CN101940552B - Chinese medicament shikimic acid powder injection - Google Patents
Chinese medicament shikimic acid powder injection Download PDFInfo
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Abstract
The invention discloses Chinese medicament shikimic acid powder injection. The Chinese medicament shikimic acid powder injection is prepared by the following steps of: dissolving 10 weight parts of 3,4-O-isopropylidene shikimic acid with water for injection; adding sodium hydroxide, sodium dihydrogen phosphate and disodium hydrogen phosphate; performing sterilization for 20 to 50 minutes at the temperature of between 110 and 140 DEG C and under the pressure condition of 0.2 to 1.4 kg/cm<2>; filtering by using a microfiltration membrane and then performing ultrafiltration; and freeze drying ultrafiltrate to prepare the Chinese medicament shikimic acid powder injection. The Chinese medicament shikimic acid powder injection has the advantages of ensuring the stability in the process of preparing the powder injection from the 3,4-O-isopropylidene shikimic acid, saving production cost and avoiding the safety problem possibly caused by using skeleton materials.
Description
The application is to be on JIUYUE 16th, 2008 applying date, and application number is 200810212048.3, and denomination of invention is divided an application for the application for a patent for invention of " isopropylidene shikimic acid powder injection ".
Technical field
The present invention relates to a kind of injectable powder of Chinese medicine, particularly injectable powder of Chinese medicine shikimic acid and preparation method thereof.
Background technology
Shikimic acid (Shikmicacid; SA-1;); Be the active ingredient that contains in the Chinese herbal medicine Magnoliaceae Illicium various plants fruit, refining forming extracted by the fruit of many stamens of Winteraceae Radix Illicii Lanceolati Illicium henrvivar.multistamineum and the mature fruit of angle other plant of genus in its source through the methanol equal solvent.Its molecular formula is C
7H
10O
5, molecular weight is 174.15.In recent years, the exploitation of thrombosis Study on Mechanism and antithrombotic reagent is received the concern of various countries the world of medicine deeply, and existing part active compound is in and the preclinical study stage clinical.
(3,4-oxo-isopropylidene-shikimic acid ISA) is one of the reactive derivative of the effective ingredient shikimic acid that from Chinese medicine Magnoliacea plant Fructus Anisi Stellati (Fructus Anisi stellati), extracts to iso propylidene shikimic acid; Chinese name: 3,4-O-iso propylidene shikimic acid, molecular formula and molecular weight: C1OHl4O5; 214; Chemical name: 3, the English chemical name of 4-O-iso propylidene shikimic acid: 3,4-oxo-isopropylidene-shikimic acid.Iso propylidene shikimic acid is used to treat cerebral thrombosis, cerebral infarction and antithrombotic.
Iso propylidene shikimic acid is mainly used in the treatment of thrombotic disease; In the treatment of thrombotic disease; Adopt non-vascular drug delivery to exist processes such as absorption, make the drug level that gets into blood reduce, iso propylidene shikimic acid is unstable in addition; So when the preparation oral formulations, also exist labile under one's belt problem.Because the unsettled characteristics of iso propylidene shikimic acid, there is bigger difficulty in the preparation ejection preparation.
Summary of the invention
Purpose of the present invention is to disclose a kind of 3 of high stability that has, the injectable powder of 4-O-iso propylidene shikimic acid.
Another object of the present invention is to disclose a kind of 3 of high stability that has, the method for preparing of the injectable powder of 4-O-iso propylidene shikimic acid.
First purpose of the present invention realizes through following technical scheme:
A kind of 3, the injectable powder of 4-O-iso propylidene shikimic acid, process by the raw material and the water for injection of following weight ratio:
3,4-O-iso propylidene shikimic acid 10 weight portion sodium hydroxide 2-5 weight portions
Sodium dihydrogen phosphate 7-10 weight portion sodium hydrogen phosphate 3-6 weight portion
Water for injection 100-1000 weight portion.
Said 3, the injectable powder of 4-O-iso propylidene shikimic acid is processed by the raw material of following preferred weight ratio:
3,4-O-iso propylidene shikimic acid 10 weight portion sodium hydroxide 2.37 weight portions
Sodium dihydrogen phosphate 8.44 weight portion sodium hydrogen phosphates 4.6 weight portions
Water for injection 300-900 weight portion.
