CN102302444A - Genistein injection and preparation method thereof - Google Patents
Genistein injection and preparation method thereof Download PDFInfo
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- CN102302444A CN102302444A CN 201110235112 CN201110235112A CN102302444A CN 102302444 A CN102302444 A CN 102302444A CN 201110235112 CN201110235112 CN 201110235112 CN 201110235112 A CN201110235112 A CN 201110235112A CN 102302444 A CN102302444 A CN 102302444A
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- genistein
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Abstract
The invention discloses a genistein injection and a preparation method thereof. The injection disclosed by the invention comprises genistein-cyclodextrin or cyclodextrin derivant clathrate. The preparation method comprises the following steps: preparing a water solution of the genistein clathrate into a water injection through sterilization; adding an appropriate amount of an osmotic pressure regulator, and carrying out autoclave sterilization to prepare medicine-carrying injection; and adding an appropriate amount of an excipient, and freezing and drying to prepare a freeze-dried injection powder. The injection disclosed by the invention acts rapidly and has stable quality, and has excellent prevention and treatment effects for diseases, such as osteoporosis, women menopause syndrome, tumor, cardiovascular and cerebrovascular diseases and the like.
Description
Technical field
The present invention relates to a kind of genistein essence injecta and preparation method thereof, specifically, the present invention relates to a kind of injection that comprises the genistein clathrate and preparation method thereof.Belong to field of medicaments.
Background technology
Genistein is dissolved in DMSO and ethanol, and water-soluble hardly, structure is following:
Genistein is the isoflavonoid that derives from bean and dentation plant, and chemistry is called 4 ', 5, the 7-trihydroxy-isoflavone.Be the main active ingredient of soybean isoflavone, have estrogen-like effects in the metabolism in vivo, be called as plant estrogen class medicine.Genistein has multiple pharmacological effect and biological activitys such as the early atherosclerosis of preventing and chronic angiopathy, antitumor, climacteric syndrome.Genistein is the inhibitor of powerful tyrosine protein kinase and topoisomerase, through the regulation and control to oncogene, thereby realizes that multipath suppresses growth of tumor and transfer.Its anticancer mechanism is unique, through growth, diffusion, the transfer of the direct anticancer of regulation and control oncogene; Genistein antitumor action mechanism comprises seven approach: Profilin tryrosinase phosphorylation; Suppress the topoisomerase enzymatic activity; Suppress cell cycle; The inducing cell differentiation; Cell death inducing; Suppress cell blood vessel hyperplasia and antioxidation.In the body, experiment in vitro and epidemiology shows that all genistein all has inhibitory action to kinds of tumors, like breast carcinoma, carcinoma of prostate, renal carcinoma, gastric cancer, colorectal cancer, bladder cancer, pulmonary carcinoma, uterus carcinoma, skin carcinoma, leukemia, lymphoma, neuroblastoma and head and neck cancer etc.Genistein not only has prevention and inhibitory action also with many antitumor drug (like tamoxifen, cisplatin, bcnu, daunorubicin, tiazofurine) the synergistic antitumor effect to be arranged to kinds of tumors separately.
Genistein is water-soluble hardly; The water solublity that it is relatively poor through the preparation that traditional formulation method is prepared from, is difficult to after oral, reach the bioavailability that the treatment disease requires; Simultaneously also big limitations process the kind of preparation, like dosage forms such as soluble powder or intravenous administration formulations.In addition; The content of genistein in preparation is lower, and in order to reach medicine concentration, can only improve curative effect through the using dosage that increases preparation; But strengthened again so to a certain extent the risk of untoward reaction taking place, but also can increase drug cost.
Summary of the invention
The present invention provides a kind of injection that comprises the genistein clathrate and preparation method thereof for solving the problem that exists in the above-mentioned prior art.
Concrete, the present invention has improved the water solublity of genistein through cyclodextrin or the cyclodextrin derivative clathration to genistein.
The present invention at first prepares the cyclodextrin or the cyclodextrin derivant clathrate of genistein, the injection that further prepares clinically the cyclodextrin of genistein or cyclodextrin derivant clathrate again to be suitable for.
