CN102293742A - Cucurbitacin E nano suspension composition and preparations thereof - Google Patents
Cucurbitacin E nano suspension composition and preparations thereof Download PDFInfo
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- CN102293742A CN102293742A CN2010102094151A CN201010209415A CN102293742A CN 102293742 A CN102293742 A CN 102293742A CN 2010102094151 A CN2010102094151 A CN 2010102094151A CN 201010209415 A CN201010209415 A CN 201010209415A CN 102293742 A CN102293742 A CN 102293742A
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Abstract
The invention discloses a cucurbitacin E nano suspension composition and a preparation method thereof. The cucurbitacin E nano suspension freeze-dried composition is successfully prepared from medicines and a surfactant by a controlled precipitation method and/or a high-pressure homogenizing method in combination with a freeze-drying technique. The cucurbitacin E nano suspension composition comprises cucurbitacin E and a surfactant, wherein the proportion of the cucurbitacin E to the surfactant is 1:300-1:1, and the surfactant is phospholipid or a combination of phospholipid and other surfactants. The composition can be directly applied, or prepared into tablets, capsules, injections and the like after adding forming agents. The nano suspension disclosed by the invention has the advantages of simple preparation technique, stable properties, high drug loading rate and high in-vivo absorption speed, and can easily implement industrial production.
Description
Technical field:
The present invention relates to medical technical field, relate to cucurbatacin E nano suspension compositions and preparation thereof, exactly it is to utilize surfactant and cucurbatacin E to form cucurbatacin E nano suspension prescription and preparation thereof.
Background technology:
The cucurbatacin E molecular formula is C
32H
44O
8Molecular weight is 556.69, have antitumor, protect the liver, multiple biological activity such as human body immunity improving power, can also promote of the picked-up of drug-resistant tumor cell to amycin, obviously be better than the two independent use with anti-tumor activity after the amycin use in conjunction, and can significantly reduce the cardiac toxicity of amycin.
Cucurbatacin E is a water-insoluble drug, and dissolubility is also lower in its oil, by being prepared into nano suspension, can improve its dissolution rate and degree, and then increases absorption in the body, guarantees the cucurbatacin E curative effect.
Nano suspension is the colloidal dispersion system of submicron particles in liquid of medicine, and diameter of aspirin particle little (mean diameter is less than 1 μ m, generally between 200～500nm), specific surface area are big.Solving the water miscible important method of insoluble drug is to adopt nanotechnology, and this The Application of Technology obtains the subsidy of national 973 problems (state key basic research development plan 2009CB903302).
The application characteristic of nano suspension:
Can improve the safety of pharmaceutical preparation.Be used at present medication preparation adjuvant some human body is had unsafe influence, by medicine being made the use that nano suspension can reduce or eliminate dangerous adjuvant.Usually the content of insoluble drug in preparation is not high, in order to reach medicine concentration, has only the dose that increases preparation, and this has strengthened the occurrence probability of untoward reaction to a certain extent.After medicine made nano suspension,, can overcome this problem to a certain extent owing to can improve medicament contg.As: the dosage of commercially available paclitaxel injection (Taxol) is 110～175mgm
-2, approximately need injection 50mL preparation under the general case, if but use 3% taxol nanosuspension, only need to inject 10mL, just can obtain same drug effect.
Improve the medicine dissolution rate.The medicine dissolution rate improves the oral absorption that can strengthen medicine, is one of method of improving the behavior of insoluble drug pharmacokinetics.That carries out on beasle dog studies show that, under the Isodose, the nano suspension of insoluble drug danazol (Danazol) can bring up to 82.3% ± 10.1% by 5.1% ± 1.9% with its bioavailability.The medicament nano suspensoid can also improve the infiltration rate of insoluble drug, and this needs the medicine (as analgesic) of quick acting to have special significance for those.Owing to the raising of medicine dissolution rate, can cause the fast Absorption of medicine in a way.
Improve drug solubility and dissolution velocity.Medicine can change its crystal formation after handling through nanorize, increases the ratio of unformed shape crystal formation in the medicine or converts unformed shape fully to, improves the dissolubility and the dissolution velocity of medicine.
