CN109044969A - A kind of preparation method of paclitaxel injection - Google Patents
A kind of preparation method of paclitaxel injection Download PDFInfo
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- CN109044969A CN109044969A CN201811236777.2A CN201811236777A CN109044969A CN 109044969 A CN109044969 A CN 109044969A CN 201811236777 A CN201811236777 A CN 201811236777A CN 109044969 A CN109044969 A CN 109044969A
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- paclitaxel injection
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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
- A61K9/08—Solutions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
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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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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Abstract
The invention discloses a kind of preparation method of paclitaxel injection, composition is 30 parts by weight of taxol, dehydrated alcohol 1000-1500 parts by volume, lactic acid 18-24 parts by volume, poly- hydrocarbon oxygen ester (35) the 1000-1500 parts by volume of castor oil.Compared with the existing technology, paclitaxel injection dissolubility prepared by the present invention is good, concentration is uniform, quality is stable, acute adverse reaction is low, and preparation process provided by the invention is simple, easily-controllable, high production efficiency, production energy consumption are low.
Description
Technical field
The invention belongs to biomedicine technical fields, and in particular to a kind of preparation method of paclitaxel injection.
Background technique
Taxol is a kind of natural plant extracts anti-tumor drug of effectively treatment kinds cancer, is widely used in ovary
The treatment of the kinds of tumors such as cancer, breast cancer, lung cancer, it is prominent to breast cancer, oophoroma curative effect, to liver cancer, lung cancer, the cancer of the esophagus, head
Neck cancer and prostate cancer also have certain curative effect, and when combining other common anti-tumor drugs, curative effect be can further improve, because
Unique anticancer mechanism is very extensive in clinical use.But taxol soluble is very poor, it is low to be insoluble in water, bioavilability,
Therefore being prepared into the preparation for being injected intravenously or being transfused, there is biggish technical difficulty.The Taxol injection listed at present
Liquid is a kind of colorless and transparent or yellowish viscosity solution, is Emulsifier EL-60-dehydrated alcohol (V:V=of taxol
50:50) solution is diluted to 0.35-1.4mmol/L intravenous injection before use.Emulsifier EL-60 has apparent toxicity, faces
Bed shows as serious allergic reaction, and the release of in-vivo tissue amine can be caused in conjunction with ethyl alcohol, several minutes after administration, that is, causes part
There is drug eruption, is short of breath, the hypersensitivity such as bronchial spasm, low blood pressure in patient, to avoid allergic reaction, before use
Often need intravenous injection 5-10mg (milligram) dexamethasone, 300mg Cimetidine in advance within 30 minutes；Or intramuscular injection 50mg benzene
Extra large Lamine, and clinical monitoring is carried out, although at present clinically generally by advance with the method for the Loratadines such as hormone
Desensitization, but still it is only capable of partial prophylaxis, and since medication process is very inconvenient, seriously limit existing paclitaxel injection
Clinical application.
In view of paclitaxel injection there are the shortcomings that, in the recent decade, domestic and international formulation scientist has carried out deeply extensive
Research, develop a large amount of taxol novel formulation.Such as it is modified with polyethylene glycol, polyvinyl alcohol, povidone, heparin etc.
The nanoparticle or taxol albumin nano suspending liquid A BI-007 of preparation.Again such as taxol is encapsulated in phosphatide, cholesterol
The liposome of membrane material, or using the complex of the paclitaxel loaded formation of hydroxypropyl cyclodextrin, and then reach solubilising and other effects.So
And above-mentioned preparation equally exists the defect that Paclitaxel precipitation is generated when the dilution of solubilization liquid, even since membrane material excessive concentration causes
The adverse reactions such as globulolysis；Or easy problems such as layering, encapsulation rate be low, easy leakage, stability difference.These are difficult to
The defect overcome seriously hinders the industrialized development and practical clinical of above-mentioned new formulation.
