CN101264064A - Vinpocetine freeze-dried powder for injection and preparation thereof - Google Patents
Vinpocetine freeze-dried powder for injection and preparation thereof Download PDFInfo
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- CN101264064A CN101264064A CNA200810089085XA CN200810089085A CN101264064A CN 101264064 A CN101264064 A CN 101264064A CN A200810089085X A CNA200810089085X A CN A200810089085XA CN 200810089085 A CN200810089085 A CN 200810089085A CN 101264064 A CN101264064 A CN 101264064A
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- vinpocetine
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Abstract
The invention discloses a new vinpocetine freeze-dried injection and the preparation method, which comprises vinpocetine, frozen-dried supporting agent mannitol and cosolvent hydrochloride. The invention is characterized in that: The salt is formed by the hydrochloride with stable and safe physicochemical properties used as cosolvent and the vinpocetine, thereby successfully producing the vinpocetine freeze-dried injection. The vinpocetine freeze-dried injection has the advantages of good solubility, stability and safety compared with prior vinpocetine freeze-dried injection.
Description
Technical field
The invention belongs to medical technical field, be specifically related to a kind of Vinpocetine freeze-dried powder for injection and preparation method thereof.
Background technology
Vinpocetine is a kind of natural extract that obtains from the Herba Catharanthi Rosei seed.Vinpocetine is as a kind of selective brain circulation improving agent, can obviously increase glucose uptake amount in the brain, improve brain artery and vein blood oxygen content, promote the utilization rate of brain oxygen, improving aspects such as cerebral circulation, memory doubly than the strong 2-4 of vincamine, the courageous and upright cerebrovascular disease of brain there is unique curative effect, and do not produce side effect such as hypotension, xerostomia, weak and tachycardia, with other drug interactional report takes place also.Its application has obtained global generally acknowledged.
Domestic preparation type about vinpocetine has tablet, injection and injection freeze-dried powder at present.Chinese patent ZL200410046419.7 discloses a kind of Vinpocetine freeze-dried powder for injection and preparation technology thereof, this lyophilized injectable powder is made up of vinpocetine, frozen-dried supporting agent and cosolvent, wherein frozen-dried supporting agent is selected from mannitol, glucose, sorbitol, dextran, sucrose or lactose, and cosolvent is selected from citric acid, tartaric acid, acetic acid, lactic acid or sorbic acid.But citric acid has blood coagulation resisting function, and lactic acid may cause lactic acidosis, may bring side effect.Tartaric acid, acetic acid and sorbic acid physicochemical property are stable inadequately, therefore can cause preparation stability not good.
Summary of the invention
In view of this, in order to solve existing Vinpocetine freeze-dried powder for injection poor stability or to have problem such as toxic and side effects, the invention provides a kind of stability, safety is better, can avoid the Vinpocetine freeze-dried powder for injection of side effect.
Another purpose of the present invention provides the preparation method of described Vinpocetine freeze-dried powder for injection.
Vinpocetine freeze-dried powder for injection of the present invention is made up of vinpocetine, frozen-dried supporting agent and cosolvent, and described frozen-dried supporting agent is a mannitol, and described cosolvent is a hydrochloric acid.
The present invention forms salt by adopting stable, the safe hydrochloric acid of physicochemical property as cosolvent with vinpocetine, successfully develops a kind of dissolubility, stability and the good Vinpocetine freeze-dried powder for injection of safety tool.
Further, described lyophilized injectable powder by weight, is made up of the vinpocetine of 10-30 part, 70～100 parts mannitol and 1.5～7 parts hydrochloric acid.
Further, described lyophilized injectable powder by weight, is made up of the vinpocetine of 10-20 part, 70～90 parts mannitol and 1.5～4 parts hydrochloric acid.
Further, described lyophilized injectable powder by weight, is made up of 10 parts vinpocetines, 90 parts mannitol and 1.5～2 parts hydrochloric acid.
Further, described lyophilized injectable powder, its specification is by the weight that contains vinpocetine, for 10mg/ props up, 20mg/ props up or 30mg/ props up.
Said weight portion can be units such as gram, milligram, jin, kilogram, ton among the present invention.
