CN102038651B - Ropivacaine mesylate freeze-dried powder injection - Google Patents
Ropivacaine mesylate freeze-dried powder injection Download PDFInfo
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Abstract
The invention relates to a ropivacaine mesylate freeze-dried powder injection which consists of ropivacaine mesylate and a PH regulator and is prepared by using the following freeze drying method: (1) a section quick-freezing stage: keeping bulked ropivacaine mesylate solution at the temperature of 0 DEG C for 10-30 minutes, and then keeping the bulked ropivacaine mesylate solution at the temperature of minus 35 DEG C-minus 45 DEG C for 1-2 hours; (2) a lyophilization stage: heating to 0 DEG C under the vacuum degree of 10-20 Pa and at the speed of 2-10 DEG C/h, and then keeping the temperature for 1-3 hours; and (3) a desorption drying stage: heating to 30 DEG C under the vacuum degree of 0-10 Pa and at the speed of 5-10 DEG C/h and keeping the temperature for 2-5 hours. The freeze-dried powder injection provided by the invention has the advantages of high yield, good re-dissolubility, more stable quality and the like.
Description
Technical field
The invention belongs to the Western medicine preparation technical field, be specifically related to a kind of Ropivacaine mesylate freeze-dried powder injection.
Background technology
S-ropivacaine mesylate is the Domestic New local anesthetics of amide derivatives after the salt acid group with Ropivacaine HCL changes methanesulfonate into, cardiac toxicity is low, the sensation retardance separates more obvious with the motion retardance, vasoconstrictor effects is arranged, and therefore need not add in use epinephrine.Because it has only blocked pain nerve in use, does not affect nervus motorius, hardly by Placenta Hominis, so have the following advantages: (1) can be the puerpera effective analgesia is provided simultaneously; (2) guarantee the nervus motorius effect of bringing into normal play, do not affect uterine contraction, increase puerpera's muscle power; (3) do not affect baby nursing and mother's postpartum recovery; (4) hypotoxicity has improved the unify safety of heart of central nervous system.Its role in clinical at childbirth and Epidural Analgesia after Operation is identified and generally acknowledges.
CN101658490A discloses a kind of preparation technology of s-ropivacaine mesylate injection.Because the injection of conventional ampoule packing is dangerous in clinical use operation, and long-time medicinal liquid contacts with packaging material, there are the hidden danger of quality such as flake, when ampoule break-off, easily produce in addition vitroclastic (outer wall of vitroclastic as without disinfection), if fall the into the liquid hidden danger that has the microbiological contamination aspect.Also roll aluminum cap packaging outward and select cillin bottle to add plug, though can avoid above-mentioned hidden danger, the quality of plug and cleaning degree can directly have influence on the quality of medicinal liquid.The final pressure sterilizing of palpus and medicinal liquid soaked with plug for a long time and contact during injection was produced, and plug surface silicone oil and some compositions very easily mix into the liquid, affect product quality and clinical drug safety.
In following patent literature, related to the preparation method of s-ropivacaine mesylate raw material and officinal salt and lyophilized injectable powder: CN100571685C, CN 1626081A, CN 1517337A, CN 1903 187A.Wherein, CN100571685C discloses a kind of preparation technology of Ropivacaine mesylate freeze-dried powder injection, yet in the disclosed technique of the document, freeze-drying time is relatively long, production cost is higher, and used a certain amount of excipient (such as mannitol) in its prescription, when clinical lumbar vertebra Epidural, had certain security risk.A kind of ropivacaine lyophilized injectable powder is disclosed among the CN 1626081A, by the treatment effective dose the ropivacaine officinal salt and can consist of by cryodesiccated additives.Its preparation technology is: the water for injection that adds 40~50 ℃ in the preparation container is an amount of, adds ropivacaine and additives, stirs and makes fully dissolving, after the cooling, injects water to capacity again, adds active carbon, absorption, decarbonization filtering; Gained filtrate is continued with 0.22 μ m filtering with microporous membrane, packing, lyophilization and get final product.Although the freeze-drying time of the disclosed lyophilized injectable powder of the document is shorter, yet product appearance shape and other pharmacy indexs of preparation are unsatisfactory, yield rate is low, place for a long time the outward appearance atrophy, redissolve slowly, and there is certain security risk in its various diluent that adopt (comprising mannitol, dextran, lactose etc.) when the lumbar vertebra Epidural uses.CN 1660094A discloses a kind of ropivacaine hydrochloride in use for injection and preparation technology thereof, it adds the support substance that pharmacology allows by Ropivacaine HCL, make stay-in-grade injection powder pin or freeze-dried powder, its support substance is mannitol, lactose, glucose, dextran.Preparation method has adopted sterile cryogenic vacuum spray drying method, yet utilizes the method to prepare the s-ropivacaine mesylate injectable powder, its complicated operation, and cost drops into very high, is not suitable for industrialized great production.
