CN102784104A - Erythromycin ethylsuccinate emulsion injection and its preparation method - Google Patents
Erythromycin ethylsuccinate emulsion injection and its preparation method Download PDFInfo
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- CN102784104A CN102784104A CN2012102573140A CN201210257314A CN102784104A CN 102784104 A CN102784104 A CN 102784104A CN 2012102573140 A CN2012102573140 A CN 2012102573140A CN 201210257314 A CN201210257314 A CN 201210257314A CN 102784104 A CN102784104 A CN 102784104A
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Abstract
The invention specifically relates to an erythromycin ethylsuccinate emulsion injection and its preparation method, belonging to the field of pharmaceutical preparations. Each 250 mL of the emulsion contains 0.75 to 4 g of erythromycin ethylsuccinate, 1 to 20 g of soybean oil for injection, 1 to 20 g of medium chain triglyceride, 1 to 5 g of soybean phospholipid for injection, 2 to 10 g of glycerin for injection, 0.01 to 0.3 g of oleic acid and 0.01 to 0.2 g of vitamin E, with the balance being injection water. The invention also provides a preparation method for the erythromycin ethylsuccinate emulsion injection. The method comprises the following steps: dissolving the main component erythromycin ethylsuccinate and a pharmaceutically acceptable emulsifier for intravenous injection, an anti-oxidant and a stabilizing agent in soybean oil for injection and medium chain triglyceride so as to prepare an oil phase; dissolving a pharmaceutically acceptable isoosmotic adjusting agent in injection water as to prepare a water phase; mixing the water phase and the oil phase and carrying out emulsification so as to prepare primary emulsion; and adding injection water into the primary emulsion until the amount of the primary emulsion is sufficient, carrying out homogenization in a high pressure homogenizer, adjusting a pH value to 7 to 8 and carrying out bottling, filling of nitrogen, embedding and autoclaving so as to obtain the erythromycin ethylsuccinate emulsion injection.
Description
Summary
The invention belongs to field of pharmaceutical preparations, more specifically, relate to ethyl succinate Emulsion injection of a kind of erythromycin and preparation method thereof.Contain in the said Emulsion of every 250mL: ethyl succinate 0.75～4 g of erythromycin; Injection soybean oil 1～20 g; Medium chain triglyceride 1～20 g; Injection soybean phospholipid 1～5 g; Glycerol for injection 2～10 g; Oleic acid 0.01～0.3g; Vitamin E 0.01～0.2g; Surplus is a water for injection.The present invention also provides a kind of ethyl succinate preparation method of emulsion injection of erythromycin; Comprise: used for intravenous injection emulsifying agent, antioxidant, the stabilizing agent of the ethyl succinate of main component erythromycin and pharmaceutically permission use are dissolved in injection soybean oil and the medium chain triglyceride, make oil phase; The isoosmotic adjusting agent that pharmaceutically allows to use is dissolved in the water for injection, makes water; With carrying out emulsifying after said water and the oil phase mixing, make colostrum again; Add water for injection to capacity to said Ruzhong just, in high pressure homogenizer, carry out homogenizing, regulate pH to 7～8, bottling, inflated with nitrogen, embedding, autoclaving promptly gets the ethyl succinate Emulsion injection of erythromycin.
Technical field
The invention belongs to technical field of medicine, related to a kind of ethyl succinate injection of erythromycin, particularly is a kind of prescription and preparation method thereof of ethyl succinate Emulsion injection of erythromycin.