Of the present invention 3, the injectable powder of 4-O-iso propylidene shikimic acid, by following method preparation:
Get 3,4-O-iso propylidene shikimic acid 10 weight portions add the dissolving of injection water, press the prescription amount and add sodium hydroxide, sodium dihydrogen phosphate, sodium hydrogen phosphate, and 110-140 ℃ of pressure condition is 0.2-1.4kg/cm
2Sterilized ultrafiltration behind the filtering with microporous membrane, ultrafiltrate lyophilization 20-50 minute.
Said sterilising conditions is preferred: 121 ℃ of hot pressing (0.7kg/cm
2), 30 minutes;
Said cryodesiccated method is: in freeze drying box, freeze to below-35 ℃, be incubated 3 hours; The open vacuum pump gets into sublimation stage, and the maximum temperature of distillation is controlled at below-14 ℃; After treating the ice crystal complete obiteration, change drying stage over to, maximum temperature is no more than 35 ℃.Wherein baking temperature the best is 30 ℃.
Second purpose of the present invention realizes through following technical scheme:
A kind of have 3 of a high stability, the method for preparing of the injectable powder of 4-O-iso propylidene shikimic acid, and this method comprises the steps:
Get 3,4-O-iso propylidene shikimic acid 10 weight portions add the dissolving of injection water 100-1000 weight portion, regulate pH value more than 5, are that 110-140 ℃, pressure condition are: 0.2-1.4kg/cm at temperature conditions
2Sterilized ultrafiltration behind the filtering with microporous membrane, ultrafiltrate lyophilization 20-50 minute.
The preferred 5-8 of said pH value; PH value most preferably 7;
The preferred 121 ℃ of hot pressing (0.7kg/cm of said sterilising conditions
2), 30 minutes;
Said cryodesiccated method is: in freeze drying box, freeze to below-35 ℃, be incubated 3 hours; The open vacuum pump gets into sublimation stage, and the maximum temperature of distillation is controlled at below-14 ℃; After treating the ice crystal complete obiteration, change drying stage over to, maximum temperature is no more than 35 ℃.Wherein baking temperature the best is 30 ℃.
Regulate pH value and can adopt conventional adding alkali to regulate,, also can adopt adding alkali and buffer salt as adding sodium hydroxide 2-5 weight portion; Wherein buffer salt is selected from: sodium hydroxide-sodium dihydrogen phosphate; Sodium hydrogen phosphate-sodium dihydrogen phosphate; TRIS buffer; Barbitol buffer solution, barbital-sodium chloride buffer, ammonia-ammonium chloride buffer, Borax-calcium chloride buffer, potassium dihydrogen phosphate-sodium hydroxide, sodium hydrogen phosphate-potassium dihydrogen phosphate, potassium dihydrogen phosphate-dipotassium hydrogen phosphate.Preferably phosphoric acid disodium hydrogen-sodium dihydrogen phosphate (pH7) is as buffer agent.Wherein the buffer salt consumption can calculate through the osmotic pressure principle; For example use the full-automatic freezing-point osmometer of FM28 type (Instrument Factory, Shanghai Medical Science Univ.); The smart 100mg thromboembolism preventing of claiming is plain; Adding 1molml-1NaOH 590 μ l adjusting pH value is 7, and sodium hydrogen phosphate-phosphate sodium dihydrogen buffer solution of the 0.2molL of the pH value 7 of adding different volumes is settled to 10ml with water; According to Chinese Pharmacopoeia two appendix IXG in 2005, adopt the osmotic pressure molar density algoscopy, measure the osmotic pressure of the thromboembolism preventing cellulose solution of variable concentrations buffer respectively; With the buffer addition osmotic pressure is mapped, fit equation is: y=39.13x+99.481, | r|=0.9991, through measuring, the osmotic pressure of 0.9% sodium chloride injection is 280mmolL-1, it is 4.61ml that the buffer salt volume that needs to add is oozed in calculating adjusting etc.
Said 3, the synthetic of 4-O-iso propylidene shikimic acid can be according to the patent No.: the ZL02130773.3 denomination of invention is the method for preparing of a kind of ISA and method preparation that new purposes is put down in writing.The element of thromboembolism preventing described in the present invention is 3, the 4-O-iso propylidene shikimic acid.
