CN106692079A - Long-acting parecoxib sodium freeze-dried powder injection preparation - Google Patents
Long-acting parecoxib sodium freeze-dried powder injection preparation Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
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- A—HUMAN NECESSITIES
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A—HUMAN NECESSITIES
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
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Abstract
The invention relates to a long-acting parecoxib sodium freeze-dried powder injection preparation. The long-acting parecoxib sodium freeze-dried powder injection preparation is prepared from, by weight, 5-15 parts of parecoxib sodium, 10-40 parts of dimyristoyl phosphatidyl choline, 10-30 parts of polyethylene glycol-phosphatidyl ethanolamine, 5-15 parts of sodium deoxycholate, 0.15-0.50 part of antioxidant, 0.5-1 part of poloxamer and 5-25 parts of freeze-dried supporting agent. The preparation can be used for intravenous administration, the problem of quality stability is effectively solved, the pharmacodynamic effect time and bioavailability of the preparation are improved, and meanwhile toxic and side effects are also relatively decreased.
Description
Technical field
The invention belongs to chemical pharmacy field, and in particular to a kind of injection SC 69124 composition of sodium and its preparation side
Method, more particularly, to long-acting freeze-dried powder of a kind of Parecoxib Sodium and preparation method thereof.
Background technology
Parecoxib Sodium is a kind of COX-2 (COX-2) specific inhibitor, belongs to the former times cloth in anti-arthritic
Class antalgesic, can be used for the short of postoperative pain, can be clinically used for the treatment of moderate or severe postoperative acute pain.
English name：Parecoxib Sodium, chemical name：N- [[4- (5- methyl -3- phenyl -4- isoxazolyls) phenyl] sulfonyl]
Propionamide sodium salt.SC 69124 is the pro-drug of Valdecoxib, SC 69124 in intravenous orIntramuscular injectionBy liver enzymeHydrolysis, it is fast
Speed is converted into the material of pharmacological activity -- Valdecoxib.Valdecoxib is selective COX-2 in clinical dosage scope
(COX-2) inhibitor, Cycloxygenase participates in prostaglandin building-up process.There are two kinds of isomers of COX-1 and COX-2.Grind
Study carefully display COX-2 as Cycloxygenase isomers by preceding-inflammatory stimulus inductive formation so that speculate COX-2 with pain, inflammation
Main effect is played in the building-up process of the prostaglandin-like mediator relevant with heating.
Liposome means the vesicle being made up of for membrane material and additives phosphatide, with bilayer structure.Due to it
Structure is similar to biomembrane, can encapsulate water-soluble and fat-soluble medicine, with medicine stability is improved, reduces drug dose, reduces
Toxicity, mitigates the advantages of allergy and immune response, the distribution in vivo of change medicine, and energy targeting release the drug and obtains wide
General attention and further investigation.
The content of the invention
Liposome preparatory techniques are applied to SC 69124 sodium freeze-dried powder injection by the present invention, drastically increase SC 69124
The bin stability and drug release time of preparation of sodium, and preparation method is easy to operate, lyophilized technique is simple, quality controllable, to people
Body is safe and reliable, is suitable to clinical practice.
The present invention provides a kind of long-acting freeze-dried powder of Parecoxib Sodium, said preparation by following weight portion composition system
Into：Parecoxib Sodium 5-15 parts, dimyristoyl phosphatidyl choline 10-40 parts, mPEG2000-DSPE 10-30 parts,
NaTDC 5-15 parts, antioxidant 0.15-0.50 parts, poloxamer 0.5-1 parts, frozen-dried supporting agent 5-25 parts.
In one of the invention preferably implementation method, said preparation is made up of the composition of following weight portion：Parecoxib Sodium 5
Part, 10 parts of dimyristoyl phosphatidyl choline, 10 parts of mPEG2000-DSPE, 5 parts of NaTDC, antioxidant
0.15 part, 0.5 part of poloxamer, 8 parts of frozen-dried supporting agent.
In one of the invention preferably implementation method, said preparation is made up of the composition of following weight portion：Parecoxib Sodium
10 parts, 20 parts of dimyristoyl phosphatidyl choline, 20 parts of mPEG2000-DSPE, 10 parts of NaTDC, antioxidant
0.3 part, 0.8 part of poloxamer, 16 parts of frozen-dried supporting agent.