To solve the above technical problem existing for the formulation for paclitaxel listed at present, it is directed to Emulsifier EL-60 for many years
Caused adverse reaction, solubility, the stability for increasing taxol reduce toxicity, increase bioavilability, prior art research and development
Personnel expand a large amount of research, are dedicated to preparing a kind of less toxic, stable paclitaxel injection.Chinese patent application
CN101816644A discloses a kind of composite injection containing taxol and phenylalanine, the weight of taxol and phenylalanine
Amount is than being 1:0.01-0.8, and the solubilizer in injection is Emulsifier EL-60, and solvent is dehydrated alcohol, polyoxyethylene caster
Although the dosage of oil and the volume ratio 1:2 of ethyl alcohol, the Emulsifier EL-60 in the injection also have reduction appropriate, but it makes
With phenylalanine and Emulsifier EL-60 usage amount it is still higher.CN101574318A discloses a kind of Taxol injection
Liquid, precentagewise in terms of prescription gross mass containing Japanese yew raw polyol 0.6%, Emulsifier EL-60 55%, dehydrated alcohol 43%,
It will be organic miscellaneous the removal of 4A type molecular sieve will to be added in preparation process in oleic acid, sodium glycocholate mixture 1% in Emulsifier EL-60
Matter.However, Emulsifier EL-60 usage amount is still higher in above-mentioned technology, adverse reaction is easily caused.Thus, the applicant causes
A kind of Emulsifier EL-60 usage amount is low and the solubility of taxol is high, stability is strong in studying for power, and bioavilability is high
The preparation method of paclitaxel injection.
Summary of the invention
Therefore, technical problem to be solved by the present invention lies in overcome existing paclitaxel injection easily to cause hypersensitivity
Technological deficiency, to propose the taxol that a kind of Emulsifier EL-60 dosage is low and product is stable, dissolubility is good, side effect is low
Injection and preparation method.
For this purpose, the present invention provides a kind of paclitaxel injection, including the poly- hydrocarbon oxygen of taxol, dehydrated alcohol, lactic acid, castor oil
Ester (35),
Wherein respectively at being grouped as are as follows:
Preferably, the paclitaxel injection is respectively at being grouped as are as follows:
The present invention also provides the preparation methods for paclitaxel injection:
A. by production prescription stock, supplementary material is weighed by recipe quantity respectively, spare；
B. the dehydrated alcohol of recipe quantity one third is added in taxol, ultrasound, the poly- of recipe quantity 4/5ths is added
Ethylene oxide castor oil, the lactic acid of recipe quantity half, is sufficiently mixed；
C. solution is lyophilized, obtains paclitaxel injection through pre-freeze, lyophilization, re-dry stage；
D. surplus dehydrated alcohol ultrasonic dissolution is added in the paclitaxel injection for taking step C to obtain, and surplus polyoxyethylene is added
Castor oil and surplus acetic acid, stirring 30min obtain paclitaxel injection.
Preferably, the freeze-drying program are as follows: solution is placed in pre-freeze 3 hours at -50 DEG C；Then it distils at -15 DEG C of temperature
It is 12 hours dry；Temperature is risen into 30 DEG C of progress re-dries again, the time is 6 hours.
The above technical solution of the present invention has the following advantages over the prior art, by carrying out part material at freeze-drying
Reason, so that taxol can both obtain complete dissolution in small amount dehydrated alcohol and Emulsifier EL-60, meanwhile, pass through
Freeze-drying reduces direct effect of most of ethoxylate castor oil to human body, therefore the present invention provides a kind of using letter
Single preparation process can reach that dissolubility is good, stability is good, quality is stable, relieving side effects caused by Emulsifier EL-60
Paclitaxel injection.In preparation process, without active carbon filtering, avoids reducing environmental pollution using active carbon, improve
Yield.Products of the present invention stability is good, and the stability of projects index such as impurity is significantly better than existing product, and this hair
The preparation process of bright offer is simple, easily-controllable, high production efficiency, production energy consumption are low.
Specific embodiment
In the present invention, if not refering in particular to, all parts, percentage are weight or volume unit, all equipment and original
Material etc. is commercially available or the industry is common.Method in following embodiments is unless otherwise instructed this field
Conventional method.
