CN101444490A - Injection preparation containing anhydrogalactitol and preparation method thereof - Google Patents
Injection preparation containing anhydrogalactitol and preparation method thereof Download PDFInfo
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- CN101444490A CN101444490A CNA2007101503972A CN200710150397A CN101444490A CN 101444490 A CN101444490 A CN 101444490A CN A2007101503972 A CNA2007101503972 A CN A2007101503972A CN 200710150397 A CN200710150397 A CN 200710150397A CN 101444490 A CN101444490 A CN 101444490A
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Abstract
The invention relates to an anhydrogalactitol injection preparation and a preparation method thereof. The preparation is characterized by being made from anhydrogalactitol, a water soluble filler, a pH regulator, water for injection and an osmoregulator, wherein, the anhydrogalactitol is 0.001-50% by weight, and the other is pharmaceutic adjuvants or water. The anhydrogalactitol injection preparation has good stability and high bioavailability, thus solving the injection requirements of treating clinical acute granulocytic leukemia and chronic granulocytic leukemia.
Description
Technical field
The invention belongs to field of pharmaceutical preparations, more particularly relate to preparation of a kind of administrated by injection that contains the active component anhydrous dulcit and preparation method thereof.
Background technology
Leukemia is a kind of malignant disease of hemopoietic system, and its characteristics are that extensively and uncontrolledly hypertrophy of a large amount of leukaemias is arranged in the body, comes across bone marrow and many other organs and tissue, and enters in the peripheral blood.Acute leukemia is anxious with its onset, progress is fast, the state of an illness is dangerous, the serious harm human health.Along with medical advance, acute leukemia is through active treatment, and most patients can both obtain alleviation, palliating leukemia no longer is the ultimate aim of treatment now, how to improve cure rate, make most of leukemia patients obtain radical cure, become the emphasis of current hematology's research.
Chronic myelocytic leukemia, it is a kind of clinically onset and develops leukemia relatively slowly.It is a kind of origin
In the malignant proliferation disease of bone marrow pluripotential hemopoietic stem cell, show as the expansion of medullary system CFU-GM pond, myelocytic series and CFU-GM undue growth thereof.Clinical main performance is that leukocyte significantly increases, and often with hepatosplenomegaly, lymphadenectasis, anemia and symptom such as hemorrhage can be arranged, and small number of patients is also with skin lesion.Malignant hematologic disease comprises: the part type among leukemia, lymphoma, myeloma and the MDS, because they have the pathological characters and the clinical manifestation of similar tumor, the general state of an illness is heavier.
The treatment of above-mentioned malignant hematologic disease mainly is a chemotherapy, promptly choose virose one or more medicine killing tumor cells of tumor cell are reached the purpose of curing the disease, but chemotherapeutics is in the tumoricidal while, normal cell has also been brought great infringement, therefore, can occur diversified toxicity as, vomiting, alopecia, bone marrow depression, organ functional lesion etc.Have a delicate constitution patient, malnutrition and through repeatedly over a long time after the chemotherapy or after the state of an illness is alleviated, continue again to use chemotherapeutics serious toxic and side effects will occur.
Melampyrin (Dulcitol), have another name called sweet and pure, hexanhexol (Dulcite).Structure is: HOCH2 (CHOH) 4CH2OH, and molecular weight: 182.18, be colourless monocline column crystallization.It is little sweet to distinguish the flavor of.Be slightly soluble in pure and mild ether; Water-soluble, particularly be soluble in boiling water.As far back as nineteen forties, China scientist is just at some commonly used Chinese medicines, as having found the dulcitol composition in Radix Tripterygii Wilfordii, the Caulis Seu Folium Euonymi Fortunei etc., and develops considerable Chinese medicine preparation and prescription.
