CN1723887A - Paclitaxel injection, and its prepn. method - Google Patents

Paclitaxel injection, and its prepn. method Download PDF

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Publication number
CN1723887A
CN1723887A CNA2005100279133A CN200510027913A CN1723887A CN 1723887 A CN1723887 A CN 1723887A CN A2005100279133 A CNA2005100279133 A CN A2005100279133A CN 200510027913 A CN200510027913 A CN 200510027913A CN 1723887 A CN1723887 A CN 1723887A
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China
Prior art keywords
injection
paclitaxel
preparation
stabilizing agent
solvent
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Pending
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CNA2005100279133A
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Chinese (zh)
Inventor
陈建明
高保安
黄尊动
陈海生
肖琴
黄成安
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Chongqing Furui Pharmaceutical Co., Ltd.
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CHONGQING FURUI PHARMACEUTICAL Co Ltd
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Application filed by CHONGQING FURUI PHARMACEUTICAL Co Ltd filed Critical CHONGQING FURUI PHARMACEUTICAL Co Ltd
Priority to CNA2005100279133A priority Critical patent/CN1723887A/en
Publication of CN1723887A publication Critical patent/CN1723887A/en
Priority to PCT/CN2006/001665 priority patent/WO2007009355A1/en
Pending legal-status Critical Current

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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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • 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
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • 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
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • 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
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • 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
    • A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid

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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

A taxi-alcohol injection is prepared from taxi-alcohol, solvent for injection and stabilizer through dissolving the stabilizer in said solvent by thermal stirring or ultrasonic stirring, adding taxi-alcohol, stirring, filtering, loading it in containers and sterilizing. It has low toxic by-effect.