A kind of embodiment 1: paclitaxel injection
Preparation method are as follows:
A. by production prescription stock, supplementary material is weighed by recipe quantity respectively, spare；
B. the dehydrated alcohol of recipe quantity one third is added in taxol, ultrasound, the poly- of recipe quantity 4/5ths is added
Ethylene oxide castor oil, the lactic acid of recipe quantity half, is sufficiently mixed；
C. solution is placed in pre-freeze 3 hours at -50 DEG C；Then at -15 DEG C of temperature lyophilization 12 hours；Again by temperature
30 DEG C of progress re-dries are risen to, the time is to obtain paclitaxel injection through pre-freeze, lyophilization, re-dry stage in 6 hours；
D. surplus dehydrated alcohol ultrasonic dissolution is added in the paclitaxel injection for taking step C to obtain, and surplus polyoxyethylene is added
Castor oil and surplus acetic acid, stirring 30min obtain paclitaxel injection.
Comparative example 1:
(1) Emulsifier EL-60 and 4A type molecular sieve are added in Agitation Tank, stir 30 minutes, mixes well, sealed,
It is to be filtered.
(2) feed liquid prepared in step (1) is subjected to sterile filters pressing by 0.22 μm of filter membrane.
(3) taxol for accurately weighing recipe quantity, the dehydrated alcohol that 10 times of taxol amounts are added in mass ratio are uniformly mixed,
Sodium hydrogensulfite, lactic mixt (mass ratio 2: 1) are added as stabilizer, is stirred completely molten to taxol and stabilizer
Dehydrated alcohol is added to recipe quantity in solution.
(4) solution prepared in step 3 is subjected to sterile filters pressing by 0.22 μm of filter membrane.
(5) the above two solution prepared is uniformly mixed, carries out sterile filters pressing.
Comparative example 2:
(1) match auxiliary liquid: Emulsifier EL-60 adds dry molecular sieve, and nitrogen charging, sealing three days spare；After active carbon activation
It is sealed in spare in drier；It is transparent that molecular sieve with dehydrated alcohol is washed till ethyl alcohol, flings to ethyl alcohol, dry, cools and is sealed in drying
It is spare in device；Emulsifier EL-60, ethyl alcohol and active carbon are mixed into (rustless steel container), ultrasonic agitation.
(2) the sterile filters pressing of auxiliary liquid: using the sterile filters pressing of miillpore filter, weighing, and calculating need to add dehydrated alcohol amount；
(3) molten main ingredient: main ingredient is dry in vacuum oven, and precision weighs main ingredient, is added in the filtrate of step (2),
Dehydrated alcohol flushing is added, high pure nitrogen is filled, is sealed, jog, ultrasound to sample is completely dissolved；
(4) the sterile filters pressing of solution: by solution ultrasound, with the sterile filters pressing of miillpore filter.
1 stability contrast result of study of experimental example
By in the embodiment of the present invention 1 paclitaxel injection and comparative example 1, comparative example 2 in the product for preparing accelerate
Test, the investigation of long term test, measure indices.
Accelerated test
Pilot sample is taken, sets and places progress accelerated test investigation in 6 months under the conditions of 40 DEG C of ± 2 DEG C/RH75 ± 5%.In
1,2,3,6 the end of month respectively sample once, according to the investigation method pair of paclitaxel injection national standard WS1- (X-026) -2001Z
Every investigation project is detected, as a result compared with 0 month.As a result such as the following table 1:
Long term test takes pilot sample, at 25 DEG C ± 2 DEG C of temperature, places and carries out under conditions of relative humidity 60% ± 10%
Long term test.It is respectively sampled once in the 0th, 6 the end of month, according to paclitaxel injection national standard WS1- (X-026) -2001Z's
Investigation method detects every investigation project, compared with 0 month result.As a result such as the following table 2:
Respectively by embodiment 1, comparative example 1, comparative example 2 paclitaxel injection be added in 0.9% sodium chloride solution into
Row medicine stability is investigated, and the results are shown in Table 3:
2 hypersensitive test of experimental example
Zoopery is carried out using injection in injection made from the embodiment of the present invention 1 and comparative example 1-2, is converted into phase
With being used after effective quantity taxol.
