CN101695493B - composition of cefmetazole acid and sodium citrate - Google Patents
composition of cefmetazole acid and sodium citrate Download PDFInfo
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- CN101695493B CN101695493B CN2009102335988A CN200910233598A CN101695493B CN 101695493 B CN101695493 B CN 101695493B CN 2009102335988 A CN2009102335988 A CN 2009102335988A CN 200910233598 A CN200910233598 A CN 200910233598A CN 101695493 B CN101695493 B CN 101695493B
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- sodium citrate
- cefmetazole acid
- cefmetazole
- acid
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- SNBUBQHDYVFSQF-HIFRSBDPSA-N cefmetazole Chemical group S([C@@H]1[C@@](C(N1C=1C(O)=O)=O)(NC(=O)CSCC#N)OC)CC=1CSC1=NN=NN1C SNBUBQHDYVFSQF-HIFRSBDPSA-N 0.000 title claims abstract description 61
- 229960003585 cefmetazole Drugs 0.000 title claims abstract description 59
- 239000002253 acid Substances 0.000 title claims abstract description 58
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 title claims abstract description 39
- 239000001509 sodium citrate Substances 0.000 title claims abstract description 38
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 21
- 239000000843 powder Substances 0.000 claims abstract description 16
- 239000003814 drug Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 3
- 239000012535 impurity Substances 0.000 abstract description 11
- 230000007774 longterm Effects 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 4
- 239000006184 cosolvent Substances 0.000 abstract description 3
- 239000011812 mixed powder Substances 0.000 abstract description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 2
- 239000011734 sodium Substances 0.000 abstract description 2
- 229910052708 sodium Inorganic materials 0.000 abstract description 2
- 238000004500 asepsis Methods 0.000 abstract 2
- 230000007547 defect Effects 0.000 abstract 1
- 231100000614 poison Toxicity 0.000 abstract 1
- 230000007096 poisonous effect Effects 0.000 abstract 1
- 238000005352 clarification Methods 0.000 description 20
- BITQGIOJQWZUPL-PBCQUBLHSA-M cefmetazole sodium Chemical compound [Na+].S([C@@H]1[C@@](C(N1C=1C([O-])=O)=O)(NC(=O)CSCC#N)OC)CC=1CSC1=NN=NN1C BITQGIOJQWZUPL-PBCQUBLHSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 1
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960002676 cefmetazole sodium Drugs 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- DSIJXEVOJMBKAM-UHFFFAOYSA-M sodium;2-methyloct-2-enoate Chemical compound [Na+].CCCCCC=C(C)C([O-])=O DSIJXEVOJMBKAM-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention discloses a composition with antibacterial effect, comprising cefmetazole acid and sodium citrate. In the invention, asepsis powder of the cefmetazole acid and the sodium citrate are combined; the sodium citrate is used as a cosolvent for the cefmetazole acid and can effectively increase the water-solubility of the cefmetazole acid and solve the defect of inconvenient clinical usage of the cefmetazole; the cefmetazole acid can well develop the antibacterial effect thereof; the composition obtained from the proportioned cefmetazole acid and the sodium citrateof has better stability; the prepared asepsis mixed powder of the cefmetazole acid and the sodium citrate can be stored in long term; the antibacterial active constitute of the cefmetazole acid has stable structure and stable and safe curative effect without generating impurities with poisonous side effect.
Description
Technical field
The present invention relates to a kind of compositions, be specifically related to the compositions of a kind of antibiotics cefmetazole acid and sodium citrate.