The preparation method of above-mentioned vinpocetine freeze-dried powder is described mannitol to be added to be stirred to dissolving in the sterile water for injection, described vinpocetine is added in the 0.5-5mol/L hydrochloric acid solution is stirred to dissolving, with described two kinds of solution mix homogeneously, add water for injection to the fill amount, the pH value of regulator solution is to 3.5-5.5, add needle-use activated carbon, heated and stirred leaves standstill, and filters, the degerming fine straining, sterile filling, lyophilization, packing.
Further, described lyophilization is a medicinal liquid-40～-30 ℃ of pre-freezes 3～5 hours, and-40～0 ℃ of distillation 15～20 hours is subsequently 20～40 ℃ of dryings 2～5 hours.
Further, described lyophilization is a medicinal liquid-35 ℃ of pre-freezes 4 hours, and-35～0 ℃ of distillation 18 hours is subsequently 30 ℃ of dryings 3.5～4.5 hours.
Further, between pH value to 4.5～5.0 with 0.5-5mol/L hydrochloric acid solution regulator solution.
The clinical using method of vinpocetine freeze-dried powder of the present invention is:
Intravenous drip.Starting dose 20mg every day can increase to 30mg every day according to the state of an illness later on, faces with behind the dilution mixing in the sodium chloride solution of 5% glucose solution that before is dissolved in 500ml or 0.9%, slowly instils.
Vinpocetine freeze-dried powder of the present invention is compared with immediate prior art, has following beneficial effect:
(1) the new vinpocetine freeze-dried powder of the present invention is compared with existing vinpocetine freeze-dried powder (ZL200410046419.7), the side effect that does not exist existing vinpocetine freeze-dried powder to bring because of cosolvent, and reduce to 1/20th when following in the amount of cosolvent, the dissolubility of principal agent does not descend; Compare bioavailability simultaneously with vinpocetine freeze-dried powder (ZL200410046419.7) and improve 12%.
(2) the cosolvent physicochemical property of vinpocetine freeze-dried powder employing of the present invention is extremely stable, thereby stability of formulation of the present invention is good than prior art;
(3) raw material economics of the present invention, technology are simple, have reduced production cost, are easy to commercial production.
Embodiment 1
Prescription is:
Vinpocetine 10g
Mannitol 90g
1mol/L hydrochloric acid 50ml
Water for injection adds to 2000ml
Prepare 1000 altogether
Preparation technology is:
1) vial, plug and aluminium lid etc. carry out aseptic process.
2) weighing supplementary material is added to mannitol in the sterile water for injection, stirs to make dissolving.Vinpocetine is joined in the hydrochloric acid solution of 1mol/L of 50ml, stir and make dissolving.Two solution are mixed, and benefit adds to the full amount of water for injection, and stirs.
3) pH value with the hydrochloric acid solution regulator solution of 0.5mol/L is 3.5.
4) needle-use activated carbon of adding 0.1% in the solution for preparing, heated and stirred 20 minutes left standstill 20 minutes, and sucking filtration takes off charcoal.
5) with aseptic microporous filter membrane (0.22 μ m) fine straining, and the clarity of inspection solution.
6) the qualified back fill of clarity is in vial, and 10mg/ props up.
7) lyophilization, pre-freeze-40 ℃ about 4 hours, dry about 18 hours of-40 ℃ of low-temperature distillations, 30 ℃ of high temperature are dry more about 4 hours.
8) jump a queue, gland, packing.
Embodiment 2:
Prescription is:
Vinpocetine 20g
Mannitol 180g
1mol/L hydrochloric acid 100ml
Water for injection adds to 5000ml
Prepare 2000 altogether
Preparation technology is:
1) vial, plug and aluminium lid etc. carry out aseptic process.
2) weighing supplementary material is added to mannitol in the sterile water for injection to stir and makes dissolving.Vinpocetine is joined in the hydrochloric acid solution of 1mol/L of 100ml, stir and make dissolving.With the two mixing, benefit adds to the full amount of water for injection, and stirs.
3) pH value with the hydrochloric acid solution regulator solution of 1mol/L is 4.5.
4) needle-use activated carbon of adding 0.1% in the solution for preparing, heated and stirred 20 minutes left standstill 20 minutes, and sucking filtration takes off charcoal.
5) with aseptic microporous filter membrane (0.22 μ m) fine straining, and the clarity of inspection solution.
