CN108815119A - A kind of pharmaceutical composition and preparation method thereof containing besifloxacin hydrochloride - Google Patents
A kind of pharmaceutical composition and preparation method thereof containing besifloxacin hydrochloride Download PDFInfo
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- CN108815119A CN108815119A CN201810905260.1A CN201810905260A CN108815119A CN 108815119 A CN108815119 A CN 108815119A CN 201810905260 A CN201810905260 A CN 201810905260A CN 108815119 A CN108815119 A CN 108815119A
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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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
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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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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- 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
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- 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
- A61K9/0048—Eye, e.g. artificial tears
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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Abstract
The pharmaceutical composition and preparation method thereof containing besifloxacin hydrochloride that the invention discloses a kind of, prescription include the component of following mass percent：Besifloxacin hydrochloride 5% ~ 10%, Amphipathilic block polymer carrier 5% ~ 65%, bacteriostatic agent 0.01% ~ 2%, thickener 0.01% ~ 20%, osmotic pressure regulator 0.01% ~ 40%, pH adjusting agent 0.01% ~ 10%, metal ion chelation agent 0.01% ~ 2% and water for injection.The stability of prepared besifloxacin hydrochloride eye drops is good, can significantly extend the action time of besifloxacin hydrochloride within the eye, improve its curative effect.
Description
Technical field
The pharmaceutical composition and preparation method thereof containing besifloxacin hydrochloride that the present invention relates to a kind of belongs to pharmaceutical preparation neck
Domain.
Background technique
Liposome（liposomes）It is a kind of pharmaceutical carrier, is taught by Bangham found in nineteen sixty-five earliest, its original
Material is lipoid substance, such as phosphatide, cholesterol etc..Because phosphatide and cholesterol have amphiphilic, i.e., one end is hydrophobic grouping, another
End is hydrophilic radical, while intermolecular hydrophilic and hydrophobic effect, the closing of the bilayer of formation phosphatide that can be spontaneous
Vesica, drug can be encapsulated in vesicle interior, using the physilogical characteristics of liposome, can specificity drug is transported to lesion group
Drug is knitted and released, to reach reduction toxicity, curative effect is improved, mitigates the therapeutic effect of side effect.Liposome technology
It is called the forth generation target administration technology of " biological missile " technology.
Phosphatide is the main membrane material for preparing liposome, mainly there is lecithin, phosphatidyl-ethanolamine（PE）, Fabaceous Lecithin,
Cholesterol, cephalin, cholesterol acetonyl ester, synthesis DPPC, synthesis PS, phosphatidylinositols（PI）, sphingomyelin（SPH）Deng.
Liposome technology can make the drug of encapsulating, and toxicity reduces, and enhances pharmacological action, extends action time, increase stability etc..And
The invention of long circulating liposome, improves circulation time and the target of liposome medicament at the shortcomings that further improving traditional liposomal
Tropism.In addition, pH sensitive liposome, thermo-responsive liposome, enzyme are oriented to liposome, photosensitive liposomes, antibody targeted liposome
Equal novel lipides are studied in also burning hot progress, and liposome technology actively answering in drug delivery field is highlighted
With.Oneself is through there is many drugs to be prepared to the form of Liposomal delivery, mainly field of antineoplastic medicaments now, and in addition there are anti-
Raw element class, antimycotic, anti parasitic class drug and vaccine etc..The form of administration being prepared to is based on injection, but in mouth
Formulation, eye-drops preparations etc. also have application.
Polyglycol derivatization phospholipid acyl ethanol amine（PEG-PE）It is degradable through U.S.'s food and drug pipe in vivo
Reason office（FDA）The drug carrier material that can be used for human body of approval has good biocompatibility and safety.PEG-PE is
A kind of linear polymer, in the conformation that surface of liposome extends in part, PEG-PE has very long polar group, can improve rouge
The hydrophily of liposome surface can be used as a kind of long-acting liposome.Due to PEG-PE critical micelle concentration（CMC）It is very low（10-6~
10-5mol/L）, the micella of formation is stable, and partial size is smaller（Less than 50nm）, the pharmaceutical carrier with wide application prospect.