Background technology
The ethyl succinate of erythromycin, another name erythromycin ethylsuccinate (erythromycin ethylsuccinate), its structural formula is: molecular formula: C
43H
75NO
16Molecular weight: 862.07
The ethyl succinate of erythromycin belongs to macrolide antibiotics; It is the regeneration product of erythromycin; Its mechanism of action is that it can see through bacterial cell membrane, combines with bacterial cell 70s ribosome 50s subunit, and it is synthetic to hinder bacterioprotein; Thereby play antibacterial or bactericidal action, have the remarkable usefulness of broad-spectrum antiseptic.These article are especially responsive to gram positive bacteria, and are effective to the penicillin fastbacteria.Be used for infection such as beta hemolytic streptococcus, staphylococcus aureus, streptococcus pneumoniae, hemophilus influenza, listeria spp, diphtheria corynebacterium, bordetella pertussis.To PCs, some pathogen that cephalo-type is invalid, has good bactericidal action especially like atypia pathogen such as Legionnella, chlamydia, mycoplasmas.It is stable than erythromycin, tasteless in gastric acid, and is almost insoluble in water, discharges erythromycin after the hydrolysis in vivo and works.Because of tasteless, and stable under one's belt, can be made into different peroral dosage forms, supply child and adult to use.Be main with peroral dosage form clinically at present,, and included, the dry suspension of producing at present in addition into Chinese Pharmacopoeia like tablet, capsule, granule etc.But peroral dosage form exists that liver is first crosses the elimination effect, and bad or swallow inconvenient patient and take also inconvenient for gastrointestinal function.The ethyl succinate of erythromycin is processed vein use injection, not only improved bioavailability, also strengthened patient's compliance to a certain extent.
The ethyl succinate of erythromycin is almost insoluble in water; This point has limited it and has been prepared into vein and uses injection; And macrolide antibiotics has administered intramuscular and can cause that local excitation, intravenous injection can cause the untoward reaction of thrombophlebitis etc., is not good selection for the patient.Therefore, to the zest of blood vessel wall, also can widen the route of administration of the ethyl succinate of erythromycin simultaneously when reducing the ethyl succinate intravenously administrable of erythromycin, it is imperative to develop new dosage form.
The ethyl succinate of erythromycin is the slightly water-soluble macrolide antibiotics; Have certain fat-solublely, also it is not prepared into the relevant report of used for intravenous injection Emulsion in the prior art, through the relevant study of pharmacy in early stage; Successfully it is prepared into the Emulsion injection; The ethyl succinate that has solved erythromycin should not be processed the difficult problem of injection because of slightly water-soluble, has also reduced its zest to blood vessel wall, has improved the bioavailability of the ethyl succinate of erythromycin.
Summary of the invention
The present invention adopts the ethyl succinate dissolving of the erythromycin that will be insoluble in water or is solubilized into and processes pastille used for intravenous injection Emulsion in the suitable oil phase; Improved solubility property and the stability of ethyl succinate in Emulsion of erythromycin on the one hand; Zest when also greatly reducing the ethyl succinate intravenous injection of erythromycin on the other hand; For the clinical practice and the suitability for industrialized production of the ethyl succinate Emulsion injection of erythromycin have been established certain basis; And solve effectively that long-term intravenous nutrition patient fatty acid provides not enough and the FAP problem that causes; Its safety on clinical treatment is guaranteed, makes that medicine discharges rapidly, curative effect improves in human body.
Therefore, the object of the present invention is to provide a kind of ethyl succinate Emulsion injection of erythromycin, its physicochemical property meets the requirement of intravenous administration, and dissolubility and good stability have reduced the medication zest, have improved patient's compliance, can be widely used in clinical.
Another object of the present invention is to provide the ethyl succinate preparation method of emulsion injection of above-mentioned erythromycin.
According to first purpose of the present invention, the present invention provides the ethyl succinate Emulsion injection of erythromycin, is made up of adjuvant necessary on ethyl succinate, oil for injection, emulsifying agent and other pharmaceuticss of the erythromycin of slightly solubility:
Component content
Ethyl succinate 0.75～the 4g of erythromycin
Oil for injection 5～30g
Emulsifying agent 1～5g
Isoosmotic adjusting agent 2～10g
Stabilizing agent 0.01～0.3g
Antioxidant 0.01～0.2g
PH to 6～10 are regulated in the pH regulator agent
Water for injection is an amount of
Described emulsifying agent is selected from one or more mixture of the mixture of ten dihydroxystearic acid macrogol esters and lecithin, tween 80, Arlacel-20, pluronic gram F-68 or fatty acid monoglyceride, preferred soybean phospholipid.
Described oil for injection is selected from one or more the mixture in soybean oil, safranine caul-fat, Semen Maydis oil, medium chain triglyceride, the Oleum Helianthi, preferred soybean oil, medium chain triglyceride.
Described isoosmotic adjusting agent preferably glycerine.
The preferred oleic acid of described stabilizing agent.