Experimentation shows 3, and the 4-O-iso propylidene shikimic acid is unstable in aqueous solution, and shikimic acid derivative is in the process of preparation injectable powder, and the problem of puzzlement is the stability problem that solves active component all the time.Technical scheme 1 of the present invention has controlled 3 through the raw material of special ratios, and 4-O-iso propylidene shikimic acid solution Ph value all efficiently solves 3 more than 5 with second technical scheme of the present invention, and the 4-O-iso propylidene shikimic acid is prepared into the stability problem of injectable powder.Any injection framework material is not used in beyond thought discovery simultaneously, 3, the 4-O-iso propylidene shikimic acid still meets the preparation requirement of injectable powder, thereby has more practiced thrift production cost, also avoid because of the use of framework material the safety issue that possibly cause.
Following embodiment all can realize the described effect of above-mentioned experimental example.
Under experimental example 1 different pH condition 3, the experiment of 4-O-iso propylidene shikimic acid stability of solution
(1) experimental technique
1, principle: in medicine stability test, not only will consider H
+Or OH
-Exclusive acid-base catalysis, to consider that also buffer forms, promptly general acid-base catalysis is to the influence of drug hydrolysis speed.These two kinds of catalytic type combine can be with apparent hydrolysis rate K
ObsBe described below:
In the formula, K
ObsIt is the apparent hydrolytic rate constant that experiment records; K
o(or solvent catalysis) speed constant when being no catalytic action; K
H+And K
OH-Be respectively exclusive acid, base catalysis speed constant; K
HXAnd K
X-Be general acid, base catalysis speed constant; [HX] and [X
-] be protonated and for protonated buffer concentration.In order to assess medicine stability fully; Eliminate the influence of buffer, be determined at the hydrolytic rate constant K in the different buffer under each pH value, K maps to buffer concentration with hydrolytic rate constant; With curve extrapolation to buffer concentration is 0; Obtain the hydrolytic rate constant K of this moment, the speed that again these extrapolations is obtained is depicted as the function of pH value, has just obtained eliminating the pH-rate profile of buffer influence.
2, experimental solutions compound method
The compound method of buffer under each pH value condition
Stability experiment is with the compound method of sample under each pH value
(2) test data and the result under each experiment condition
1.pH=0, plain stability test data of thromboembolism preventing and result under 25 ℃ of conditions
PH=0, the plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the solution under 25 ℃ of conditions
Through measuring, sample was prepared back 10 minutes, had decomposed basically to finish.By 2 return regression equation: y=-0.2126x+1.0026, correlation coefficient | r|=1, calculate degradation rate constant
2.pH=1, plain stability test data of thromboembolism preventing and result under 25 ℃ the condition
PH=1, the plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result under 25 ℃ the condition
3.pH=2, plain stability test data of thromboembolism preventing and result under t=25 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the pH=2 t=25 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=2 t=25 ℃
4.pH=3, plain stability test data of thromboembolism preventing and result under the different temperatures
(1) pH=3, the plain stability test of thromboembolism preventing under t=85 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the pH=3 t=85 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=3 t=85 ℃
(2) pH=3, the plain stability test of thromboembolism preventing under t=70 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the pH=3 t=70 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=3 t=70 ℃
(3) pH=3, the plain stability test of thromboembolism preventing under t=55 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the pH=3 t=55 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=3 t=55 ℃
(4) pH=3, the plain stability test of thromboembolism preventing under t=40 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the pH=3 t=40 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=3 t=40 ℃
Buffer concentration is to the plain apparent hydrolysis rate influence of thromboembolism preventing in the time of pH=3 t=40 ℃
5.pH4 buffer in the plain stability test of thromboembolism preventing
(1) pH=4, the plain stability test of thromboembolism preventing under t=85 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the pH=4 t=85 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=4 t=85 ℃
(2) pH=4, the plain stability test of thromboembolism preventing under t=80 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the H=4 t=80 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=4 t=80 ℃
(3) pH=4, the plain stability test of thromboembolism preventing under t=55 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the pH=4 t=55 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=4 t=55 ℃
(4) pH=4, the plain stability test of thromboembolism preventing under t=40 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in t=40 ℃ of variable concentrations buffer of table 2-1 pH=4
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=4 t=40 ℃
6.pH5 buffer in the plain stability test of thromboembolism preventing
(1) pH=5, the plain stability test of thromboembolism preventing under t=85 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the pH=5 t=85 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=5 t=85 ℃
(2) pH=5, the plain stability test of thromboembolism preventing under t=80 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the pH=5 t=80 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=5 t=80 ℃
(3) pH=5, the plain stability test of thromboembolism preventing under t=55 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the pH=5 t=55 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=5 t=55 ℃
(4) pH=5, the plain stability test of thromboembolism preventing under t=40 ℃ the condition
The plain apparent hydrolytic rate constant of thromboembolism preventing is measured the result in the pH=5 t=40 ℃ of variable concentrations buffer
The plain apparent hydrolytic rate constant of thromboembolism preventing in the variable concentrations buffer in the time of pH=5 t=40 ℃
(5) pH=5, the plain stability prediction of thromboembolism preventing under the condition of room temperature (t=25 ℃)
(1) according to the Arrhenius law, with logK 1/T is made linear regression: according to the result of the test of hydrolysis at each temperature, the logarithm logK of speed constant and the reciprocal value 1/T of thermodynamic temperature see table 2-2.