Chinese patent（CN103860467A）Having used mPEG2000-DSPE is carrier, is prepared for Bromfenac
Sodium lipidosome eye drops.The bromfenac sodium liposome eye drops can significantly increase the diagonal permeability of the membrane of drug, and extend medicine
The action time of object within the eye, improve curative effect.Similar, Chinese patent（CN103860466A）Also use polyethylene glycol-
Phosphatidyl-ethanolamine is carrier, is prepared for Loteprednol eye drops.The Loteprednol nano-micelle eye drops similarly can be significant
Enhance infiltration of the Loteprednol to cornea, and the action time of Loteprednol within the eye can be extended.
Besifloxacin hydrochloride（Besifloxacin hydrochloride）It is fluoroquinolone drug, by
Bausch & Lomb Inc of the U.S.（Bausch & Lomb Inc.）Exploitation, and it is approved by the FDA in the United States listing in May, 2009, it is first
It is a to use fluoroquinolones exclusively for the non-systemic of ophthalmic remedy exploitation.Besifloxacin hydrochloride listing dosage form and specification be
0.6% besifloxacin hydrochloride suspension, trade name Besivance are clinically used for the treatment of bacterial conjunctivitis.
Besifloxacin hydrochloride chemical name is (R) -7- [3- amino hexahydro -1H- azepine -1- base] chloro- 1- cyclopropyl -6- fluoro- 1 of -8-,
4- dihydro -4- oxo -3- quinoline carboxylic acid hydrochloride, chemical structural formula are as follows：
。
Besifloxacin hydrochloride system have N- cyclopropyl 8- chlorine flouroquinolone drugs, by inhibit DNA of bacteria gyrase and
Topoisomerase Ⅳ plays anti-gram positive bacteria and negative bacterium effect.DNA gyrase is bacterium DNA replication, transcription and repairing institute
The key enzyme needed；Key enzyme needed for chromosomal DNA separates when Topoisomerase Ⅳ is bacterium division.Besifloxacin hydrochloride is facing
Extraordinary bactericidal effect is shown in bed test, and to causing the eye pathogenic bacteria of bacterial conjunctivitis to have broad-spectrum antiseptic living
Property.
Although besifloxacin hydrochloride bactericidal effect is strong, has a broad antifungal spectrum, but if besifloxacin hydrochloride is prepared into common molten
, there is the following in liquid type eye drops：（1）The stability of besifloxacin hydrochloride is poor, is easier to degrade in the solution,
Especially to the stability sharp fall of light；（2）The dissolubility of besifloxacin hydrochloride is bad, is also not easy to be prepared into solution-type eye
Use preparation；（3）Regular solution type eye drops is easily lost during blink, is unfavorable for besifloxacin hydrochloride and is played within the eye
Its antibacterial action.
Summary of the invention
The pharmaceutical composition and preparation method thereof containing besifloxacin hydrochloride that the purpose of the present invention is to provide a kind of, it is intended to
Solve the problems, such as besifloxacin hydrochloride eye drip agent method made above.
The purpose of the present invention can be achieved by the following measures：
A kind of pharmaceutical composition containing besifloxacin hydrochloride provided by the invention is a kind of liposome nano-micelle eye drops,
Prescription includes the component of following mass percent：Besifloxacin hydrochloride 5% ~ 10%, Amphipathilic block polymer carrier 5% ~ 65%, suppression
Microbial inoculum 0.01% ~ 2%, thickener 0.01% ~ 20%, osmotic pressure regulator 0.01% ~ 40%, pH adjusting agent 0.01% ~ 10%, metal ion
Chelating agent 0.01% ~ 2%, remaining is water for injection.
Besifloxacin hydrochloride liposome nano-micelle eye drops provided by the invention, used carrier are two kinds of polymerizations
The Amphipathilic block polymer of object composition, the material of hydrophilic area are polyethylene glycol, in polyoxyethylene, polyvinylpyrrolidone
One kind, the material of hydrophobic region are one of polyoxypropylene, polystyrene, polylactic acid, phosphatidyl-ethanolamine.It is preferred amphipathic
Block polymer carrier is mPEG2000-DSPE.MPEG2000-DSPE polymer is by FDA batches
The quasi- pharmaceutic adjuvant that can be used for being injected intravenously, has many advantages, such as nontoxic, low immunogenicity, degradable in vivo, by Germany
The production of Lipoid company.