In one of the invention preferably implementation method, said preparation is made up of the composition of following weight portion：Parecoxib Sodium
15 parts, 40 parts of dimyristoyl phosphatidyl choline, 30 parts of mPEG2000-DSPE, 15 parts of NaTDC, antioxidant
0.45 part, 1 part of poloxamer, 24 parts of frozen-dried supporting agent.
In a specific embodiment of the invention, wherein described antioxidant is sodium thiosulfate and vitamin E
Combination, the proportioning of the two is 2：1.
In a specific embodiment of the invention, wherein the frozen-dried supporting agent is selected from mannitol, lactose, sweet ammonia
Acid, sucrose, sorbierite, sodium chloride, one or more of glycine.
In one preferred embodiment of the invention, described frozen-dried supporting agent is sodium chloride, mannitol and glycine
Combination, the mass ratio of three is 1:2:1.
In one preferred embodiment of the invention, said preparation is made up of the composition of following weight portion：Parecoxib Sodium 5
Part, 10 parts of dimyristoyl phosphatidyl choline, 10 parts of mPEG2000-DSPE, 5 parts of NaTDC, antioxidant
0.15 part, 0.5 part of poloxamer, 8 parts of frozen-dried supporting agent；Antioxidant is the combination of sodium thiosulfate and vitamin E, and the two is matched somebody with somebody
Than being 2：1；Frozen-dried supporting agent is the combination of sodium chloride, mannitol and glycine, and the mass ratio of three is 1:2:1.
In one of the invention preferably implementation method, said preparation is made up of the composition of following weight portion：Parecoxib Sodium
10 parts, 20 parts of dimyristoyl phosphatidyl choline, 20 parts of mPEG2000-DSPE, 10 parts of NaTDC, antioxidant
0.3 part, 0.8 part of poloxamer, 16 parts of frozen-dried supporting agent；Antioxidant is the combination of sodium thiosulfate and vitamin E, and the two is matched somebody with somebody
Than being 2：1；Frozen-dried supporting agent is the combination of sodium chloride, mannitol and glycine, and the mass ratio of three is 1:2:1.
In one of the invention preferably implementation method, said preparation is made up of the composition of following weight portion：Parecoxib Sodium
15 parts, 40 parts of dimyristoyl phosphatidyl choline, 30 parts of mPEG2000-DSPE, 15 parts of NaTDC, antioxidant
0.45 part, 1 part of poloxamer, 24 parts of frozen-dried supporting agent；Antioxidant is the combination of sodium thiosulfate and vitamin E, and the two is matched somebody with somebody
Than being 2：1；Frozen-dried supporting agent is the combination of sodium chloride, mannitol and glycine, and the mass ratio of three is 1:2:1.
Another aspect of the present invention is related to the preparation method of the described long-acting freeze-dried powder of Parecoxib Sodium, preparation process
Including：
(1) by dimyristoyl phosphatidyl choline, mPEG2000-DSPE, NaTDC, antioxidant, pool
Luo Shamu is dissolved in organic solvent, is well mixed, and the solution decompression that then will be formed removes organic solvent, prepares lipid film；
(2) configuration pH is the buffer salt solution of 8-8.5, and cushioning liquid is added in the lipid film prepared in step (1),
After after the complete aquation of lipid film, blank liposome is prepared with homogenate equipment, it is standby；
(3) Parecoxib Sodium is weighed, is dissolved in step (2) in obtained blank liposome, add frozen-dried supporting agent, mixed
Close uniform, place 10-30 minutes, then degerming through filtering with microporous membrane, filling in cillin bottle, freeze-drying is obtained final product.
In a specific embodiment of the invention, wherein described antioxidant is sodium thiosulfate and vitamin E
Combination, the proportioning of the two is 2：1.
In a specific embodiment of the invention, wherein the frozen-dried supporting agent is selected from mannitol, lactose, sweet ammonia
Acid, sucrose, sorbierite, sodium chloride, one or more of glycine.
In one preferred embodiment of the invention, described frozen-dried supporting agent is sodium chloride, mannitol and glycine
Combination, the mass ratio of three is 1:2:1.