Eliminate the hydrolytic rate constant value of buffer influence during table 2-2 pH=5 under each test temperature
According to the Arrhenius law, with logK 1/T is made linear regression, get linear equation:
logK＝-3877.41/T+9.7091 |r|＝0.9970
With room temperature (t=25 ℃, 298K) substitution linear equation, the hydrolytic rate constant under room temperature condition during pH=5:
Effect duration under room temperature when trying to achieve pH=5 (t=25 ℃) condition:
7. the hydrolytic rate constant under the different experimental conditions
Hydrolytic rate constant under the different experimental conditions
Experimental result shows pH value more than 5,3, and the 4-O-iso propylidene shikimic acid all has stability preferably.
Definite experiment of experimental example 2 baking temperatures
According to embodiment 1 prescription preparation sample, put into freezer dryer and carry out pre-freeze, the open vacuum pump gets into sublimation stage subsequently.After treating the ice crystal complete obiteration, begin to heat up, every at a distance from 5 ℃ be a range, be the macro examination index with the mouldability of solid, the maximum temperature of observation preparation temperature rise period.The result sees table.
Confirming of baking temperature
Can know that by experimental result it is influential that temperature is higher than 35 ℃ of mouldabilities to preparation.
The selection of experimental example 3 lyophilizing proppants
Outward appearance and redissolution with goods after the lyophilizing are index, to add mannitol as proppant with do not compare with proppant, the result sees the following form.
The proppant screening experiment
Conclusion: above experiment can find out, add mannitol as proppant with direct lyophilizing can not obtain the lyophilized formulations of outward appearance homogeneous with proppant, redissolve back solution clarification.
Following embodiment all can realize the effect of above-mentioned experimental example.
Embodiment 1
3,4-O-iso propylidene shikimic acid 10g
Sodium hydroxide 2.37g
Sodium dihydrogen phosphate 8.44g
Sodium hydrogen phosphate 4.6g
Get 3, the 4-O-iso propylidene shikimic acid adds injection water 1000g dissolving, presses the prescription amount and adds sodium hydroxide, sodium dihydrogen phosphate, sodium hydrogen phosphate, 121 ℃ of hot pressing 0.7kg/cm
2Sterilized 30 minutes, ultrafiltration behind the filtering with microporous membrane, ultrafiltrate is sub-packed in cillin bottle, in freeze drying box, freezes to below-35 ℃, is incubated 3 hours; The open vacuum pump gets into sublimation stage, and the maximum temperature of distillation is controlled at below-14 ℃; After treating the ice crystal complete obiteration, change drying stage over to, baking temperature is 30 ℃.Be prepared into 200 bottles.
Intravenous drip.One time 1～2,1 time on the one.Use after being diluted to 250～500ml with 5% glucose or 0.9% sodium chloride injection.
Embodiment 2
Take by weighing plain 10 grams of thromboembolism preventing, add sodium hydroxide, sodium hydrogen phosphate, sodium dihydrogen phosphate, regulating ph value is 7, rarely is assigned to 1000 milliliters, and microporous filter membrane (aperture 0.22 μ m) filters, and is sub-packed in the cillin bottle, adorns 5ml for every, and lyophilization promptly gets.Test, preparation technology's repeatability is good, sees the following form.