Genistein clathrate provided by the invention is made up of genistein and inclusion agents, and the consumption of preparation used genistein of genistein clathrate and inclusion agents is counted with weight portion:
Genistein 1-100
Inclusion agents 5-800
The consumption of used genistein and inclusion agents is preferably in weight portion:
Genistein 10-100
Inclusion agents 50-600.
The consumption of used genistein and inclusion agents is preferably in weight portion again:
Genistein 10-30
Inclusion agents 200-500
The consumption of used genistein and inclusion agents is in weight portion more preferably:
Genistein 10-20
Inclusion agents 400-500
The consumption of used genistein and inclusion agents most preferably is in weight portion:
Genistein 10
Inclusion agents 300
The source of genistein can be through extracted form natural plant or chemosynthesis and gets among the present invention.
Inclusion agents according to the invention is preferably cyclodextrin or cyclodextrin derivative, can be selected from one or more the combination in alpha-cyclodextrin, gamma-cyclodextrin, hydroxyethyl-, HP-, dihydroxypropyl beta-schardinger dextrin-, methyl-beta-schardinger dextrin-, glucose ring dextrin, maltose cyclodextrin, maltotriose cyclodextrin, carboxymethyl cyclodextrin, the sulfoalkyl cyclodextrin.Inclusion agents more preferably HP-, dihydroxypropyl beta-schardinger dextrin-or HP-and glucose ring dextrin by weight 1: 2 combination.
The method for preparing of genistein clathrate can adopt any in the methods such as solvent method, polishing, ultrasonic method, freeze-drying, spray drying method among the present invention.
The method for preparing of genistein cyclodextrin or cyclodextrin derivant clathrate among the present invention; Can be that cyclodextrin or cyclodextrin derivative and genistein are placed colloid mill or mortar; Adding suitable solvent stirs; Make into pastel; Ground 1～5 hour, and got the viscous pastes of homogeneous, filter; 40 ℃～80 ℃ dryings promptly get solid genistein cyclodextrin or cyclodextrin derivant clathrate.
The method for preparing of genistein cyclodextrin or cyclodextrin derivant clathrate among the present invention; Can also be genistein to be joined among the NaOH of an amount of 0.01mol/L dissolve; Weight part ratio according to genistein and cyclodextrin or cyclodextrin derivative; Cyclodextrin or cyclodextrin derivative are added wherein; Stir to clarify clear solution; Regulate pH value to neutral with the dilute hydrochloric acid of 1.0mol/L then, promptly get liquid genistein cyclodextrin or cyclodextrin derivant clathrate.
The method for preparing of genistein cyclodextrin or cyclodextrin derivant clathrate among the present invention; Can be that liquid genistein cyclodextrin or cyclodextrin derivant clathrate are concentrated into cyclodextrin or the cyclodextrin derivative concentration range solution at 10～15% (W/V); Cold preservation 12 hours; Make it separate out white precipitate; Filter; In 40 ℃～80 ℃ dryings, promptly get solid genistein cyclodextrin or cyclodextrin derivant clathrate.
The preferred for preparation method of genistein clathrate provided by the invention comprises the steps:
(a) genistein is joined in the suitable solvent after the dissolving, add inclusion agents;
(b) heating, stir, to clear solution, promptly get liquid genistein clathrate.
Step (b) preferably under temperature 25-80 ℃, magnetic agitation 0.5-2 hour.More preferably temperature is that 40 ℃ of lower magnetic forces stirred 0.5 hour.
The preferred for preparation method of genistein clathrate provided by the invention comprises the steps: that also (c) is dry with liquid genistein prime ring clathrate, promptly gets solid genistein clathrate.Step (c) is preferable under 40 ℃～80 ℃ the temperature dry.Most preferably 60 ℃.
The said drying means of step (c) can use drying meanss such as convection drying, spray drying, lyophilization.
In the method for preparing of genistein clathrate provided by the invention; Said solvent is selected from a kind of or any two kinds and the above mixed solvent in water, ethanol, methanol, propanol, isopropyl alcohol, ethylene glycol, propylene glycol, glycerin, the acetone, wherein most preferably is ethanol.
With this area method commonly used, genistein clathrate of the present invention can be prepared into various injections.
Injection of the present invention comprises solution type injection agent and freeze-dried powder; Solution type injection agent comprises aqueous injection and the transfusion of medicine carrying type.
