CN102119920A - Edaravone injection and preparation method thereof - Google Patents
Edaravone injection and preparation method thereof Download PDFInfo
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- CN102119920A CN102119920A CN 201010224564 CN201010224564A CN102119920A CN 102119920 A CN102119920 A CN 102119920A CN 201010224564 CN201010224564 CN 201010224564 CN 201010224564 A CN201010224564 A CN 201010224564A CN 102119920 A CN102119920 A CN 102119920A
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- edaravone
- injection
- hydroxide solution
- sodium hydroxide
- water
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- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 229950009041 edaravone Drugs 0.000 title claims abstract description 54
- 238000002347 injection Methods 0.000 title claims abstract description 31
- 239000007924 injection Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000008215 water for injection Substances 0.000 claims abstract description 12
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229960001305 cysteine hydrochloride Drugs 0.000 claims abstract description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 235000010265 sodium sulphite Nutrition 0.000 claims description 10
- 230000001954 sterilising effect Effects 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- 238000004659 sterilization and disinfection Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000003708 ampul Substances 0.000 claims description 5
- 238000005262 decarbonization Methods 0.000 claims description 4
- 239000012982 microporous membrane Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 1
- 229940090044 injection Drugs 0.000 description 23
- 206010008118 cerebral infarction Diseases 0.000 description 9
- 208000026106 cerebrovascular disease Diseases 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 208000006011 Stroke Diseases 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003978 infusion fluid Substances 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 206010008190 Cerebrovascular accident Diseases 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000002490 cerebral effect Effects 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 230000023611 glucuronidation Effects 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- 210000002381 plasma Anatomy 0.000 description 3
- 239000002510 pyrogen Substances 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- -1 3-methyl isophthalic acid-phenyl-2-pyrazoline Chemical compound 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229940123457 Free radical scavenger Drugs 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 206010025482 malaise Diseases 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 230000000324 neuroprotective effect Effects 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229940001482 sodium sulfite Drugs 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001180 sulfating effect Effects 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 108010022579 ATP dependent 26S protease Proteins 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 206010048962 Brain oedema Diseases 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- 235000004692 Eucalyptus globulus Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000004958 brain cell Anatomy 0.000 description 1
- 208000006752 brain edema Diseases 0.000 description 1
- 208000009973 brain hypoxia - ischemia Diseases 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
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- 230000004064 dysfunction Effects 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 229940093181 glucose injection Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008354 sodium chloride injection Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention discloses edaravone injection and a preparation method thereof. The edaravone injection is characterized by comprising 1.5g of edaravone, 0.5g of cysteine hydrochloride, 1.0g of sodium bisulfite and 1,000ml of water for injection. The invention solves the problem that the edaravone injection is not available for clinical application at present.
Description
Technical field
The present invention relates to medicine field, in particular to a kind of Edaravone Injection and preparation method.
Background technology
In China, apoplexy is the second largest cause of death after malignant tumor and main invalid reason, annual sickness rate 120～1,80/,100,000, mortality rate 60～1,20/,100,000.Different with western developed country, China's stroke onset rate is 4～6 times of myocardial infarction, and the ratio of the apoplexy of survival/myocardial infarction prevalence also reaches 2.7 times.Apoplexy comprises cerebral infarction, cerebral hemorrhage, subarachnoid hemorrhage etc., and wherein based on cerebral infarction, accounts for 3/4 of whole sickness rate.After cerebral infarction took place, acute stages treated had decisive role for prognosis.The therapeutic goal of cerebral infarction priorly also is to reduce function of nervous system's infringement except saving life, alleviate invalidly, promotes rehabilitation, so neuroprotective is essential in acute stages treated.Along with scientific research has disclosed the nervous lesion behind the cerebral hypoxia ischemia and poured into excessive generation of the free radical that causes again substantial connection is arranged, free radical scavenger is coming into one's own day by day based on the neuroprotective in all kinds of apoplexy treatments of cerebral infarction.