Assay
Embodiment 3
Get 3,4-O-iso propylidene shikimic acid 5g adds injection water 250g dissolving, and adding sodium hydroxide adjusting pH is 7,121 ℃ of hot pressing 0.7kg/cm
2Sterilized 30 minutes, ultrafiltration behind the filtering with microporous membrane, ultrafiltrate is sub-packed in cillin bottle, in freeze drying box, freezes to below-35 ℃, is incubated 3 hours; The open vacuum pump gets into sublimation stage, and the maximum temperature of distillation is controlled at below-14 ℃; After treating the ice crystal complete obiteration, change drying stage over to, baking temperature is 30 ℃.
Claims (8)
1. the injectable powder of a Chinese medicine shikimic acid is characterized in that being processed by the raw material of following weight ratio:
3,4-O-iso propylidene shikimic acid 10 weight portions, sodium hydroxide 2-5 weight portion, sodium dihydrogen phosphate 7-10 weight portion, sodium hydrogen phosphate 3-6 weight portion water for injection 100-1000 weight portion.
2. injectable powder as claimed in claim 1 is characterized in that being processed by the raw material of following weight ratio:
3,4-O-iso propylidene shikimic acid 10 weight portion sodium hydroxide 2.37 weight portion sodium dihydrogen phosphate 8.44 weight portion sodium hydrogen phosphates 4.6 weight portion water for injection 300-900 weight portions.
3. according to claim 1 or claim 2 the method for preparing of injectable powder is characterized in that this method is:
Get 3,4-O-iso propylidene shikimic acid 10 weight portions add the dissolving of injection water, press the prescription amount and add sodium hydroxide, sodium dihydrogen phosphate, sodium hydrogen phosphate, and 110-140 ℃ of pressure condition is 0.2-1.4kg/cm
2Sterilized ultrafiltration behind the filtering with microporous membrane, ultrafiltrate lyophilization 20-50 minute.
4. the method for preparing of injectable powder as claimed in claim 3 is characterized in that sterilising conditions is in this method for preparing: 121 ℃, pressure are 0.7kg/cm
2, sterilized 30 minutes.
5. the method for preparing of injectable powder as claimed in claim 3 is characterized in that cryodesiccated method is in this method: in freeze drying box, freeze to below-35 ℃, be incubated 3 hours; The open vacuum pump gets into sublimation stage, and the maximum temperature of distillation is controlled at below-14 ℃; After treating the ice crystal complete obiteration, change drying stage over to, maximum temperature is no more than 35 ℃.
6. the method for preparing of injectable powder as claimed in claim 5 is characterized in that baking temperature is 30 ℃.
7.3 the method for preparing of the injectable powder of 4-O-iso propylidene shikimic acid is characterized in that this method comprises the steps:
Get 3,4-O-iso propylidene shikimic acid 10 weight portions add the dissolving of injection water 100-1000 weight portion, regulate pH value 5-7, are that 110-140 ℃, pressure condition are: 0.2-1.4kg/cm at temperature conditions
2Sterilized ultrafiltration behind the filtering with microporous membrane, ultrafiltrate lyophilization 20-50 minute.
8. the method for preparing of injectable powder as claimed in claim 7 is characterized in that sterilising conditions is in this method for preparing: 121 ℃, pressure are 0.7kg/cm
2, sterilized 30 minutes.
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|---|---|---|---|
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|---|---|---|---|
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1163104A (en) * | 1997-02-03 | 1997-10-29 | 北京中医药大学 | Medicinal preparation containing shikimic acid and its derivatives, and its use in preparing anti-thrombosis and analgesic medicine |
| CN1442415A (en) * | 2002-09-26 | 2003-09-17 | 北京中医药大学 | Preparation method of iso propylidene shikimic acid and its new use |
-
2008
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1163104A (en) * | 1997-02-03 | 1997-10-29 | 北京中医药大学 | Medicinal preparation containing shikimic acid and its derivatives, and its use in preparing anti-thrombosis and analgesic medicine |
| CN1442415A (en) * | 2002-09-26 | 2003-09-17 | 北京中医药大学 | Preparation method of iso propylidene shikimic acid and its new use |
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