A kind of pharmaceutical composition containing besifloxacin hydrochloride provided by the invention, the bacteriostatic agent in component are that benzene pricks chlorine
One of ammonium, benzalkonium bromide and ethyl hydroxy benzoate.
A kind of pharmaceutical composition containing besifloxacin hydrochloride provided by the invention, the thickener in component are hydroxypropyl first
One of base cellulose, polycarbophil, polyvinyl alcohol and hydroxypropyl cellulose are a variety of.
A kind of pharmaceutical composition containing besifloxacin hydrochloride provided by the invention, the osmotic pressure regulator in component are
One of sodium chloride, glucose, mannitol, glycerol, xylitol, sorbierite, boric acid are a variety of.
There are two ways to nano-micelle is often used is prepared, one is direct dissolution method, another kind is dialysis, prepares micella
Method depend on the dissolubility of polymer in water.Under room temperature or higher temperature, the polymer of good water solubility can be directly molten
In Xie Yushui or aqueous solution（PBS buffer solution or physiological saline）, the micellar solution of clear is formed when being greater than CMC.Water
The polymer of dissolubility difference must be then first dissolved in organic solvent miscible with water, then be removed by solvent evaporated method or dialysis
Organic solvent, in the process, polymer gradually form the nano-micelle of stable structure.Dialysis is that laboratory prepares polymer
The common method of micella, but it is not suitable for mass production.There are commonly solvents ethyl alcohol, dimethyl sulfoxide, N, N- dimethyl methyl
Amide etc..
The preparation method of the above-mentioned nano-micelle eye drops containing besifloxacin hydrochloride provided by the invention, including following step
Suddenly：
（1）The polycarbophil of recipe quantity, natrium adetate are weighed, mannitol is added in suitable water for injection, stirs at room temperature
Mix swelling 10 ~ 12 hours, obtained solution 1；
（2）The benzalkonium chloride and sodium chloride for weighing recipe quantity are added in solution 1, stir evenly obtained after adding suitable quantity of water to dissolve
Solution 2；
（3）The mPEG2000-DSPE and besifloxacin hydrochloride for weighing recipe quantity are dissolved in the dehydrated alcohol of 300mL,
Stirring after being dried with nitrogen instrument removal solvent, is then added to 300mL water for injection, is stirring evenly and then adding into being completely dissolved
Into solution 2, pH value is adjusted to 6.2 ~ 6.5 with 10% sodium hydroxide solution, water for injection is added and adjusts volume to 1000mL.
It is prepared by a kind of above pharmaceutical composition and preparation method thereof containing besifloxacin hydrochloride provided by the invention
Liposome nano-micelle eye drops, the stability of besifloxacin hydrochloride is good, can significantly extend besifloxacin hydrochloride within the eye
Action time improves its curative effect.
Specific embodiment
Following exemplary embodiments are used to illustrate the present invention, the letter that technical staff in the art is the present invention
Single replacement or improvement etc. belong within the technical solution that the present invention is protected.
Embodiment 1：The preparation of besifloxacin hydrochloride eye drops
Composition is as follows：
Besifloxacin hydrochloride 6.56g
MPEG2000-DSPE 39.36g
Polycarbophil 3.28g
Natrium adetate 0.03g
Benzalkonium chloride 0.03g
Mannitol 6.56g
Sodium chloride 3.28g
10% sodium hydroxide solution is appropriate
Water for injection adds to 1000mL
Preparation method：
（1）The polycarbophil of recipe quantity, natrium adetate are weighed, mannitol is added in suitable water for injection, stirs at room temperature
Mix swelling 10 ~ 12 hours, obtained solution 1；
（2）The benzalkonium chloride and sodium chloride for weighing recipe quantity are added in solution 1, stir evenly obtained after adding suitable quantity of water to dissolve
Solution 2；
（3）The mPEG2000-DSPE and besifloxacin hydrochloride for weighing recipe quantity are dissolved in the dehydrated alcohol of 300mL,
Stirring after being dried with nitrogen instrument removal solvent, is then added to 300mL water for injection, is stirring evenly and then adding into being completely dissolved
Into solution 2, pH value is adjusted to 6.2 ~ 6.5 with 10% sodium hydroxide solution, water for injection is added and adjusts volume to 1000mL.
