CN102671210A - Clathrate compound of beta-cyclodextrin or derivatives of beta-cyclodextrin for Nifuroxazide and preparation method for preparation of clathrate compound - Google Patents
Clathrate compound of beta-cyclodextrin or derivatives of beta-cyclodextrin for Nifuroxazide and preparation method for preparation of clathrate compound Download PDFInfo
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- CN102671210A CN102671210A CN2012101414594A CN201210141459A CN102671210A CN 102671210 A CN102671210 A CN 102671210A CN 2012101414594 A CN2012101414594 A CN 2012101414594A CN 201210141459 A CN201210141459 A CN 201210141459A CN 102671210 A CN102671210 A CN 102671210A
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Abstract
The invention relates to a clathrate compound of beta-cyclodextrin or derivatives of the beta-cyclodextrin for Nifuroxazide and a preparation method for a preparation of the clathrate compound. The clathrate compound consists of the following raw materials in weight ratio: 1 percent of Nifuroxazide, 0.125-0.25 percent of povidone K30 and 5-25 percent of beta-cyclodextrin or derivatives of the beta-cyclodextrin. The invention aims to solve the problems that traditional market products are low in water solubility and dissolution rate generally, sediments are often generated and colors are darkened during the application process and the like. According to the invention, clathration is performed on the Nifuroxazide by adopting the beta-cyclodextrin or the derivatives of the beta-cyclodextrin, so that the Nifuroxazide can be easily dissolved in water, and meanwhile, the stability of the Nifuroxazide is improved; the form of the preparation is expanded; the route of administration is enlarged; and an application effect is promoted.
Description
Technical field
The present invention relates to the veterinary drug technical field, relate to feed additive field simultaneously, also relate to a kind of preparation of nifuroxazide cyclodextrin clathrate, be specially a kind of clathrate of nifuroxazide beta-schardinger dextrin-or derivatives thereof and the method for preparing of preparation.
Background technology
Nifuroxazide (Nifuroxazide) has another name called nifuroxazide, and people's medical science section is the itrofurans antineoplastic agent, clinically is usually used in treating colitis and diarrhoea etc.The nifuroxazide has a broad antifungal spectrum, antibacterial activity is high, and Mlc is low, does not have cross resistance with sulfonamides, Du-6859a and other antibiotic, and its antimicrbial power receives other organic influence, effect stability hardly.Because this product can effectively be prevented and treated intestinal or the urinary tract systemic disease that poultry escherichia coli, Salmonella, pasteurellosis bacillus, Richter scale bacillus, aerobacteria, Bacillus proteus, necrobacillus and staphylococcus etc. cause; Can effectively prevent dysentery, promote animal to search for food, by the European Community legal be unique new and effective feed additive of animal specific.China is in recent years also by veterinary drug and feed additive manufacturing enterprise Application and Development; Be mainly used in the coccidiosis of control chicken at veterinary clinic; Diseases such as white comb that leukocytozoon causes and blackhead; In aquatic animal, be used for antibacterial, vibrio and fungus-caused intestinal and systemic disease, the susceptibility effect in water is far above other antimicrobial drug.In feed additive industry, be mainly used in the interpolation in pig, chicken and the aquatic animal feed, can effectively prevent dysentery, promote that animal searches for food.
Nifuroxazide, its chemistry 4-hydroxyl-2 by name
' -(5-nitrofuran methene)-phenylhydrazide is yellow or foresythia powder, is insoluble in water usually or is slightly soluble in water; Because this product water solublity is low; Cause bioavailability low, influence giving full play to of drug effect, directly influence the absorption after the poultry medication; It is big the effect diversity often to occur, has limited the approach of parenterai administration simultaneously.At present domestic many with the crude drug of content >=98.5% and the powder supply the market of content 20%, also there is not product-feed market fine, very convenient application to the veterinary drug and the feed additive of these article, affect the extensive use of this product.Again it; At present the commercially available prod ubiquity water solublity of supply is low, dissolution is low and application process in problems such as deposition produces, darkens are often arranged.The present invention adopts the beta-schardinger dextrin-or derivatives thereof that nifuroxazide is carried out enclose, can improve its dissolubility and bioavailability.Cooperate each dosage form to add corresponding auxiliary material again and process preparation, thereby improved the dissolubility of preparation in water that contains nifuroxazide greatly, make the pharmacologically active of effective ingredient in the product and physicochemical property reliable and stable.Through retrieval, do not find to have to relate to the patent of nifuroxazide with the clathrate of beta-schardinger dextrin-or derivatives thereof.