6) the qualified back fill of clarity is in vial, and 10mg/ props up.
7) lyophilization, pre-freeze-35 ℃ about 4 hours, dry about 18 hours of-30 ℃ of low-temperature distillations, 30 ℃ of high temperature are dry more about 4 hours.
8) jump a queue gland, packing.
Embodiment 3:
Prescription is:
Vinpocetine 30g
Mannitol 250g
1mol/L hydrochloric acid 150ml
Water for injection adds to 5000ml
Prepare 3000 altogether
Preparation technology is:
1) vial, plug and aluminium lid etc. carry out aseptic process.
2) weighing supplementary material is added to mannitol in the sterile water for injection, stirs to make dissolving.Vinpocetine is joined in the hydrochloric acid solution of 1mol/L of 150ml, stir and make dissolving.With the two mixing, benefit adds to the full amount of water for injection, and stirs.
3) pH value with the hydrochloric acid solution regulator solution of 2mol/L is 4.0.
4) needle-use activated carbon of adding 0.1% in the solution for preparing, heated and stirred 20 minutes left standstill 20 minutes, and sucking filtration takes off charcoal.
5) with aseptic microporous filter membrane (0.22 μ m) fine straining, and the clarity of inspection solution.
6) the qualified back fill of clarity is in vial, and 10mg/ props up.
7) lyophilization, pre-freeze-35 ℃ about 4 hours, dry about 20 hours of 0 ℃ of low-temperature distillation, 30 ℃ of high temperature are dry more about 4 hours.
8) jump a queue gland, packing.
Embodiment 4
Prescription is:
Vinpocetine 20g
Mannitol 100g
1mol/L hydrochloric acid 150ml
Water for injection adds to 4000ml
Prepare 1000 altogether
Preparation technology is:
1) vial, plug and aluminium lid etc. carry out aseptic process.
2) weighing supplementary material is added to mannitol in the sterile water for injection, stirs to make dissolving.Vinpocetine is joined in the hydrochloric acid solution of 1mol/L of 150ml, stir and make dissolving.With the two mixing, benefit adds to the full amount of water for injection, and stirs.
3) pH value with the hydrochloric acid solution regulator solution of 2mol/L is 5.5.
4) needle-use activated carbon of adding 0.1% in the solution for preparing, heated and stirred 20 minutes left standstill 20 minutes, and sucking filtration takes off charcoal.
5) with aseptic microporous filter membrane (0.22 μ m) fine straining, and the clarity of inspection solution.
6) the qualified back fill of clarity is in vial, and 20mg/ props up.。
7) lyophilization, pre-freeze-35 ℃ about 4 hours, dry about 18 hours of-10 ℃ of low-temperature distillations, 30 ℃ of high temperature are dry more about 4 hours.
8) jump a queue gland, packing.
Test example 1
Cosolvent in the lyophilized injectable powder of the present invention and the selected cosolvent of Chinese patent ZL200410046419.7 are to the contrast experiment of vinpocetine hydrotropy effect:
Get vinpocetine 1g, add the 5mmol cosolvent, add an amount of water for injection again, limit edged jolting until dissolving fully, is calculated the dissolubility of vinpocetine, the results are shown in Table 1.
The experiment of table 1 choice of Solvent
Conclusion: by measuring vinpocetine dissolubility in the solution of the different cosolvents of same amount, hydrochloric acid is best to the solubilization-aid effect of vinpocetine as can be seen.
The vinpocetine freeze-dried powder that 2 the present invention of test example are new and the stable contrast experiment of Chinese patent ZL200410046419.7 freeze-dried powder
Laboratory sample:
Vinpocetine freeze-dried powder of the present invention, prescription and preparation method are seen embodiment 1-4;
The described vinpocetine freeze-dried powder of patent ZL200410046419.7,10mg/ props up.
Proposing under the meter terms of packing, vinpocetine freeze-dried powder of the present invention and the described vinpocetine freeze-dried powder of patent ZL200410046419.7 sample are investigated the clarity of its appearance character, solution and color, clarity, pH value, related substance, vinpocetine content etc. through accelerated test 6 months.
With above-mentioned two kinds of samples, be to place under 75% ± 5% condition 6 months at 40 ℃ ± 2 ℃ of temperature, relative humidity, respectively at the 1st, 2,3,6 the end of month sampling and testing, relatively after the outward appearance test other investigate index.The results are shown in Table 2.
