CN105622635A - Ceftizoxime sodium novel crystal form capable of reducing anaphylactic reactions and preparation thereof - Google Patents
Ceftizoxime sodium novel crystal form capable of reducing anaphylactic reactions and preparation thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
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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
- A61K9/0012—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
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/12—Separation; Purification
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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Abstract
The invention discloses a ceftizoxime sodium novel crystal form capable of reducing anaphylactic reactions, a preparation method and a pharmaceutic preparation of the ceftizoxime sodium novel crystal form. Ceftizoxime sodium is measured through an X-ray powder diffraction method, and feature diffraction peaks are displayed at the 6.8-degree position, the 11.5-degree position, the 14.6-degree position, the 15.8-degree position, the 19.4-degree position, the 20.2-degree position, the 21.8-degree position, the 24.0-degree position, the 27.4-degree position and the 30.5-degree position of an X ray powder diffraction pattern expressed by a 2 theta +/-0.2-degree diffraction angle. The content of ceftizoxime sodium compound impurities is obviously reduced compared with the prior art, and the ceftizoxime sodium novel crystal form has the advantages of being good in stability and fluidity, not prone to absorb moisture, high in dissolution speed, good in clinical effect, low in occurrence rate of adverse reactions and very suitable for clinical application.
Description
Technical field
The present invention relates to antibiotic medicine field, it is specifically related to a kind of powder ampoule agent for injection and its preparation method that comprise ceftizoxime sodium novel crystal form.
Background technology
Ceftizoxime sodium; chemical name is: [6R-[6a; 7b (Z)]]-7 [[2; 3-bis-hydrogen-2-imino--4-thiazolyl) (methoxyimino) ethanoyl] amino]-8-oxo-5-thia-1-azabicyclic [4.2.0] oct-2-ene-2-carboxylic acid sodium salt; molecular formula C13H12N5NaO5S2, molecular weight 405.38.
Ceftizoxime sodium belongs to third generation cephalosporin, tool broad-spectrum antibacterial action, the wide spectrum lactamase (comprising penicillinase and cephalosporinase) that multiple gram positive organism and gram-negative bacteria produce is stablized, the enterobacteriaceae lactobacteriaceaes such as escherichia coli, Klebsiella Pneumoniae, Proteus mirabilis are had powerful anti-microbial effect, and the Rhodopseudomonass such as Pseudomonas aeruginosa and acinetobacter are poor to this product susceptibility. Relatively first, second cynnematin for poor in generation to the effect of streptococcus aureus and staphylococcus epidermidis for ceftizoxime sodium, and methicillin-resistant staphylococcus aureus and enterococcus spp are to this product resistance, and various suis is all extremely sensitive to this product. The anerobes such as dyspepsiacoccus, peptostreptococcus and part Bacteroides are many in responsive to this product, and clostridium difficile is to this product resistance. Ceftizoxime sodium mechanism of action is reach germicidal action by the biosynthesizing of anti-bacteria cell wall mucopeptide, is applicable to meningitis and Simple gonorrhea caused by the lower respiratory infection caused by sensitive organism, urinary tract infections, abdominal cavity infection, pelvic infection, septicemia, skin soft-tissue infection, bone and the infection of joint, streptococcus pneumoniae or hemophilus influenzae.
Ceftizoxime for inj be the powder injection of its sodium salt (ceftizoxime sodium) extensively for clinical, be one of current most widely used antibiotic medicine, its preparation is all aseptic subpackaged obtained by ceftizoxime sodium raw materials. It is not high to there is purity in most of ceftizoxime sodium raw materials, and after dissolving, clarity is poor, stability is poor in the aqueous solution, the problems such as side effect is bigger. Thus, seriously have impact on the application of ceftizoxime or its salt.
Chinese patent CN101348492A discloses the method preparing high-purity ceftizoxime sodium, wants to be converted into ceftizoxime sodium in water ceftizoxime acid, obtains ceftizoxime acid crude with organic reagent extraction, peroxidation aluminium chromatography column, remove the solvent in gained moving phase, add lower alcohol and dissolve, add alkali and propose product, the method uses alumina chromatographic column, also to be used a large amount of eluents, cost height, contaminate environment, complicated operation, is not suitable for suitability for industrialized production.
Chinese patent CN102180889A discloses a kind of ceftizoxime sodium crystalline hydrate thing, and the molecular formula of this ceftizoxime sodium crystalline hydrate thing is C13H12N5NaO5S2��nH2O, n=1.5-1.85. This ceftizoxime sodium crystalline hydrate thing has good stability in storage, but the method uses chloroform, methylene dichloride equal solvent.