Edaravone is first cerebral protective agent in the world; it is free radical scavenger; English by name: Edaravone; chemistry is by name: 3-methyl isophthalic acid-phenyl-2-pyrazoline; Edaravone can effectively be removed oxygen-derived free radicals; suppress lipid peroxidation, improve the function of brain cell (vascular endothelial cell, neurocyte).Edaravone acts on cerebral infarction in earlier stage; suppress cerebral edema, dwindle the cerebral infarction district, alleviate the outbreak of neural syndrome, the death of the tardy property neurocyte of inhibition and the appearance and the progress (promptly worsening) of ischemic cerebral vascular obstacle, the 26S Proteasome Structure and Function of protection cerebral tissue.Edaravone can effectively alleviate nervous symptoms and the dysfunction that brain tissue impairment causes behind the cerebral infarction.But can not use at present the injection of Edaravone clinically, and, the preparation method of any Edaravone Injection is not disclosed in the prior art yet.
Summary of the invention
At the problem that does not have spendable Edaravone Injection clinically in the prior art and propose the present invention, for this reason, main purpose of the present invention is to provide a kind of Edaravone Injection and preparation method, to address the above problem.
According to an aspect of the present invention, provide a kind of Edaravone Injection, having comprised: Edaravone 1.5g, cysteine hydrochloride 0.5g, sodium sulfite 1.0g and water for injection 1000ml.。
According to a further aspect in the invention, a kind of preparation method of above-mentioned Edaravone Injection also is provided, comprise: 60% the water for injection of getting total amount of preparation 1000ml, the Edaravone, the cysteine hydrochloride of 0.5g, the sodium sulfite of 1.0g, the needle-use activated carbon 0.02% (W/V) or 0.05% that add 1.5g stir; Filtering decarbonization; Add injection and be used for water, and regulate pH to 3.5-5.0 with sodium hydroxide solution to 1000ml; Filter, fill the nitrogen embedding in ampoule, sterilization.
Preferably, described sodium hydroxide solution is the sodium hydroxide solution of 0.1mol/L.
Preferably, regulate pH to 4.5 with sodium hydroxide solution.
Preferably, described ampoule is 10ml, and the specification of described Edaravone Injection is 10ml:15mg.
Preferably, the temperature of described water for injection is 70 ℃.
Preferably, after sodium hydroxide solution adjusting pH to 3.5-5.0, extremely clear and bright with 0.22 micron filtering with microporous membrane.
By the present invention, solved the problem that does not have spendable Edaravone Injection at present clinically.
Description of drawings
Accompanying drawing described herein is used to provide further understanding of the present invention, constitutes the application's a part, and illustrative examples of the present invention and explanation thereof are used to explain the present invention, do not constitute improper qualification of the present invention.In the accompanying drawings:
Fig. 1 is the Edaravone preparation technology flow chart according to the embodiment of the invention.
The specific embodiment
The Edaravone prescription that provides in the present embodiment is as follows:
Edaravone 1.5g
Cysteine hydrochloride 0.5g
Sodium sulfite 1.0g
Water for injection ad 1000ml
In the present embodiment, preferred Edaravone Injection specification is: 10ml:15mg.
Edaravone is almost insoluble in water, and is molten at acetone or ethyl acetate part omitted, easily molten in chloroform or methanol.And the prescription in the present embodiment through the test, Edaravone: 1.5g, cysteine hydrochloride: 0.5g, sodium sulfite: 1.0g, water for injection adds to 1000ml.Dissolving in order.After sterilizing and deposit more than half a year, achromatism and clarity still.
The pH value test of Edaravone Injection.Table one is the test situation of different pH value.
Table one
According to the injection of using for intravenous drip, general pH should be controlled between the 3.0-8.5, intends being controlled at 3.5-5.0 through test this product pH value, and Edaravone Injection is stable in this scope.The adjusting of pH value can use dilute hydrochloric acid and 0.1mol/L sodium hydroxide solution to regulate.
The charcoal test of Edaravone Injection
In order to reach best adsorption effect and minimum principal agent adsorbance, in the present embodiment the consumption of active carbon is tested.
One, prescription:
The actual inventory of recipe quantity 1. 2.
Edaravone (100%) 1.5g 15.0276g 7.9017g
Cysteine hydrochloride 0.5g 5.0340g 2.5270g
Sodium sulfite 1.0g 10.0099g 5.0602g
Water for injection 1000ml 10000ml 5000ml
Active carbon (0.05%/0.02%) 0.5g 5.017g 1.0588g
Two, experimental procedure:
The hot water for injection (70 ℃) of getting total amount of preparation about 60% adds Edaravone, cysteine hydrochloride, sodium sulfite successively, after being stirred to dissolving fully, add active carbon 0.05% (W/V) and 0.02% (W/V) more respectively, stirred 15 minutes, filtering decarbonization adds water to full dose.Survey its pH value, be adjusted to about 4.5 with the sodium hydroxide solution of 1mol/L.Fill, 115 ℃ the sterilization 30 minutes.