Improve the stability of pharmaceutical preparation.The medicine of unstable chemcial property is made nano suspension can prevent drug degradation.Surfactant molecule in the nano suspension and high molecular polymer have improved the chemical stability of preparation to the medicine crystal structure of particulate protective effect of medicament nano and nano-scale.JanMoschwitzer etc. successfully make nano suspension with omeprazole (Omeprazole) by the high pressure homogenization method.Adopt the high-performance liquid chromatography method medicament contg after one month in preparation, found that the omeprazole solution Chinese medicine content of 5mg/100mL obviously descends solution changes color; Omeprazole nano suspension with concentration then shows good chemical stability.
Improve the bioadhesive of medicine.Nano suspension Chinese medicine particle grain size is little, has good bioadhesive, can promote the absorption of medicine.
Realize the target administration purpose.Particle diameter by control nano suspension Chinese medicine particle and carry out the target administration that finishing can realize medicine.Applied widely, almost be applicable to all insoluble drugs, and prescription is simple, preparation is fast.
Nano suspension can satisfy different needs with combining of conventional formulation form.As can be directly oral with the liquid suspension form, this administering mode be particularly useful for being inconvenient to take the child or the old man of solid preparation; Also can change preparation into solid form, make tablet, pill, capsule, suppository, gel and aerosol etc., take and transport with convenient adult by lyophilization, spray drying.
Nano suspension preparation technology is simple.The nano suspension preparation method is various, and production process is simple, can realize industrialized great production.The input of new drug development increases day by day at present, and particularly synthesizing of new chemicals needs to consume a large amount of resources especially.Can utilize those drug effects good but because the medicine that poor solubility is abandoned using improves the reference role that reality is arranged to the dosage form of new drug development and old product again by medicine being made nano suspension.
The tert-butyl alcohol has characteristics such as high-melting-point, high vapour pressure, hypotoxicity, and a spot of tert-butyl alcohol joins in the aqueous solution, forms the acicular crystal (see figure 1) when freezing, the effusion of water vapour after more helping distilling.In addition, organic solvent or organic solvent/water cosolvent can strengthen the stability of solution or lyophilization product, reduce degradation rate.The butanol/water cosolvent has begun to be used for the lyophilization production of some injectable drugs at present, for example, prostaglandin E is the very poor medicine of stability, the butanol/water cosolvent of employings such as Teagarden 20% dissolves medicine and lactose jointly, obtain after the lyophilization stablizing the lyophilized powder pin, the prostaglandin E aseptic powdery preparation CAVERJECT that adopts this freeze drying process to produce goes on the market abroad.Select the good solvent of the tert-butyl alcohol according to above characteristics as medicine.
Summary of the invention
The purpose of this invention is to provide a kind of cucurbatacin E nano suspension compositions and preparation thereof, its preparation technology is simple, the drug loading height, and external dissolution rate is fast, oral absorption availability height.
The present invention is achieved by the following scheme:
The present invention prepares nano suspension by control precipitation and/or high pressure homogenization method, select phospholipid and/or other surfactant stabilizing agent as nano suspension, preparation nano suspension compositions, related nano suspension compositions is made up of cucurbatacin E and surfactant, the mass ratio of its Chinese medicine cucurbatacin E and surfactant is 1: 300～1: 1, preferred 1: 300～1: 50.
Described surfactant is the compositions of phospholipid or phospholipid and other surfactant.
Described phospholipid is natural origin, synthetic, the artificial semi-synthetic or manually modified phospholipid substance that two fat hydrocarbon chains respectively contain 8～18 saturated or unsaturated carbon atoms, be selected from lecithin, cuorin, dioleoyl phospholipid phatidylcholine, DOPG, distearoyl phosphatidylcholine, distearyl phosphatidyl glycerol, dipalmitoyl phosphatidyl choline, the two palmityl PHOSPHATIDYL ETHANOLAMINE one or more, or one or more of wherein any derivant.
