CN1879647A - Solid dispersion of protopanaxadiol and preparation method thereof - Google Patents
Solid dispersion of protopanaxadiol and preparation method thereof Download PDFInfo
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- CN1879647A CN1879647A CN 200610050598 CN200610050598A CN1879647A CN 1879647 A CN1879647 A CN 1879647A CN 200610050598 CN200610050598 CN 200610050598 CN 200610050598 A CN200610050598 A CN 200610050598A CN 1879647 A CN1879647 A CN 1879647A
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Abstract
The invention provides a protopanaxadiol solid dispersion and its preparing method, wherein the weight ratio of the protopanaxadiol and carrier material is 1:1-50, and protopanaxadiol solid dispersion can be prepared through melting method, solvent method, solvent-melting method, grinding method, spray-drying method or freeze drying method. The preparation can be made into the dosage forms of capsules, tablets, suppositories and drop pills.
Description
Technical field
The present invention relates to medical technical field, exactly relate to solid dispersion of protopanaxadiol and preparation method thereof.
Background technology
The screening anti-tumor active ingredient has become one of focus of research in the world from Chinese medicine.The tonic Radix Ginseng has the history in thousands of years in the application of countries in Asia, and its main active is the ginsenoside, has various pharmacological activities.Research worker finds that ginsenoside Rg3, Rh2, C-K (Compound K) and aglycon protopanoxadiol, Protopanaxatriol etc. have stronger anti-tumor activity both at home and abroad in recent years, and activity is subjected to the influence of glycosyl bigger, and the strong and weak rule of anti-tumor activity is: and aglycon＞monoglycosides＞bioside＞three glucosides＞tetrose glycosides (Dou Deqiang etc. Shenyang Pharmaceutical University's journal 1999; 16 (2): 151-156.David G, et al.Archives ofBiochemistry and Biophysics 2002; 406:1-8.), so protopanoxadiol has bigger market prospect as antitumor drug exploitation.
But protopanoxadiol is an insoluble drug, can't directly prepare qualified preparation by crude drug, and oral absolute biological degree is low.Adopt suitable method, protopanoxadiol is scattered in physiology inertia, and the solid-state carrier that water solublity is big compatible with body makes solid dispersion, can increase the dissolubility and the gastrointestinal degree of absorption of medicine, thereby improve bioavailability of medicament.And the research of solid dispersion of protopanaxadiol does not appear in the newspapers both at home and abroad.
Summary of the invention
The purpose of this invention is to provide a kind of solid dispersion of protopanaxadiol and preparation method thereof.
The technical solution adopted for the present invention to solve the technical problems is:
One. solid dispersion of protopanaxadiol comprises:
Contain active component protopanoxadiol and carrier material;
The weight ratio of protopanoxadiol and carrier material is 1: 2～50;
Described protopanoxadiol be 20 (S)-protopanoxadiols, 20 (R)-protopanoxadiols or 20 (R, S)-protopanoxadiol;
Described carrier material is one or more mixtures in polyvinylpyrrolidone, crospolyvinylpyrrolidone, Macrogol 4000, polyethylene glycol 6000, poloxamer, cyclodextrin, microcrystalline Cellulose, hydroxypropyl methylcellulose, hydroxypropyl cellulose, lactose, the mannose.
Two. the preparation method of solid dispersion of protopanaxadiol: adopt polishing, fusion method, solvent method, solvent-fusion method, spray drying method or freeze-drying.
1) carrier material is polyvinylpyrrolidone, crospolyvinylpyrrolidone, Macrogol 4000, polyethylene glycol 6000, cyclodextrin, microcrystalline Cellulose or lactose in the described polishing.
2) carrier material is poloxamer, Macrogol 4000 or polyethylene glycol 6000 in the described fusion method.
3) carrier material is Macrogol 4000, polyethylene glycol 6000, poloxamer, crospolyvinylpyrrolidone, polyvinylpyrrolidone, hydroxypropyl cellulose, lactose or mannose in the described solvent method.
4) carrier material is poloxamer, Macrogol 4000 or polyethylene glycol 6000 in described solvent-fusion method.
5) carrier material is Macrogol 4000, polyethylene glycol 6000, poloxamer, cyclodextrin, crospolyvinylpyrrolidone, polyvinylpyrrolidone, lactose or mannose in the described spray drying method.
6) carrier material is Macrogol 4000, polyethylene glycol 6000, poloxamer, cyclodextrin, crospolyvinylpyrrolidone, polyvinylpyrrolidone, lactose or mannose in the described freeze-drying.