Described antioxidant preferred vitamin E.
The preferred sodium hydroxide of described pH regulator agent.
In the most preferred embodiment of the present invention, the ethyl succinate Emulsion injection of described erythromycin in the 250mL injection, comprises:
The ethyl succinate 1.5g of erythromycin
Injection soybean oil (LCT) 12.5g
Medium chain triglyceride (MCT) 12.5g
Soybean phospholipid 3g
Glycerol 5.5g
Oleic acid 0.1g
Vitamin E 0.125g
The water for injection surplus
According to another object of the present invention, the present invention provides the ethyl succinate preparation method of emulsion injection of erythromycin, and in the ethyl succinate Emulsion injection of preparation 250mL erythromycin, method is:
Step 1: the ethyl succinate, injection soybean oil, medium chain triglyceride, soybean phospholipid, oleic acid and the vitamin E that take by weighing or measure erythromycin by formula ratio mix stirring and dissolving under 50～80 ℃ of conditions, get oil phase;
Step 2: measure glycerol and proper amount of water for injection is mixed stirring and dissolving under 50～80 ℃ of conditions by prescription, water;
Step 3: under high-speed stirred, water is slowly added in the oil phase, get colostrum;
Step 4: colostrum is settled to formula ratio with the water for injection dilution, transfers to and carry out homogenizing in the high pressure homogenizer;
Step 5: the Emulsion behind the homogenizing is regulated pH to 7～8 with sodium hydroxide, bottling, inflated with nitrogen, embedding, autoclaving promptly gets the ethyl succinate Emulsion injection of erythromycin.
More specifically, this method step is specific as follows:
Step 1: ethyl succinate, 12.5g injection soybean oil, 12.5g medium chain triglyceride and the 3g soybean phospholipid of 1.5g erythromycin mixed being heated to 70 ℃ in the rearmounted constant temperature blender with magnetic force; After mixing to whole dissolvings; Again 0.1g oleic acid and 0.125g vitamin E are scattered in the above-mentioned mixture; Be incubated behind the mix homogeneously, make oil phase;
Step 2: 5.5 g glycerol for injection are scattered in 70% the water for injection, put and be heated to 70 ℃ in the constant temperature blender with magnetic force, be incubated after mixing to whole dissolvings, make water;
Step 3: use high shearing mixing emulsor, with 9000rmin
-1Rotating speed high speed shear oil phase, water slowly is added drop-wise in the oil phase, continue to shear 10min, make colostrum;
Step 4: colostrum is settled to recipe quantity with remaining 70 ℃ of waters for injection dilution, transfers to again in the high pressure homogenizer, with the pressure homogenizing of 1000bar 5 times;
Step 5: the Emulsion that makes through homogenizing in the step 4 is used 0.2molL
-1Sodium hydroxide solution is regulated pH to 8, bottling, and envelope is irritated nitrogen, gland, autoclaving 30min promptly gets the ethyl succinate Emulsion injection of erythromycin.
Product is a milky homogeneous liquid, and drug loading is 6 ± 1mgmL
-1, mean diameter is about 208.0 ± 5 nm, and current potential is-35.3 ± 3mV, and pH is 7～9.
Compared with prior art; The invention provides a kind of ethyl succinate Emulsion injection of erythromycin; The ethyl succinate that wherein is insoluble in the erythromycin of water is the active component of performance pharmacological action; Be dissolved in the microgranule that forms oil-in-water type in injection soybean oil and the medium chain triglyceride under the function of stabilizer of at the emulsifying agent soybean phospholipid, pharmaceutically allow using, avoided and the contacting of the external world, can't contact with air, water etc. and take place to go bad; Can not degrade yet, reaction such as hydrolysis, stability is improved.Simultaneously, also in the ethyl succinate Emulsion injection of erythromycin, add antioxidant, the rotten probability of oxidation reaction because of taking place in the ethyl succinate that has further reduced erythromycin, and stability further improves.In addition, the preparation technology of the ethyl succinate Emulsion injection of erythromycin provided by the invention is simple, and cost is lower, is easy to large-scale production.