The prepared nano suspension of the present invention adds behind an amount of excipient its lyophilization, but directly uses after this preparation aquation, or further processing and preparing becomes tablet, granule, capsule etc.
Its prescription is composed as follows:
Cucurbatacin E: 0.001%～1% (w/v);
Surfactant: 0.1～20% (w/v);
Good solvent: 0%～30% (v/v);
Excipient: 1～20% (w/v);
Distilled water: surplus.
The preparation method of cucurbatacin E nano suspension adopts the control sedimentation method and/or high pressure homogenization method.The control precipitation genealogy of law joins drug solution in the water that contains stabilizing agent by medicine dissolution is formed drug solution in the good solvent of a certain amount of and water immiscible phase with certain speed, medicine is separated out crystallization rapidly because of reach supersaturation in water.Can disperse by high shear, ultrasonic and/or microjet method control precipitation.Ultrasound wave is complicated to the influence of crystallization process, and the most basic influence is the pressure that it is applied alternation to continuous fluid.Under low-intensity, this pressure can promote fluid local flow and mixing; Under high strength, local pressure can be reduced to below the fluidic vapour pressure in the fluid, generate some vesicles and hole, local temporary transient negative pressure in fluid increases, and vesicle wherein will be grown up, and subsides suddenly when arriving to a certain degree, form more hole, be cavitation, provide special space and energy, impel crystalline formation for nucleus forms.Ultrasound wave has significant heat effect and melange effect to solution equally, thereby crystallization process is produced material impact.Can pass through medicine joining day, adding speed, aspects such as ultrasonic temperature, ultrasonic power, ultrasonic time are investigated, and optimize preparation technology.The high pressure homogenization method is that the medicine coarse-grain is spared matter through high pressure, to obtain the drug crystallization of desired particle size.
Formed drug crystallization is a Unstable Systems, needs to add surfactant as stabilizing agent in prescription.Described surfactant is the compositions of phospholipid or phospholipid and other surfactant.
Prepared nano suspension adds the excipient postlyophilization, preserves more stable with the state of freeze-dried powder.Described excipient comprises one or more the combination in mannitol, sucrose, lactose, glucose, trehalose, maltose, sorbitol, the dextran, and its consumption is 1%～20% (w/v).
This freeze-dried powder further processing and preparing becomes tablet, capsule, injection etc.
Adopt classical counterbalanced procedure to measure the cucurbatacin E dissolubility, recording the equilbrium solubility of cucurbatacin E in pure water is 0.155 μ g.mL
-1, according to " Chinese pharmacopoeia judges that it is a water-insoluble drug.And surfactant can reach more than 500 times of its dissolubility to its solubilising power weak (seeing Table 1) and be prepared into its drug loading of nano suspension.
Table 1 surfactant is to the solubilising of CuE
Adopt laser granulometry to measure cucurbatacin E nano suspension granularity and distribution, instrument parameter is provided with as follows: medium index of refraction (n=1.330), temperature are 25 ℃.Light source is He-Ne laser (λ
0=632.8nm), select wide (channel width) automatically, measuring the angle is 90 °, Solid Particle pattern, power: 75mW, temperature: 25 ℃, the particle mean size of prepared cucurbatacin E nano suspension is that granulometry the results are shown in Figure 2 between 150nm～300nm.Outward appearance is observed as shown in Figure 3, is blue opalescence.Its electron micrograph is seen Fig. 4, and distribution of particles is even.Zeta potential is-25.2mV.Freeze-dried preparation color and luster homogeneous, surfacing, exquisite quality; Nanometer suspension liquid is translucent milky liquid after the redissolution aquation, shows slightly blue opalescence.
Sample DSC scanning spectra is seen shown in Figure 5, sweep parameter: with the aluminum dish is reference, and nitrogen is carrier gas, and initial temperature is 28 ℃, rises to 300 ℃ with the speed of 10 ℃/min.The X-Ray powder diffraction spectrum is seen shown in Figure 5, adopts Cu target K alpha ray; Scanning speed is 1.2 °/min; Accelerating potential is that 40kV, electric current are 200mA; 2-Thea:5.0 °～50.0 °.By the result as can be known cucurbatacin E nano suspension Chinese medicine exist with the metamict crystals form.