The beneficial effect that the present invention has is: can increase drug solubility, accelerate the dissolution rate of medicine.Experiment showed, that through stripping medicine former spice of 45min accumulative total stripping percentage in dissolution medium improves 2～5 times, the present invention can be made into tablet, capsule, drop pill or suppository.
Description of drawings
Accompanying drawing is the x-ray diffraction pattern of embodiment 6.
The solid dispersion of curve 1.20 (S)-protopanoxadiol-polyvinylpyrrolidone K30 (1: 8);
The physical mixture of curve 2.20 (S)-protopanoxadiol-polyvinylpyrrolidone K30 (1: 8);
Curve 3. polyvinylpyrrolidone K30;
Curve 4.20 (S)-protopanoxadiol.
The specific embodiment
Protopanoxadiol of the present invention (Hainan Yazhou Pharmaceutical Co., Ltd provides) solid dispersion can be distinguished preparation as follows:
1. polishing
Get carrier material and protopanoxadiol mixing, put in the mortar and grind, rotating speed 100～600rpm, milling time 20～60min.Take out, cross 60～100 mesh sieves, promptly get solid dispersion of the present invention.The gained solid dispersion can be made into tablet or capsule.
Wherein the weight ratio of protopanoxadiol and carrier material is 1: 2～50, and described carrier material is polyvinylpyrrolidone, crospolyvinylpyrrolidone, Macrogol 4000, polyethylene glycol 6000, cyclodextrin, microcrystalline Cellulose or lactose.
2. fusion method
Get carrier material and protopanoxadiol mixing, heated and stirred is to fusion fully, also can be with behind the carrier heating and melting, add again protopanoxadiol stir molten, then with fused mass under vigorous stirring, put in the cryosel bath and be cooled to solid rapidly, placed the exsiccator drying at room temperature 1～5 day, or vacuum drying 5～24h, grind, cross 60～100 mesh sieves, promptly get solid dispersion of the present invention.The gained solid dispersion can be made into tablet, capsule, drop pill or suppository.
Wherein the weight ratio of protopanoxadiol and carrier material is 1: 2～50, and described carrier material is poloxamer, Macrogol 4000 or polyethylene glycol 6000.
3. solvent method
Get carrier material and protopanoxadiol, behind the adding organic solvent dissolution, adopt rotary evaporation to remove and desolvate; Or carrier material and protopanoxadiol be dissolved in the organic solvent, add the auxiliary materials and mixing that is insoluble to this solvent, adopt rotary evaporation to remove and desolvate, vacuum drying 5～24h grinds, and crosses 60～100 mesh sieves, promptly gets solid dispersion of the present invention.The gained solid dispersion can be made into tablet or capsule.
Wherein the weight ratio of protopanoxadiol and carrier material is 1: 2～50, and described carrier material is Macrogol 4000, polyethylene glycol 6000, poloxamer, crospolyvinylpyrrolidone or polyvinylpyrrolidone; Insoluble adjuvant is hydroxypropyl cellulose, lactose or mannose; Organic solvent is methanol, ethanol, acetone, ether, chloroform or dichloromethane.
4. solvent-fusion method
Get carrier material, heating makes its fusion in 50～90 ℃ of water-baths, adds the protopanoxadiol with organic solvent dissolution, and is evenly mixed, boil off organic solvent, place cryosel to bathe and be cooled to solid, vacuum drying 5～24h rapidly, grind, cross 60～100 mesh sieves, promptly get solid dispersion of the present invention.The gained solid dispersion can be made into tablet, capsule, drop pill or suppository.
Wherein the weight ratio of protopanoxadiol and carrier material is 1: 2～50, and described carrier material is poloxamer, Macrogol 4000 or polyethylene glycol 6000; Organic solvent is methanol, ethanol, acetone, ether, chloroform or dichloromethane.
5. spray drying method
With carrier material and protopanoxadiol mixing, be dissolved in 60～90% ethanol, spray drying eliminates solvent and promptly gets solid dispersion of the present invention.The gained solid dispersion can be made into tablet or capsule.
Wherein the weight ratio of protopanoxadiol and carrier material is 1: 4～50, and described carrier material is Macrogol 4000, polyethylene glycol 6000, poloxamer, cyclodextrin, crospolyvinylpyrrolidone, polyvinylpyrrolidone, lactose or mannose.
6. freeze-drying
Get carrier material, be dissolved in water, add protopanoxadiol again, put in the mortar and grind, rotating speed 100～600rpm, milling time 20～60min.Lyophilization, freeze-drying time are 12～30h.Grind, cross 60～100 mesh sieves, promptly get solid dispersion of the present invention.The gained solid dispersion can be made into tablet or capsule.