In a word, in order to guarantee good lyophilizing outward appearance, the prior art of preparation ropivacaine lyophilized injectable powder has all added excipient, such as mannitol etc., thereby solves the problem that product appearance is poor, yield rate is low.Yet, the security risks (clinical safety of mannitol when the excipient such as mannitol may bring the administration of lumbar vertebra Epidural, little equality of summer, adverse effect magazine the 4th phase in 2003), therefore, as the anesthetis ropivacaine of epidural injection administration, if in the process of preparation injectable powder, can reduce or not add any excipient, the clinical safety of this medicine will have been increased to a great extent.
Summary of the invention
Based on the deficiencies in the prior art, a kind of solubility and good stability, the safer Ropivacaine mesylate freeze-dried powder injection of clinical practice have been the object of the present invention is to provide.This lyophilized injectable powder does not contain any excipient, and preparation technology is simple, lyophilization cycle is short, and production cost is low, and product appearance is good after the lyophilizing, yield rate is high, and indices all meets standards of pharmacopoeia.
In order to realize purpose of the present invention, the inventor studies by lot of experiments, has finally obtained following technical scheme:
A kind of Ropivacaine mesylate freeze-dried powder injection is comprised of s-ropivacaine mesylate and PH regulator, and adopts following freeze-drying method preparation:
(1) the segmentation quick-freezing stage: the s-ropivacaine mesylate solution that fill is good keeps 10~30min at 0 ℃, then keeps 1~2h at-35 ℃~-45 ℃;
(2) the sublimation drying stage: at vacuum 10~20Pa, temperature keeps 1~3h after being warming up to 0 ℃ with 2~10 ℃/h;
(3) the parsing-desiccation stage: at 0~10Pa, temperature is warming up to 30 ℃ with 5~10 ℃/h in vacuum, and keeps 2~5h.
Above-mentioned Ropivacaine mesylate freeze-dried powder injection, wherein said PH regulator are sodium hydroxide or/and phosphoric acid, and regulates described s-ropivacaine mesylate solution to PH 4~7.
Preferably, above-mentioned Ropivacaine mesylate freeze-dried powder injection, described freeze-drying method is:
(1) the segmentation quick-freezing stage: after the s-ropivacaine mesylate solution that fill is good is put into freeze dryer, first freeze dryer flaggy temperature is down to 0 ℃ and keeps 10~30min, be down to again-35 ℃~-45 ℃ and keep 1~2h;
(2) the sublimation drying stage: vacuum is at 10~20Pa in the control freeze drying box, and the flaggy temperature is warming up to 0 ℃ with 2~10 ℃/h of constant rate of speed, and keeps 1~3h.
(3) the parsing-desiccation stage: vacuum is at 0~10Pa in the control freeze drying box, and the flaggy temperature is warming up to 30 ℃ with 5~10 ℃/h of constant rate of speed, and keeps 2~5h.
Above-mentioned any one Ropivacaine mesylate freeze-dried powder injection, the heating rate in described sublimation drying stage is preferably 5 ℃/h.
Compared with prior art, Ropivacaine mesylate freeze-dried powder injection of the present invention has following useful technique effect:
When (1) Ropivacaine mesylate freeze-dried powder injection of the present invention does not contain any excipient, guaranteed good lyophilizing outward appearance, the security risks when having avoided the administration of lumbar vertebra Epidural, clinical practice is safer.
(2) Ropivacaine mesylate freeze-dried powder injection of the present invention adopts the pre-freeze mode of segmentation, so that the product rate of temperature fall is faster, less and the homogeneous of the crystallization particle diameter that forms, outward appearance is loose evenly after the lyophilizing, solubility is better, the security risks when having overcome prior art and be the lumbar vertebra Epidural administration that a large amount of excipient that the good lyophilizing outward appearance of assurance adds bring.
(3) investigate result of the test as can be known by outward appearance, solubility, content and the related substance of the Ropivacaine mesylate freeze-dried powder injection of embodiment 5, compared with prior art, it is high that Ropivacaine mesylate freeze-dried powder injection of the present invention has yield rate, solubility is good, the advantages such as more stable quality, whole freeze-dry process is consuming time shorter, has greatly shortened production cost, has alleviated patient economy burden.