The specific embodiment
The ethyl succinate content 1500mg/250mL of embodiment 1 prescription 1 erythromycin
The ethyl succinate 1.5g of erythromycin
Injection soybean oil (LCT) 12.5g
Medium chain triglyceride (MCT) 12.5g
Soybean phospholipid 3g
Glycerol 5.5g
Oleic acid 0.1g
Vitamin E 0.125g
The water for injection surplus
The preparation of the ethyl succinate intravenous injection emulsion of erythromycin:
Step 1: ethyl succinate, 12.5g injection soybean oil, 12.5g medium chain triglyceride and the 3g soybean phospholipid of 1.5g erythromycin mixed being heated to 70 ℃ in the rearmounted constant temperature blender with magnetic force; After mixing to whole dissolvings; Again 0.1g oleic acid and 0.125 g vitamin E are scattered in the above-mentioned mixture; Be incubated behind the mix homogeneously, make oil phase;
Step 2: the 5.5g glycerol for injection is scattered in 70% the water for injection, puts and be heated to 70 ℃ in the constant temperature blender with magnetic force, mix to whole dissolvings after, insulation makes water;
Step 3: with high shearing mixing emulsor with 9000rmin
-1Rotating speed high speed shear oil phase, water slowly is added drop-wise in the oil phase, continue to shear 10min, make colostrum;
Step 4: colostrum is settled to recipe quantity with the dilution of remaining 70 ℃ water for injection, transfers to again in the high pressure homogenizer, with the pressure homogenizing of 1000bar 5 times;
Step 5: the Emulsion that makes through homogenizing in the step 4 is used 0.2molL
-1Sodium hydroxide solution is regulated pH to 8, bottling, and envelope is irritated nitrogen, gland, autoclaving 30min promptly gets the ethyl succinate Emulsion injection of erythromycin.
The ethyl succinate 1000mg/250mL of embodiment 2 prescriptions 2 erythromycin
The ethyl succinate 1.0g of erythromycin
Injection soybean oil (LCT) 15g
Medium chain triglyceride (MCT) 10g
Soybean phospholipid 3g
Glycerol 5.5g
Oleic acid 0.1g
Vitamin E 0.125g
The water for injection surplus
The preparation of the ethyl succinate intravenous injection emulsion of erythromycin:
Step 1: ethyl succinate, 15g injection soybean oil, 10g medium chain triglyceride and the 3g soybean phospholipid of 1.0g erythromycin mixed being heated to 70 ℃ in the rearmounted constant temperature blender with magnetic force; After mixing to whole dissolvings; Again 0.1g oleic acid and 0.125 g vitamin E are scattered in the said mixture; Be incubated behind the mix homogeneously, make oil phase;
Step 2: 5.5 g glycerol for injection are scattered in 70% the water for injection, put and be heated to 70 ℃ in the constant temperature blender with magnetic force, mix to whole dissolvings after, insulation makes water;
Step 3: with high shearing mixing emulsor with 9000rmin
-1Rotating speed high speed shear oil phase slowly is added drop-wise to water in the oil phase, continues to shear 10min, makes colostrum;
Step 4: colostrum is settled to recipe quantity with the dilution of remaining 70 ℃ water for injection, transfers to again in the high pressure homogenizer, with 1000bar pressure homogenizing 5 times;
Step 5: the Emulsion that makes through homogenizing in the step 4 is used 0.2molL
-1Sodium hydroxide solution is regulated pH to 8, bottling, and envelope is irritated nitrogen, gland, autoclaving 30min promptly gets the ethyl succinate Emulsion injection of erythromycin.