At the beginning of the seventies in last century, the U.S. has found a kind of material from a kind of tingia Folium Mayteni hookeri plant by name in Africa, through being accredited as dulcitol, find that it has significant antitumaous effect.China in 1972 has found that also Folium Mayteni hookeri distributes.After this, Chinese medicine institute in Guangxi produces from Guangxi to separate the Folium Mayteni hookeri and obtains dulcitol.For further eliminating the toxicity and the side effect of dulcitol, dulcitol with plant extract is the synthetic mitolactol (Dibromogalactitol of raw material, DBG), diacetyl two anhydrous dulcit (diacetyldianhydrogalactitol, DADAG) be called for short anhydrous dulcit, chronic myelocytic leukemia is had better curative effect.
Summary of the invention
The purpose of this invention is to provide and be fit to clinical acute, injectable drug that the chronic myelocytic leukemia treatment requires, the present invention is an active component with diacetyl two anhydrous dulcit, invented preparation of drug administration by injection and preparation method thereof, especially intravenous administration has solved demand acute, that chronic myelocytic leukemia is treated.
Technical scheme of the present invention: a kind of preparation that contains active component anhydrous dulcit administrated by injection is characterized in that pressing regulator to form thoroughly by active component anhydrous dulcit 0.001-50% and water-soluble filler, PH regulator, solubilizing agent, antioxidant, water for injection, Seepage.
The preparation of administrated by injection of the present invention is characterized in that described preparation is meant freeze-dried powder, small injection and the primary infusion that contains anhydrous dulcit.
The preparation of administrated by injection of the present invention is characterized in that described preparation is:
A. the percentage by weight of lyophilized preparation Chinese medicine composition and other pharmaceutic adjuvant is 0.1-50%;
B. the concentration of small injection Chinese medicine is 50mg/ml-0.5mg/ml;
C. the concentration of primary infusion Chinese medicine is 1mg/ml-0.02mg/ml.
The preparation of administrated by injection of the present invention is characterized in that described primary infusion is meant the compound injection that anhydrous dulcit and water are formed.
The preparation of administrated by injection of the present invention is characterized in that water-soluble filler is manna or tween; The PH regulator is nonvolatile acid and potassium hydroxide, sodium hydroxide, sodium carbonate or sodium bicarbonate salt, sodium phosphate or potassium or ammonium salts such as citric acid, phosphoric acid, malic acid; Solubilizing agent is polyvinylpyrrolidone, PEG6000, PEG4000, poloxamer, carbomer, Tween 80, low molecular dextran or Tris; Antioxidant is sodium sulfite, sodium pyrosulfite, sodium thiosulfate or sodium sulfite; Organic sulfur antioxidant is thioglycerol, thiourea or 1-thio sorbitol.
The present invention contains the preparation method of active component anhydrous dulcit administrated by injection preparation, it is characterized in that this method comprises the following steps:
I, composition
(1) lyophilized preparation: anhydrous dulcit 0.1%-30%,, water-soluble filler 50%-70%, solubilizing agent 0.1%-12%, antioxidant 0.003%-3% ， Seepage is saturating to press 0.9%;
(2) small injection: anhydrous dulcit 0.05%-1.0%, solubilizing agent 0.1%-8%, antioxidant 0.001%-5%, water for injection 70%-90%;
(3) primary infusion: anhydrous dulcit 0.005-0.1%, solubilizing agent 0.1%-8%, antioxidant 0.003%-1% ， Seepage is saturating to press 0.9%, water for injection 88%-98%;
The preparation method of II. different administrated by injection preparations comprises the following steps:
(1) lyophilized preparation: get anhydrous dulcit and water-soluble filler, solubilizing agent, antioxidant, Seepage presses agent etc. thoroughly, it is an amount of to add water for injection, regulates pH value and makes its dissolving to 4-10, adds water to scale, add the 0.1-0.5% active carbon, stirred 10-60 minute down at 20-50 ℃, the filtering with microporous membrane degerming is adopted in decarburization, filtrate is carried out packing, adopt freeze-drying, make the white loose block, seal promptly;
(2) small injection: get anhydrous dulcit and water-soluble filler, solubilizing agent, antioxidant, Seepage presses agent etc. thoroughly, it is an amount of to add water for injection, regulate pH value and make its dissolving to 4-10, add water to scale, add the 0.1-0.5% active carbon, stirred 10-60 minute decarburization, fine straining, embedding, sterilization down at 20-50 ℃;
(3) primary infusion: get anhydrous dulcit and water-soluble filler, solubilizing agent, antioxidant, osmotic pressure agent etc., add water for injection an amount of about 20%, regulate pH value and make its dissolving to 4-10, add the 0.1-0.5% active carbon, stirred 10-60 minute down at 20-50 ℃, decarburization adds water to scale, fine straining, embedding, sterilization.