The specific embodiment
Below be specific embodiments of the invention, technical scheme of the present invention is further described, but protection scope of the present invention is not limited to these embodiment.Every do not deviate from the change of the present invention design or be equal to substitute include within protection scope of the present invention.
The preparation of embodiment 1 Ropivacaine mesylate freeze-dried powder injection
Prescription: s-ropivacaine mesylate 89.4g
Water for injection adds to 1000mL
Make 1000
Preparation: take by weighing s-ropivacaine mesylate 89.4g, add 80% recipe quantity and be chilled to the water for injection of room temperature, stirring makes fully dissolving, sodium hydroxide or phosphoric acid are regulated medicinal liquid PH to 4~7, add 0.5 ‰ needle-use activated carbon, stirring and adsorbing 10 minutes, rear decarburization is filtered, add water for injection to 1000mL, stir.By 0.22 μ m degerming filter membrane twin-stage aseptic filtration, filtrate sampling detects semi-finished product content, and according to the medicinal liquid of content fill standard quantity in the cillin bottle of cleaning, the false add plug is put into the freeze dryer lyophilization.Freeze drying process is as follows, and lyophilizing finishes, aluminium lid is rolled in the vacuum tamponade outward, visual inspection, packs.
Freeze drying process:
1) the pre-freeze stage: after the s-ropivacaine mesylate semi-finished product are put into freeze dryer, first freeze dryer flaggy temperature is down to 0 ℃ with rapid rate, kept 30 minutes, be down to-45 ℃ with rapid rate again, kept 1.5 hours.
2) the sublimation drying stage: vacuum 10~20Pa in the control freeze drying box, the flaggy temperature is warming up to 0 ℃ with 5 ℃/hour of constant rate of speeds, and keeps 2 hours.
3) the parsing-desiccation stage: vacuum 0~10Pa in the control freeze drying box, the flaggy temperature is warming up to 30 ℃ with 10 ℃/hour of constant rate of speeds, and keeps 3 hours, namely gets s-ropivacaine mesylate powder pin.
The preparation of embodiment 2 Ropivacaine mesylate freeze-dried powder injections
Prescription: s-ropivacaine mesylate 47.7g
Water for injection adds to 1000mL
Make 1000
Preparation: take by weighing s-ropivacaine mesylate 47.7g, add 80% recipe quantity and be chilled to the water for injection of room temperature, stirring makes fully dissolving, sodium hydroxide or phosphoric acid are regulated medicinal liquid PH to 4~7, add 1 ‰ needle-use activated carbon, stirring and adsorbing 10 minutes, rear decarburization is filtered, add water for injection to 1000mL, stir.By 0.22 μ m degerming filter membrane twin-stage aseptic filtration, filtrate sampling detects semi-finished product content, and according to the medicinal liquid of content fill standard quantity in the cillin bottle of cleaning, the false add plug is put into the freeze dryer lyophilization.Freeze drying process is as follows, and lyophilizing finishes, aluminium lid is rolled in the vacuum tamponade outward, visual inspection, packs.
Freeze drying process:
1) the pre-freeze stage: after the s-ropivacaine mesylate semi-finished product are put into freeze dryer, first freeze dryer flaggy temperature is down to 0 ℃ with rapid rate, kept 20 minutes, be down to-40 ℃ with rapid rate again, kept 2 hours.
2) the sublimation drying stage: vacuum 10~15Pa in the control freeze drying box, the flaggy temperature is warming up to 0 ℃ with 10 ℃/hour of constant rate of speeds, and keeps 2 hours.
3) the parsing-desiccation stage: vacuum 0~10Pa in the control freeze drying box, the flaggy temperature is warming up to 30 ℃ with 10 ℃/hour of constant rate of speeds, and keeps 5 hours, namely gets s-ropivacaine mesylate powder pin.
The preparation of embodiment 3 Ropivacaine mesylate freeze-dried powder injections
Prescription: s-ropivacaine mesylate 89.4g
Water for injection adds to 500mL
Make 1000
Preparation: take by weighing s-ropivacaine mesylate 89.4g, add 80% recipe quantity and be chilled to the water for injection of room temperature, stirring makes fully dissolving, sodium hydroxide or phosphoric acid are regulated medicinal liquid PH to 4~7, add 1 ‰ needle-use activated carbon, stirring and adsorbing 10 minutes, rear decarburization is filtered, add water for injection to 500mL, stir.By 0.22 μ m degerming filter membrane twin-stage aseptic filtration, filtrate sampling detects semi-finished product content, and according to the medicinal liquid of content fill standard quantity in the cillin bottle of cleaning, the false add plug is put into the freeze dryer lyophilization.Freeze drying process is as follows, and lyophilizing finishes, aluminium lid is rolled in the vacuum tamponade outward, visual inspection, packs.
