CN116036014B - Octreotide acetate injection and preparation method thereof - Google Patents

Octreotide acetate injection and preparation method thereof Download PDF

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Publication number
CN116036014B
CN116036014B CN202310207272.8A CN202310207272A CN116036014B CN 116036014 B CN116036014 B CN 116036014B CN 202310207272 A CN202310207272 A CN 202310207272A CN 116036014 B CN116036014 B CN 116036014B
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injection
octreotide acetate
sodium
stirring
preparation
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CN116036014A (en
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王会勇
熊心磊
郭芬
唐维
徐敬
李乐枫
丁晶
倪萌
褚炜
陈诗
李明霞
肖盼
卢子龙
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Wuhan Humanwell Pharmaceutical Co ltd
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
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    • A61K38/00Medicinal preparations containing peptides
    • A61K38/04Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/08Peptides having 5 to 11 amino acids
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    • A61K47/18Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
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Abstract

The invention discloses octreotide acetate injection and a preparation method thereof, and relates to the technical field of pharmacy. On the basis of optimizing the buffering agent, the invention enhances the high temperature and illumination stability of the active ingredients by matching with the antioxidant such as disodium edentate, greatly improves the stability of the octreotide acetate injection, can be stored for 18 months or more under the condition of not higher than 20 ℃ without being protected from light during production and use, and can obtain ideal stability without using inert gas to control residual oxygen during the preparation.