Three, experimental result:
| ? | Sample 1. | Sample 2. |
| PH value before transferring | 4.06 | 4.22 |
| Transfer the back pH value | 4.48 | 4.62 |
| Sterilization back pH value | 4.10 | 4.10 |
| Add the preceding content % of charcoal | 99.8％ | 97.6％ |
| Take off content % behind the charcoal | 86.4％ | 96.9％ |
| Related substance before the sterilization | Up to specification | Up to specification |
| Sterilization back related substance | Up to specification | Up to specification |
| Pyrogen | Up to specification | Up to specification |
Experimental result proves, active carbon with 0.05%, can reach the result of required removal pyrogen, but principal agent absorption is too many, and with 0.02% active carbon, can reach the result of required removal pyrogen, can make drug content descend fewly again, therefore, the active carbon of employing 0.02% adsorbs.
Preparation technology
Fig. 1 is the Edaravone preparation technology flow chart according to the embodiment of the invention, as shown in Figure 1, get the hot water for injection (70 ℃) of total amount of preparation about 60%, add Edaravone, cysteine hydrochloride, sodium sulfite, the needle-use activated carbon 0.02% (W/V) of recipe quantity successively, stir 15min.Filtering decarbonization.Add water to full dose.Regulate pH to 4.5 with 10% sodium hydroxide solution, measure semi-finished product content and be controlled at 100%.Filter, extremely clear and bright with 0.22 micron filtering with microporous membrane.Fill the nitrogen embedding in the 10ml ampoule.115 ℃ of 30min sterilizations promptly.
The stability test of Edaravone Injection and common infusion fluid compatibility
During clinical use, need Edaravone Injection is added the common infusion fluid iv drip, provide reference frame, behind Edaravone Injection and three kinds of common infusion fluid compatibilities, carry out the study on the stability in 6 hours for giving clinical use.
During clinical use, according in clinical operating position, experimenter's consumption is 0.5mg/kg, and the eucalyptus globulus average weight is by 60kg, and general consumption is 30mg.For this reason, carry out compatibility as follows.
The stability test of Edaravone Injection and common infusion fluid compatibility
Test temperature: 18～25 ℃
The situation of change of drug content behind Edaravone Injection and the common infusion fluid compatibility
Conclusion: behind Edaravone Injection and 5% glucose injection, Dextrose and Sodium Chloride Inj., 0.9% sodium chloride injection, the compatibility, its color and luster, clarity, drug content have no significant change in 6 hours, but the clinical compatibility of prompting uses.
The supplementary material source and the quality standard thereof of present embodiment: the cysteine hydrochloride quality standard meets Chinese Pharmacopoeia 2005 editions, and the sodium sulfite quality standard meets Chinese Pharmacopoeia 2005 editions.
Pharmacokinetic parameter also is provided in the present embodiment: with 2mg/kg single dose intravenous injection Edaravone, the blood plasma radioactive concentration of male, female rats, male beasle dog is eliminated half-life (t
1/2 β) be respectively: 5.07,5.31,12.1 hours.The t of prototype medicine
1/2 βBe respectively: 1.26,5.09,0.70 hours.The AUC of blood plasma mesarcs medicine
0-∞For: male rat 0.79 μ g.hr/ml; Female rats 0.82 μ g.hr/ml; Male beasle dog 0.66 μ g.hr/ml.Be distributed to whole body rapidly behind the injection Edaravone 2mg/kg, high concentration in kidney, occurs, reach valid density 0.59 μ g/g in the brain, and be distributed to the gamogenesis organ.It has the ability that distributes to fetus, milk.After the administration 24 hours, the concentration in tissue reaches low value.Repetitively administered has the tendency of accumulating.The plasma protein binding rate of Edaravone is to rat 86%, Canis familiaris L. 52%.The accretion rate of Edaravone is fast, is sulfating product and glucuronidation product for the main metabolites of rat and Canis familiaris L..The Edaravone principal agent after administration in 24 hours through feces, urine excretion, almost exhale to drain, can pass through bile excretion, but less.