Obtain national science progress prize card in December, 2001 " research of ��-lactam antibitics anaphylaxis ", prize-winning unit: pharmaceutical biological product institute of China (now rename: Chinese food drug inspection research institute). Fuan medicine company group Qing Yutang pharmacy company limited reached cooperation agreement application " research of ��-lactam antibitics anaphylaxis " in 2015 with Chinese food drug inspection research institute's chemistry room and carries out the transformation of scientific and technical result, it is comprised the cephalosporin analog antibiotic improvement of production process of ceftizoxime sodium, reduce cephalosporin analog antibiotic impurity, reach and improve the quality of products, reduce the object of cephalosporin analog antibiotic anaphylaxis.
Summary of the invention
Based on project cooperation achievement, the present invention provides the brilliant type of a kind of ceftizoxime sodium compound, preparation method and pharmaceutical preparation thereof, and concrete scheme is as follows:
A kind of ceftizoxime sodium crystal, employing x-ray powder diffraction measures, and the X-ray powder diffraction pattern represented with 2 �� �� 0.2 �� diffraction angle demonstrates characteristic diffraction peak at 6.8 ��, 11.5 ��, 14.6 ��, 15.8 ��, 19.4 ��, 20.2 ��, 21.8 ��, 24.0 ��, 27.4 �� and 30.5 �� of places.
The X-ray powder diffraction of the ceftizoxime sodium crystal of the present invention is as shown in Figure 1.
The preparation method of the ceftizoxime sodium crystal of the present invention comprises the steps: 1) ceftizoxime sodium is dissolved in water, the pH value 6.3-6.9 of control solution, temperature 20-30 DEG C, the mixed solvent adding Virahol and tetrahydrofuran (THF) under stirring in solution is muddy to solution; 2) it is warming up to 40-50 DEG C, leaves standstill and support brilliant 3-5 hour; Adding dehydrated alcohol under stirring, slow cooling is to 20-30 DEG C simultaneously; Leave standstill 1-2 hour; 3) continue to be cooled to 5-10 DEG C under stirring, leave standstill 1-2 hour; 4) filtering, washing, vacuum-drying, obtains ceftizoxime sodium crystal.
As optimal technical scheme, the volume ratio of Virahol and tetrahydrofuran (THF) is 1-3:1.
As optimal technical scheme, the mixed solvent of Virahol and tetrahydrofuran (THF) adopts a mode added to add, and rate of addition is 300-400ml/h. Further preferably, the stirring velocity dripping the added-time is 180-250 rev/min.
As optimal technical scheme, the volume ratio of the mixed solvent of dehydrated alcohol and Virahol and tetrahydrofuran (THF) is 1:2-3.
As optimal technical scheme, dehydrated alcohol adopts a mode added to add, and rate of addition is 50-100ml/h. Further preferably, the stirring velocity dripping the added-time is 100-150 rev/min.
As optimal technical scheme, adopt absolute ethanol washing 1-3 time.
The present invention also provides a kind of ceftizoxime sodium preparation, comprises ceftizoxime sodium crystal and suitable auxiliary material, carrier or the auxiliary agent of the present invention. The ceftizoxime sodium of the present invention comprises injection freeze-dried powder, aseptic subpackaged powder injection, great transfusion preparation for the preparation of solid preparation, suppository, injection, wherein injection, wherein, great transfusion preparation comprises two rooms instant-matching type infusion solutions, the non-PVC instant-matching type infusion solutions that liquid two rooms instant-matching type infusion solutions, non-PVC multi-layer co-extruded film are made admittedly; Tablet, capsule, granule etc. Such as, freeze-dried powder is prepared by following method: the preparation method of freeze-dried powder is: get ceftizoxime sodium crystalline hydrate thing, pharmaceutically acceptable frozen-dried supporting agent or auxiliary shape agent, stablizer, water for injection can be added, it is stirred to dissolve, if desired, available pharmaceutically acceptable acid-alkali accommodation pH is 6.0��8.0, add activated carbon 0.005��0.5% (W/V) and stir 15��45min, filter, moisturizing, sterile filtration, by 0.5��2g/ bottle packing, lyophilize, tamponade, obtains finished product.