Description

Octreotide acetate injection and preparation method thereof
Technical Field
The invention belongs to the technical field of pharmacy, and particularly relates to octreotide acetate injection and a preparation method thereof.
Background
Octreotide acetate is an analogue of somatostatin, and is a synthetic 8-peptide drug, and the chemical name of the octreotide acetate is D-phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophanyl-L-lysyl-L-threonyl-N- [ (1R, 2R) -2-hydroxy-1- (hydroxymethyl) propyl ] -L-cysteinamide ring (2- & gt 7) -disulfide acetate. Has the functions of controlling and treating acromegaly, relieving symptoms related to functional gastrointestinal pancreatic (GEP) endocrine tumor, preventing postoperative complications of pancreas, treating hemorrhage caused by gastric-esophageal varices of patients with liver cirrhosis, stopping bleeding, preventing rebleeding and the like, is mainly a small-volume injection clinically, and has convenient use and reliable curative effect.
The stability of the peptide chain is poor, and acid, alkali, metal ions and the like can cause the degradation of the peptide chain, so that octreotide acetate is extremely easy to degrade under the conditions of high temperature, illumination, acid, alkali and the like. The production and transportation process need to be protected from light and refrigerated. The prior art has made many improvements to improve the stability of octreotide acetate formulations.
Patent (CN 114983936A) discloses an octreotide acetate injection, wherein the injection consists of octreotide acetate with the concentration of 0.001-0.05% (w/v), an osmotic pressure regulator, a pH regulator and water for injection, the pH of the injection is 4.0-4.5, and the osmotic pressure of the injection is 285-320mOsmol/kg. The components and the proportion for preparing the octreotide acetate injection are scientifically screened, the preparation process and the parameters are optimized, the stability of the octreotide acetate injection is obviously improved, the octreotide acetate injection is well compatible with any one or combination of normal saline and 5% glucose, the risk of microbial infection is obviously reduced or even avoided, the quality of medicines is obviously improved, and the safety and the effectiveness of clinical medication are ensured.
Patent (CN 113318218A) and octreotide acetate injection and preparation process thereof. According to the invention, CO 2 is used as a shielding gas to prepare the octreotide acetate injection, so that the stability of the octreotide acetate injection is improved to a certain extent, and the osmotic pressure of the octreotide acetate injection is improved, so that the osmotic pressure of the octreotide acetate injection is basically consistent with that of a reference preparation.
The patent (CN 114288385A) relates to a preparation method of octreotide acetate preparation, which comprises the following steps of taking injection water accounting for 50-80% of the total amount, introducing protective gas until the residual oxygen content is below 8%, adding an antioxidant, adding octreotide acetate raw material medicine after dissolution to obtain a solution a, adding an isotonic agent into the injection water, adding lactic acid after dissolution, regulating the pH value to obtain a solution b, uniformly mixing the solution a and the solution b, and regulating the pH value to 3.9-4.5 to obtain the octreotide acetate preparation. The method can effectively improve the stability of the octreotide acetate injection, so that the octreotide acetate injection still has stable pH value, total octreotide acetate and low maximum single impurity and total impurity percentage after being stored for 5 days and 10 days on the preparation day. According to the packaging method provided by the invention, the stability of the octreotide acetate injection is further improved by adding the process link of filling carbon dioxide protective gas, so that the octreotide acetate injection still maintains high octreotide acetate content and low maximum single impurity and total impurity percentage after being stored for 30 days.
The patent (CN 113350276A) discloses a preparation method and a packaging method of octreotide acetate injection, wherein the preparation method comprises the steps of (1) mixing lactic acid with water for injection, (2) mixing mannitol with the mixture obtained in the step (1), (3) adjusting the pH value of the mixture obtained in the step (2) and then adding octreotide acetate, (4) filtering to obtain octreotide acetate injection, and (5) adding water for injection to the total amount. The method can effectively improve the stability of the octreotide acetate injection, so that the octreotide acetate injection still has stable pH value, total octreotide acetate and low maximum single impurity and total impurity percentage after being stored for 5 days and 10 days. The packaging method comprises the step of filling carbon dioxide, so that the stability of the octreotide acetate injection under high temperature and illumination conditions can be improved, and the octreotide acetate injection can still keep high octreotide acetate content and low maximum single impurity and total impurity percentage after being stored for 5 days, 10 days and 30 days.