Freeze drying process:
1) the pre-freeze stage: after the s-ropivacaine mesylate semi-finished product are put into freeze dryer, first freeze dryer flaggy temperature is down to 0 ℃ with rapid rate, kept 10 minutes, be down to-35 ℃ with rapid rate again, kept 1 hour.
2) the sublimation drying stage: vacuum 10~20Pa in the control freeze drying box, the flaggy temperature is warming up to 0 ℃ with 10 ℃/hour of constant rate of speeds, and keeps 1 hour.
3) the parsing-desiccation stage: vacuum 0~10Pa in the control freeze drying box, the flaggy temperature is warming up to 30 ℃ with 5 ℃/hour of constant rate of speeds, and keeps 2 hours, namely gets s-ropivacaine mesylate powder pin.
The preparation of embodiment 4 Ropivacaine mesylate freeze-dried powder injections
Prescription: s-ropivacaine mesylate 47.7g
Water for injection adds to 500mL
Make 1000
Preparation: take by weighing s-ropivacaine mesylate 47.7g, add 80% recipe quantity and be chilled to the water for injection of room temperature, stirring makes fully dissolving, sodium hydroxide or phosphoric acid are regulated medicinal liquid PH to 4~7, add 0.5 ‰ needle-use activated carbon, stirring and adsorbing 10 minutes, rear decarburization is filtered, add water for injection to 500mL, stir.By 0.22 μ m degerming filter membrane twin-stage aseptic filtration, filtrate sampling detects semi-finished product content, and according to the medicinal liquid of content fill standard quantity in the cillin bottle of cleaning, the false add plug is put into the freeze dryer lyophilization.Freeze drying process is as follows, and lyophilizing finishes, aluminium lid is rolled in the vacuum tamponade outward, visual inspection, packs.
Freeze drying process:
1) the pre-freeze stage: after the s-ropivacaine mesylate semi-finished product are put into freeze dryer, first freeze dryer flaggy temperature is down to 0 ℃ with rapid rate, kept 15 minutes, be down to-40 ℃ with rapid rate again, kept 1 hour.
2) the sublimation drying stage: vacuum 10~20Pa in the control freeze drying box, the flaggy temperature is warming up to 0 ℃ with 8 ℃/hour of constant rate of speeds, and keeps 1 hour.
3) the parsing-desiccation stage: vacuum 0~10Pa in the control freeze drying box, the flaggy temperature is warming up to 30 ℃ with 8 ℃/hour of constant rate of speeds, and keeps 3 hours, namely gets s-ropivacaine mesylate powder pin.
The outward appearance of embodiment 5 Ropivacaine mesylate freeze-dried powder injections of the present invention, solubility, content and related substance are investigated test
Investigate group: the preparation method according to the embodiment of the invention 1 prepares Ropivacaine mesylate freeze-dried powder injection
Adopt the Ropivacaine mesylate freeze-dried powder injection of embodiment 1 preparation among the CN100571685C
Adopt the Ropivacaine mesylate freeze-dried powder injection of embodiment 1 preparation among the CN1626081A
Investigate index: the outward appearance of product, solubility, content and related substance
The investigation method:
Content, related substance detection method are Same Way, all adopt high performance liquid chromatography (according to two appendix VD of Chinese Pharmacopoeia version in 2010) to measure.
Chromatographic condition: be filler with octadecylsilane chemically bonded silica.Be mobile phase with acetonitrile-phosphate buffer (get the sodium dihydrogen phosphate 1.3ml of 1mol/L, 0.05mol/L disodium phosphate soln 32.5ml adds water to 1000ml, is adjusted to pH8.0) (600: 400); Wavelength is 240nm, and theoretical cam curve is calculated by the s-ropivacaine mesylate peak and is not less than 2000.
Algoscopy: get the content under the content uniformity item, mix homogeneously, precision takes by weighing this product an amount of (approximately being equivalent to s-ropivacaine mesylate 50mg), put in the volumetric flask of 50ml, with water dissolution and be diluted to scale, shake up, precision takes by weighing 20ul injection liquid chromatography, the record chromatogram; It is an amount of that other gets the s-ropivacaine mesylate reference substance, accurately weighed, makes the solution that contains s-ropivacaine mesylate 0.24mg among every 1ml with water dissolution and dilution, measures with method.Press external standard method with calculated by peak area, and get final product.