The ethyl succinate 500mg/250mL of embodiment 3 prescriptions 3 erythromycin
The ethyl succinate 0.5g of erythromycin
Injection soybean oil (LCT) 17.5g
Medium chain triglyceride (MCT) 7.5g
Soybean phospholipid 3g
Glycerol 5.5g
Oleic acid 0.1g
Vitamin E 0.125g
The water for injection surplus
The preparation of the ethyl succinate intravenous injection emulsion of erythromycin:
Step 1: ethyl succinate, 17.5g injection soybean oil, 7.5g medium chain triglyceride and the 3g soybean phospholipid of 0.5g erythromycin mixed being heated to 70 ℃ in the rearmounted constant temperature blender with magnetic force; After mixing to whole dissolvings; Again 0.1g oleic acid and 0.125g vitamin E are scattered in the said mixture; Be incubated behind the mix homogeneously, make oil phase;
Step 2: the 5.5g glycerol for injection is scattered in 70% the water for injection, puts and be heated to 70 ℃ in the constant temperature blender with magnetic force, mix to whole dissolvings after, insulation makes water;
Step 3: with high shearing mixing emulsor with 9000rmin
-1Rotating speed high speed shear oil phase slowly is added drop-wise to water in the oil phase, continues to shear 10min, makes colostrum;
Step 4: colostrum is settled to recipe quantity with the dilution of remaining 70 ℃ water for injection, transfers to again in the high pressure homogenizer, with 1000bar pressure homogenizing 5 times;
Step 5: the Emulsion that makes through homogenizing in the step 4 is used 0.2molL
-1Sodium hydroxide solution is regulated pH to 8, bottling, and envelope is irritated nitrogen, gland, autoclaving 30min promptly gets the ethyl succinate Emulsion injection of erythromycin.
The stability instance
1 outward appearance
The outward appearance of the ethyl succinate Emulsion injection of the erythromycin of perusal instantiation 1, instance 2 and instance 3 preparations is milky even emulsion liquid.
2 study on the stability
1) quickens centrifuging
The ethyl succinate Emulsion injection 10mL of erythromycin that gets embodiment 1, embodiment 2 and embodiment 3 preparations in centrifuge tube, 4000rmin
-1Centrifugal 15min, it is transparent that the bottom shows slightly, and do not see that breast analyses, and promptly reverts to even Emulsion up and down after the overturning several times; With 3750rmin
-1The centrifugal 5h of speed is equivalent to place the natural layering effect in 1 year, does not also see layering, can think the Emulsion steady quality.
2) jolting experiment
Get the ethyl succinate Emulsion injection 15mL of the erythromycin of embodiment 1, embodiment 2 and embodiment 3 preparations, fill nitrogen, be sealed in the cillin bottle, place constant temperature oscillator, 100shakemin under 25 ℃
-1Jolting, respectively at 0h, 12h, 24h, 48h, 72h sampling is measured the outward appearance of Emulsion under each sample time, centrifugal stability parameter and microscopically to observe＞the oil droplet number of 2 μ m.
Result of the test shows that jolting is little to the outward appearance of Emulsion, the influence of centrifugal stability parameter continuously, and sample still is the milky uniform liquid, and the long-time continuous jolting has larger oil droplet to produce, so Emulsion should be avoided long-term thermal agitation.
3) hot test
The ethyl succinate Emulsion injection of getting the erythromycin of embodiment 1, embodiment 2 and embodiment 3 preparations fills nitrogen, sealing; Respectively at the condition held of 40 ℃, 60 ℃ temperature 10 days; And investigate outward appearance, pH value and the content of Emulsion respectively at the 0th day, 5 days and 10 days, and contrasted in the 0th day.
Each experimental condition held, the content of Emulsion has no significant change.Place after 10 days for 40 ℃, the basic no change of Emulsion outward appearance, good fluidity does not have lamination, and pH value, content slightly descend; Place after 10 days for 60 ℃, the Emulsion color begins flavescence, and content slightly descends, and pH value descends bigger, and analysis possibly take place for the hydrolysis of phospholipid hydrolysis or oil, produces due to a large amount of free fatties.The result shows that high temperature (40 ℃) does not have influence basically to the physical stability of this preparation at short notice, and chemical stability is had certain influence.But temperature too high (60 ℃) has produced certain influence to emulsion stability, so the Emulsion storage should be avoided high temperature.
4) long-time stability are investigated
Get three samples of the ethyl succinate Emulsion injection of the erythromycin for preparing by embodiment 1, embodiment 2 and embodiment 3; Sterilization back was 30 ± 2 ℃, the condition held of RH 65 ± 5% 6 months; Place under the lucifuge condition and preserve; Respectively at the 0th, 1,2,3 and June sampling, outward appearance, pH value, particle diameter and the content of Emulsion are investigated.