Therefore, the stability of octreotide acetate injection can be improved to a certain extent by optimizing the raw material types or the preparation process, in particular to adopting an inert gas to control residual oxygen. However, the stability of the octreotide acetate injection is still not very ideal, so that the screening of a proper prescription further improves the stability of the octreotide acetate injection.
Disclosure of Invention
Aiming at the problems existing in the prior art, the invention provides octreotide acetate injection and a preparation method thereof. On the basis of optimizing the buffering agent, the invention enhances the high temperature and illumination stability of the active ingredients by matching with the antioxidant such as disodium edentate, greatly improves the stability of the octreotide acetate injection, can be stored for 18 months or more without being protected from light in the production and use process, and can obtain ideal stability without using inert gas to control residual oxygen in the preparation process.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
In the first aspect, the invention provides octreotide acetate injection, which comprises 50-1000mg of octreotide acetate, 0.5-5g of buffer solution, 0.1-1.0g of antioxidant, 1-10g of osmotic pressure regulator, a proper amount of pH regulator for regulating pH to 2.0-6.0 and a proper amount of solvent for adding 1000mL, wherein the buffer solution is at least one selected from succinic acid, citric acid and acetic acid, and the antioxidant is at least one selected from disodium edentate, calcium sodium edentate and methionine.
In a preferred embodiment, the injection comprises, per 1000mL of the injection, 100mg of octreotide acetate, 0.5-5g of buffer solution, 1g of antioxidant, 7g of osmotic pressure regulator, a proper amount of pH regulator for regulating the pH to 3.7-4.7, and a proper amount of solvent for adding to 1000mL.
In a preferred embodiment, the buffer is succinic acid.
In a preferred embodiment, the pH adjuster is selected from sodium hydroxide, sodium succinate, sodium citrate, sodium acetate, more preferably sodium hydroxide, sodium acetate trihydrate.
In a preferred embodiment, the antioxidant is disodium edentate.
In a preferred embodiment, the osmolality adjusting agent is selected from sodium chloride and/or mannitol, more preferably sodium chloride.
In a preferred embodiment, the solvent is selected from the group consisting of water for injection, oil for injection, ethanol, propanol, isopropanol, propylene glycol, ethyl acetate, dimethyl sulfoxide and glycerol.
Compared with the common buffer lactic acid, the buffer used in the invention has better stability, and the antioxidant such as disodium edentate is matched for use, so that the high temperature and illumination stability of active ingredients are enhanced, the stability of octreotide acetate injection is greatly improved, the octreotide acetate injection can be stored for 18 months or more without being protected from light in the production and use process, and the ideal stability can be obtained without using inert gas to control residual oxygen in the preparation process.
In a preferred embodiment, the injection further comprises an enhancer selected from one or more of beta-cyclodextrin, polysorbate 80, glycerin, propylene glycol.
In a second aspect, the application also provides a preparation method of the octreotide acetate injection, which comprises the following steps:
1) Preparation of liquid medicine
Adding a cold solvent with the quantity lower than the preparation quantity, adding raw materials except octreotide acetate and a pH regulator, stirring and dissolving, regulating the pH by using the pH regulator, adding octreotide acetate, stirring and dissolving, and fixing the volume to a scale by using the cold solvent;
2) Sterilizing and filtering;
3) Filling;
4) Lamp inspection, leak detection and packaging;
In a preferred embodiment, step 2) the medical fluid is filtered using a filter or filter membrane selected from the group consisting of PES, PVDF and PTFE having a pore size of 0.45 μm or 0.22 μm, and step 3) the medical fluid is filled into a packaging container of at least one of ampoule, penicillin bottle and cartridge type according to 1.15 ml/bottle. Wherein, the PES filter element or the filter membrane has less adsorption to the octreotide acetate active ingredient except for sterilization and quality removal.
In a preferred embodiment, the filter element or filter membrane in step 2) is made of PES, the pore size is 0.22 μm, and the packaging container in step 3) is an ampoule bottle.
In a preferred embodiment, step 4) the product is packaged after light inspection, leak detection.
Compared with the prior art, the invention has the following beneficial effects:
1. On the basis of optimizing the buffering agent, the invention enhances the high temperature and illumination stability of the active ingredient by matching with the antioxidant such as disodium edentate, greatly improves the stability of octreotide acetate injection, and can obtain ideal stability without using inert gas to control residual oxygen in the preparation process.