Table 2 vinpocetine freeze-dried powder accelerated test is investigated result's (sample is embodiment 1)
The result shows, vinpocetine freeze-dried powder of the present invention through accelerated test after 6 months sample appearance do not change, related substance slightly increases, and indicates content and does not change, investigate the result show qualified.And the described vinpocetine freeze-dried powder of patent ZL200410046419.7 after 6 months sample appearance, pH value, sign content and related substance significant change is all arranged, illustrate that vinpocetine freeze-dried powder stability of the present invention is than the described vinpocetine freeze-dried powder of patent ZL200410046419.7 good stability.
With embodiment 2-4 is that the result of the test of the result of the test of sample and embodiment is close, therefore outlines.
Compared by bright vinpocetine freeze-dried powder of the present invention of above test illustration and the described vinpocetine freeze-dried powder of patent ZL200410046419.7, safety and stability improve greatly, have guaranteed clinical drug safety, effective, stable, controlled.
The selection of cosolvent amount ranges in test example 3 lyophilized injectable powders of the present invention:
, and its consumption selected as cosolvent with hydrochloric acid.Get vinpocetine 5g, add 1mol/L hydrochloric acid 10ml, 15ml, 20ml, 25ml, 50ml, 75ml, 100ml respectively, add an amount of water for injection again to 500ml, the dissolving situation is observed in limit edged jolting, the results are shown in Table 3.
The selection experiment of table 3 cosolvent consumption
According to the result of dissolution experiment, the 5g vinpocetine is partly dissolved in 1mol/L hydrochloric acid 15ml, and 20,25,50,75,100ml dissolves fully, the solution clarification does not have muddy and separates out the solid phenomenon through placing.Therefore, the consumption of the cosolvent 1mol/L hydrochloric acid of 5g vinpocetine is that 20～100ml (is equivalent to hydrochloric acid 0.73～3.65g), take all factors into consideration dissolubility and acidity, (it is comparatively suitable to be equivalent to hydrochloric acid 0.73～1.825g), and (it is the most suitable to be equivalent to hydrochloric acid 0.73～0.9125g) for 20～25ml for 20～50ml.The selection of proppant kind in test example 4 lyophilized injectable powders of the present invention:
Dried frozen aquatic products will have preferably profile and be easy to lyophilizing, and the selection of suitable proppant is very important.In experimentation of the present invention, two kinds of proppant of manna alcohol and glucose are contrasted,, select the proppant of this preparation according to comprehensive comparison to outward appearance, mouldability, structural strength, dissolubility and water content etc.Experimental result sees Table 4, wherein vinpocetine: the frozen-dried supporting agent weight ratio is 1: 30 (a disclosed optimal proportion among the patent ZL200410046419.7).
The selection of table 4 proppant
Annotate :+expression can ++ represent fine
The two is suitable aspect outward appearance, structural strength and water content; Mannitol is better aspect mouldability and dissolubility, and the water content of dried frozen aquatic products is minimum during with mannitol.It is the proppant of this preparation that analysis-by-synthesis is selected mannitol.
The selection of proppant consumption in test example 5 lyophilized injectable powders of the present invention:
The selection of suitable proppant is very important, but the difference of its consumption is also very important to the influence of preparation.The present invention has carried out vinpocetine: the screening of a plurality of ratios of mannitol, for example: vinpocetine: mannitol 1: 5,1: 7,1: 9,1: 10,1: 20,1: 30 etc., 50mg, 70mg, 90mg, 100mg, 200mg and 300mg mannitol are added in the sterile water for injection of total dosing amount 40-60% stirring and dissolving; The vinpocetine of 10mg is joined in the hydrochloric acid solution of 1mol/L of 0.05ml stirring and dissolving; With the two mixing, benefit adds to the full amount of water for injection, and stirs, and adds 0.1% needle-use activated carbon in the solution for preparing, and heated and stirred leaves standstill, and makes the vinpocetine freeze-dried powder.By comprehensive comparison, select best mannitol consumption to outward appearance, mouldability, structural strength, dissolubility and water content etc.Experimental result sees Table 5:
The selection of table 5 proppant consumption
Annotate :+it is poor to represent-represent
As seen from the above table, the dissolubility of six batch samples and water content and outward appearance all do not have significantly difference; Mouldability and structural strength with the increase sample of mannitol consumption all make moderate progress, mouldability begins variation during mannitol 200mg consumption, and waste adjuvant, analysis-by-synthesis, the consumption of mannitol is decided to be 70～100mg (be vinpocetine: mannitol is 1: 7～10), the consumption of mannitol is that 70～90mg (be vinpocetine: mannitol is 1: 7～9) is comparatively suitable, and the consumption of mannitol is that 90mg (be vinpocetine: mannitol is 1: 9) is optimum.