Summary of the invention
The present invention provides a kind of clathrate of nifuroxazide beta-schardinger dextrin-or derivatives thereof and the method for preparing of preparation thereof for problems such as the poor solubility that solves prior art nifuroxazide preparation and exist, dissolution rate, poor storage performance.This method is utilized the cyclodextrin inclusion compound effect, with the nifuroxazide enclose, makes it soluble in water, improves its stability simultaneously, expands preparation formulation simultaneously, enlarges medicine-feeding way, promotes effect.
The beta-schardinger dextrin-or derivatives thereof has the tubular molecular structure, and is soluble in water, and the enclose amount is big; The characteristics that toxicity is low, and can be used for tablet, capsule, granule, injection, in inclusion process; The beta-schardinger dextrin-or derivatives thereof can be combined in pharmaceutical pack in the tubular molecule; Can the nifuroxazide enclose be formed clathrate through test beta-schardinger dextrin-or derivatives thereof, its clathrate dissolubility improves a lot, and reaches soluble in water by being slightly soluble in water.
The beta-schardinger dextrin-or derivatives thereof that adopts among the present invention comprises beta-schardinger dextrin-(β-CD), hydroxypropyl (HP-β-CYD), SBE-beta-schardinger dextrin-; The β-CDBao He rate is relatively low in above-mentioned β-CD, HP-β-CYD and the SBE-beta-schardinger dextrin-; HP-β-CYD and SBE-beta-cyclodextrin inclusion compound rate are higher; And do not have hemolytic reaction, the application of suitable especially injection with small volume and high-capacity injection preparation uses HP-the most extensive at present.
The objective of the invention is to realize by following technical scheme, a kind of clathrate of nifuroxazide beta-schardinger dextrin-or derivatives thereof by following raw material by weight forming:
Nifuroxazide: 30 POVIDONE K 30 BP/USP 30: beta-schardinger dextrin-or derivatives thereof=1: (0.125～0.25): (5～25).
Described beta-schardinger dextrin-can also be substituted by other cyclodextrin, and used ratio is consistent.
A kind of clathrate of nifuroxazide beta-schardinger dextrin-or derivatives thereof is prepared by following method; The beta-schardinger dextrin-or derivatives thereof is added water and is heated to 40 ℃～45 ℃; Make its whole dissolvings, process beta-schardinger dextrin-or derivatives thereof solution, mass concentration is 2～4%; With the organic solvent dissolution of nifuroxazide with 5～10 times, add 30 POVIDONE K 30 BP/USP 30 stirrings again and make dissolving in addition, organic solvent generally adopts ethanol or methanol; Adopt electric mixing device will contain 30 POVIDONE K 30 BP/USP 30 under rotating speed is 300～350 rev/mins stirring nifuroxazide drips of solution to be added in the aqueous solution that contains the beta-schardinger dextrin-or derivatives thereof; After treating all to drip; Stop heating, continue to stir 4-6 hour, stop to stir; Reactant liquor is put 2 ℃～4 ℃ environment left standstill 24 hours, sucking filtration, the adding distil water filtering and washing is 2 times on filter, and 35 ℃～40 ℃ dryings get loose powder shape nifuroxazide clathrate.