" Chinese pharmacopoeia (appendix C X) dissolution determination method (three therapeutic methods of traditional Chinese medicine) has compared cucurbatacin E nano suspension and the dissolution of the thick suspendible system of cucurbatacin E-phospholipid in dissolution medium 10% alcohol-water and PBS (pH 6.8) according to 2005 editions.The results are shown in shown in Figure 7.Cucurbatacin E is prepared into nano suspension has significantly improved dissolution rate.
Based on selecting for use phospholipid as the nano suspension stabilizing agent, phospholipid can be considered by spontaneous formation liposome in water, according to the method correct of document, is marker with the calcein, measures the content of liposome in the CuE nano suspension.Measurement result sees Table 2, by the result as can be known, has 26% phospholipid to form liposome approximately
The content of table 2 cucurbatacin E nano suspension liposome
Small intestinal is the main position that drug oral absorbs, research medicine little intestinal absorption mainly contain vitro method, in kinds of experiments methods such as body method and intracorporal methods, can under the situation of blood circulation, nervous system and metabolic function that animal is kept perfectly, obtain dynamics data in the body method, and method is easy, and the time spent is few.Wherein unidirectional perfusion model is stable because of absorption rate, with body in have good dependency to be widely used.The cucurbatacin E rat sees shown in Figure 8 in the unidirectional perfusion experiment method of body intestinal absorption.The thick suspendible system of cucurbatacin E nano suspension and cucurbatacin E-phospholipid of having studied is in body intestinal absorption kinetics, by its comparison at the absorption rate constant and the apparent absorption coefficient at small intestinal position, all there are significant difference (P＜0.05) in the absorption rate constant and the apparent absorption coefficient that show two kinds of preparations, and wherein nano suspension is better in the absorption at small intestinal position.Record absorption rate constant and apparent absorption coefficient the results are shown in Table 3.
The thick suspendible system of table 3 cucurbatacin E nano suspension and cucurbatacin E-phospholipid is at body intestinal absorption kinetic parameter
Advantage of the present invention is: preparation technology is simple, realizes commercialization easily, stable in properties, and drug loading is big, and infiltration rate is fast in the body.
Description of drawings:
Fig. 1: the tertiary butanol and water cosolvent freezes the cool-drying photo
Fig. 2: cucurbatacin E nano suspension particle size determination
Fig. 3: cucurbatacin E nano suspension outward appearance
Fig. 4: cucurbatacin E coarse-grain and nano suspension electron micrograph
A-cucurbatacin E coarse-grain; B-cucurbatacin E nano suspension
Fig. 5: sample DSC scanning spectra
The nanometer suspension freeze-dried sample of A-cucurbatacin E; The blank adjuvant (phospholipid) of B-; The C-physical mixture; D-cucurbatacin E coarse-grain
Fig. 6: sample X-Ray powder diffraction spectrum
The nanometer suspension freeze-dried sample of A-cucurbatacin E; The blank adjuvant (phospholipid) of B-; The C-physical mixture; D-cucurbatacin E coarse-grain
Fig. 7: the thick suspendible system of cucurbatacin E nano suspension and cucurbatacin E-phospholipid dissolution relatively
Fig. 8: rat is in the unidirectional perfusion experiment method of body intestinal absorption
The 1-thermometer; The 2-water-bath; The 3-stirrer; The 4-small intestinal; 5; The perfusate collecting pipe
The specific embodiment:
The preparation of embodiment 1 cucurbatacin E nano suspension
Prescription:
Cucurbatacin E 5.0mg
Soybean lecithin 0.75g
Tert-butyl alcohol 5.0mL
Distilled water 45.0mL
Preparation technology:
Ultrasonic control intermediate processing prepares the cucurbatacin E nano suspension to pop one's head in.By recipe quantity cucurbatacin E is dissolved in and prepares organic facies in the tert-butyl alcohol, soybean lecithin is dispersed in the water as water, in ultrasonic working hour organic facies is added aqueous phase in the mode of quick injection, ultrasonic power is 400W, ultrasonic time is 6min, and ultrasonic procedure needs to carry out under ice bath.