Wherein the weight ratio of protopanoxadiol and carrier material is 1: 4～50, and described carrier material is Macrogol 4000, polyethylene glycol 6000, poloxamer, cyclodextrin, crospolyvinylpyrrolidone, polyvinylpyrrolidone, lactose or mannose.
The present invention adopts the X-ray diffraction analysis that prepared all kinds of solid dispersion are investigated.The X-ray diffraction result shows that protopanoxadiol has strong diffraction maximum between 2-22 °, make solid dispersion after, the crystal diffraction peak of medicine disappears, show medicine with molecular forms or unformed state high degree of dispersion in above-mentioned carrier material.
The present invention adopts the stripping situation of dissolution in vitro measuring medicine, and the result shows that it is all right in external stripping, has clear improvement than crude drug.The result is as follows:
1. the three therapeutic methods of traditional Chinese medicine (little agar diffusion method) mensuration medicine dissolution in vitro in the Chinese Pharmacopoeia version appendix in 2005 press in dissolution in vitro experiment.Medium is 0.35% sodium lauryl sulphate (SDS) aqueous solution, and rotating speed is 50rpm, and temperature is 37 ± 0.5 ℃.
2. the dissolution in vitro experiment is contrast with the protopanoxadiol crude drug, measures solid dispersion of protopanaxadiol of the present invention in external stripping situation.The result shows material medicine 45min cumulative in vitro stripping percentage rate for being 20.3%, and solid dispersion of the present invention then can reach 42.7～100.1% (labelled amounts).Wherein be the solid dispersion of preparing carriers with poloxamer 188, polyvinylpyrrolidone, crospolyvinylpyrrolidone or HP-, dissolution rate improves particularly remarkable.
Embodiment 1
Get 800mg polyvinylpyrrolidone K30 and 200mg 20 (S)-protopanoxadiol mixing, put in the mortar and grind, rotating speed 200rpm, milling time 30min.Take out, cross 100 mesh sieves, promptly.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 40.5 ± 2.3% (n=6).
Embodiment 2
Get 4000mg microcrystalline Cellulose and 200mg 20 (R)-protopanoxadiol mixing, put in the mortar and grind, rotating speed 100rpm, milling time 60min.Take out, cross 80 mesh sieves, this invention solid dispersion 45min cumulative in vitro stripping percentage rate is 48.7 ± 1.4% (n=6).
Embodiment 3
Get the 1600mg poloxamer-188 and 200mg 20 (S)-protopanoxadiol is put in the evaporating dish, heated and stirred is to fusion fully in 60 ℃ of water-baths, then with fused mass under vigorous stirring, put in the cryosel bath and be cooled to solid rapidly, placed the exsiccator drying at room temperature 2d days, and took out, grind, cross 60 mesh sieves, promptly.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 98.1 ± 3.4% (n=6).
Embodiment 4
Getting the 5000mg polyethylene glycol 6000 puts in the evaporating dish, in 60 ℃ of water-baths, be heated to complete fusion, add 100mg 20 (R again, S)-protopanoxadiol stir molten, then with fused mass under vigorous stirring, put cryosel and be cooled to solid rapidly in bathing, place vacuum drying oven drying at room temperature 24h, grind, cross 60 mesh sieves, promptly get solid dispersion of the present invention.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 95.7 ± 2.5% (n=6).
Embodiment 5
Get the 1000mg crospolyvinylpyrrolidone and 200mg 20 (S)-protopanoxadiol is put in the round-bottomed flask, add 15ml dichloromethane ultrasonic dissolution.In 45 ℃ of water-baths, reduce pressure 30min except that desolvating with Rotary Evaporators.Room temperature continues dry 24h in vacuum drying oven, takes out, and grinds, and crosses 80 mesh sieves, promptly.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 99.4 ± 1.6% (n=6).
Embodiment 6
Get 1600mg polyvinylpyrrolidone K30 and 200mg 20 (S)-protopanoxadiol is put in the round-bottomed flask, add 20ml dehydrated alcohol ultrasonic dissolution.In 55 ℃ of water-baths, reduce pressure 45min except that desolvating with Rotary Evaporators.Room temperature continues dry 12h in vacuum drying oven, takes out, and grinds, and crosses 80 mesh sieves, promptly.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 95.4 ± 1.6% (n=6).
X-ray diffraction contrast figure sees shown in the accompanying drawing.