In a specific embodiment of the invention, organic solvent is selected from ethanol, acetone, isopropanol, the tert-butyl alcohol
One or more of combination.
In a specific embodiment of the invention, the cushioning liquid is selected from phosphate buffer, citrate and delays
One or more in fliud flushing, carbonate buffer solution, borate buffer solution, acetate buffer.
Third aspect present invention is related to state application of the note long-acting freeze-dried powder of Parecoxib Sodium in antalgesic is prepared.
Weight portion can be converted into arbitrary unit of weight in the present invention.
The long-acting freeze-dried powder of Parecoxib Sodium of the invention is expanded on further with reference to specific embodiment.
Specific embodiment
Embodiment 1：
(1) recipe quantity dimyristoyl phosphatidyl choline, mPEG2000-DSPE, NaTDC, sulphur are weighed
Sodium thiosulfate, vitamin E, poloxamer are dissolved in ethanol, are well mixed, and liposome solutions are formed, by liposome solutions in thin
On film evaporator, decompression abjection ethanol is obtained lipid film.
(2) configuration pH is 8.1 phosphate buffer, and cushioning liquid is added in the lipid film prepared in step (1),
After after the complete aquation of lipid film, blank liposome is prepared with homogenate equipment, it is standby；
(3) Parecoxib Sodium is weighed, is dissolved in step (2) in obtained blank liposome, add sodium chloride, mannitol
And glycine, it is well mixed, place 10-30 minutes, then degerming through filtering with microporous membrane, filling in cillin bottle, freezing is dry
It is dry, obtain final product.
Embodiment 2：
(1) recipe quantity dimyristoyl phosphatidyl choline, mPEG2000-DSPE, NaTDC, sulphur are weighed
Sodium thiosulfate, vitamin E, poloxamer are dissolved in ethanol, are well mixed, and liposome solutions are formed, by liposome solutions in thin
On film evaporator, decompression abjection ethanol is obtained lipid film.
(2) configuration pH is 8.3 phosphate buffer, and cushioning liquid is added in the lipid film prepared in step (1),
After after the complete aquation of lipid film, blank liposome is prepared with homogenate equipment, it is standby；
(3) Parecoxib Sodium is weighed, is dissolved in step (2) in obtained blank liposome, add sodium chloride, mannitol
And glycine, it is well mixed, place 10-30 minutes, then degerming through filtering with microporous membrane, filling in cillin bottle, freezing is dry
It is dry, obtain final product.
Embodiment 3：
(1) recipe quantity dimyristoyl phosphatidyl choline, mPEG2000-DSPE, NaTDC, sulphur are weighed
Sodium thiosulfate, vitamin E, poloxamer are dissolved in ethanol, are well mixed, and liposome solutions are formed, by liposome solutions in thin
On film evaporator, decompression abjection ethanol is obtained lipid film.
(2) configuration pH is 8.2 phosphate buffer, and cushioning liquid is added in the lipid film prepared in step (1),
After after the complete aquation of lipid film, blank liposome is prepared with homogenate equipment, it is standby；
(3) Parecoxib Sodium is weighed, is dissolved in step (2) in obtained blank liposome, add sodium chloride, mannitol
And glycine, it is well mixed, place 10-30 minutes, then degerming through filtering with microporous membrane, filling in cillin bottle, freezing is dry
It is dry, obtain final product.
Comparative example 1：(soybean lecithin replacement dimyristoyl phosphatidyl choline)
Other are with embodiment 1.
Comparative example 2：(cholesterol replacement NaTDC)
Other are with embodiment 1.
Comparative example 3：(omission sodium thiosulfate)
Other are with embodiment 1.
Comparative example 4：(omission vitamin E)
Other are with embodiment 1.
Comparative example 5：(omission poloxamer)
Other are with embodiment 1.
Comparative example 6：(omission sodium chloride)
Other are with embodiment 1.
Comparative example 7：(omission mannitol)
Other are with embodiment 1.
Comparative example 8：(omission glycine)
Other are with embodiment 1.
Comparative example 9：(omission mPEG2000-DSPE)
Other are with embodiment 1.
