycine.
Freeze-dried powder injection of the present invention can also contain solubilizing agent and pH regulator agent, and wherein solubilizing agent is polyoxyethylene castor oil or poloxamer (poloxamer), and the pH regulator agent is phosphoric acid and salt thereof.
Injection freeze-dried powder preparation method of the present invention can adopt conventional preparation method preparation, but the preparation method of preferred lyophilized injectable powder of the present invention is: get protopanoxadiol, add the injection solvent dissolving, can add solubilizing agent as required, add proppant, activated carbon adsorption, filtration, packing then, adopt conventional freeze-dry process lyophilizing promptly, wherein when containing low boiling point solvent in the injection solvent that adopts, should before lyophilizing, boil off this low boiling point solvent.
The protopanoxadiol injection is transfusion among the present invention, the present invention transfusion contain protopanoxadiol, injection solvent, etc. ooze adjusting, wherein protopanoxadiol be 20 (R)-protopanoxadiols, 20 (S)-protopanoxadiols or 20 (R, S)-protopanoxadiol; Injection solvent is a kind of, two or more the combination in water, ethanol, propylene glycol, glycerol, isopropyl alcohol, isobutanol and the Polyethylene Glycol; Isoosmotic adjusting agent is one or more sorbitol, fructose, sodium chloride, calcium chloride, potassium chloride, magnesium chloride, ammonium sulfate, glucose, Chile saltpeter, potassium nitrate, Borax, the boric acid in the following material, preferred isoosmotic adjusting agent is sodium chloride or glucose, and wherein the isoosmotic adjusting agent addition can add as the case may be in right amount.
The present invention infuses, and liquid can also contain solubilizing agent, wherein solubilizing agent is polyoxyethylene castor oil or poloxamer.
Protopanoxadiol injection of the present invention has good effect, bioavailability height, steady quality.
The specific embodiment
Embodiment 1
Take by weighing 0.50g 20 (R)-protopanoxadiol, add 50g PEG-400, make the saponin dissolving; The phosphate buffer of preparation 50g pH5.5 takes by weighing the 0.20g procaine hydrochloride, the 0.02g sodium sulfite joins in the above-mentioned phosphate buffer; Buffer is joined in the PEG solution of saponin, mix homogeneously adds 100 ℃ of insulations of 0.01% needle-use activated carbon 30 minutes, G
3Sintered glass funnel filters, the filtering with microporous membrane of 0.22um, and filtered liquid medicine is distributed into 50 of the injections that 2ml/ props up, and divides the directly tamponade of injection, the jewelling that install to cover into injection.
Embodiment 2
Take by weighing 0.50g 20 (S)-protopanoxadiol, add 50g PEG-400, make the saponin dissolving.The phosphate buffer of preparation 50g PH5.5 takes by weighing the 0.20g procaine hydrochloride, the 0.02g sodium sulfite joins in the above-mentioned phosphate buffer; Buffer is joined in the PEG solution of saponin, mix homogeneously adds 100 ℃ of insulations of 0.01% needle-use activated carbon 30 minutes, G
3Sintered glass funnel filters, the filtering with microporous membrane of 0.22um; Filtered liquid medicine is distributed in the cillin bottle that 2ml/ props up, and makes freeze-dried powder through the freeze dryer lyophilizing.
Embodiment 3
Take by weighing 1.00g 20 (R, S)-protopanoxadiol, add 20ml ethanol saponin is melted fully, add 40ml glycerol mix homogeneously again, the EDTA-2Na of 0.20g tetracaine hydrochloride, 0.02g is joined in the 40ml water for injection, adjuvant is dissolved fully, and above-mentioned aqueous solution joined in the drug solution, mix homogeneously, regulating pH value with the sodium hydroxide of 0.01mol/L and dilute hydrochloric acid is 5.5 ± 1.0,85 ℃ of insulations of the needle-use activated carbon of adding 0.1% 15 minutes, G
3Sintered glass funnel filters, the filtering with microporous membrane of 0.22um, and filtrate is sub-packed in the 7ml cillin bottle, every loading amount 2ml.