Think the sugar alcohols active anticancer at present mainly from its α, the tension force of two three-membered rings of ω diepoxide, its can and the DNA combination of cancerous cell, destruction DNA, thus stop it to duplicate, the propagation of anticancer.Introduce the fat-soluble increase of DADAG of two acetyl group, easily by cell membrane, performance is to the potentiality of DNA alkanisation, so the curative effect of DADAG is better than DAD.Chongqing medical college Li Wei letter waits people [7,8] described " cellular contraction necrosis " such as [6] carry out " slow grain " treatment with DAD Ultrastructural observation result and Kerr and " apoptosis " that renamed as afterwards is consistent on form shows.But whether the DADAG antitumor action still imperfectly understands at present with apoptosis-induced relevant.In this experiment, HL-60 and K562 cell are after the DADAG effect, and its DNA is through the distinctive biochemical variation of agarose gel electrophoresis apoptosis cells---scalariform band; Flow cytometer detects apoptotic peak equally, and is certain dose-effect and time-effect relationship, and this explanation DADAG antitumor action is relevant with cell death inducing.DADAG is to the IC50 of K562 cell and induce the apoptotic dosage of K562 obviously greater than HL-60, and does not influence the cell cycle distribution of K562 cell, and this is relevant with the activated Bcr/Abl tyrosine kinase of K562 cell continuous expression.Studies show that: the expression of Bcr/Abl can suppress the removal and the inductive apoptosis of Vp-16 of somatomedin, the function of Abl tyrosine kinase and the bcl-2 similar [9,10] that suppresses apoptosis.This shows that apoptosis has cell type specificity, and the apoptotic signal approach of HL-60 and K562 cell is different.To the further investigation of K562 cellular biochemical approach, will help to illustrate the K562 cell to the insensitive and drug-fast mechanism of most of chemotherapeutic.
(diacetyldianhydrogalactitol, DADAG) antitumor action has in vivo and in vitro carried out pharmacological evaluation, inquires into the relation of its antitumor action and cell death inducing to diacetyl two anhydrous dulcit in the present invention.Method: set up mice intracranial inoculation ehrlich carcinoma model, observe anti-tumor effect in the DADAG body; Mtt assay is observed the growth inhibited effect of DADAG to human promyelocytic leukemia cell strain HL-60 and human erythroleukemia cell's strain K562, DNA electrophoresis and flow cytometry analysis HL-60 and the apoptotic situation of K562.
Result: DADAG10mg/kgip, every day 1 time, successive administration 7 days, but significant prolongation mice median survival time; HL-60 and K562 are all had the growth inhibited effect, and the IC50 of drug effect 72h is respectively 3.7mg/L and 25.5mg/L; Effect HL-60 and K562 cell rear electrophoresis show apoptotic cell distinctive " scalariform " band, and inferior G1 peak appears in the DNA rectangular histogram.
Conclusion: the DADAG antitumor action is relevant with cell death inducing.To the rat w256 tumour inhibiting rate is 90.6% (2mg/kg, ip * 6), and the Lewis lung cancer tumour inhibiting rate is 52.1% (3mg/kg, ip * 7), B16 melanoma tumour inhibiting rate is 72.6% (3mg/kg, ip * 7), EAC solid tumor tumour inhibiting rate is 32.8% (8mg/kg, ip * 7) (waiting to deliver).We have observed the effect of DADAG to intracerebral transplantation EAC solid tumor, found that under the 10mg/kg high dose, and DADAG is 29% to the increase in life span of intracranial tumor-bearing mice, show that DADAG might see through blood brain barrier.DADAG shows that it has the inside and outside antitumor action, for the DADAG clinical practice provides theoretical foundation to the inhibitory action of cerebroma with to the growth inhibited effect of HL-60, K562 cell.