Background technology
Cefmetazon (Sankyo) (Cefmetazole Sodium) is the novel cephalosporin class antibiotic that three common companies develop alone the earliest, three altogether companies obtain permission in August, 1978 with the trade name of Cefmetazon, start selling injection from February, 1980, the Cefmetazon (Sankyo) chemistry is by name: sulfur (6R-cis)-7-[[[(cyanogen methyl)] acetyl] amido]-7-methoxy-3-[[(1-methyl isophthalic acid H-5-tetrazole base) sulfur]-methyl]-8-oxo-5-thia-1-azabicyclic [4.2.0] oct-2-ene-2-carboxylic acid sodium salt.Structural formula is shown below:
Its active component is a cefmetazole acid, but because its polarity is less, poorly water-soluble, use for convenient clinically, make dosage form with its sodium salt, cefmetazole acid commonly used adds sodium carbonate or sodium bicarbonate becomes sodium salt, regulate about pH=6, adopt freeze-dry process to prepare freeze-dried powder then.But cefmetazole acid sodium itself does not have crystal formation, so character less stable, the cefmetazole acid structure easily changes in freeze-drying process and in the follow-up storage, be transformed into other material, in quality standard control, other its related substances is higher, simultaneously since impurity content than higher, side reaction and anaphylaxis easily produce the secondary injury than higher to patient in clinical use.
Summary of the invention
Goal of the invention: technical problem to be solved by this invention is to overcome the deficiencies in the prior art, and a kind of product quality height and steady quality are provided, the compositions of the novel cefmetazole acid of large-scale industrial production preferably.
Technical scheme: in order to realize above purpose, the compositions with antibacterial action of the present invention, it is made up of cefmetazole acid and sodium citrate.
Compositions with antibacterial action of the present invention, the weight ratio of cefmetazole acid and sodium citrate is 1: 0.4 to 1: 2 in the compositions.
As preferred version, the weight ratio of cefmetazole acid and sodium citrate is 1: 0.4 to 1: 0.8 in the compositions.
As preferred scheme, the weight ratio of cefmetazole acid and sodium citrate is 1: 0.65 in the compositions.
Compositions with antibacterial action of the present invention, have wherein that cefmetazole acid is antimicrobial active component in the compositions of antibacterial action, it and sodium citrate are used in combination, sodium citrate is as cosolvent, can effectively solve the difficult problem of cefmetazole acid poorly water-soluble, and the bactericidal composition formed of cefmetazole acid and sodium citrate injection or the injectable powder steady quality made, can long term storage, be difficult for being transformed into other materials through the experimentation cefmetazole acid, impurity content is few, can make things convenient for to formulate quality standard accurately, and because steady quality, side reaction and irritated rate are lower in the use, quality safety.
Compositions with antibacterial action of the present invention, can be through conventional method, get cefmetazole acid and sodium citrate in proportion and prepare the antibacterials of injection dosage form, perhaps get the medicine that cefmetazole acid and sodium citrate prepare the injectable powder dosage form in proportion.
When the compositions that the present invention is made up of cefmetazole acid and sodium citrate is made the injectable powder dosage form, its technical scheme is: in aseptic batch plant, take by weighing cefmetazole acid and sodium citrate sterile bulk drug according to the prescription ratio, pour in the efficient three-dimensional motion mixer, setting the three-dimensional rotating speed that mixes the powder machine is 5 to 8 rev/mins, begins to mix the powder operation according to mixed powder packaging standard rule of operation, mix 60min～90min, behind the mix homogeneously, discharging divides packing promptly.
Beneficial effect: the compositions with antibacterial action provided by the invention is compared with prior art and is had the following advantages:
1, the compositions with antibacterial action provided by the invention, screen through lot of experiments, with cefmetazole acid and sodium citrate combination, the two is coordinated mutually, mutually promote, sodium citrate can effectively increase the water solublity of cefmetazole acid as the cosolvent of cefmetazole acid, shortcoming, the especially cefmetazole acid and the sodium citrate that solve the clinical use inconvenience of sodium citrate have excellent water solublity when weight ratio is combination in 1: 0.65.
2, the compositions with antibacterial action provided by the invention, the two scientific matching of cefmetazole acid and sodium citrate, cefmetazole acid can its antibacterial action of fine performance, the compositions that obtains after the two proportioning has good stability, the injectable powder that makes can long term storage, antibacterial activity composition cefmetazole acid Stability Analysis of Structures, can not produce the impurity of toxic and side effects, stable curative effect safety.