Hypersensitive test method: taking cavy 18, be randomly divided into three groups, and 6mg/mL paclitaxel injection is injected intraperitoneally respectively,
Only, 1 time every other day, continuous 3 times, the 14th day and the 21st day after injecting for the first time, each group takes 3 cavys to dosage 3mg/ every time, by 6mg/
Only intravenous injection is attacked, and determines allergic reaction score value by 4 systemic anaphylaxis rating scale of table.
The results are shown in Table 5 (average value):
As seen from the results in Table 5, paclitaxel injection allergic reaction of the present invention is between 0-1 grades, Japanese yew in comparative example 1-2
Alcohol injection allergic reaction illustrates serious possessed by the substantially reduced former paclitaxel injection of the present invention between 1-2 grades
Allergic reaction.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or
It changes still within the protection scope of the invention.
Claims (4)
1. a kind of paclitaxel injection, it is characterised in that including taxol, dehydrated alcohol, lactic acid, the poly- hydrocarbon oxygen ester (35) of castor oil,
Wherein respectively at being grouped as are as follows:
2. paclitaxel injection according to claim 1, it is characterised in that respectively at being grouped as are as follows:
3. the preparation method of paclitaxel injection described in a kind of one of claim 1-2, which is characterized in that include the following steps
The present invention also provides the preparation methods for paclitaxel injection:
A. by production prescription stock, supplementary material is weighed by recipe quantity respectively, spare；
B. the dehydrated alcohol of recipe quantity one third is added in taxol, the polyoxy second of recipe quantity 4/5ths is added in ultrasound
Alkene castor oil, the lactic acid of recipe quantity half；
C. solution is lyophilized, obtains paclitaxel injection through pre-freeze, lyophilization, re-dry stage；
D. surplus dehydrated alcohol ultrasonic dissolution is added in the paclitaxel injection for taking step C to obtain, and surplus polyoxyethylene caster is added
Oil and surplus acetic acid, stirring 30min obtain paclitaxel injection.
4. Taxol injection liquid and preparation method thereof according to claim 3, it is characterised in that the freeze-drying program are as follows: solution is set
Pre-freeze 3 hours at -50 DEG C；Then at -15 DEG C of temperature lyophilization 12 hours；Temperature 30 DEG C are risen to again to be done again
Dry, the time is 6 hours.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811236777.2A CN109044969B (en) | 2018-10-23 | 2018-10-23 | Preparation method of paclitaxel injection |
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| CN201811236777.2A CN109044969B (en) | 2018-10-23 | 2018-10-23 | Preparation method of paclitaxel injection |
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| CN109044969A true CN109044969A (en) | 2018-12-21 |
| CN109044969B CN109044969B (en) | 2020-04-10 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110882213A (en) * | 2019-11-21 | 2020-03-17 | 海南紫杉园制药有限公司 | Paclitaxel injection and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101816644A (en) * | 2009-02-27 | 2010-09-01 | 海南四环医药有限公司 | Composition of taxol and phenylalanine and preparation method thereof |
| CN103833693A (en) * | 2014-03-04 | 2014-06-04 | 悦康药业集团有限公司 | Taxol compound and medicine composition containing same |
| CN106880589A (en) * | 2017-03-07 | 2017-06-23 | 华北制药股份有限公司 | A kind of paclitaxel injection and preparation method thereof |
-
2018
- 2018-10-23 CN CN201811236777.2A patent/CN109044969B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101816644A (en) * | 2009-02-27 | 2010-09-01 | 海南四环医药有限公司 | Composition of taxol and phenylalanine and preparation method thereof |
| CN103833693A (en) * | 2014-03-04 | 2014-06-04 | 悦康药业集团有限公司 | Taxol compound and medicine composition containing same |
| CN106880589A (en) * | 2017-03-07 | 2017-06-23 | 华北制药股份有限公司 | A kind of paclitaxel injection and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110882213A (en) * | 2019-11-21 | 2020-03-17 | 海南紫杉园制药有限公司 | Paclitaxel injection and preparation method thereof |
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Denomination of invention: A preparation method of paclitaxel injection Effective date of registration: 20230317 Granted publication date: 20200410 Pledgee: Industrial Bank Co.,Ltd. Haikou Branch Pledgor: HAINAN CHOITEC PHARMACEUTICAL CO.,LTD. Registration number: Y2023980034716 |
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