Clathrate among the present invention can adopt other method preparation; As adopt ultrasound wave to replace stirring means, and also can adopt Ginding process, the nifuroxazide ethanol or the methanol solution that are about to contain 30 POVIDONE K 30 BP/USP 30 add in the moisture cyclodextrin that grinds well; Grind evenly, dry clathrate.
Nifuroxazide and 30 POVIDONE K 30 BP/USP 30 are 1 with the beta-schardinger dextrin-weight ratio in the clathrate among the present invention: (0.125～0.25): (5～25); Wherein with 1: (0.125～0.25): (6～12) ratio; Dissolubility is maximum; 1: (0.125～0.25): during 8 ratios, content of dispersion, inclusion rate is the highest; With the HP-weight ratio be 1: (0.125～0.25): (5～25), wherein think 1: (0.125～0.25): (4～8) ratio, dissolubility is maximum, 1: (0.125～0.25): during 5 ratios, content of dispersion, inclusion rate is the highest; With SBE-beta-schardinger dextrin-weight ratio be 1: (0.125～0.25): (5～25), wherein think 1: (0.125～0.25): (3～6) ratio, dissolubility is maximum, 1: (0.125～0.25): during 4 ratios, content of dispersion, inclusion rate is the highest.
The inventive method makes the clathrate preparation of nifuroxazide beta-schardinger dextrin-or derivatives thereof; Said preparation can be prepared with different pharmaceutic adjuvants; Adopt corresponding prepared to become multiple dosage form; Like solid preparation (comprising tablet, capsule, granule etc.), liquid preparation (comprising oral administration solution, small-volume injection, bulk capacity injection etc.).
The present invention utilizes microscopic method, changes according to lattice arrangement, utilizes the clathrate of microscopically pastille different with the clathrate shape of pastille not, makes the judgement of inclusion rate through analysis package compound lattice variations and phase-state change.
The present invention adopts and adds high molecular weight water soluble polymer 30 POVIDONE K 30 BP/USP 30 in the enclose medium, can increase the clathration of medicine and CD effectively, improves inclusion rate and enclose quality, increases the solubilising efficient of CD to nifuroxazide.
Product of the present invention is nifuroxazide and 30 POVIDONE K 30 BP/USP 30 to be dissolved in organic solvent ethanol or methanol carry out enclose with beta-schardinger dextrin-and derivant thereof and process clathrate; Product is stablized to be improved; Improved its dissolubility in water, this has very big effect to the bioavailability of improving nifuroxazide, can realize developing the different dosage form product; Enlarge route of administration; Promote the purpose of clinical application effect, the clathrate product of nifuroxazide beta-schardinger dextrin-or derivatives thereof of the present invention can also be used as feed additive, compares with the existing market product; Have very big application advantage, provide a kind of new formulation products that wide application prospect is arranged the development of aquaculture.
The specific embodiment
Below in conjunction with embodiment the present invention is further described, but it is not a limitation of the present invention.
Embodiment 1
Get nifuroxazide 100g, be dissolved in the 500ml ethanol, adding 30 POVIDONE K 30 BP/USP 30 25g make dissolving and stir; Other gets beta-schardinger dextrin-800g and is dissolved in the 39200ml distilled water, is heated to 40 ℃～45 ℃, makes its whole dissolvings; It is 300 rev/mins that speed of agitator is set, and nifuroxazide and 30 POVIDONE K 30 BP/USP 30 alcoholic solutions slowly is added dropwise in β-CD aqueous solution, after treating all to drip; Stop heating, continue to stir 4～6 hours, stop to stir; Place 2 ℃～4 ℃ environment to leave standstill 24 hours reactant liquor, sucking filtration, the adding distil water filtering and washing is 2 times on filter; 35 ℃～40 ℃ dryings get loose powder shape nifuroxazide Benexate Hydrochloride.