The present invention also provides the application of a kind of ceftizoxime sodium in the medicine of the disease of the human or animal caused by preparation treatment or prevention Gram-positive or negative bacteria sensitive organism, and described disease comprises respiratory system, liver and gall, face, urinary tract infections, abdominal cavity infection, pelvic infection, septicemia, skin soft-tissue infection, bone and the infection of joint, meningitis and Simple gonorrhea.
Useful effect: the ceftizoxime sodium Crystal impurity content of the present invention obviously reduces, and product is fine particle shape, even particle size distribution, in process of production, it is not necessary to pulverize, without electrostatic, for suitability for industrialized production has saved equipment, power and human cost. The ceftizoxime sodium crystal Determination of Residual Organic Solvents of the present invention is low, reduces the pungency to body when being prepared into drug regimen and preparation; Effectively improve product stability and Drug safety. The ceftizoxime sodium crystal not easily moisture absorption of the present invention, has good mobility, not easily causes producing blocking during packing when carrying out aseptic subpackaged because of the moisture absorption and makes loading amount generation difference cause dosage not enough, thus brings the defective of product; The ceftizoxime sodium crystal of the present invention has good dissolving out capability so that it is easily rapidly absorbed into blood circulation, improves bioavailability, and is conducive to playing its effect fast.
Accompanying drawing explanation
Accompanying drawing 1 is the X powder diffraction collection of illustrative plates of ceftizoxime sodium crystal of the present invention
Embodiment
Embodiment 1
Ceftizoxime sodium crude product 100g is dissolved in water, the pH value 6.5 of control solution, temperature 25 DEG C, dripping the mixed solvent (volume ratio 2:1) adding Virahol and tetrahydrofuran (THF) under stirring in solution muddy to solution, stirring velocity is 250 revs/min, and rate of addition is 300ml/h; It is warming up to 50 DEG C, leaves standstill and support brilliant 3 hours; Stirring lower and add dehydrated alcohol, stirring velocity is 100 revs/min, simultaneously slow cooling to 25 DEG C; Rate of addition is 80ml/h, dropwises, and leaves standstill 2 hours; Continue under stirring to be cooled to 10 DEG C, leave standstill 1 hour; Filtering, absolute ethanol washing 3 times, 30 DEG C of vacuum-dryings, obtain ceftizoxime sodium crystal. Particle diameter is 50-70 ��m, receipts rate 96.4%, HPLC content 99.95%. As shown in Figure 1, the X-ray powder diffraction pattern represented with 2 �� �� 0.2 �� diffraction angle demonstrates characteristic diffraction peak at 6.8 ��, 11.5 ��, 14.6 ��, 15.8 ��, 19.4 ��, 20.2 ��, 21.8 ��, 24.0 ��, 27.4 �� and 30.5 �� of places to the X-ray powder diffractogram that use Cu-K alpha-ray measurement obtains.
Embodiment 2
Ceftizoxime sodium crude product 100g is dissolved in water, the pH value 6.8 of control solution, temperature 30 DEG C, dripping the mixed solvent (volume ratio 1:1) adding Virahol and tetrahydrofuran (THF) under stirring in solution muddy to solution, stirring velocity is 250 revs/min, and rate of addition is 350ml/h; It is warming up to 50 DEG C, leaves standstill and support brilliant 3 hours; Stirring lower and add dehydrated alcohol, stirring velocity is 100 revs/min, simultaneously slow cooling to 25 DEG C; Rate of addition is 80ml/h, dropwises, and leaves standstill 2 hours; Continue under stirring to be cooled to 10 DEG C, leave standstill 1 hour; Filtering, absolute ethanol washing 3 times, 30 DEG C of vacuum-dryings, obtain ceftizoxime sodium crystal. Particle diameter is 50-70 ��m, receipts rate 95.9%, HPLC content 99.96%. The X-ray powder diffraction using Cu-K alpha-ray measurement to obtain is consistent with the result of embodiment 1.
Embodiment 3
Ceftizoxime sodium crude product 100g is dissolved in water, the pH value 6.3 of control solution, temperature 25 DEG C, dripping the mixed solvent (volume ratio 3:1) adding Virahol and tetrahydrofuran (THF) under stirring in solution muddy to solution, stirring velocity is 250 revs/min, and rate of addition is 400ml/h; It is warming up to 50 DEG C, leaves standstill and support brilliant 4 hours; Stirring lower and add dehydrated alcohol, stirring velocity is 100 revs/min, simultaneously slow cooling to 25 DEG C; Rate of addition is 80ml/h, dropwises, and leaves standstill 2 hours; Continue under stirring to be cooled to 10 DEG C, leave standstill 1 hour; Filtering, absolute ethanol washing 3 times, 30 DEG C of vacuum-dryings, obtain ceftizoxime sodium crystal. Particle diameter is 50-70 ��m, receipts rate 94.6%, HPLC content 99.95%. The X-ray powder diffraction using Cu-K alpha-ray measurement to obtain is consistent with the result of embodiment 1.