Embodiment 2：The preparation of besifloxacin hydrochloride eye drops
Composition is as follows：
Besifloxacin hydrochloride 6.56g
MPEG2000-DSPE 52.26g
Polycarbophil 4.20g
Natrium adetate 0.10g
Benzalkonium chloride 0.10g
Mannitol 22.00g
Sodium chloride 4.50g
10% sodium hydroxide solution is appropriate
Water for injection adds to 1000mL
Preparation method：
（1）The polycarbophil of recipe quantity, natrium adetate are weighed, mannitol is added in suitable water for injection, stirs at room temperature
Mix swelling 10 ~ 12 hours, obtained solution 1；
（2）The benzalkonium chloride and sodium chloride for weighing recipe quantity are added in solution 1, stir evenly obtained after adding suitable quantity of water to dissolve
Solution 2；
（3）The mPEG2000-DSPE and besifloxacin hydrochloride for weighing recipe quantity are dissolved in the dehydrated alcohol of 300mL,
Stirring after being dried with nitrogen instrument removal solvent, is then added to 300mL water for injection, is stirring evenly and then adding into being completely dissolved
Into solution 2, pH value is adjusted to 6.2 ~ 6.5 with 10% sodium hydroxide solution, water for injection is added and adjusts volume to 1000mL.
Embodiment 3：The preparation of besifloxacin hydrochloride eye drops
Composition is as follows：
Besifloxacin hydrochloride 6.56g
MPEG2000-DSPE 65.60g
Polycarbophil 4.20g
Natrium adetate 0.10g
Benzalkonium chloride 0.10g
Mannitol 22.00g
Sodium chloride 4.50g
10% sodium hydroxide solution is appropriate
Water for injection adds to 1000mL
Preparation method：
（1）The polycarbophil of recipe quantity, natrium adetate are weighed, mannitol is added in suitable water for injection, stirs at room temperature
Mix swelling 10 ~ 12 hours, obtained solution 1；
（2）The benzalkonium chloride and sodium chloride for weighing recipe quantity are added in solution 1, stir evenly obtained after adding suitable quantity of water to dissolve
Solution 2；
（3）The mPEG2000-DSPE and besifloxacin hydrochloride for weighing recipe quantity are dissolved in the dehydrated alcohol of 300mL,
Stirring after being dried with nitrogen instrument removal solvent, is then added to 300mL water for injection, is stirring evenly and then adding into being completely dissolved
Into solution 2, pH value is adjusted to 6.2 ~ 6.5 with 10% sodium hydroxide solution, water for injection is added and adjusts volume to 1000mL.
Embodiment 4：The stability contrast of besifloxacin hydrochloride eye drops
Inspection method：HPLC method（《Chinese Pharmacopoeia》The two annex V D of version in 2010）；
Apparatus：Shimadzu Corporation of Shimadzu LC-20AD high performance liquid chromatograph Japan；
Detector：UV detector；
Experimental condition：Chromatographic column is Kromasil-C18 chromatographic column（Specification：250mm × 4.6mm, 5m）, Detection wavelength is
275nm, mobile phase are：Acetonitrile：Water=75:25.
Stability contrast result is as follows：
Claims (7)
1. a kind of pharmaceutical composition containing besifloxacin hydrochloride, prescription includes the component of following mass percent：Hydrochloric acid shellfish
Xisha star 5% ~ 10%, Amphipathilic block polymer carrier 5% ~ 65%, bacteriostatic agent 0.01% ~ 2%, thickener 0.01% ~ 20%, osmotic pressure
Regulator 0.01% ~ 40%, pH adjusting agent 0.01% ~ 10%, metal ion chelation agent 0.01% ~ 2%, remaining is water for injection.