Embodiment 2
Get nifuroxazide 100g, be dissolved in the 1000ml methanol, adding 30 POVIDONE K 30 BP/USP 30 12.5g make dissolving and stir; Other gets HP-(HP-CD) 500g, is dissolved in the 12000ml distilled water, is heated to 40 ℃～45 ℃; Make its whole dissolvings, it is 300 rev/mins that speed of agitator is set, and nifuroxazide and 30 POVIDONE K 30 BP/USP 30 alcoholic solutions slowly are added dropwise in the HP-aqueous solution; After treating all to drip, stop heating, continue to stir 4～6 hours; Stop to stir, place 2 ℃～4 ℃ environment to leave standstill sucking filtration 24 hours reactant liquor; The adding distil water filtering and washing is 2 times on filter, and vacuum decompression is dry, gets loose powder shape nifuroxazide hydroxypropyl-beta-cyclodextrin inclusion.
Embodiment 3
Change the whipping process among the embodiment 1 into ultrasonic concussion, ultrasonic 20min, other is operated with embodiment 1, obtains loose powder shape nifuroxazide Benexate Hydrochloride.
Embodiment 4
Change the whipping process among the embodiment 2 into ultrasonic concussion, ultrasonic 25min, other is operated with embodiment 2, obtains loose powder shape nifuroxazide hydroxypropyl-beta-cyclodextrin inclusion.
Embodiment 5
Get nifuroxazide 100g, be dissolved in the 1000ml ethanol, adding 30 POVIDONE K 30 BP/USP 30 12.5g make dissolving and stir; Get SBE-beta-schardinger dextrin-400g, be dissolved in the 9600ml distilled water, be heated to 40 ℃～45 ℃; Make its whole dissolvings, it is 350 rev/mins that speed of agitator is set, and nifuroxazide and 30 POVIDONE K 30 BP/USP 30 alcoholic solutions slowly are added dropwise in the SBE-beta-schardinger dextrin-aqueous solution; After treating all to drip, stop heating, continue to stir 4～8 hours; Stop to stir, place 2 ℃～4 ℃ environment to leave standstill sucking filtration 24 hours reactant liquor; The adding distil water filtering and washing is 2 times on filter, through 35 ℃～40 ℃ dryings, gets loose powder shape nifuroxazide SBE-Benexate Hydrochloride.
Embodiment 6
Preparation nifuroxazide Benexate Hydrochloride tablet
Get nifuroxazide Benexate Hydrochloride 900 grams of embodiment 1 preparation; Microcrystalline Cellulose 500g, lactose 350g, hydroxypropyl cellulose 180g; Magnesium stearate 70g; The nifuroxazide Benexate Hydrochloride of getting above-mentioned recipe quantity mixes with microcrystalline Cellulose, with an amount of moistening of dehydrated alcohol, at wetting state and abundant mixing.With above-mentioned moistening material intensive drying in 50 ℃ of air dry ovens, it is subsequent use to cross 80 mesh sieves.Drying mistake 80 mesh sieves are subsequent use in advance to take by weighing other each adjuvant of residue by recipe quantity.It is even to take by weighing residue each adjuvant and pretreated raw materials mix by recipe quantity, adds tabletting behind the magnesium stearate mix homogeneously, processes 4000, must tablet.
Embodiment 7
Preparation nifuroxazide hydroxypropyl-beta-cyclodextrin inclusion granule
Take by weighing the nifuroxazide hydroxypropyl-beta-cyclodextrin inclusion 600g of embodiment 2 preparations, dextrin 2100g, hydroxypropyl cellulose 150g, sodium cyclohexyl sulfamate 150g.Nifuroxazide hydroxypropyl-beta-cyclodextrin inclusion, dextrin, hydroxypropyl cellulose, sodium cyclohexyl sulfamate are weighed by prescription weight; Dextrin, hydroxypropyl cellulose and sodium cyclohexyl sulfamate are pulverized the back with pulverizer cross 120 mesh sieves, direct mistake 120 mesh sieves of nifuroxazide hydroxypropyl-beta-cyclodextrin inclusion mixed 40 minutes with the grooved blender; Process soft material with purified water then; Process 16 purpose granules with granulator, with granule with 35 ℃～40 ℃ freeze-day with constant temperature, 14 mesh sieve granulate; Packing is processed 2000 bags, gets granule.