The selection of test example 6 lyophilized injectable powder freeze-dry process of the present invention:
Lyophilization has three phases: pre-freeze, low-temperature distillation drying and high temperature are dry again.This experimental design three freeze-dry process, the preparation sample comprehensively compares its outward appearance, mouldability, dissolubility, structural strength and water content etc. respectively at carrying out lyophilizing under three kinds of lyophilisation conditions, selects optimum freeze-dry process.
Freeze-dry process and experimental result see the following form:
Table 6 freeze-dry process
The evaluation of table 7 experimental result
Annotate :+it is poor to represent-represent
As seen from the above table, the mouldability and the structural strength of the sample of making through 1# technology are very poor, and the quality of making sample through 2# and 3# is better, but 2# technology is consuming time oversize, waste bigger.Analysis-by-synthesis is with the freeze-dry process of technology 3# as this preparation.That is: pre-freeze-35 is ℃ about 4 hours, about 18 hours of-35～0 ℃ of distillation, and 30 ℃ of high temperature are dry more about 4 hours.
Determining of test example 7 lyophilized injectable powder acidity of the present invention:
Between pH3.0～6.5, prepare sample, and simulation accelerated experiment condition places 40 ℃ of environment 3 months with sample, investigate its stability.
Experimental result sees the following form:
The stability of table 8 sample under different pH condition
The sample of selecting between pH3.5～5.5 according to testing sieve is good through investigating its stable in properties, and is especially the most stable during at 4.5-5.0 at pH.
Claims (9)
1, a kind of Vinpocetine freeze-dried powder for injection is characterized in that, is made up of vinpocetine, frozen-dried supporting agent and cosolvent, and described frozen-dried supporting agent is a mannitol, and described cosolvent is a hydrochloric acid.
According to the described Vinpocetine freeze-dried powder for injection of claim 1, it is characterized in that 2, by weight, described lyophilized injectable powder is made up of the vinpocetine of 10-30 part, 70～100 parts mannitol and 1.5～7 parts hydrochloric acid.
According to the described Vinpocetine freeze-dried powder for injection of claim 2, it is characterized in that 3, by weight, described lyophilized injectable powder is made up of the vinpocetine of 10-20 part, 70～90 parts mannitol and 1.5～4 parts hydrochloric acid.
According to the described Vinpocetine freeze-dried powder for injection of claim 3, it is characterized in that 4, by weight, described lyophilized injectable powder is made up of 10 parts vinpocetine, 90 parts mannitol and 1.5～2 parts hydrochloric acid.
According to claim 1,2,3 or 4 described Vinpocetine freeze-dried powder for injection, it is characterized in that 5, described lyophilized injectable powder specification is divided into by the weight that contains vinpocetine that 10mg/ props up, 20mg/ props up or 30mg/ props up.
6, according to the preparation method of claim 1,2,3 or 4 described Vinpocetine freeze-dried powder for injection, it is characterized in that, described mannitol is added to is stirred to dissolving in the sterile water for injection, described vinpocetine is added in the 0.5-5mol/L hydrochloric acid solution is stirred to dissolving,, add water for injection to the fill amount with described two kinds of solution mix homogeneously, the pH value of regulator solution adds needle-use activated carbon, heated and stirred to 3.5-5.5, leave standstill, filter degerming fine straining, sterile filling, lyophilization, packing.
7, according to the described preparation method of claim 6, it is characterized in that, between pH value to 4.5～5.0 with 0.5-5mol/L hydrochloric acid solution regulator solution.
According to the described preparation method of claim 6, it is characterized in that 8, described lyophilization is a medicinal liquid-40～-30 ℃ of pre-freezes 3～5 hours ,-40～0 ℃ of distillation 15～20 hours is subsequently 20～40 ℃ of dryings 2～5 hours.