2. The production and use processes of the invention can avoid light, the octreotide acetate injection prepared by the invention can be stored for 18 months or more at the temperature of not higher than 20 ℃,
Detailed Description
It is to be noted that the raw materials used in the present invention are all common commercial products, and the sources thereof are not particularly limited.
Example 1
The prescription is as follows:
Component (A) Dosage of
Octreotide acetate 100mg
Succinic acid 1g
Sodium chloride 7g
Edetic acid disodium salt 1g
Sodium hydroxide Proper amount of pH is regulated to 3.7-4.7
Water for injection Constant volume to 1000ml
Preparation method of octreotide acetate injection
Step 1, adding 800ml of cooled water for injection into a container, starting stirring, adding prescribed amounts of sodium chloride, succinic acid and edetate disodium, stirring to dissolve, adjusting the pH to 4.2 by using a sodium hydroxide solution, adding prescribed amounts of octreotide acetate, stirring to dissolve, and fixing the volume to 1000ml by using the cooled water for injection.
Step 2, sterilization filtration was performed using a 0.22 μm PES filter.
And 3, sterilizing the 1ml ampoule bottle by a tunnel oven, removing heat sources, filling the liquid medicine into the 1ml ampoule bottle according to 1.15 ml/branch, and wire drawing and sealing.
And 4, performing lamp inspection, leakage detection and packaging on the product.
Example 2
The prescription is as follows:
Component (A) Dosage of
Octreotide acetate 100mg
Citric acid 1g
Mannitol (mannitol) 7g
Edetate calcium sodium 1g
Sodium hydroxide Proper amount of pH is regulated to 3.7-4.7
Water for injection Constant volume to 1000ml
Preparation method of octreotide acetate injection
Step 1, adding 800ml of cooled water for injection into a container, starting stirring, adding mannitol, citric acid and calcium sodium edetate in a prescription amount, stirring to dissolve, adjusting the pH to 4.2 by using a sodium hydroxide solution, adding octreotide acetate in the prescription amount, stirring to dissolve, and fixing the volume to 1000ml by using the cooled water for injection.
Step 2, sterilization filtration was performed using a 0.22 μm PES filter.
And 3, sterilizing the 1ml ampoule bottle by a tunnel oven, removing heat sources, filling the liquid medicine into the 1ml ampoule bottle according to 1.15 ml/branch, and wire drawing and sealing.
And 4, performing lamp inspection, leakage detection and packaging on the product.
Example 3
The prescription is as follows:
Component (A) Dosage of
Octreotide acetate 100mg
Glacial acetic acid 2g
Sodium chloride 7g
Methionine 1g
Sodium acetate trihydrate 2g
Water for injection Constant volume to 1000ml
Preparation method of octreotide acetate injection
Step 1, adding 800ml of cooled water for injection into a container, starting stirring, adding the prescribed amounts of sodium chloride, glacial acetic acid, methionine and sodium acetate trihydrate, and stirring to dissolve. Octreotide acetate in the prescribed amount was added, stirred to dissolve, and cooled water for injection was used to fix the volume to 1000ml.
Step 2, sterilization filtration was performed using a 0.22 μm PES filter.
And 3, sterilizing the 1ml ampoule bottle by a tunnel oven, removing heat sources, filling the liquid medicine into the 1ml ampoule bottle according to 1.15 ml/branch, and wire drawing and sealing.
And 4, performing lamp inspection, leakage detection and packaging on the product.
Comparative example 1
The prescription is as follows:
Component (A) Dosage of
Octreotide acetate 100mg
Lactic acid 3.4g
Mannitol (mannitol) 45g
Sodium bicarbonate Proper amount of pH is regulated to 3.7-4.7
Water for injection Constant volume to 1000ml
Preparation method of octreotide acetate injection
Step 1, adding 800ml of cooled water for injection into a container, starting stirring, adding the mannitol and lactic acid with the prescribed amount, stirring to dissolve, adding octreotide acetate with the prescribed amount, stirring to dissolve, and adjusting the pH to 4.2 by using sodium bicarbonate solution. Cooled water for injection was used to volume to 1000ml.
Step 2, sterilization filtration was performed using a 0.22 μm PES filter.
And 3, sterilizing the 1ml ampoule bottle by a tunnel oven, removing heat sources, filling the liquid medicine into the 1ml ampoule bottle according to 1.15 ml/branch, and wire drawing and sealing.
And 4, performing lamp inspection, leakage detection and packaging on the product.
Comparative example 2
The prescription is as follows:
preparation method of octreotide acetate injection
Step 1, adding 800ml of cooled water for injection into a container, starting stirring, introducing carbon dioxide below the liquid surface to make the dissolved oxygen content less than 5ppm, continuously introducing carbon dioxide until the filtration is finished, adding the mannitol and lactic acid with the prescribed amount, stirring to dissolve, adding the octreotide acetate with the prescribed amount, and stirring to dissolve. The pH was adjusted to 4.2 using sodium bicarbonate solution. Cooled water for injection was used to volume to 1000ml.