Intravenous injection 0.5mg/kg/30 branch between healthy normal person 2 times 2 days on the 1st, blood plasma mesarcs medicine Cmax is after the administration: 888 ± 171ng/ml.t
1/2 α, t
1/2 βBe respectively: 0.27 ± 0.11hr, 2.27 ± 0.80hr; AUC
0-∞, CL, Vdss is respectively 742 ± 95nghr/ml, 683 ± 98ml/kg/hr, 0.93 ± 0.20L/kg.The Edaravone major metabolite is hydrosulphate and glucuronidation product, mainly forms at liver, kidney respectively.Repeated intravenous injection Edaravone 1mg/kg/40min/day between healthy normal person 2 times 7 days on the 1st, drug main will be through urine excretion (66-91%, according to the dosage conversion), sulfating product in the urine (5.8-6.6%), glucuronidation product (70.1-78.0%).
The adult uses Edaravone in cerebral infarction showed effect back 24 hours, each 30mg instils with 0.9% normal saline dilution posterior vein before the administration, or directly instils with the 100ml transfusion vein, continues 30 minutes at every turn, and every day, each once continued medication 14 days sooner or later.
The above is the preferred embodiments of the present invention only, is not limited to the present invention, and for a person skilled in the art, the present invention can have various changes and variation.Within the spirit and principles in the present invention all, any modification of being done, be equal to replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (7)
1. an Edaravone Injection is characterized in that, comprising: Edaravone 1.5g, cysteine hydrochloride 0.5g, sodium sulfite 1.0g and water for injection 1000ml.
2. the preparation method of Edaravone Injection according to claim 1 is characterized in that, comprising:
Get 60% the water for injection of total amount of preparation 1000ml, add Edaravone, the cysteine hydrochloride of 0.5g, the sodium sulfite of 1.0g, the needle-use activated carbon 0.02% (W/V) or 0.05% of 1.5g, stir; Filtering decarbonization; Add injection and be used for water, and regulate pH to 3.5-5.0 with sodium hydroxide solution to 1000ml; Filter, fill the nitrogen embedding in ampoule, sterilization.
3. method according to claim 2 is characterized in that, described sodium hydroxide solution is the sodium hydroxide solution of 0.1mol/L.
4. method according to claim 2 is characterized in that, regulates pH to 4.5 with sodium hydroxide solution.
5. according to each described method in the claim 2 to 4, it is characterized in that described ampoule is 10ml, the specification of described Edaravone Injection is 10ml:15mg.
6. according to each described method in the claim 2 to 4, it is characterized in that the temperature of described water for injection is 70 ℃.
7. according to each described method in the claim 2 to 4, it is characterized in that, after sodium hydroxide solution adjusting pH to 3.5-5.0, extremely clear and bright with 0.22 micron filtering with microporous membrane.
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| CN102349893A (en) * | 2011-08-19 | 2012-02-15 | 福建天泉药业股份有限公司 | Edaravone pharmaceutical composition |
| CN103245621A (en) * | 2012-02-10 | 2013-08-14 | 陕西健民制药有限公司 | Quality test method of edaravone injection |
| CN103751104A (en) * | 2014-01-23 | 2014-04-30 | 扬子江药业集团南京海陵药业有限公司 | Edaravone injection and preparation method thereof |
| CN105012230A (en) * | 2014-04-30 | 2015-11-04 | 长春海悦药业有限公司 | A kind of pharmaceutical composition of Edaravone |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102349893A (en) * | 2011-08-19 | 2012-02-15 | 福建天泉药业股份有限公司 | Edaravone pharmaceutical composition |
| CN103245621A (en) * | 2012-02-10 | 2013-08-14 | 陕西健民制药有限公司 | Quality test method of edaravone injection |
| CN103245621B (en) * | 2012-02-10 | 2014-12-17 | 陕西健民制药有限公司 | Quality test method of edaravone injection |
| CN103751104A (en) * | 2014-01-23 | 2014-04-30 | 扬子江药业集团南京海陵药业有限公司 | Edaravone injection and preparation method thereof |
| CN105012230A (en) * | 2014-04-30 | 2015-11-04 | 长春海悦药业有限公司 | A kind of pharmaceutical composition of Edaravone |
| CN105012230B (en) * | 2014-04-30 | 2018-01-16 | 长春海悦药业股份有限公司 | Edaravone pharmaceutical composition |
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Application publication date: 20110713 |