The aqueous solution of genistein clathrate of the present invention can be prepared into aqueous injection through sterilization.
Genistein clathrate aqueous solution of the present invention adds an amount of osmotic pressure regulator and can be made into the transfusion of medicine carrying type through pressure sterilizing, comprises sodium chloride injection and glucose injection.
The aqueous solution of genistein clathrate of the present invention adds an amount of excipient and can be made into freeze-dried powder through lyophilization.In the method for preparing of preferred genistein clathrate freeze-dried powder provided by the invention, the weight portion of genistein clathrate and excipient is respectively:
Genistein clathrate 15～30
Excipient 5～60
The weight portion of genistein clathrate and excipient is preferably:
Genistein clathrate 20～30
Excipient 15～50
The weight part ratio of genistein clathrate and excipient most preferably is:
Genistein clathrate 20～25
Excipient 40～50
Excipient in the above-mentioned freeze-dried powder can adopt various pharmaceutical excipients commonly used, is preferably in mannitol, glucose, sorbitol, sodium chloride, dextran, sucrose, lactose, gelatin hydrolysate and the Polyethylene Glycol one or more; Further be preferably in mannitol, sorbitol, dextran, lactose, gelatin hydrolysate and the Polyethylene Glycol one or more.
The invention provides a kind of injection that comprises above-mentioned genistein clathrate and preparation method thereof, it comprises the steps:
A, take by weighing the genistein clathrate, and get pH value regulator, medical active carbon and water for injection ready by recipe quantity;
b, in the preparation of the container by adding an appropriate amount of water for injection, take weighed genistein inclusion Join preparation container, stirring to dissolve completely, fill with water for injection to the full amount, adjusted to pH
adding medicinal charcoal stir adsorption
minutes, the weight of carbon medication
filter.Fill promptly got after filtrating added adjuvant according to the requirement of above-mentioned different dosage form.
The above-mentioned regulator that is used to regulate pH value can be used hydrochloric acid, acetic acid, citric acid, tartaric acid, acidic amino acid, sodium bicarbonate, sodium acetate, ethylenediamine, basic amino acid etc., and in preferably citric acid, tartaric acid, sodium bicarbonate or the sodium acetate one or more.
Cyclodextrin or cyclodextrin derivative be a kind of toxicity less the water solublity pharmaceutic adjuvant; The present invention carries out enclose through cyclodextrin or cyclodextrin derivative to genistein; Genistein is embedded in the tubular structure of cyclodextrin or cyclodextrin derivative molecule; Become the clathrate of genistein cyclodextrin or cyclodextrin derivative; Thereby improve the water solublity of genistein; Make this active component of genistein directly apply to liquid dosage form, solved the shortcoming that the genistein water solublity is low, can not directly be used for injection type with the form of clathrate.
The invention provides various stable injections, injection provided by the invention has improved the bioavailability of genistein greatly.Injection provided by the invention is used for muscle and intravenous administration, have easy to use, curative effect is rapid, characteristics such as safe and reliable, particularly to not eating or gastrointestinal function obstacle and patient that can not oral administration can intravenously administrables; Preparation provided by the invention has good preventing and therapeutic effect for osteoporosis, climacteric syndrome, tumor and cardio-cerebrovascular diseases.
In addition, production technology provided by the invention skill easy, economical, be easy to suitability for industrialized production, economic and social benefits height.
The specific embodiment
Be described further below in conjunction with embodiment, but not as to qualification of the present invention.
Embodiment 1: the preparation of genistein freezing-dried powder
Take by weighing genistein 2.0g respectively; 60.0 gram HP-; Mannitol 126g; Earlier genistein is dissolved in the 130ml ethanol; Add HP-after the stirring and dissolving; Magnetic agitation 2 hours; 50 ℃ of temperature, behind the enclose, ethanol is removed in decompression; Add mannitol and water for injection 1000ml stirring and make it dissolving; After-teeming is penetrated water to the 2000ml full dose, with citron acid for adjusting pH to 3.3, adds medical active carbon stirring and adsorbing 15 minutes; The amount of used medicinal charcoal is 0.03%; Filter, filtrating is sub-packed in the cillin bottle lyophilization; Take out behind the vacuum gland, jewelling lid labeling promptly gets the lyophilizing finished product.