Embodiment 7
Getting 600mg poloxamer 188 puts in the round-bottomed flask with 200mg 20 (R)-protopanoxadiol, after adding 25ml dehydrated alcohol ultrasonic dissolution, add the 800mg low-substituted hydroxypropyl cellulose, in 55 ℃ of water-baths, adopt rotary evaporation decompression 45min to remove and desolvate, room temperature continues dry 12h in vacuum drying oven, take out, grind, cross 60 mesh sieves, promptly.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 100.1 ± 1.8% (n=6).
Embodiment 8
Getting 1000mg poloxamer 407 puts in the evaporating dish, heating makes its fusion in 70 ℃ of water-baths, stir the 100mg 20 that adds down with the 0.5ml anhydrous alcohol solution (R, S)-protopanoxadiol, evenly mixed, after flinging to solvent, place cryosel to bathe and be cooled to solid rapidly, room temperature continues dry 6h in vacuum drying oven, take out, grind, cross 80 mesh sieves, promptly.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 96.8 ± 1.0% (n=6).
Embodiment 9
Getting 2000mg PEG4000 puts in the evaporating dish, heating makes its fusion in 60 ℃ of water-baths, stir 100mg 20 (the S)-protopanoxadiol that adds down with the 0.5ml acetone solution, evenly mixed, fling to solvent after, place cryosel to bathe and be cooled to solid rapidly, room temperature continues dry 12h in vacuum drying oven, takes out, and grinds, cross 100 mesh sieves, promptly.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 92.4 ± 1.8% (n=6).
Embodiment 10
Get 5000mg polyvinylpyrrolidone K30, add 75% ethanol 500ml dissolving, add 500mg 20 (S)-protopanoxadiol mixing again, carry out spray drying with electric heating mini spray exsiccator with 50ml 90% dissolve with ethanol, inlet temperature is 70 ℃, and application of sample speed is 25ml/min.Promptly get solid dispersion of the present invention.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 80.2 ± 2.2% (n=6).
Embodiment 11
Get 1000mg polyethylene glycol 6000 and 2000mg lactose, add the 30ml water dissolution, add 500mg 20 (R)-protopanoxadiol mixing again, carry out spray drying with electric heating mini spray exsiccator with the 100ml95% dissolve with ethanol, inlet temperature is 70 ℃, and application of sample speed is 25ml/min.Promptly get solid dispersion of the present invention.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 88.5 ± 1.8% (n=6).
Embodiment 12
Get 1000mg polyvinylpyrrolidone K29/32 and 5000mg mannose, add the 100ml water dissolution, add 200mg 20 (R)-protopanoxadiol again, put in the mortar and grind, rotating speed 200rpm, milling time 60min.Medicinal liquid is transferred in the 500ml round-bottomed flask-20 ℃ of pre-freeze 4h, lyophilization 20h.Take out, grind, cross 80 mesh sieves, promptly.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 98.2 ± 2.3% (n=6).
Embodiment 13
Get the 2000mg HP-, add the 100ml water dissolution, add 200mg 20 (S)-protopanoxadiol again, put in the mortar and grind, rotating speed 300rpm, milling time 45min.Medicinal liquid is transferred in the 500ml round-bottomed flask-20 ℃ of pre-freeze 4h, lyophilization 20h.Take out, grind, cross 80 mesh sieves, promptly.This invention solid dispersion 45min cumulative in vitro stripping percentage rate is 99.8 ± 2.7% (n=6).
Claims (8)
1, solid dispersion of protopanaxadiol is characterized in that:
Contain active component protopanoxadiol and carrier material;
The weight ratio of protopanoxadiol and carrier material is 1: 2～50;
Described protopanoxadiol be 20 (S)-protopanoxadiols, 20 (R)-protopanoxadiols or 20 (R, S)-protopanoxadiol;
Described carrier material is one or more mixtures in polyvinylpyrrolidone, crospolyvinylpyrrolidone, Macrogol 4000, polyethylene glycol 6000, poloxamer, cyclodextrin, microcrystalline Cellulose, hydroxypropyl methylcellulose, hydroxypropyl cellulose, lactose, the mannose.
2, the preparation method of solid dispersion of protopanaxadiol is characterized in that: adopt polishing, fusion method, solvent method, solvent-fusion method, spray drying method or freeze-drying.
3, the preparation method of solid dispersion of protopanaxadiol according to claim 2 is characterized in that: carrier material is polyvinylpyrrolidone, crospolyvinylpyrrolidone, Macrogol 4000, polyethylene glycol 6000, cyclodextrin, microcrystalline Cellulose or lactose in the described polishing.
4, solid dispersion of protopanaxadiol according to claim 2 is characterized in that: carrier material is poloxamer, Macrogol 4000 or polyethylene glycol 6000 in the described fusion method.