According to the described preparation method of claim 8, it is characterized in that 9, described lyophilization is a medicinal liquid-35 ℃ of pre-freezes 4 hours ,-35～0 ℃ of distillation 18 hours is subsequently 30 ℃ of dryings 3.5～4.5 hours.
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| CN200810089085XA CN101264064B (en) | 2008-04-17 | 2008-04-17 | Vinpocetine freeze-dried powder for injection and preparation thereof |
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| CN200810089085XA CN101264064B (en) | 2008-04-17 | 2008-04-17 | Vinpocetine freeze-dried powder for injection and preparation thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102091030A (en) * | 2011-01-20 | 2011-06-15 | 罗军 | Vinpocetine injection and preparation method thereof |
| CN101874776B (en) * | 2009-04-28 | 2012-06-13 | 中国人民解放军军事医学科学院毒物药物研究所 | Dry emulsion of vinpocetine and preparation method thereof |
| CN102526042A (en) * | 2010-12-09 | 2012-07-04 | 常建晖 | Stable liquid medicinal composition |
| CN104083329A (en) * | 2014-02-21 | 2014-10-08 | 杭州长典医药科技有限公司 | Vinpocetine special ultrafine powder lyophilized preparation and preparation method thereof |
| CN105213323A (en) * | 2014-05-30 | 2016-01-06 | 海南通用康力制药有限公司 | A kind of preparation method of injection vinpocetine lyophilized powder |
| CN105267160A (en) * | 2015-11-24 | 2016-01-27 | 河北智同生物制药有限公司 | Vinpocetine freeze-drying preparation composition for injection and preparing method thereof |
| CN109364021A (en) * | 2018-10-26 | 2019-02-22 | 山西普德药业有限公司 | A kind of injection vinpocetine |
Family Cites Families (5)
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| CN100366250C (en) * | 2003-06-11 | 2008-02-06 | 山东绿叶制药有限公司 | Freeze dried vinpocetine powder injection and its preparation process |
| CN1723896A (en) * | 2004-07-19 | 2006-01-25 | 胡才忠 | Vinthitine liposome |
| CN1919195A (en) * | 2005-08-24 | 2007-02-28 | 姜昱 | Vinpocetine drop pills and its preparation method |
| CN101103962A (en) * | 2006-07-13 | 2008-01-16 | 华中科技大学同济医学院 | Vinpocetine oral self-micro-emulsification medicine-releasing system and preparation method thereof |
| CN100522163C (en) * | 2006-09-28 | 2009-08-05 | 郑州羚锐制药有限公司 | Small volume vincamine injection and its preparation process |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101874776B (en) * | 2009-04-28 | 2012-06-13 | 中国人民解放军军事医学科学院毒物药物研究所 | Dry emulsion of vinpocetine and preparation method thereof |
| CN102526042A (en) * | 2010-12-09 | 2012-07-04 | 常建晖 | Stable liquid medicinal composition |
| CN102526042B (en) * | 2010-12-09 | 2013-12-11 | 常建晖 | Stable liquid medicinal composition |
| CN102091030A (en) * | 2011-01-20 | 2011-06-15 | 罗军 | Vinpocetine injection and preparation method thereof |
| CN104083329A (en) * | 2014-02-21 | 2014-10-08 | 杭州长典医药科技有限公司 | Vinpocetine special ultrafine powder lyophilized preparation and preparation method thereof |
| CN105213323A (en) * | 2014-05-30 | 2016-01-06 | 海南通用康力制药有限公司 | A kind of preparation method of injection vinpocetine lyophilized powder |
| CN105267160A (en) * | 2015-11-24 | 2016-01-27 | 河北智同生物制药有限公司 | Vinpocetine freeze-drying preparation composition for injection and preparing method thereof |
| CN105267160B (en) * | 2015-11-24 | 2019-05-14 | 河北智同生物制药股份有限公司 | A kind of injection vinpocetine lyophilized preparation composition and preparation method thereof |
| CN109364021A (en) * | 2018-10-26 | 2019-02-22 | 山西普德药业有限公司 | A kind of injection vinpocetine |
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| CN101264064B (en) | 2011-04-20 |
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