2. a kind of pharmaceutical composition containing besifloxacin hydrochloride according to claim 1, the amphiphilic that includes in prescription
Property block polymer carrier hydrophilic area material be one of polyethylene glycol, polyoxyethylene, polyvinylpyrrolidone, dredge
The material in pool is one of polyoxypropylene, polystyrene, polylactic acid, phosphatidyl-ethanolamine.
3. a kind of pharmaceutical composition containing besifloxacin hydrochloride according to claim 1, the amphiphilic that includes in prescription
Property block polymer carrier be mPEG2000-DSPE.
4. a kind of pharmaceutical composition containing besifloxacin hydrochloride according to claim 1, include in prescription is antibacterial
Agent is one of benzalkonium chloride, benzalkonium bromide and ethyl hydroxy benzoate.
5. a kind of pharmaceutical composition containing besifloxacin hydrochloride according to claim 1, the thickening that includes in prescription
Agent is one of hypromellose, polycarbophil, polyvinyl alcohol and hydroxypropyl cellulose or a variety of.
6. a kind of pharmaceutical composition containing besifloxacin hydrochloride according to claim 1, the infiltration that includes in prescription
Pressure regulator is one of sodium chloride, glucose, mannitol, glycerol, xylitol, sorbierite, boric acid or a variety of.
7. a kind of pharmaceutical composition containing besifloxacin hydrochloride, preparation method described according to claim 1 ~ 6 are as follows：
（1）The polycarbophil of recipe quantity, natrium adetate are weighed, mannitol is added in suitable water for injection, stirs at room temperature
Mix swelling 10 ~ 12 hours, obtained solution 1；
（2）The benzalkonium chloride and sodium chloride for weighing recipe quantity are added in solution 1, stir evenly obtained after adding suitable quantity of water to dissolve
Solution 2；
（3）The mPEG2000-DSPE and besifloxacin hydrochloride for weighing recipe quantity are dissolved in the dehydrated alcohol of 300mL,
Stirring after being dried with nitrogen instrument removal solvent, is then added to 300mL water for injection, is stirring evenly and then adding into being completely dissolved
Into solution 2, pH value is adjusted to 6.2 ~ 6.5 with 10% sodium hydroxide solution, water for injection is added and adjusts volume to 1000mL.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021250635A1 (en) * | 2020-06-11 | 2021-12-16 | Vyome Therapeutics Inc. | Acid salts of fluoroquinolone carboxylic acid based compositions and methods of making and using the same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102114020A (en) * | 2009-12-30 | 2011-07-06 | 北京德众万全医药科技有限公司 | Pharmaceutical composition containing besivance or salts thereof and preparation method thereof |
| US20130345297A1 (en) * | 2007-12-31 | 2013-12-26 | Samyang Biopharmaceuticals Corporation | Method for stabilizing amphiphilic block copolymer micelle composition containing poorly water-soluble drug |
| CN105412003A (en) * | 2014-09-12 | 2016-03-23 | 广东东阳光药业有限公司 | Besifloxacin hydrochloride eye drops and preparation method thereof |
| US11179334B1 (en) * | 2019-02-04 | 2021-11-23 | Florida A&M University | Targeted carriers for tacrolimus for ocular inflammation |
-
2018
- 2018-08-10 CN CN201810905260.1A patent/CN108815119B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130345297A1 (en) * | 2007-12-31 | 2013-12-26 | Samyang Biopharmaceuticals Corporation | Method for stabilizing amphiphilic block copolymer micelle composition containing poorly water-soluble drug |
| CN102114020A (en) * | 2009-12-30 | 2011-07-06 | 北京德众万全医药科技有限公司 | Pharmaceutical composition containing besivance or salts thereof and preparation method thereof |
| CN105412003A (en) * | 2014-09-12 | 2016-03-23 | 广东东阳光药业有限公司 | Besifloxacin hydrochloride eye drops and preparation method thereof |
| US11179334B1 (en) * | 2019-02-04 | 2021-11-23 | Florida A&M University | Targeted carriers for tacrolimus for ocular inflammation |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021250635A1 (en) * | 2020-06-11 | 2021-12-16 | Vyome Therapeutics Inc. | Acid salts of fluoroquinolone carboxylic acid based compositions and methods of making and using the same |
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