Embodiment 4
Take by weighing 1.50g 20 (R)-protopanoxadiol, add 20ml ethanol and stir, saponin is dissolved fully, in above-mentioned alcoholic solution, add the 15.00g poloxamer, be heated to 50 ℃ poloxamer is melted, add the 0.10g benzyl alcohol again, stir and make dissolving; 0.9% sodium chloride solution 80ml with tartaric acid and salt thereof preparation pH5.5 adds the 0.02g ascorbic acid in sodium chloride solution, stir and make dissolving fully; Sodium chloride solution is joined in the saponin solution, make mix homogeneously, add 80 ℃ of 0.05% needle-use activated carbons insulation 15 minutes, filter successively with the microporous filter membrane of sintered glass funnel and 0.22um, filtrate dress 100ml infusion bottle is made the ginsenoside-Rh2 and is infused.
Embodiment 5
Take by weighing 1.50g 20 (S)-protopanoxadiol, adding 20ml ethanol stirs, saponin is dissolved fully, in above-mentioned alcoholic solution, add the 15.00g poloxamer, being heated to 50 ℃ melts poloxamer, add the 0.10g benzyl alcohol again, stir and make dissolving, with the aqueous solution 80ml of tartaric acid and salt preparation pH5.5 thereof, in sodium chloride solution, add the 0.02g ascorbic acid, stirring makes dissolving fully, and sodium chloride solution is joined in the saponin solution, makes mix homogeneously, add 80 ℃ of insulations of 0.05% needle-use activated carbon 15 minutes, microporous filter membrane with sintered glass funnel and 0.22um filters successively, and be filled in the 7ml cillin bottle filtrate branch, can be made into injection.
Embodiment 6
(R S)-protopanoxadiol, uses an amount of anhydrous alcohol solution, adds 5.00g polyoxyethylene castor oil acid esters, makes dissolving fully, adds glucose injection and is diluted to 100ml, adds the dissolving of 0.02g methionine to take by weighing 1.00g 20; Add 80 ℃ of 0.05% needle-use activated carbons insulation 15 minutes, filter successively with the microporous filter membrane of sintered glass funnel and 0.22um, filtrate is adorned the 100ml infusion bottle and is made ginsenoside-Rh
2Transfusion.
Embodiment 7
Take by weighing 1.00g20 (R)-protopanoxadiol, use an amount of anhydrous alcohol solution, add 5.00g polyoxyethylene castor oil acid esters, make dissolving fully; 60 degree drying under reduced pressure are removed ethanol, add glucose injection and be diluted to 100ml, add the dissolving of 0.02g methionine, 4% mannitol, add 0.05% needle-use activated carbon afterwards and be incubated 15 minutes for 80 ℃, filter successively with the microporous filter membrane of sintered glass funnel and 0.22um; Packing, freeze-dried powder is made in lyophilizing.
Embodiment 8
Take by weighing 1.00g20 (S)-protopanoxadiol, use an amount of anhydrous alcohol solution, add single month esters of silicon acis of 8.00g cetomacrogol 1000, make dissolving fully, add 0.9% sodium chloride injection and be diluted to 100ml, add the dissolving of 0.02g glycosides propylhomoserin, add 80 ℃ of insulations of 0.05% needle-use activated carbon 15 minutes, microporous filter membrane with sintered glass funnel and 0.22um filters successively, and filtrate dress 100ml infusion bottle is made the panax saponin-Re transfusion; Filtrate also can be divided and is filled in the 7ml cillin bottle, makes the injection that 2ml/ props up.
Embodiment 9
Take by weighing the 1.00g protopanoxadiol, use an amount of anhydrous alcohol solution, add single month esters of silicon acis of 8.00g cetomacrogol 1000, make dissolving fully, 60 degree drying under reduced pressure are removed ethanol, add 0.9% sodium chloride injection and be diluted to 100ml, add the dissolving of 0.02g glycosides propylhomoserin, add 4% mannitol, add 80 ℃ of insulations of 0.05% needle-use activated carbon 15 minutes, microporous filter membrane with sintered glass funnel and 0.22um filters successively, and filtrate, packing, lyophilizing are made and contained ginsenoside Re 20mg/ and prop up freeze-dried powder.