Description

A kind of paclitaxel injection and preparation method thereof
Technical field
The present invention relates to medical technical field, be specifically related to dissolve the anticarcinogen paclitaxel and share new prescription and the preparation method that suitable stabilizing agent is prepared into a kind of novel paclitaxel injection with solvent for injection.
Background technology
Paclitaxel (Paclitaxel, trade name Taxol) is the efficient anticarcinogen that extracts from Taxus taxaceae plant mountain mahogany (Taxusbrevidolia, Pacific yew), and it is a kind of diterpene-kind compound of complexity, and molecular formula is C 47H 51NO 14, relative molecular mass is 853.9.Paclitaxel has good anti-cancer activity, is used for the treatment of ovarian cancer, breast carcinoma, colon cancer, nonsmall-cell lung cancer, neck cancer, melanoma etc., has better curative effect.
The dissolubility of paclitaxel in water is very little, water-soluble hardly (＜0.004mg/ml), the oral administration bioavailability is poor, can only pass through intravenous administration.Existing clinical formulation for paclitaxel commonly used is that the oil preparation (Cremophor  EL) that is mixed and made at 1: 1 with polyoxyethylene castor oil and dehydrated alcohol is a paclitaxel Cremophor preparation, can discharge histamine during polyoxyethylene castor oil degradation in vivo in this double solvent, thereby cause severe anaphylactic reaction.The expensive precious company of U.S. Bu Maishi is at the paclitaxel injection (commodity are called taxol) of China's registration, point out " for preventing severe anaphylactic reaction; all accept this medicine patient should give corticosteroid (as dexamethasone), diphenhydramine and bisfentidine (as cimetidine, ranitidine) in advance " in its description, and the administration process need be carried out the strictness monitoring, and whole process is inconvenience very.The Cremophor preparation is poor at the dilution rear stability in addition, easily separates out precipitation, has reduced clinical application safety, has influenced absorbing of paclitaxel simultaneously.Shama A, a scape Qing have been done research (Sharma A, et al., Int J Cancer, 1997,71 (1): 103 to Paclitaxel liposome; Open the scape Qing, West China pharmaceutical journal, 2001,16 (1): 23), the stable temperature influence of liposome is big, and the resting period is short, because the particle diameter of liposome is bigger, its main targeting moiety is liver, spleen, and other site distribution is very low, and its curative effect to some tumor can not reach requirement.Csethati has prepared multiple paclitaxel wrappage (Cserhati T with various cyclodextrin, et al., J Pharm Biomed Anal, 1995,13:533-541.), but cyclodextrin has bigger anaphylaxis and haemolysis, the extensive use of bigger untoward reaction restriction paclitaxel cyclodextrin wrappage.Open to teach to eat etc. paclitaxel, phospholipid and cholate are dissolved in the organic solvent, make injectable powder (CN1148957 with freeze-drying, 1997.), directly add 5% glucose during use or 0.9% sodium chloride injection dissolving posterior vein instils, but easily have paclitaxel to separate out during dilution.In a word, comprise other preparation such as microemulsion, pro-liposome, topical etc.,, can not replace paclitaxel Cremophor preparation fully because of there is certain problem in it at aspects such as envelop rate, stability, side effect, bioavailability or convenient drug administration.
Summary of the invention
The invention provides a kind of novel paclitaxel injection and preparation method thereof.Promptly dissolve paclitaxel and share suitable stabilizing agent and be prepared into injection with solvent for injection.This injection is diluted to 5%, 10% glucose or 0.9% sodium chloride solution that the injection rear stability is good, side effect is little, has guaranteed the safety of medication, does not have the phenomenon of separating out that is prone to after other dosage form dilution, has further guaranteed effective utilization of paclitaxel.
Paclitaxel injection of the present invention is made up of following component:
Component W/v% content
Paclitaxel stabilizing agent solvent for injection 0.01-2 1-70 surplus
Wherein stabilizing agent comprises but is not limited to injection soybean phospholipid, egg yolk lecithin, tween 80, cholesterol, sodium cholate, poloxamer 188 (F68) or glycerin mono-fatty acid ester etc., selects one or more mixture for use.
Solvent for injection includes but not limited to dehydrated alcohol, glycerol, propylene glycol, Polyethylene Glycol etc., selects one or more mixture for use.
The preparation method of paclitaxel injection of the present invention is as follows:
Take by weighing in the stabilizing agent adding solvent for injection by formula ratio, room temperature or heated and stirred or the ultrasonic stabilizing agent that makes dissolve, and the temperature of heating is 40-90 ℃, adds paclitaxel again, and stirring or the ultrasonic paclitaxel that makes dissolve fully, filter, and packing, sterilization gets paclitaxel injection.
Earlier stabilizing agent is dissolved in the solvent for injection in the described preparation method, adds paclitaxel again, purpose is a paclitaxel decomposes when avoiding the heating for dissolving stabilizing agent.
Filtration device in the described preparation method includes but not limited to microporous filter membrane, sand filtration rod, vertical molten funnel, filter press device etc., adopts a kind of independent use or more than one common uses.
Sterilization in the described preparation method is meant sterilization such as the method that includes but not limited to flowing steam, high steam, temperature 100-121 ℃, time 5-120 minute.