Embodiment 2: the preparation of genistein sodium chloride injection
Take by weighing 40.0g HP-, genistein 1.0g and 9.0g sodium chloride for injection respectively; Genistein is joined in the 60ml ethanol; Add HP-and sodium chloride for injection after the stirring and dissolving; Magnetic agitation 1 hour (speed controlling does not outwards produce at liquid and splashes); 60 ℃ of temperature are observed the genistein hydroxypropyl-beta-cyclodextrin inclusion solution that obtains clear.Ethanol is removed in decompression; Adding water for injection stirs to 600ml; Back after-teeming is penetrated water to the 1000ml full dose; With winestone acid for adjusting pH to 3.8; Added medical active carbon stirring and adsorbing 20 minutes, the amount of used medicinal charcoal is 0.03%, filters; Be sub-packed in the infusion bottle by predetermined close, 115 ℃ of pressure sterilizings promptly got in 30 minutes.
Embodiment 3: the preparation of genistein glucose injection
Take by weighing 50.0g HP-, genistein 2.0g, glucose for injection 50g respectively; Genistein is joined in the 150ml ethanol; Add HP-after the stirring and dissolving; Magnetic agitation 1 hour (speed controlling does not outwards produce at liquid and splashes); 55 ℃ of temperature are observed the genistein hydroxypropyl-beta-cyclodextrin inclusion solution that obtains clear.Ethanol is removed in decompression.After glucose for injection added injection water 100ml stirring and dissolving; Glucose Liquid is poured in the clathrate; Moisturizing is to 800ml; With winestone acid for adjusting pH to 3.8; Added medical active carbon stirring and adsorbing 20 minutes, the amount of used medicinal charcoal is 0.03%, filters; Be sub-packed in the infusion bottle by predetermined close, 115 ℃ of pressure sterilizings promptly got in 30 minutes.
Embodiment 4: preparation genistein aseptic powder injection
Indoor in the sterile working; Take by weighing 30.0g HP-and genistein 1.0g; Add 80ml ethanol stirring and dissolving; Add HP-after the stirring and dissolving; Magnetic agitation 1.5 hours (speed controlling does not outwards produce at liquid and splashes); 70 ℃ of temperature are observed the genistein hydroxypropyl-beta-cyclodextrin inclusion solution that obtains clear.Moisturizing with winestone acid for adjusting pH to 3.5, added medical active carbon stirring and adsorbing 20 minutes to 1000ml after the inclusion complex in solution drying under reduced pressure that obtains removed ethanol, and the amount of used medicinal charcoal is 0.03%, filter, and lyophilization, packing promptly gets.
Embodiment 5: the preparation of genistein injection
Take by weighing genistein 2.0g, 70.0 gram HP-respectively, earlier genistein is dissolved in the 140ml ethanol, add HP-after the stirring and dissolving; Magnetic agitation 2 hours, 80 ℃ of temperature are behind the enclose; Ethanol is removed in decompression; Add water for injection 800ml stirring and make it dissolving, after-teeming is penetrated water to the 1000ml full dose, with citron acid for adjusting pH to 3.3; Added medical active carbon stirring and adsorbing 15 minutes; The amount of used medicinal charcoal is 0.03%, filters, and packing promptly gets.
Embodiment 6: the preparation of genistein freezing-dried powder
Take by weighing genistein 3.0g respectively; 100.0 gram HP-; Mannitol 258g; Earlier genistein is dissolved in the 200ml ethanol; Add HP-after the stirring and dissolving; Magnetic agitation 1.5 hours; 55 ℃ of temperature, behind the enclose, ethanol is removed in decompression; Add mannitol and water for injection 2000ml stirring and make it dissolving; After-teeming is penetrated water to the 3000ml full dose, with winestone acid for adjusting pH to 3.7, adds medical active carbon stirring and adsorbing 20 minutes; The amount of used medicinal charcoal is 0.03%; Filter, filtrating is sub-packed in the cillin bottle lyophilization; Take out behind the vacuum gland, jewelling lid labeling promptly gets the lyophilizing finished product.