The result that long-time stability are investigated shows: the ethyl succinate Emulsion injection of erythromycin was 30 ± 2 ℃, the condition held of RH 65 ± 5% 6 months; Its outward appearance is good, and the uniform liquid that is creamy white is better mobile; Oil droplet does not appear in the surface, does not have lamination; Size slightly increased after 6 months, and pH value changes not obvious, and content reduces slightly.Physical stability and chemical stability result show that the basic no change of each item index of the ethyl succinate Emulsion injection of erythromycin has good stability.
Claims (7)
1. the ethyl succinate Emulsion injection of an erythromycin is characterized in that, contains in the said Emulsion of every 250mL:
The ethyl succinate of erythromycin (erythromycin ethylsuccinate) 0.75～4g
Pharmaceutically acceptable oil for injection 5～30g
Injection emulsifying agent 1～5g
Pharmaceutically acceptable stabilizing agent 0.01～0.3g
Pharmaceutically acceptable isoosmotic adjusting agent 2～10g
Pharmaceutically acceptable antioxidant 0.01～0.2g
Surplus is pharmaceutically acceptable water for injection 200～242g
A kind of ethyl succinate Emulsion injection of erythromycin is characterized in that containing ethyl succinate, oil for injection, emulsifying agent, pH regulator agent, isoosmotic adjusting agent, stabilizing agent and antioxidant, the water for injection of active component erythromycin.
2. the ethyl succinate Emulsion injection of erythromycin according to claim 1 is characterized in that described oil for injection is selected from one or more the mixture in soybean oil, safranine caul-fat, Semen Maydis oil, medium chain triglyceride, the Oleum Helianthi.
3. the ethyl succinate Emulsion injection of erythromycin according to claim 1 is characterized in that described emulsifying agent is selected from one or more mixture of the mixture of ten dihydroxystearic acid macrogol esters and lecithin, tween 80, Arlacel-20, pluronic gram F-68 or fatty acid monoglyceride.
4. the ethyl succinate Emulsion injection of erythromycin according to claim 1 is characterized in that described pH regulator agent is sodium hydroxide or hydrochloric acid.
5. the ethyl succinate Emulsion injection of erythromycin according to claim 1 is characterized in that described isoosmotic adjusting agent is glycerol, sorbitol, mannitol or glucose.
6. the ethyl succinate Emulsion injection of erythromycin according to claim 1 is characterized in that described stabilizing agent is oleic acid or enuatrol.
7. the ethyl succinate Emulsion injection of erythromycin according to claim 1 is characterized in that described antioxidant is vitamin E or ascorbic acid.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104906041A (en) * | 2015-06-30 | 2015-09-16 | 武汉大学 | Erythromycin ethylsuccinate emulsion injection and preparation method thereof |
| CN111358754A (en) * | 2020-03-13 | 2020-07-03 | 广州白云山汉方现代药业有限公司 | Long-circulating emulsion of macrolide antibiotics and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1602887A (en) * | 2004-08-18 | 2005-04-06 | 江苏省药物研究所 | Erythromycin ethylsuccinate for injection and its preparation process and application |
| CN101066245A (en) * | 2007-05-25 | 2007-11-07 | 朱芳海 | Orally taken emulsion and its prepn |
| CN101411686A (en) * | 2008-12-11 | 2009-04-22 | 刘玉辉 | Clarithromycin sub-microemulsion injection and preparation method thereof |
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2012
- 2012-07-24 CN CN2012102573140A patent/CN102784104A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1602887A (en) * | 2004-08-18 | 2005-04-06 | 江苏省药物研究所 | Erythromycin ethylsuccinate for injection and its preparation process and application |
| CN101066245A (en) * | 2007-05-25 | 2007-11-07 | 朱芳海 | Orally taken emulsion and its prepn |
| CN101411686A (en) * | 2008-12-11 | 2009-04-22 | 刘玉辉 | Clarithromycin sub-microemulsion injection and preparation method thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104906041A (en) * | 2015-06-30 | 2015-09-16 | 武汉大学 | Erythromycin ethylsuccinate emulsion injection and preparation method thereof |
| CN111358754A (en) * | 2020-03-13 | 2020-07-03 | 广州白云山汉方现代药业有限公司 | Long-circulating emulsion of macrolide antibiotics and preparation method thereof |
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Application publication date: 20121121 |