Comparative example 1
Get the ceftizoxime sodium crude product that 10g is to be purified, it is dissolved in 200ml water, add the ethyl acetate that volume accounts for described aqueous solution volume 40% every time, extract 2 times, after fully stirring, leave standstill 1 hour, then separate organic phase, obtain the aqueous phase containing ceftizoxime sodium. 15% ammoniacal liquor adding 50ml in above-mentioned aqueous phase processes, and the treatment time is 2 hours, stirs in treating processes, until the pH value of the aqueous solution reaches 9-10. The sedimentation and filtration of precipitation is fallen. The ceftizoxime sodium water solution obtained being increased to 60-70 DEG C, removes remaining ammonia in solution, concentrate simultaneously, obtaining liquor capacity is 120ml. Then adding the ethanol of concentration 75% in this aqueous solution, its volume accounts for aqueous solution volume 65%, is slowly cooled to 12 DEG C. Optional input ceftizoxime sodium crystal seed in temperature-fall period. Slowly crystallize out, place 10 hours until no longer include crystal precipitate out, whizzer is centrifugal, filter, air dries, and obtains white ceftizoxime sodium 9.0g, and it is 94.10% that receipts rate 90%, HPLC records the content of ceftizoxime.
Embodiment 4: stability test
Sample: embodiment 1-3 is numbered samples 1-3 respectively, commercially available ceftizoxime sodium numbered samples 4, comparative example 1 numbered samples 5 product in contrast.
1. high temperature test and exposure experiments to light
High temperature test: the ceftizoxime sodium crystalline compounds simulation listing packaging that Example 1-3 prepares, put in sealing clean container, place 10 days at 40 �� 2 DEG C of temperature, in the 5th day and sampling in the 10th day, investigating project by stability emphasis to detect, test-results compared with 0 day.
Exposure experiments to light: under sample is put YB 1 type visible foreign body detector, illumination was 4500 scholar 500Lx, the 5th, the ten day every index of sampling and measuring.
Test-results is as shown in table 1:
Table 1 high temperature and exposure experiments to light
Result shows: the ceftizoxime sodium crystalline compounds that the present invention prepares, its good stability, and foreign matter content is low, under high temperature and high light conditions, equal retention is stablized, and its solution colour is without considerable change, impurity change is little, and stability is obviously better than commercially available prod and reference substance.
2, wettability test
This test example has investigated the water absorbability of ceftizoxime sodium compound provided by the invention. This test example is respectively at 25 DEG C, and when humidity 75% and 95%, each sample thief 5g is placed on electronic balance, and time recording weight, to detect moisture absorption degree, the results are shown in Table 2.
Table 2 hygroscopicity test results
As known from Table 2, relative to commercially available ceftizoxime sodium, the ceftizoxime sodium compound water absorbability prepared by the present invention is little, is obviously better than commercially available prod and reference substance.
3, fluidity test
Adopt fixed funnel method, suitable height funnel being placed on graph paper, ceftizoxime sodium compound is freely flowed down from flare opening, until the cone top formed contacts with flare opening, measures the hypotenuse of ceftizoxime sodium compound accumulation horizon and the angle (slope of repose ��) of sea line. Test-results is such as table 3.
Table 3 ceftizoxime sodium compound fluidity test result
| Sample number into spectrum | 1 | 2 | 3 | 4 | 5 |
| �ȡ� | 20 | 20 | 21 | 35 | 37 |
As can be seen from Table 3, compared with ceftizoxime sodium of the prior art, the ceftizoxime sodium compound prepared by the present invention has very excellent mobility, is conducive to improving the accuracy of packing, and is easy to mix when mixing with other composition.
4, dissolution time measures
The dissolution time of sample 1-4 ceftizoxime sodium compound of the present invention is detected, gets each 1g of ceftizoxime sodium compound, add to leave standstill after 10ml water for injection carries out shaking 3 times and observe dissolution time.