Embodiment 10
Take by weighing 0.80g20 (R)-protopanoxadiol, adding 30ml ethanol melts saponin fully, add 30ml isopropyl alcohol mix homogeneously again, 0.10g hydrochloric acid first is sent caine, the sodium pyrosulfite of 0.02g joins in the 40ml water for injection, make dissolving fully, and above-mentioned aqueous solution joined in the drug solution, mix homogeneously, it is 5.5 ± 1.0 that triethanolamine with 10% and sodium bicarbonate are regulated pH value, the needle-use activated carbon 85 degree insulations of adding 0.1% 15 minutes, G
3Sintered glass funnel filters, the filtering with microporous membrane of 0.22um, and filtrate is sub-packed in the 7ml cillin bottle, every loading amount 2ml.
Embodiment 11
Take by weighing 1.00g 20 (S)-protopanoxadiol, the propylene glycol that adds 20ml n-butyl alcohol and 30ml melts saponin fully, and the citric acid of 0.15g tetracaine hydrochloride, 0.02g is joined in the 40ml water for injection, makes dissolving fully, and above-mentioned aqueous solution joined in the drug solution mix homogeneously; Regulating pH value with Borax and boric acid is 5.5 ± 1.0; 85 ℃ of insulations of the needle-use activated carbon of adding 0.1% 30 minutes, G
3Sintered glass funnel filters, the filtering with microporous membrane of 0.22um; Filtrate is sub-packed in the 7ml cillin bottle, every loading amount 2ml.
Claims (18)
1. antineoplastic injection is characterized by and contains protopanoxadiol, injection solvent and additives, and wherein injection solvent is a kind of, two or more combination in water for injection, ethanol, propylene glycol, glycerol, isopropyl alcohol, isobutanol, the Polyethylene Glycol; Additives are a kind of, two or more the combination in pH regulator agent, stabilizing agent, isoosmotic adjusting agent and the proppant.
2. injection according to claim 1, it is characterized in that protopanoxadiol be content in injection be 0.1-50% (w/v) 20 (R)-protopanoxadiols, 20 (S)-protopanoxadiols or 20 (R, S)-protopanoxadiol.
3. injection according to claim 1, be characterized as also contain solubilizing agent, wherein solubilizing agent is 0.1～30% polyglycol distearate, tween (Tween), poloxamer (Poloxamer) or a polyoxyethylene castor oil of injection volume.
4. according to the described injection of claim 1, it is characterized in that wherein pH regulator agent can be one or more in the following material: phosphoric acid and salt thereof, sodium hydroxide, hydrochloric acid, organic amine, potassium hydroxide, calcium hydroxide, tartaric acid and salt thereof, carbonic acid and salt thereof, borate family, citric acid and salt thereof, lactic acid and salt thereof; Stabilizing agent can be one or more in the following material: sodium sulfite, sodium sulfite, sodium pyrosulfite, ascorbic acid, EDTA, glycine, cysteine, citric acid and salt thereof, tartaric acid and salt thereof, methionine; Isoosmotic adjusting agent can be one or more in the following material: sorbitol, glycerol, fructose, sodium chloride, calcium chloride, potassium chloride, magnesium chloride, ammonium sulfate, glucose, Chile saltpeter, potassium nitrate, Borax, boric acid.
5. according to the arbitrary described injection of claim 1-2, it is characterized by injection.
6. injection according to claim 5 is characterized by above-mentioned injection and contains protopanoxadiol, injection solvent and PH regulator, and wherein injection solvent is two or more combination in water for injection, ethanol, glycerol, propylene glycol and the Polyethylene Glycol; The pH regulator agent is phosphoric acid and salt, tartaric acid and salt thereof, borate or dilute sodium hydroxide.
7. injection according to claim 6 is characterized in that injection solvent is the double solvents of PEG-water, alcohol-water, PEG-alcohol-water or glycerol-alcohol-water; The PH regulator is phosphoric acid and salt buffer solution thereof.
8. injection according to claim 7 is characterized in that injection solvent is the 20-50% that PEG accounts for the double solvents volume, and ethanol accounts for the 20-50% of double solvents volume, and all the other are the PEG-alcohol-water double solvents of water for injection.
9. injection according to claim 6, it is characterized by also contain solubilizing agent, wherein solubilizing agent is polyoxyethylene castor oil or poloxamer (Poloxamer).
10. according to claim 6 or 9 described injections, it is characterized by above-mentioned injection and also contain stabilizing agent, wherein stabilizing agent is EDTA-2Na, tartaric acid or sodium sulfite.