3, the compositions with antibacterial action provided by the invention can make things convenient for and make injection or injectable powder according to a conventional method, the convenient storage and use.
The specific embodiment
Below in conjunction with specific embodiment, further illustrate the present invention, should understand these embodiment only is used to the present invention is described and is not used in and limit the scope of the invention, after having read the present invention, those skilled in the art all fall within the application's claims institute restricted portion to the modification of the various equivalent form of values of the present invention.
Embodiment 1
By cefmetazole acid and sodium citrate preparation of compositions injectable powder: in aseptic batch plant, mix proportion scheme according to table 1 takes by weighing cefmetazole acid and the common 50kg of sodium citrate sterile bulk drug, pour in the efficient three-dimensional motion mixer, setting the three-dimensional rotating speed that mixes the powder machine is 5 rev/mins, begin to mix the powder operation according to mixed powder packaging standard rule of operation, mix 60min～90min to mix homogeneously, discharging, divide packing, obtain injectable powder.
Get the pH value of each sample of sample detection of each proportioning, be prepared into conventional instillation of human body with water for injection then and use the liquid medicine of concentration, detect the water solublity of each sample solution, concrete experimental result is as shown in table 1.
The pH value of the cefmetazole acid of the different proportionings of table 1 and sodium citrate compositions and water solublity testing result
| Group | Cefmetazole acid (g) | Sodium citrate (g) | PH | Clarity |
| 1 | 1.0 | 0.4 | 4.57 | Settled solution |
| 2 | 1.0 | 0.5 | 4.65 | Settled solution |
| 3 | 1.0 | 0.6 | 4.83 | Settled solution |
| 4 | 1.0 | 0.65 | 4.90 | Settled solution |
| 5 | 1.0 | 0.7 | 4.99 | Settled solution |
| 6 | 1.0 | 0.8 | 5.13 | Settled solution |
| 7 | 1.0 | 2.0 | 5.65 | Settled solution |
Show by table 1 experimental result, the cefmetazole acid of different proportionings and the injectable powder that the sodium citrate combined preparation obtains all have pH value preferably, cefmetazole acid Stability Analysis of Structures under this pH value condition, be difficult for changing other impurity of generation, side reaction and anaphylaxis rate are low, and the injectable powder that experimental result shows each proportioning all has good water solublity after with the water for injection dilution, and clarity is good, color is more shallow, noresidue impurity.
Embodiment 2 cefmetazole acids and sodium citrate composition stable Journal of Sex Research
Press the long-term experiment (3 months) and accelerated tests (3 months) the experimental implementation standard of medicine registered standard, detect above group and be 1,4,6 and 7 the cefmetazole acid and the stability of sodium citrate compositions, and compare with single Cefmetazon (Sankyo).Wherein cefmetazole acid and the related impurities content that is transformed into by cefmetazole acid adopt high performance liquid chromatography (HPLC) to detect, and use waters2487 type high performance liquid chromatograph, are filler with octadecyl silane; So that ammonium dihydrogen phosphate (take by weighing Ammonium biphosphate 5.75g, add water 700ml dissolving)-(700: 280: 20: 12.8) (regulate pH to 4.5 ± 0.1 with phosphoric acid) was mobile phase to methanol-oxolane-10% TBAH; The detection wavelength is 254nm; Column temperature is a method for 30 ℃, adopts area normalization method to calculate cefmetazole acid and the percentage composition of the related impurities that is transformed into by cefmetazole acid then, concrete experimental result as table 2 to shown in the table 5.