The specific embodiment
The present invention is described further below in conjunction with embodiment, and embodiment only is indicative explanation, means that never it limits the scope of the invention by any way.
Embodiment 1
Get anhydrous dulcit 3g, place container, add solubilizing agent polyvinylpyrrolidone 0.1g, water for injection 80ml, hydro-oxidation sodium 0.2g stirs and makes dissolving, the citric acid that adds 1mol/L is regulated PH to 7-9.0, and adding mannitol 28g, stirring make dissolving, mend and add water to 100ml.Add the 0.5g activated carbon, stirred 20 minutes down at 30 ℃, the filtering with microporous membrane degerming is adopted in decarburization, and filtrate is carried out packing by every 1ml, after the pre-freeze 2 hours, freezing down drying under reduced pressure 12 hours, to sample temperature after room temperature, dry 5 hours again, make the white loose block, seal and promptly get the anhydrous dulcit freeze-dried powder.
Embodiment 2
Get anhydrous dulcit 50g, place container, add PEG-60002g, water for injection 180ml stirs and makes dissolving, regulates PH to 5.0-9.0 with hydrochloric acid or the sodium hydroxide of 1mol/L, adds mannitol 80g, sorbitol 20g, stirs and makes dissolving, mends and adds water to 2000ml.Add the 0.5g activated carbon, stirred 20 minutes down at 30 ℃, the filtering with microporous membrane degerming is adopted in decarburization, and filtrate is carried out packing by every 2ml, after the pre-freeze 2 hours, freezing down drying under reduced pressure 18 hours, to sample temperature after room temperature, dry 5 hours again, make the white loose block, seal and promptly get the anhydrous dulcit freeze-dried powder.
Embodiment 3
Get anhydrous dulcit 10g, xylitol 0.3g, join among the water for injection 440ml that dissolves the 5g sodium lauryl sulphate, add 2g sodium thiosulfate stirring and dissolving, adding sodium bicarbonate adjusting PH is 5.5-8.5, add the 0.5g active carbon, stirring at room absorption 30 minutes, carbon removal is mended and is added water to 500ml, fine straining, with every 5ml embedding, sterilization, promptly get the anhydrous dulcit injection.
Embodiment 4
Get anhydrous dulcit 10g, xylitol 0.3g among the water for injection 440ml of Tris 5g, adds 2g EDTA-2Na stirring and dissolving, adding sodium bicarbonate adjusting PH is 7.5-9.0, benefit adds water to 500ml, adds the 5g active carbon, stirring at room absorption 30 minutes, carbon removal, fine straining with every 2ml embedding, sterilization, promptly gets the anhydrous dulcit injection.
Embodiment 5
Get anhydrous dulcit 1g, xylitol 0.1g adds among the water for injection 180ml, add 0.5 gram NaOH stirring and make dissolving, add the 3g sodium pyrosulfite, stirring and dissolving, regulating PH is 7.0-9.0, add water for injection to 200ml, add the 2g active carbon, stirring and adsorbing 30 minutes, carbon removal, fine straining, with every 2ml embedding, sterilization, promptly get the anhydrous dulcit injection.
Embodiment 6
Get anhydrous dulcit 5g, xylitol 0.5g adds 15g sodium hydrogen phosphate and 90g sodium chloride, adds injection water 2000ml again, stirs and makes dissolving, regulating PH is 7.5-9.0, add the 10g active carbon, stirring and adsorbing 30 minutes, carbon removal, benefit adds water to 10000ml, fine straining, every bottle of 100ml of embedding, sterilization promptly gets the anhydrous dulcit sodium chloride injection.