Step 2, sterilization filtration was performed using a 0.22 μm PES filter.
Step 3, 1ml ampoule bottles are sterilized by a tunnel oven to remove heat sources, the liquid medicine is filled into 1ml ampoule bottles according to 1.15 ml/branch, the air in the bottles is replaced by carbon dioxide, and the ampoule bottles are subjected to wiredrawing and sealing.
And 4, performing lamp inspection, leakage detection and packaging on the product.
Comparative example 3
The prescription is as follows:
Component (A) Dosage of
Octreotide acetate 100mg
Succinic acid 1g
Sodium chloride 7g
Sodium metabisulfite 0.1g
Sodium hydroxide Proper amount of pH is regulated to 3.7-4.7
Water for injection Constant volume to 1000ml
Preparation method of octreotide acetate injection
Step 1, adding 800ml of cooled water for injection into a container, starting stirring, adding prescribed amounts of sodium chloride, succinic acid and sodium metabisulfite, stirring to dissolve, and adjusting the pH to 4.2 by using sodium hydroxide solution. Octreotide acetate in the prescribed amount was added, stirred to dissolve, and cooled water for injection was used to fix the volume to 1000ml.
Step 2, sterilization filtration was performed using a 0.22 μm PES filter.
And 3, sterilizing the 1ml ampoule bottle by a tunnel oven, removing heat sources, filling the liquid medicine into the 1ml ampoule bottle according to 1.15 ml/branch, and wire drawing and sealing.
And 4, performing lamp inspection, leakage detection and packaging on the product.
Comparative example 4
The prescription is as follows:
preparation method of octreotide acetate injection
Step 1, adding 800ml of cooled water for injection into a container, starting stirring, adding prescribed amount of sodium chloride, lactic acid and edetate disodium, stirring to dissolve, adjusting pH to 4.2 with sodium hydroxide solution, adding prescribed amount of octreotide acetate, stirring to dissolve, and fixing volume to 1000ml with cooled water for injection.
Step 2, sterilization filtration was performed using a 0.22 μm PES filter.
And 3, sterilizing the 1ml ampoule bottle by a tunnel oven, removing heat sources, filling the liquid medicine into the 1ml ampoule bottle according to 1.15 ml/branch, and wire drawing and sealing.
And 4, performing lamp inspection, leakage detection and packaging on the product.
Test examples
The substances and contents of the substances of examples 1 to 2 and comparative examples were measured according to the method of "Chinese pharmacopoeia" (second edition 2020).
The chromatographic conditions are as follows:
The column was a Xtimate C18.6mm.times.250mm column, a tetramethylammonium hydroxide solution (20 ml of a 10% tetramethylammonium hydroxide solution, 880ml of water was added, the pH was adjusted to 5.4 with a 10% phosphoric acid solution) -acetonitrile (900:100) was used as mobile phase A, a tetramethylammonium hydroxide solution (20 ml of a 10% tetramethylammonium hydroxide solution, 380ml of water was added, the pH was adjusted to 5.4 with a 10% phosphoric acid solution) -acetonitrile (400:600) was used as mobile phase B, and gradient elution was carried out as in Table 1, the detection wavelength was 210nm, and the sample volume was 100. Mu.l.
TABLE 1 elution conditions
Time (minutes) Mobile phase a (%) Mobile phase B (%)
0 73 27
30 55 45
31 73 27
37 73 27
The test results are shown in Table 2:
TABLE 2 content of substances related to examples 1-and comparative examples 2
Note that "ND" indicates undetected.
Influence factor study results table 3 shows:
TABLE 3 examples 1-comparative example 2 related substances, contents under different conditions
The formulations of examples 1-3 exhibited unpredictable improvements in light stability over comparative examples 1-4. The thermal stability was also significantly higher than in comparative examples 1-4.
The stability study results are shown in table 4:
TABLE 3 Long term stability of examples 1-and comparative example 2
The impurities of comparative example 1, comparative example 2, comparative example 3 and comparative example 4 exceeded the standard limit for a long period of 12 months (25 deg. C, RH%) and the impurities of examples 1-3 were significantly smaller than the comparative example, within the standard limit, but exceeded the standard limit for 18 months.
The impurities in comparative example 1, comparative example 2, comparative example 3 and comparative example 4 were about to reach the standard limit for a long period of 12 months (20℃, RH%) and exceeded the standard limit for a long period of 18 months. Examples 1-3 were significantly less contaminated than the comparative examples and were stable for 18 months at this temperature with 18 months of extended 18 month contamination within standard limits.
Finally, it should be noted that the above description is only for illustrating the technical solution of the present invention, and not for limiting the scope of the present invention, and that the simple modification and equivalent substitution of the technical solution of the present invention can be made by those skilled in the art without departing from the spirit and scope of the technical solution of the present invention.