Other index detects all and requires to measure according to Chinese Pharmacopoeia version appendix in 2010.
Investigate the result as follows referring to table 1:
The table 1 product number of rejects and percent defective (with every batch of 1000 bottles of calculating)
Get each 10 of the injectable powder of each group preparation, add 5ml particulate matter inspection water dissolution, check product solubility, redissolve clarity and the visible foreign matters of rear medicinal liquid, the result participates in table 2
The result is investigated in the contrast of table 2 product solubility
Get the semi-finished product medicinal liquid of each assembly system, under room temperature, together place and investigate stability, detect indices behind the 8h, the results are shown in Table 3.
Table 3 semi-finished product medicinal liquid room temperature is placed definitiveness and is investigated result's contrast
Get that lyophilized injectable powder of each group preparation is an amount of to detect related item with putting under 40 ℃, RH75% constant temperature and humidity condition respectively at sampling in 0,3,6,12 month, the results are shown in Table 4.
Table 4 product 1, contrast product 2 and 3 study on the stability results contrast
Claims (2)
1. Ropivacaine mesylate freeze-dried powder injection, it is characterized in that: it is comprised of s-ropivacaine mesylate and pH adjusting agent, and adopts following freeze-drying method preparation:
(1) the segmentation quick-freezing stage: after the s-ropivacaine mesylate solution that fill is good is put into freeze dryer, first freeze dryer flaggy temperature is down to 0 ℃ and keeps 10~30min, be down to again-35 ℃~-45 ℃ and keep 1~2h;
(2) the sublimation drying stage: vacuum is at 10~20Pa in the control freeze drying box, and the flaggy temperature is warming up to 0 ℃ with 2~10 ℃/h of constant rate of speed, and keeps 1~3h.
(3) the parsing-desiccation stage: vacuum is at 0~10Pa in the control freeze drying box, and the flaggy temperature is warming up to 30 ℃ with 5~10 ℃/h of constant rate of speed, and keeps 2~5h;
Described pH adjusting agent is sodium hydroxide or/and phosphoric acid, and regulates described s-ropivacaine mesylate solution to pH 4~7.
2. Ropivacaine mesylate freeze-dried powder injection as claimed in claim 1, it is characterized in that: the heating rate in described sublimation drying stage is 5 ℃/h.
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CN103705473B (en) * | 2013-12-26 | 2016-02-10 | 山东博迈康药物研究有限公司 | A kind of Lansoprazole freeze-dried injection and preparation method thereof |
US11224593B2 (en) | 2015-07-13 | 2022-01-18 | Neon Laboratories Limited | Hyperbaric injection solution of ropivacaine hydrochloride and process for preparation thereof |
EP3331567B1 (en) | 2015-07-24 | 2020-09-23 | Neon Laboratories Ltd. | Stabilized injectable emulsion of propofol and ketamine |
CN105125486A (en) * | 2015-10-15 | 2015-12-09 | 扬子江药业集团南京海陵药业有限公司 | Preparation method for ropivacaine mesylate injection solution |
CN106109423A (en) * | 2016-07-13 | 2016-11-16 | 山西普德药业有限公司 | A kind of injection Vistamycin lyophilized injectable powder and preparation method thereof |
CN112460924A (en) * | 2020-10-16 | 2021-03-09 | 河北常山生化药业股份有限公司 | Freeze-drying process of exenatide precursor |
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CN1660094A (en) * | 2004-12-13 | 2005-08-31 | 黄健鹏 | Ropivacaine hydrochloride in use for injection and preparation technique |
CN100998567A (en) * | 2007-01-05 | 2007-07-18 | 山东鲁抗辰欣药业有限公司 | Ropivacaine, and its pharmaceutical salt freeze-dried powder-injection preparation and art for preparing the same |
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CN1626081A (en) * | 2003-12-10 | 2005-06-15 | 北京博尔达生物技术开发有限公司 | Ropivacaine freeze-dried powder and injection preparation in use for injection and preparation method |
CN1660094A (en) * | 2004-12-13 | 2005-08-31 | 黄健鹏 | Ropivacaine hydrochloride in use for injection and preparation technique |
CN101125126A (en) * | 2006-08-16 | 2008-02-20 | 丛繁滋 | Method for preparing medical freeze-dried powder (injection) preparation |
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