Embodiment 7
Get anhydrous dulcit 10g, add 15g sodium hydroxide and 1g xylitol, the 15g sodium pyrosulfite, add injection water 2000ml again, stirring makes dissolving, and regulating PH is 5.0-8.0, adds the 10g active carbon, stirring and adsorbing 30 minutes, carbon removal is mended and is added water to 10000ml, fine straining, every bottle of 100ml of embedding, sterilization promptly gets the anhydrous dulcit Xylitol injection.
Embodiment 8
Get anhydrous dulcit 3.0g, xylitol 0.5g adds PEG-400020g, water for injection 2000ml stirs and makes dissolving, adds 15g sodium hydrogen phosphate and 500g low molecular dextran again, 15g EDTA-2Na stirs and makes dissolving, and adjusting PH is 7.0-8.5, add the 10g active carbon, stirring and adsorbing 30 minutes, carbon removal, benefit adds water to 5000ml, fine straining, every bottle of 50ml of embedding, sterilization promptly gets anhydrous dulcit low molecular dextran injection.
Although more than the present invention done detailed description in conjunction with its special embodiment; but clearly still can make various changes and improvements concerning the skilled people in present technique field, these can not depart from the spirit and the protection domain of claim of the present invention.
Claims (6)
1, a kind of preparation that contains active component anhydrous dulcit administrated by injection is characterized in that being made up of active component anhydrous dulcit 0.001-50% and water-soluble filler, PH regulator, solubilizing agent, antioxidant, water for injection, osmotic pressure regulator.
2, the preparation of administrated by injection as claimed in claim 1 is characterized in that described preparation is meant freeze-dried powder, small injection and the primary infusion that contains anhydrous dulcit.
3, the preparation of administrated by injection as claimed in claim 1 is characterized in that described preparation is:
A. the percentage by weight of lyophilized preparation Chinese medicine composition and other pharmaceutic adjuvant is 0.1-50%;
B. the concentration of small injection Chinese medicine is 50mg/ml-0.5mg/ml;
C. the concentration of primary infusion Chinese medicine is 1mg/ml-0.02mg/ml.
4, the preparation of administrated by injection as claimed in claim 3 is characterized in that described primary infusion is meant the compound injection that anhydrous dulcit and water are formed.
5, the preparation of administrated by injection according to claim 1 is characterized in that water-soluble filler is manna or tween; The PH regulator is nonvolatile acid and potassium hydroxide, sodium hydroxide, sodium carbonate or sodium bicarbonate salt, sodium phosphate or potassium or ammonium salts such as citric acid, phosphoric acid, malic acid; Solubilizing agent is polyvinylpyrrolidone, PEG6000, PEG4000, poloxamer, carbomer, Tween 80, low molecular dextran or Tris; Antioxidant is sodium sulfite, sodium pyrosulfite, sodium thiosulfate or sodium sulfite; Organic sulfur antioxidant is thioglycerol, thiourea or 1-thio sorbitol.