The preparation of embodiment 2 cucurbatacin E nano suspensions
Prescription:
Cucurbatacin E 50mg
Soybean lecithin 50mg
Distilled water 45.0mL
Preparation technology:
Prepare the cucurbatacin E nano suspension with high pressure homogenization method.By recipe quantity cucurbatacin E and soybean lecithin are added in the entry, after the dispersed with stirring, first suspension is carried out the high pressure homogenize, condition is 200bar circulation 2 times, and 800bar circulation 10 times promptly gets the cucurbatacin E nano suspension.
The preparation of embodiment 3 cucurbatacin E nano suspensions
Prescription:
Cucurbatacin E 10.0mg
Soybean lecithin 3.0g
Poloxamer 188 0.2g
Ethanol 4.0mL
Distilled water 45.0mL
Preparation technology:
Ultrasonic control intermediate processing prepares the cucurbatacin E nano suspension to pop one's head in.By recipe quantity cucurbatacin E is dissolved in and prepares organic facies in the ethanol, soybean lecithin is dispersed in the water as water, in ultrasonic working hour organic facies is added aqueous phase in the mode of quick injection, ultrasonic power is 300W, ultrasonic time is 8min, and ultrasonic procedure needs to carry out under ice bath.
The preparation of embodiment 4 cucurbatacin E nano suspensions
Prescription:
Cucurbatacin E 10.0mg
Soybean lecithin 1.0g
Ethanol 2.0mL
Distilled water 45.0mL
Preparation technology:
Ultrasonic control intermediate processing prepares the cucurbatacin E nano suspension to pop one's head in.By recipe quantity cucurbatacin E is dissolved in and prepares organic facies in the ethanol, Tween 80 is dispersed in the water as water, in ultrasonic working hour organic facies is added aqueous phase in the mode of quick injection, ultrasonic power is 200W, ultrasonic time is 5min, and ultrasonic procedure needs to carry out under ice bath.
The preparation of embodiment 5 cucurbatacin E nano suspensions
Prescription:
Cucurbatacin E 5.0mg
Ovum Gallus domesticus Flavus lecithin 1.0g
Lactose 8.0g
Ethanol 2.0mL
Distilled water 45.0mL
Preparation technology:
With high shear decentralised control precipitation, the method for associating microjet homogenize prepares the cucurbatacin E nano suspension.By recipe quantity cucurbatacin E is dissolved in and prepares organic facies in the ethanol, egg lecithin, lactose are dispersed in the water as water, in the high shear dispersive process, organic facies is added aqueous phase, high speed shear 5min in the mode of quick injection.This suspension is crossed microjet carry out putting into freezer dryer and carrying out the sample lyophilizing after homogenize handles, freeze drying process is-74 ℃ of pre-freezes 8 hours,-35 ℃ of evacuation 1 hour, temperature is increased to-25 ℃, keeps 12 hours, temperature is increased to 20 ℃, keeps 3 hours.
The preparation of embodiment 6 cucurbatacin E nano suspensions
Prescription:
Cucurbatacin E 5.0mg
Ovum Gallus domesticus Flavus lecithin 1.0g
Trehalose 1.0g
Tert-butyl alcohol 2.0mL
Distilled water 45.0mL
Preparation technology:
With high shear decentralised control precipitation, the method for associating microjet homogenize prepares the cucurbatacin E nano suspension.By recipe quantity cucurbatacin E is dissolved in and prepares organic facies in the tert-butyl alcohol, Ovum Gallus domesticus Flavus lecithin, trehalose are dispersed in the water as water, in the high shear dispersive process, organic facies is added aqueous phase, high speed shear 5min in the mode of quick injection.This suspension is crossed microjet carry out putting into freezer dryer and carrying out the sample lyophilizing after homogenize handles, freeze drying process is-74 ℃ of pre-freezes 5 hours,-35 ℃ of evacuation 1 hour, temperature is increased to-25 ℃, keeps 7 hours, temperature is increased to 20 ℃, keeps 1 hour.