5, solid dispersion of protopanaxadiol according to claim 2 is characterized in that: carrier material is Macrogol 4000, polyethylene glycol 6000, poloxamer, crospolyvinylpyrrolidone, polyvinylpyrrolidone, hydroxypropyl cellulose, lactose or mannose in the described solvent method.
6, solid dispersion of protopanaxadiol according to claim 2 is characterized in that: carrier material is poloxamer, Macrogol 4000 or polyethylene glycol 6000 in described solvent-fusion method.
7, solid dispersion of protopanaxadiol according to claim 2 is characterized in that: carrier material is Macrogol 4000, polyethylene glycol 6000, poloxamer, cyclodextrin, crospolyvinylpyrrolidone, polyvinylpyrrolidone, lactose or mannose in the described spray drying method.
8, solid dispersion of protopanaxadiol according to claim 2 is characterized in that: carrier material is Macrogol 4000, polyethylene glycol 6000, poloxamer, cyclodextrin, crospolyvinylpyrrolidone, polyvinylpyrrolidone, lactose or mannose in the described freeze-drying.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101298502B (en) * | 2007-04-30 | 2010-08-11 | 福建省医学科学研究所 | Method for increasing chitose water-solubility |
| CN101229172B (en) * | 2007-12-28 | 2010-10-27 | 天津药物研究院 | Solid dispersing agent of glycyrrhetinic acid 30-acylamide derivatives, preparing method and uses thereof |
| CN102178956A (en) * | 2011-04-21 | 2011-09-14 | 李国玉 | Preparation, medical application and composition of 20S-protopanaxadiol beta-cyclodextrin inclusion compound |
| 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 |
| EP2510924A4 (en) * | 2009-12-08 | 2013-10-09 | Il Hwa Co Ltd | SOLID DISPERSIONS CONTAINING 20-O-ß-D-GLUCOPYRANOSYL-20(S)-PROTOPANAXADIOL |
| CN103816133A (en) * | 2014-02-25 | 2014-05-28 | 吉林英联尚德科技开发有限公司 | Q808 solid dispersion used for antiepileptic drug and preparing method thereof |
| WO2017004733A1 (en) * | 2015-07-03 | 2017-01-12 | 浙江海正药业股份有限公司 | Ginsenoside c-k oral solid preparation and preparation method thereof |
| CN114177149A (en) * | 2021-11-17 | 2022-03-15 | 中国医学科学院药用植物研究所 | Solid dispersion loaded with 20(S) -protopanaxadiol and preparation method and application thereof |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101298502B (en) * | 2007-04-30 | 2010-08-11 | 福建省医学科学研究所 | Method for increasing chitose water-solubility |
| CN101229172B (en) * | 2007-12-28 | 2010-10-27 | 天津药物研究院 | Solid dispersing agent of glycyrrhetinic acid 30-acylamide derivatives, preparing method and uses thereof |
| EP2510924A4 (en) * | 2009-12-08 | 2013-10-09 | Il Hwa Co Ltd | SOLID DISPERSIONS CONTAINING 20-O-ß-D-GLUCOPYRANOSYL-20(S)-PROTOPANAXADIOL |
| CN102178956A (en) * | 2011-04-21 | 2011-09-14 | 李国玉 | Preparation, medical application and composition of 20S-protopanaxadiol beta-cyclodextrin inclusion compound |
| CN102178956B (en) * | 2011-04-21 | 2013-06-19 | 李国玉 | Preparation, medical application and composition of 20S-protopanaxadiol beta-cyclodextrin inclusion compound |
| 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 |
| CN103816133A (en) * | 2014-02-25 | 2014-05-28 | 吉林英联尚德科技开发有限公司 | Q808 solid dispersion used for antiepileptic drug and preparing method thereof |
| CN103816133B (en) * | 2014-02-25 | 2016-07-06 | 吉林英联尚德科技开发有限公司 | A kind of Q808 solid dispersion for antiepileptic medicine and preparation method thereof |
| WO2017004733A1 (en) * | 2015-07-03 | 2017-01-12 | 浙江海正药业股份有限公司 | Ginsenoside c-k oral solid preparation and preparation method thereof |
| CN107735080B (en) * | 2015-07-03 | 2020-10-23 | 浙江海正药业股份有限公司 | Ginsenoside C-K oral solid preparation and preparation method thereof |
| CN114177149A (en) * | 2021-11-17 | 2022-03-15 | 中国医学科学院药用植物研究所 | Solid dispersion loaded with 20(S) -protopanaxadiol and preparation method and application thereof |
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