6, a kind of preparation method that contains active component anhydrous dulcit administrated by injection preparation is characterized in that this method comprises the following steps:
I, composition
(1) lyophilized preparation: anhydrous dulcit 0.1%-30%,, water-soluble filler 50%-70%, solubilizing agent 0.1%-12%, antioxidant 0.003%-3%, osmotic pressure 0.9%;
(2) small injection: anhydrous dulcit 0.05%-1.0%, solubilizing agent 0.1%-8%, antioxidant 0.001%-5%, water for injection 70%-90%;
(3) primary infusion: anhydrous dulcit 0.005-0.1%, solubilizing agent 0.1%-8%, antioxidant 0.003%-1% ， Seepage is saturating to press 0.9%, water for injection 88%-98%;
The preparation method of II. different administrated by injection preparations comprises the following steps:
(1) lyophilized preparation: get anhydrous dulcit and water-soluble filler, solubilizing agent, antioxidant, osmotic pressure agent etc., it is an amount of to add water for injection, regulates pH value and makes its dissolving to 4-10, adds water to scale, add the 0.1-0.5% active carbon, stirred 10-60 minute down at 20-50 ℃, the filtering with microporous membrane degerming is adopted in decarburization, filtrate is carried out packing, adopt freeze-drying, make the white loose block, seal promptly;
(2) small injection: get anhydrous dulcit and water-soluble filler, solubilizing agent, antioxidant, Seepage presses agent etc. thoroughly, it is an amount of to add water for injection, regulate pH value and make its dissolving to 4-10, add water to scale, add the 0.1-0.5% active carbon, stirred 10-60 minute decarburization, fine straining, embedding, sterilization down at 20-50 ℃;
(3) primary infusion: get anhydrous dulcit and water-soluble filler, solubilizing agent, antioxidant, osmotic pressure agent etc., add water for injection an amount of about 20%, regulate pH value and make its dissolving to 4-10, add the 0.1-0.5% active carbon, stirred 10-60 minute down at 20-50 ℃, decarburization adds water to scale, fine straining, embedding, sterilization.
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| Application Number | Priority Date | Filing Date | Title |
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| CNA2007101503972A CN101444490A (en) | 2007-11-26 | 2007-11-26 | Injection preparation containing anhydrogalactitol and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CNA2007101503972A CN101444490A (en) | 2007-11-26 | 2007-11-26 | Injection preparation containing anhydrogalactitol and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014004376A2 (en) | 2012-06-26 | 2014-01-03 | Del Mar Pharmaceuticals | Methods for treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations employing dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulcitol, or analogs or derivatives thereof |
| CN106389351A (en) * | 2015-07-29 | 2017-02-15 | 广西梧州制药（集团）股份有限公司 | Application of controlling moisture content of dianhydrogalactol lyophilized powder for injection in keeping stability of dianhydrogalactol lyophilized powder for injection |
| CN106389352A (en) * | 2015-07-29 | 2017-02-15 | 广西梧州制药（集团）股份有限公司 | Stable dianhydrogalactol lyophilized powder for injection |
| CN115054591A (en) * | 2022-08-18 | 2022-09-16 | 中唯国际生命科技有限公司 | Application of dulcitol in medicine for preventing and treating rheumatoid arthritis |
-
2007
- 2007-11-26 CN CNA2007101503972A patent/CN101444490A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014004376A2 (en) | 2012-06-26 | 2014-01-03 | Del Mar Pharmaceuticals | Methods for treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations employing dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulcitol, or analogs or derivatives thereof |
| CN104797267A (en) * | 2012-06-26 | 2015-07-22 | 德玛医药 | Methods for treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations employing dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulcitol, or analogs or derivatives thereof |
| JP2015526410A (en) * | 2012-06-26 | 2015-09-10 | デル マー ファーマシューティカルズ | Treating tyrosine kinase inhibitor resistant malignancies in patients with genetic polymorphisms or dysregulation or mutation of AHI1 using dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulucitol, or analogs or derivatives thereof How to |
| EP2872161A4 (en) * | 2012-06-26 | 2016-07-20 | Del Mar Pharmaceuticals | Methods for treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations employing dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulcitol, or analogs or derivatives thereof |
| CN106389351A (en) * | 2015-07-29 | 2017-02-15 | 广西梧州制药（集团）股份有限公司 | Application of controlling moisture content of dianhydrogalactol lyophilized powder for injection in keeping stability of dianhydrogalactol lyophilized powder for injection |
| CN106389352A (en) * | 2015-07-29 | 2017-02-15 | 广西梧州制药（集团）股份有限公司 | Stable dianhydrogalactol lyophilized powder for injection |
| CN115054591A (en) * | 2022-08-18 | 2022-09-16 | 中唯国际生命科技有限公司 | Application of dulcitol in medicine for preventing and treating rheumatoid arthritis |
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Open date: 20090603 |