Blood vessel irritation with the genistein hydroxypropyl-beta-cyclodextrin inclusion carries out is tested as follows:
Get 10 of rabbit and be divided into two groups, i.e. test group and matched group, test group is by rabbit ear edge vein this clathrate that slowly instils, and once a day, dosage 1.62g/kg adds 5% glucose injection 40ml, drips successive administration 3 days fast 1.5ml/ minute; Matched group gives 10% glacial acetic acid; In the negative contrast of 5% glucose injection of instiling of the offside rabbit ear; Successive administration 3 days; The result shows: test group successive administration 3 days; Local no abnormality seen; With the same, and inject visible contrafluxion, thickening behind 10% glacial acetic acid, ooze out side injection 5% glucose injection.
This description of test, this clathrate that instils is little to the vascular stimulation of animal, is suitable for this clathrate is prepared into injection type.
Genistein essence injecta study on the stability of the present invention is tested as follows:
One, influence factor's test
High temperature, exposure experiments to light
Get each 2 parts of genistein freezing-dried powder and genistein injection, carry out high temperature and exposure experiments to light respectively:
1. hot test: sample is put in the sealing clean container, 60 ℃ of condition held 5 days, and sampling check and analysis, result and sample comparison in 0 day.
2. exposure experiments to light: sample places the transparent sealing container, is placed in the lighting box that daylight lamp is housed, and in the condition held of 4500 ± 500LX illuminance 5 days, the analysis of taking a sample to check, result and 0 day sample are relatively.
The sample size of table 15 day accelerated test is measured the result
Conclusion: under the accelerated test condition, genistein essence injecta appearance color does not have change, and content reduces seldom, the basic no change of impurity, and the result shows that genistein chemical property behind enclose is stable.
Two, long-time stability are investigated test
Get genistein freezing-dried powder and injection,, investigate 0,3,6,9 intending under the listing packing GMP storage condition, relevant indexs such as the character of sample, acidity, clarity of solution and color, related substance, changes of contents in the time of 12,24 months, result of the test is following:
Table 2 genistein freezing-dried powder long-time stability are investigated test
Table 3 genistein injection experimental result
Result of the test, genistein freezing-dried powder and injection are good at 24 months internal stabilities.
Obviously, the above embodiment of the present invention only be for clearly the present invention is described and is done for example, and be not to be qualification to embodiment of the present invention.For the those of ordinary skill in affiliated field, on the basis of above-mentioned explanation, can also make other multi-form variation or change.Here need not also can't give exhaustive to all embodiments.And these belong to conspicuous variation or the change that spirit of the present invention extended out and still are among protection scope of the present invention.
Claims (23)
1. injection that comprises the genistein clathrate is characterized in that in the genistein clathrate, genistein and inclusion agents are counted with weight portion:
Genistein 1-100
Inclusion agents 5-800
2. injection according to claim 1 is characterized in that genistein and inclusion agents count with weight portion:
Genistein 10-100
Inclusion agents 50-600.
3. injection according to claim 2 is characterized in that genistein and inclusion agents count with weight portion:
Genistein 10-30
Inclusion agents 200-500
4. injection according to claim 3 is characterized in that genistein and inclusion agents count with weight portion:
Genistein 10-20
Inclusion agents 400-500
5. injection according to claim 4 is characterized in that genistein and inclusion agents count with weight portion:
Genistein 10
Inclusion agents 300
6. according to the described injection of arbitrary claim among the claim 1-5, the source that it is characterized in that genistein is for getting through extracted form natural plant or chemosynthesis.
7. according to the described injection of arbitrary claim among the claim 1-5, it is characterized in that said inclusion agents is selected from and be cyclodextrin or cyclodextrin derivative.
8. injection according to claim 7 is characterized in that said inclusion agents is selected from one or more the combination in alpha-cyclodextrin, gamma-cyclodextrin, hydroxyethyl-, HP-, dihydroxypropyl beta-schardinger dextrin-, methyl-beta-schardinger dextrin-, glucose ring dextrin, maltose cyclodextrin, maltotriose cyclodextrin, carboxymethyl cyclodextrin, the sulfoalkyl cyclodextrin.
9. injection according to claim 8 is characterized in that said inclusion agents is selected from HP-and dihydroxypropyl beta-schardinger dextrin-.