The stability experiment of embodiment 4
Lyophilized formulations prepared by embodiment of the present invention 1-3 and comparative example 1-8, under 60 ± 2 DEG C, RH75% acceleration environments
Place 30 days, determine Parecoxib Sodium changes of contents, carry out study on the stability, it is as a result as follows：
The stability of the SC 69124 sodium freeze-dried powder injection of table 1
| Group | SC 69124 sodium content (%) |
| Embodiment 1 | 99.95% |
| Embodiment 2 | 99.98% |
| Embodiment 3 | 99.92% |
| Comparative example 1 | 95.34% |
| Comparative example 2 | 95.67% |
| Comparative example 3 | 95.72% |
| Comparative example 4 | 96.31% |
| Comparative example 5 | 97.25% |
| Comparative example 6 | 96.43% |
| Comparative example 7 | 97.63% |
| Comparative example 8 | 96.84% |
The result of table 1 shows that the long-acting freeze-dried powder of the Parecoxib Sodium that embodiment of the present invention 1-3 is prepared has
Stability higher, 30 days contents of Parecoxib Sodium of placement will not change substantially under 60 ± 2 DEG C, RH75% acceleration environments
Become, and the content of Parecoxib Sodium can be significantly reduced in comparative example 1-8.
The safety testing of embodiment 5
(1) sensitivity test：Long-acting freeze-dried powder 5mg prepared by embodiment 1-3 adds 0.9% sodium chloride solution
2mL, dissolving shakes up, and the auricular vein to cavy carries out the test of sensitivity response, after exciting administration twice, does not observe and takes office
What sensitization phenomenon, shows that freeze-dried powder of the invention does not have sensitization to animal subject thing.
(2) vascular stimulation tests：Long-acting freeze-dried powder 5mg prepared by embodiment 1-3 adds 0.9% sodium chloride
Solution 2mL, is injected for rabbit auricular vein, and its Histopathology result shows：Ear vein tube wall is intact, has no bad
Extremely, blood engorgement in tube chamber, has no thrombus, and the intact nothing of vascular endothelial cell comes off, and has no any notable blood vessel irritation reaction.
The pharmacokinetic studies of embodiment 6
BABL/c mouse 20 are taken, 6-8 weeks, male and female half and half were randomly divided into control group and experimental group, every group 10, control
Group and experimental group give the Parecoxib Sodium of equivalent.
Control group：Parecoxib Sodium freeze-dried powder prepared by injection comparative example 9, every mouse dose 0.2ml, tail is quiet
Arteries and veins is administered once.In taking blank blood before administration, 5 minutes after administration, 15 minutes, 30 minutes, 60 minutes, 120 minutes eyeball veins
Blood is taken, centrifuging and taking blood plasma after anticoagulant heparin is added, concentration of the Parecoxib Sodium in different time points in HPLC measure blood plasma；
Experimental group：The long-acting freeze-dried powder of Parecoxib Sodium prepared by embodiment 1, every mouse dose 0.2ml, tail is quiet
Arteries and veins is administered once.In taking blank blood before administration, 5 minutes after administration, 15 minutes, 30 minutes, 60 minutes, 120 minutes eyeballs take blood,
Centrifuging and taking blood plasma after anticoagulant heparin is added, concentration of the Parecoxib Sodium in different time points in HPLC measure blood plasma.
The Parecoxib Sodium of table 2 different time points determination of plasma concentration result upon administration
| Time (minute) | Control group blood concentration (mg/L) | Experimental group blood concentration (mg/L) |
| 5 | 7.56 | 6.93 |
| 15 | 4.13 | 4.93 |
| 30 | 2.34 | 3.74 |
| 60 | 0.13 | 1.42 |
| 120 | 0.002 | 0.52 |
Claims (8)
1. the long-acting freeze-dried powder of a kind of Parecoxib Sodium, it is characterised in that said preparation is made up of the composition of following weight portion：
Parecoxib Sodium 5-15 parts, dimyristoyl phosphatidyl choline 10-40 parts, mPEG2000-DSPE 10-30 parts, take off
5-15 parts, antioxidant 0.15-0.50 parts, poloxamer 0.5-1 parts, frozen-dried supporting agent 5-25 parts of oxycholic acid sodium.