The novel paclitaxel injection of the present invention's preparation is colourless or light yellow transparent liquid.Drug loading is 0.1-20mg paclitaxel/ml.Injection of the present invention can directly be dissolved in 5%, 10% glucose or 0.9% sodium chloride solution becomes the injection posterior vein to instil.
The novel paclitaxel injection that does not contain polyoxyethylene castor oil provided by the invention, it has good stable and water solublity, the product drug loading is big, can directly be dissolved in 5%, 10% glucose or 0.9% sodium chloride solution and become the injection posterior vein to instil, and is easy to use.Injection after 72 hours its content be the 98%-102% of labelled amount, exhibit stabilization improves greatly.And need not desensitization and strict monitoring before the administration, make patient acceptant, improved clinical drug safety, alleviated patient's burden simultaneously.This injection also has certain targeting.The toxic and side effects of paclitaxel injection of the present invention is well below paclitaxel cremophor preparation.Paclitaxel injection of the present invention has overcome a series of problems that various in the past dosage forms exist at aspects such as envelop rate, stability, side effect, bioavailability and convenient drug administration, is common pursue, the comparatively ideal dosage form of vast medical personnel and patient.Paclitaxel injection preparation technology method of the present invention is simple, is applicable to a large amount of preparations and suitability for industrialized production.
The specific embodiment
The novel paclitaxel injection of embodiment 1 preparation
Measure 30 milliliters of dehydrated alcohol, add injection soybean phospholipid 15 grams, cholesterol 1.66 grams, tween 80 50 grams, 45 ℃ of heated and stirred make dissolving, add 600 milligrams of paclitaxels, be stirred to dissolving, add dehydrated alcohol to 100 milliliter, filter with microporous filter membrane (0.22um), packing, routine disinfection gets final product.
The novel paclitaxel injection of embodiment 2 preparations
Measure 20 milliliters of dehydrated alcohol, add injection soybean phospholipid 10 grams, sodium cholate 0.1 gram, tween 80 5 grams, 60 ℃ of heated and stirred make dissolving, add 500 milligrams of paclitaxels, be stirred to dissolving, add dehydrated alcohol to 100 milliliter, filter with medium size sand filtration rod, packing, routine disinfection gets final product.
The novel paclitaxel injection of embodiment 3 preparations
Measure 5 milliliters of dehydrated alcohol, 5 milliliters of Polyethylene Glycol, mix, add injection soybean phospholipid 12 grams, poloxamer (F68) 1.5 grams, sodium cholate 0.1 gram, ultrasonicly make its dissolving, add 400 milligrams of paclitaxels, be stirred to dissolving, add dehydrated alcohol to 100 milliliter, filter with vertical molten funnel (No. 6), packing, routine disinfection gets final product.
The novel paclitaxel injection of embodiment 4 preparations
Measure 20 milliliters of dehydrated alcohol, 10 milliliters of glycerol, mix, add tween 80 5 grams, stir and make dissolving, add 300 milligrams of paclitaxels, ultrasonic to dissolving, add dehydrated alcohol to 100 milliliter, filter with the filter press device, packing, routine disinfection gets final product.
The novel paclitaxel injection of embodiment 5 preparations
Measure 15 milliliters of dehydrated alcohol, 15 milliliters of propylene glycol, mix, add injection soybean phospholipid 15 grams, cholesterol 1.5 grams, tween 80 10 grams, 75 ℃ of heated and stirred make dissolving, add 1500 milligrams of paclitaxels, ultrasonic to dissolving, add dehydrated alcohol to 100 milliliter, with filter press device coarse filtration, use microporous filter membrane (0.22um) fine straining then earlier, packing, routine disinfection gets final product.
The novel paclitaxel injection of embodiment 6 preparations
Measure 30 milliliters of propylene glycol, add injection soybean phospholipid 10 grams, cholesterol 1.5 grams, tween 80 5 grams, 85 ℃ of heated and stirred make dissolving, add 20 milligrams of paclitaxels, are stirred to dissolving, add propylene glycol to 100 milliliter, with medium size sand filtration rod coarse filtration, use microporous filter membrane (0.22um) fine straining then, packing earlier, routine disinfection gets final product.Embodiment 7 novel paclitaxel injections (with the injection of embodiment 1 preparation) and paclitaxel Cremophor injection apparent comparison in 5% glucose diluent of preparing with polyoxyethylene castor oil see Table 1.
Table 1
Time (h) 0 2 4 8 12 18 24 36 48 60 72
Injection of the present invention Clarification Clarification Clarification Clarification Clarification Clarification Clarification Clarification Clarification Clarification Slightly turbid
The Cremophor injection Clarification Clarification Clarification Clarification Slightly turbid Slightly turbid Muddy Muddy Precipitation Precipitation Precipitation
。
Embodiment 8 novel paclitaxel injections stable content test in 5% glucose diluent (is example with embodiment 1 injection)
Measure the content of novel paclitaxel injection different time in 5% glucose diluent with HPLC, separate out and make measurement result can not react actual drug content for fear of having medicine, so in the preparation need testing solution, after earlier test sample being crossed the microporous filter membrane filtration of 0.22um, and then be configured to need testing solution.The result who records like this is only real medicament contg.Result of the test sees Table 2.
Table 2
Time (h) 0 2 4 8 12 18 24 36 48 60 72
Paclitaxel concentration mg/ml 0.3620 0.3620 0.3628 0.3622 0.3618 0.3619 0.3616 0.3612 0.3588 0.3556 0.3540
Labelled amount (%) 100.00 100.00 100.22 100.05 99.94 99.97 99.89 99.78 99.12 98.23 97.79
。