Embodiment 7
Take by weighing the cucurbatacin E nanosuspension frozen powder of 1.0g, add 0.5g starch by the preparation of embodiment 6 methods, the mixing that sieves, the encapsulating capsule gets capsule.
Claims (10)
1. cucurbatacin E nano suspension prescription and preparation thereof, it is characterized in that: described cucurbatacin E nano suspension prescription is made up of cucurbatacin E and surfactant, and the mass ratio of cucurbatacin E and surfactant is 1: 300～1: 1.
2. cucurbatacin E nano suspension prescription according to claim 1 and preparation thereof is characterized in that: the mass ratio of cucurbatacin E and surfactant is 1: 300～1: 50.
3. cucurbatacin E nano suspension prescription according to claim 1 and 2 and preparation thereof is characterized in that: described surfactant is the compositions of phospholipid or phospholipid and other surfactant.
4. cucurbatacin E nano suspension prescription according to claim 3 and preparation thereof, it is characterized in that: described phospholipid is the natural origin that two fat hydrocarbon chains respectively contain 8～18 saturated or unsaturated carbon atoms, synthetic, artificial semi-synthetic or manually modified phospholipid substance, be selected from lecithin, cuorin, the dioleoyl phospholipid phatidylcholine, DOPG, distearoyl phosphatidylcholine, the distearyl phosphatidyl glycerol, dipalmitoyl phosphatidyl choline, in the two palmityl PHOSPHATIDYL ETHANOLAMINE one or more, or one or more of wherein any derivant.
5. cucurbatacin E nano suspension prescription according to claim 1 and preparation thereof is characterized in that: described cucurbatacin E nano suspension prescription adopts the control sedimentation method and/or the preparation of high pressure homogenization method.
6. cucurbatacin E nano suspension prescription according to claim 5 and preparation thereof is characterized in that: the described control sedimentation method can be disperseed by high shear, ultrasonic and/or microjet method control precipitation.
7. cucurbatacin E nano suspension prescription according to claim 1 and preparation thereof is characterized in that: when adopting the control sedimentation method to prepare the cucurbatacin E nano suspension, the medicine good solvent that is adopted is the ethanol or the tert-butyl alcohol.
8. cucurbatacin E nano suspension prescription according to claim 1 and preparation thereof, it is characterized in that: described cucurbatacin E and surfactant are prepared into and add behind the nano suspension behind an amount of excipient its lyophilization or spray drying, directly use after the aquation, its prescription consists of:
Cucurbatacin E: 0.001%～1% (w/v);
Surfactant: 0.1～20% (w/v);
Good solvent: 0%～30% (v/v);
Excipient: 1～20% (w/v);
Distilled water: surplus.
9. cucurbatacin E nano suspension prescription according to claim 8 and preparation thereof is characterized in that: described nano suspension prescription and preparation thereof can directly be used or further processing and preparing becomes tablet, capsule, injection.
10. cucurbatacin E nano suspension prescription according to claim 8 and preparation thereof is characterized in that: described excipient is one or more the combination in mannitol, sucrose, lactose, glucose, trehalose, maltose, sorbitol, the dextran.
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| CN103637984A (en) * | 2013-12-24 | 2014-03-19 | 宁夏医科大学 | Baicalin nanometer crystal and preparation method thereof |
| CN104473168A (en) * | 2014-12-26 | 2015-04-01 | 江南大学 | Processing method for increasing solubility and bioavailability of fat-soluble active component |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103637984A (en) * | 2013-12-24 | 2014-03-19 | 宁夏医科大学 | Baicalin nanometer crystal and preparation method thereof |
| CN104473168A (en) * | 2014-12-26 | 2015-04-01 | 江南大学 | Processing method for increasing solubility and bioavailability of fat-soluble active component |
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