The long-term experiment result of table 2 cefmetazole acid and sodium citrate compositions
The long-term experiment result of table 3 Cefmetazon (Sankyo)
The accelerated tests result of table 4 cefmetazole acid and sodium citrate compositions
| Group | Month | Cefmetazole acid percentage composition (%) | PH value | Color | Clarity | Related impurities percentage composition (%) |
| 1 | 0 | 97.2 | 4.59 | ＜Y2# | Clarification | 0.6 |
| 1 | 97.2 | 4.58 | ＜Y2# | Clarification | 0.6 | |
| 2 | 97.2 | 4.56 | ＜Y2# | Clarification | 0.6 | |
| 3 | 97.1 | 4.57 | ＜Y2# | Clarification | 0.7 | |
| 4 | 0 | 97.1 | 4.90 | ＜Y2# | Clarification | 0.7 |
| 1 | 97.1 | 4.88 | ＜Y2# | Clarification | 0.7 | |
| 2 | 97.1 | 4.92 | ＜Y2# | Clarification | 0.8 | |
| 3 | 97.1 | 4.91 | ＜Y2# | Clarification | 0.8 | |
| 6 | 0 | 97.3 | 5.13 | ＝Y2# | Clarification | 0.6 |
| 1 | 97.3 | 5.15 | ＝Y2# | Clarification | 0.6 | |
| 2 | 97.2 | 5.11 | ＝Y2# | Clarification | 0.6 | |
| 3 | 97.2 | 5.13 | ＝Y2# | Clarification | 0.7 | |
| 7 | 0 | 97.2 | 5.66 | ＜Y2# | Clarification | 0.6 |
| 1 | 97.2 | 5.69 | ＜Y2# | Clarification | 0.6 | |
| 2 | 97.1 | 5.65 | ＜Y2# | Clarification | 0.7 | |
| 3 | 97.1 | 5.64 | ＝Y2# | Clarification | 0.7 |
The accelerated tests result of table 5 Cefmetazon (Sankyo)
| Group | Month | Cefmetazole acid percentage composition (%) | PH value | Color | Clarity | Related impurities percentage composition (%) |
| 1 | 0 | 94.6 | 4.81 | ＜Y3# | Clarification | 1.73 |
| 1 | 1 | 94.5 | 4.77 | ＜Y3# | Clarification | 1.84 |
| 1 | 2 | 93.8 | 4.84 | ＜Y3# | Clarification | 2.05 |
| 1 | 3 | 93.2 | 4.80 | ＝Y3# | Clarification | 2.10 |
The long-term experiment and the accelerated tests result that are mixed sodium citrate and Cefmetazon (Sankyo) by above cefmetazole acid show, the cefmetazole acid of different proportionings provided by the invention and sodium citrate compositions have better stability than the Cefmetazon (Sankyo) of one-component, and has better color and clarity, cefmetazole acid is difficult for being transformed into other impurity in the storage process, antibacterial activity composition cefmetazole acid steady quality, the content height can long term storage, quality safety.
Claims (4)
1. the compositions with antibacterial action is characterized in that, it is made up of cefmetazole acid and sodium citrate, and wherein, the weight ratio of cefmetazole acid and sodium citrate is 1: 0.4 to 1: 2.
2. the compositions with antibacterial action according to claim 1 is characterized in that, the weight ratio of cefmetazole acid and sodium citrate is 1: 0.4 to 1: 0.8 in the compositions.
3. the compositions with antibacterial action according to claim 2 is characterized in that, the weight ratio of cefmetazole acid and sodium citrate is 1: 0.65 in the compositions.
4. according to each described compositions of right claim 1 to 3, it is characterized in that: be made into the injectable powder drug form with antibacterial action.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102335988A CN101695493B (en) | 2009-10-23 | 2009-10-23 | composition of cefmetazole acid and sodium citrate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102335988A CN101695493B (en) | 2009-10-23 | 2009-10-23 | composition of cefmetazole acid and sodium citrate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101695493A CN101695493A (en) | 2010-04-21 |
| CN101695493B true CN101695493B (en) | 2011-12-28 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2009102335988A Expired - Fee Related CN101695493B (en) | 2009-10-23 | 2009-10-23 | composition of cefmetazole acid and sodium citrate |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112641729B (en) * | 2020-12-24 | 2022-11-18 | 金河牧星（重庆）生物科技有限公司 | High-water-solubility chlortetracycline hydrochloride soluble powder and preparation method thereof |
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- 2009-10-23 CN CN2009102335988A patent/CN101695493B/en not_active Expired - Fee Related
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