Claims (7)

1. paclitaxel injection is characterized in that it is made up of following component:
Component W/V% content
Paclitaxel 0.01-2
Stabilizing agent 1-70
The solvent for injection surplus.
2. paclitaxel injection as claimed in claim 1 is characterized in that described stabilizing agent is selected from one or more the mixture in soybean phospholipid, egg yolk lecithin, tween 80, cholesterol, sodium cholate, poloxamer 188 or the glycerin mono-fatty acid ester.
3. paclitaxel injection as claimed in claim 1 is characterized in that described solvent for injection is selected from one or more the mixture in dehydrated alcohol, glycerol, propylene glycol or the Polyethylene Glycol.
4. the preparation method of a paclitaxel injection is characterized in that by claim 1 prescription, takes by weighing stabilizing agent and adds in the solvent for injection, 40-90 ℃ of stirring of room temperature or heating or the ultrasonic stabilizing agent that makes dissolve, and add paclitaxel again, and stirring or the ultrasonic paclitaxel that makes dissolve, filter, packing, sterilization is promptly.
5. preparation method as claimed in claim 4 is characterized in that being selected from one or more mixture in soybean phospholipid, egg yolk lecithin, tween 80, cholesterol, sodium cholate, poloxamer 188 or the glycerin mono-fatty acid ester at stabilizing agent described in the preparation method.
6. preparation method as claimed in claim 4 is characterized in that being selected from one or more mixture in dehydrated alcohol, glycerol, propylene glycol or the Polyethylene Glycol at solvent for injection described in the preparation method.
7. preparation method as claimed in claim 4 is characterized in that at the device of filtration described in the preparation method, adopts a kind of independent use or more than one common uses in microporous filter membrane, sand filtration rod, vertical molten funnel or the filter press device.
CNA2005100279133A 2005-07-20 2005-07-20 Paclitaxel injection, and its prepn. method Pending CN1723887A (en)

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PCT/CN2006/001665 WO2007009355A1 (en) 2005-07-20 2006-07-13 Paclitaxel injection and preparation method thereof

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008098415A1 (en) * 2007-02-14 2008-08-21 Beijing Century Biocom Pharmaceutical Technology Co., Ltd. Pharmaceutical composition containing taxane and its preparation process and application
CN101190214B (en) * 2007-01-31 2010-09-15 广东庆发药业有限公司 Paclitaxel injection and preparation method thereof
CN101574318B (en) * 2009-05-31 2011-06-15 海口市制药厂有限公司 Preparation method of taxol injection
CN101190213B (en) * 2006-11-30 2011-07-13 天津天士力集团有限公司 Docetaxel injection and preparation method thereof
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

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019081285A1 (en) 2017-10-27 2019-05-02 Basf Se Method for producing ethyleneamines
WO2019081283A1 (en) 2017-10-27 2019-05-02 Basf Se Method for the production of ethyleneamines
CN115634195B (en) * 2022-10-26 2024-08-06 华北制药集团动物保健品有限责任公司 Preparation method of compound butafos injection

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1241561C (en) * 2002-12-16 2006-02-15 天津大学 Taxane injecta preparation
JP2005225818A (en) * 2004-02-13 2005-08-25 Otsuka Pharmaceut Factory Inc Medicinal composition of paclitaxel or docetaxel
CN1714785A (en) * 2004-06-28 2006-01-04 胡宇方 Concentrated emulsifier containing taxol compound and its using method

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101190213B (en) * 2006-11-30 2011-07-13 天津天士力集团有限公司 Docetaxel injection and preparation method thereof
CN101190214B (en) * 2007-01-31 2010-09-15 广东庆发药业有限公司 Paclitaxel injection and preparation method thereof
WO2008098415A1 (en) * 2007-02-14 2008-08-21 Beijing Century Biocom Pharmaceutical Technology Co., Ltd. Pharmaceutical composition containing taxane and its preparation process and application
CN101574318B (en) * 2009-05-31 2011-06-15 海口市制药厂有限公司 Preparation method of taxol injection
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

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