11. injection according to claim 10, it is characterized by stabilizing agent is the EDTA-2Na that accounts for 0.002～0.02% (w/v) of injection total amount.
12., it is characterized by the frozen powder for injection pin according to claim 1 or 2 arbitrary described injections.
13. injection according to claim 12, it is characterized by above-mentioned frozen powder for injection pin and contain protopanoxadiol, injection solvent and proppant, wherein injection solvent is a kind of in water, ethanol, propylene glycol, glycerol, isopropyl alcohol, isobutanol and the Polyethylene Glycol, two or more combination; Proppant is glycine, mannitol, lactose, sucrose, sodium chloride or dextran.
14. injection according to claim 13 is characterized by above-mentioned frozen powder for injection pin and also contains solubilizing agent and PH regulator, wherein solubilizing agent is polyoxyethylene castor oil or poloxamer (poloxamer); The PH regulator is phosphoric acid and salt thereof.
15., it is characterized by transfusion according to the arbitrary described injection of claim 1-2.
16. injection according to claim 15, it is characterized by above-mentioned transfusion and contain protopanoxadiol, injection solvent and isoosmotic adjusting agent, wherein injection solvent is a kind of, two or more the combination in water, ethanol, propylene glycol, glycerol, isopropyl alcohol, isobutanol and the Polyethylene Glycol; Isoosmotic adjusting agent is sorbitol, fructose, sodium chloride, calcium chloride, potassium chloride, magnesium chloride, ammonium sulfate, glucose, Chile saltpeter, potassium nitrate, Borax, boric acid or glycerol.
17. injection according to claim 16 is characterized in that isoosmotic adjusting agent is a glucose.
18. injection according to claim 16 is characterized by that above-mentioned transfusion also contains solubilizing agent, wherein solubilizing agent is polyoxyethylene castor oil or poloxamer (poloxamer).
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2004100021095A CN1526407A (en) | 2003-01-06 | 2004-01-06 | Antitumor protopanoxadiol injection and its prepn process |
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| Application Number | Priority Date | Filing Date | Title |
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| CN03100025 | 2003-01-06 | ||
| CN03100025.8 | 2003-01-06 | ||
| CNA2004100021095A CN1526407A (en) | 2003-01-06 | 2004-01-06 | Antitumor protopanoxadiol injection and its prepn process |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007143930A1 (en) * | 2006-06-09 | 2007-12-21 | Shanghai Innovative Research Center Of Traditional Chinese Medicine | Use of 20(s)-protopanoxadiol in manufacture of antidepressants |
| CN100391468C (en) * | 2006-02-27 | 2008-06-04 | 杭州创新中药标准化研究所有限公司 | Protopanaxadiol lyophilized agent and its preparing method |
| CN102631322A (en) * | 2012-04-23 | 2012-08-15 | 上海中医药大学 | 20 (S)-protopanoxadiol dry suspension agent and preparation method thereof |
| CN104688669A (en) * | 2013-12-10 | 2015-06-10 | 沈阳药科大学 | Ginsenoside concentrated liquid and medical application thereof |
-
2004
- 2004-01-06 CN CNA2004100021095A patent/CN1526407A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100391468C (en) * | 2006-02-27 | 2008-06-04 | 杭州创新中药标准化研究所有限公司 | Protopanaxadiol lyophilized agent and its preparing method |
| WO2007143930A1 (en) * | 2006-06-09 | 2007-12-21 | Shanghai Innovative Research Center Of Traditional Chinese Medicine | Use of 20(s)-protopanoxadiol in manufacture of antidepressants |
| US8148354B2 (en) | 2006-06-09 | 2012-04-03 | Shanghai Innovative Research Center Of Traditional Chinese Medicine | Use of 20(S)-protopanaxadiol in manufacture of antidepressants |
| CN102631322A (en) * | 2012-04-23 | 2012-08-15 | 上海中医药大学 | 20 (S)-protopanoxadiol dry suspension agent and preparation method thereof |
| CN102631322B (en) * | 2012-04-23 | 2014-08-06 | 上海中医药大学 | 20 (S)-protopanoxadiol dry suspension agent and preparation method thereof |
| CN104688669A (en) * | 2013-12-10 | 2015-06-10 | 沈阳药科大学 | Ginsenoside concentrated liquid and medical application thereof |
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