10. injection according to claim 8 is characterized in that said inclusion agents is HP-and glucose ring dextrin by weight 1: 2 combination.
11., it is characterized in that comprising aqueous injection, transfusion or freeze-dried powder according to the described injection of arbitrary claim among the claim 1-10.
12. injection according to claim 11 is characterized in that method for preparing comprises:
The aqueous solution of genistein clathrate is prepared into aqueous injection through sterilization;
Or genistein clathrate aqueous solution adds an amount of osmotic pressure regulator and processes the transfusion of medicine carrying type through pressure sterilizing, comprises sodium chloride injection and glucose injection;
Or an amount of excipient of the aqueous solution of genistein clathrate adding is processed freeze-dried powder through lyophilization.
13. injection according to claim 12 is characterized in that in the method for preparing of described freeze-dried powder, the weight portion of genistein clathrate and excipient is respectively:
Genistein clathrate 15～30
Excipient 5～60
14. injection according to claim 13 is characterized in that in the method for preparing of described freeze-dried powder, the weight portion of genistein clathrate and excipient is:
Genistein clathrate 20～30
Excipient 15～50
15. injection according to claim 14 is characterized in that in the method for preparing of described freeze-dried powder, the weight portion of genistein clathrate and excipient is:
The weight part ratio of genistein clathrate and excipient most preferably is:
Genistein clathrate 20～25
Excipient 40～50
16., it is characterized in that described excipient is selected from one or more in mannitol, glucose, sorbitol, sodium chloride, dextran, sucrose, lactose, gelatin hydrolysate and the Polyethylene Glycol according to the injection described in the arbitrary claim of claim 12-15.
17. injection according to claim 16 is characterized in that described excipient is selected from one or more in mannitol, sorbitol, dextran, lactose, gelatin hydrolysate and the Polyethylene Glycol.
18. the method for preparing of a genistein clathrate injection is characterized in that comprising the steps:
(a) genistein is joined in the suitable solvent after the dissolving, add inclusion agents;
(b) under temperature 25-80 ℃, magnetic agitation 0.5-2 hour,, promptly get liquid genistein clathrate to clear solution.
19. method for preparing according to claim 18 is characterized in that also comprising the steps: that (c) is dry under 40 ℃～80 ℃ temperature with liquid genistein clathrate.
20., it is characterized in that solvent described in the step (a) is selected from a kind of or any two kinds and the above mixed solvent in water, ethanol, methanol, propanol, isopropyl alcohol, ethylene glycol, propylene glycol, glycerin, the acetone according to claim 18 or 19 described method for preparinies.
21. method for preparing according to claim 20 is characterized in that solvent is an ethanol described in the step (a); Step (b) is to stir 0.5 hour at 40 ℃ of lower magnetic forces; Step (c) is 60 ℃ of dryings down.
22., it is characterized in that also comprising the steps: according to the described method for preparing of arbitrary claim among the claim 18-21
Take by weighing the genistein clathrate by recipe quantity, and get pH value regulator, medical active carbon and water for injection ready;
In the preparation of the container by adding an appropriate amount of water for injection, take weighed genistein inclusion Join preparation container, stirring to dissolve completely, fill with water for injection to the full amount, adjusted to pH
adding drug stirring with activated carbon adsorption
min, the weight of carbon medication
filtering.
23. method for preparing according to claim 22; It is characterized in that said pH value regulator is selected from hydrochloric acid, acetic acid, citric acid, tartaric acid, acidic amino acid, sodium bicarbonate, sodium acetate, ethylenediamine, basic amino acid etc., and in preferably citric acid, tartaric acid, sodium bicarbonate or the sodium acetate one or more.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102579400A (en) * | 2012-03-26 | 2012-07-18 | 扬州大学 | Method for preparing microcapsules capable of controlling to release magnetic medicines in timing mode |
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Non-Patent Citations (1)
| Title |
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| 《中国药学杂志》 20041108 雷英杰等 染料木素-beta-环糊精包合物的制备和鉴定 , 第11期 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102579400A (en) * | 2012-03-26 | 2012-07-18 | 扬州大学 | Method for preparing microcapsules capable of controlling to release magnetic medicines in timing mode |
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Application publication date: 20120104 |