2. the long-acting freeze-dried powder of Parecoxib Sodium according to claim 1, wherein described antioxidant is thio sulphur
The combination of sour sodium and vitamin E, the proportioning of the two is 2：1.
3. the long-acting freeze-dried powder of Parecoxib Sodium according to claim 1, wherein the frozen-dried supporting agent be selected from it is sweet
Dew alcohol, lactose, glycine, sucrose, sorbierite, sodium chloride, one or more of glycine.
4. the long-acting freeze-dried powder of Parecoxib Sodium according to claim 3, it is characterised in that described lyophilized support
Agent is the combination of sodium chloride, mannitol and glycine, and the mass ratio of three is 1:2:1.
5. the preparation method of the long-acting freeze-dried powder of Parecoxib Sodium described in any one of claim 1-4, preparation process bag
Include：
(1) by dimyristoyl phosphatidyl choline, mPEG2000-DSPE, NaTDC, antioxidant, Bo Luosha
Nurse is dissolved in organic solvent, is well mixed, and the solution decompression that then will be formed removes organic solvent, prepares lipid film；
(2) configuration pH is the buffer salt solution of 8-8.5, and cushioning liquid is added in the lipid film prepared in step (1), treats fat
After the complete aquation of plasma membrane, blank liposome is prepared with homogenate equipment, it is standby；
(3) Parecoxib Sodium is weighed, is dissolved in step (2) in obtained blank liposome, add frozen-dried supporting agent, mixing is equal
It is even, place 10-30 minutes, then degerming through filtering with microporous membrane, filling in cillin bottle, freeze-drying is obtained final product.
6. the preparation method of the long-acting freeze-dried powder of Parecoxib Sodium according to claim 5, it is characterised in that organic
Solvent is selected from the combination of one or more in ethanol, acetone, isopropanol, the tert-butyl alcohol.
7. the preparation method of the long-acting freeze-dried powder of Parecoxib Sodium according to claim 5, the cushioning liquid choosing
One kind from phosphate buffer, citrate buffer, carbonate buffer solution, borate buffer solution, acetate buffer
Or it is several.
8. application of the long-acting freeze-dried powder of Parecoxib Sodium in antalgesic is prepared is noted as described in claim 1-4 is any.
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| CN201611218713.0A CN106692079A (en) | 2016-12-26 | 2016-12-26 | Long-acting parecoxib sodium freeze-dried powder injection preparation |
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| CN201611218713.0A CN106692079A (en) | 2016-12-26 | 2016-12-26 | Long-acting parecoxib sodium freeze-dried powder injection preparation |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108828127A (en) * | 2018-06-21 | 2018-11-16 | 上药东英（江苏）药业有限公司 | Liquid-phase chromatography method in relation to substance in a kind of detection Parecoxib Sodium and synthetic intermediate |
| CN108969494A (en) * | 2018-09-25 | 2018-12-11 | 珠海赛隆药业股份有限公司 | A kind of Parecoxib Sodium durative action preparation and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2478500A1 (en) * | 2002-03-15 | 2003-09-25 | Pharmacia Corporation | Crystalline parecoxib sodium |
| CN102512383A (en) * | 2011-12-25 | 2012-06-27 | 天津市嵩锐医药科技有限公司 | Parecoxib sodium pharmaceutical composition for injection |
-
2016
- 2016-12-26 CN CN201611218713.0A patent/CN106692079A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2478500A1 (en) * | 2002-03-15 | 2003-09-25 | Pharmacia Corporation | Crystalline parecoxib sodium |
| CN102512383A (en) * | 2011-12-25 | 2012-06-27 | 天津市嵩锐医药科技有限公司 | Parecoxib sodium pharmaceutical composition for injection |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108828127A (en) * | 2018-06-21 | 2018-11-16 | 上药东英（江苏）药业有限公司 | Liquid-phase chromatography method in relation to substance in a kind of detection Parecoxib Sodium and synthetic intermediate |
| CN108969494A (en) * | 2018-09-25 | 2018-12-11 | 珠海赛隆药业股份有限公司 | A kind of Parecoxib Sodium durative action preparation and preparation method thereof |
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Application publication date: 20170524 |
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| RJ01 | Rejection of invention patent application after publication |