The table 4 sample dissolution time
| Sample 1 | Sample 2 | Sample 3 | Sample 4 | Sample 5 | |
| Dissolution time when 0 DEG C | 6s | 6s | 6s | 20s | 18s |
| Dissolution time when 15 DEG C | 5s | 5s | 5s | 15s | 14s |
| Dissolution time when 25 DEG C | 4s | 4s | 4s | 12s | 12s |
From the interpretation of table 4, the dissolution rate of the ceftizoxime sodium compound that embodiment of the present invention 1-3 prepares is fast, is more applicable to the needs of clinical application.
The ceftizoxime sodium crystal that the present invention proposes and preparation method thereof are described by embodiment, person skilled obviously can not depart from content of the present invention, spirit and scope, ceftizoxime sodium described herein and its preparation method are changed or suitably change with combination, realize the technology of the present invention. Special needs to be pointed out is, all mutually similar replacements and change apparent to those skilled in the art, they are all deemed to be included in the spirit of the present invention, scope and content.
Claims (10)
1. the crystal of a ceftizoxime sodium compound, it is characterized in that, employing x-ray powder diffraction measures, and the X-ray powder diffraction pattern represented with 2 �� �� 0.2 �� diffraction angle demonstrates characteristic diffraction peak at 6.8 ��, 11.5 ��, 14.6 ��, 15.8 ��, 19.4 ��, 20.2 ��, 21.8 ��, 24.0 ��, 27.4 �� and 30.5 �� of places.
2. ceftizoxime sodium crystal as claimed in claim 1, it is characterised in that, the X-ray powder diffraction of described crystal is as shown in Figure 1.
3. the preparation method of ceftizoxime sodium crystal as claimed in claim 1, it is characterized in that, comprise the steps: 1) ceftizoxime sodium is dissolved in water, the pH value 6.3-6.9 of control solution, temperature 20-30 DEG C, the mixed solvent adding Virahol and tetrahydrofuran (THF) under stirring in solution is muddy to solution; 2) it is warming up to 40-50 DEG C, leaves standstill and support brilliant 3-5 hour; Adding dehydrated alcohol under stirring, slow cooling is to 20-30 DEG C simultaneously; Leave standstill 1-2 hour; 3) continue to be cooled to 5-10 DEG C under stirring, leave standstill 1-2 hour; 4) filtering, washing, vacuum-drying, obtains ceftizoxime sodium crystal.
4. preparation method as claimed in claim 3, it is characterised in that, the volume ratio of Virahol and tetrahydrofuran (THF) is 1-3:1.
5. preparation method as claimed in claim 4, it is characterised in that, the mixed solvent of Virahol and tetrahydrofuran (THF) adopts and drips the mode added and add, and rate of addition is 300-400ml/h; The stirring velocity dripping the added-time is 180-250 rev/min.
6. preparation method as described in claim 4 or 5, it is characterised in that, the volume ratio of the mixed solvent of dehydrated alcohol and Virahol and tetrahydrofuran (THF) is 1:2-3.
7. preparation method as claimed in claim 6, it is characterised in that, dehydrated alcohol adopts and drips the mode added and add, and rate of addition is 50-100ml/h; The stirring velocity dripping the added-time is 100-150 rev/min.
8. preparation method as claimed in claim 3, it is characterised in that, adopt absolute ethanol washing 1-3 time.
9. a ceftizoxime sodium preparation, comprises the ceftizoxime sodium crystal described in claim 1 or 2 and suitable auxiliary material, carrier or auxiliary agent.
10. ceftizoxime sodium as claimed in claim 1 is treated in preparation or is prevented the application in the medicine of the disease of the human or animal caused by Gram-positive or negative bacteria sensitive organism, and described disease comprises respiratory system, liver and gall, face, urinary tract infections, abdominal cavity infection, pelvic infection, septicemia, skin soft-tissue infection, bone and the infection of joint, meningitis and Simple gonorrhea.
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| CN109160921A (en) * | 2017-07-26 | 2019-01-08 | 王秀香 | A kind of 1/2 water ceftizoxime sodium compound |
| CN109160920A (en) * | 2017-07-20 | 2019-01-08 | 海南美大制药有限公司 | An a kind of water ceftizoxime sodium compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109160920A (en) * | 2017-07-20 | 2019-01-08 | 海南美大制药有限公司 | An a kind of water ceftizoxime sodium compound |
| CN109160921A (en) * | 2017-07-26 | 2019-01-08 | 王秀香 | A kind of 1/2 water ceftizoxime sodium compound |
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| CN105622635B (en) | 2017-03-15 |
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