Claims (3)

1. The octreotide acetate injection is characterized by comprising the following components of 100mg of octreotide acetate, 1g of succinic acid, 7g of sodium chloride, 1g of edetate disodium, and a proper amount of sodium hydroxide for regulating the pH value to 3.7-4.7, wherein the volume of water for injection is regulated to 1000mL;
The preparation method of the octreotide acetate injection comprises the following steps:
Step 1, adding 800mL of cooled water for injection into a container, starting stirring, and adding the prescribed amount of sodium chloride and sodium succinate
Stirring to dissolve the perc acid and the edetate disodium, regulating the pH value to 4.2 by using a sodium hydroxide solution, adding the octreotide acetate with a prescription amount, stirring to dissolve, and fixing the volume to 1000mL by using cooled water for injection;
Step 2, performing sterilization filtration by using a 0.22 mu m PES filter;
Step 3, sterilizing the 1mL ampoule bottle by a tunnel oven, removing heat sources, filling the liquid medicine into the 1mL ampoule bottle according to 1.15 mL/branch, and wire drawing and sealing;
and 4, performing lamp inspection, leakage detection and packaging on the product.
2. The octreotide acetate injection is characterized by comprising the following components of 100mg octreotide acetate, 1g of citric acid, 7g of mannitol, 1g of calcium sodium edetate, a proper amount of sodium hydroxide, adjusting the pH value to 3.7-4.7, and fixing the volume of water for injection to 1000mL;
The preparation method of the octreotide acetate injection comprises the following steps:
Adding 800mL of cooled water for injection into a container, starting stirring, adding mannitol, citric acid and calcium sodium edetate with a prescription amount, stirring to dissolve, adjusting the pH to 4.2 with a sodium hydroxide solution, adding octreotide acetate with a prescription amount, stirring to dissolve, and fixing the volume to 1000mL with the cooled water for injection;
Step 2, performing sterilization filtration by using a 0.22 mu m PES filter;
Step 3, sterilizing the 1mL ampoule bottle by a tunnel oven, removing heat sources, filling the liquid medicine into the 1mL ampoule bottle according to 1.15 mL/branch, and wire drawing and sealing;
and 4, performing lamp inspection, leakage detection and packaging on the product.
3. The octreotide acetate injection is characterized by comprising the following components of 100mg of octreotide acetate, 2g of glacial acetic acid, 7g of sodium chloride, 1g of methionine, sodium acetate trihydrate and water for injection to 1000mL in volume per 1000mL of injection;
The preparation method of the octreotide acetate injection comprises the following steps:
Adding 800mL of cooled water for injection into a container, starting stirring, adding the prescribed amount of sodium chloride, glacial acetic acid, methionine and sodium acetate trihydrate, adding the prescribed amount of octreotide acetate, stirring to dissolve, and using the cooled water for injection to fix the volume to 1000mL;
Step 2, performing sterilization filtration by using a 0.22 mu m PES filter;
Step 3, sterilizing the 1mL ampoule bottle by a tunnel oven, removing heat sources, filling the liquid medicine into the 1mL ampoule bottle according to 1.15 mL/branch, and wire drawing and sealing;
and 4, performing lamp inspection, leakage detection and packaging on the product.
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Citations (2)

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Publication number Priority date Publication date Assignee Title
CN101647773A (en) * 2009-05-25 2010-02-17 李红力 Octreotide acetate injection
CN114288385A (en) * 2021-12-27 2022-04-08 苏州天马医药集团天吉生物制药有限公司 Preparation method of octreotide acetate preparation

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US20100086597A1 (en) * 2008-10-06 2010-04-08 Oakwood Laboratories LLC Microspheres for the sustained release of octreotide with a low initial burst
CN102416001B (en) * 2011-12-09 2013-06-05 重庆煜澍丰医药有限公司 Octreotide acetate freeze-dried powder injection for injection and preparation method thereof
CN110678194B (en) * 2017-05-15 2024-08-06 太阳制药有限公司 Octreotide injection
CN113350276A (en) * 2021-06-21 2021-09-07 上海上药第一生化药业有限公司 Preparation method and packaging method of octreotide acetate injection

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Publication number Priority date Publication date Assignee Title
CN101647773A (en) * 2009-05-25 2010-02-17 李红力 Octreotide acetate injection
CN114288385A (en) * 2021-12-27 2022-04-08 苏州天马医药集团天吉生物制药有限公司 Preparation method of octreotide acetate preparation

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