Embodiment 8
Preparation nifuroxazide hydroxypropyl-beta-cyclodextrin inclusion injection with small volume
Take by weighing the nifuroxazide hydroxypropyl-beta-cyclodextrin inclusion 60g of embodiment 2 preparations, benzyl alcohol 10g, lidocaine hydrochloride 10g, propylene glycol 280ml, Macrogol 200 150ml, ethanol 60ml, hydrochloric acid is an amount of, and water for injection adds 1000ml to.
Propylene glycol, ethanol, the Macrogol 200 of recipe quantity are added in about 400ml water for injection; Mix homogeneously; The nifuroxazide hydroxypropyl-beta-cyclodextrin inclusion that adds above-mentioned recipe quantity again is stirred to dissolving, adds benzyl alcohol, lidocaine hydrochloride then, is stirred to dissolving evenly; Using dilute hydrochloric acid to regulate pH value is 5.0～6.0, adds remaining water for injection to capacity.With the solution of gained with 0.22 μ m filtering with microporous membrane after, the filtrating embedding is processed 100 in the 10ml ampoule, through 110 ℃ of autoclavings 30 minutes, promptly get.
Embodiment 9
Preparation nifuroxazide SBE-Benexate Hydrochloride high-capacity injection
Take by weighing the nifuroxazide SBE-beta-schardinger dextrin-50g of embodiment 5 preparations, sodium chloride 5g, sodium sulfite 1g, cysteine hydrochloride 0.25g, propylene glycol 500ml, ethanol 50ml, hydrochloric acid is an amount of, and water for injection adds 1000ml to.
Propylene glycol, the ethanol of recipe quantity are added in about 300ml water for injection, and mix homogeneously adds nifuroxazide SBE-Benexate Hydrochloride, sodium chloride, sodium sulfite, the cysteine hydrochloride of above-mentioned recipe quantity again; Stirring makes dissolving, and using hydrochloric acid to regulate pH value is 5.0～6.0, adds water for injection to 1000ml; With the needle-use activated carbon of dose volume 0.1% amount about 30 minutes of stirring and adsorbing under 80 ℃ of temperature; Behind the filtering decarbonization, with 0.22 μ m filtering with microporous membrane, filtrating is filled in the 100ml infusion bottle; Sterilization is 30 minutes under 115 ℃ of flowing steams, promptly gets.
Claims (10)
1. the clathrate of a nifuroxazide beta-schardinger dextrin-or derivatives thereof is characterized in that by following raw material by weight forming: nifuroxazide: 30 POVIDONE K 30 BP/USP 30: beta-schardinger dextrin-or derivatives thereof=1: (0.125～0.25): (5～25); Described beta-cyclodextrin derivative is HP-or SBE-beta-schardinger dextrin-.
2. the method for preparing of the clathrate of a kind of nifuroxazide beta-schardinger dextrin-or derivatives thereof according to claim 1; It is characterized in that by the preparation of following method: the beta-schardinger dextrin-or derivatives thereof is added water and is heated to 40 ℃～45 ℃; Make its whole dissolvings; Process beta-schardinger dextrin-or derivatives thereof solution, mass concentration is 2～4%; With organic solvent ethanol or the dissolve with methanol of nifuroxazide, add 30 POVIDONE K 30 BP/USP 30 stirrings again and make dissolving in addition with 5～10 times; The nifuroxazide drips of solution that under rotating speed is 300～350 rev/mins stirring, will contain 30 POVIDONE K 30 BP/USP 30 is added in the aqueous solution that contains the beta-schardinger dextrin-or derivatives thereof, after treating all to drip, stops heating, continues to stir 4-6 hour, stops to stir; Reactant liquor is put 2 ℃～4 ℃ environment left standstill 24 hours, sucking filtration, the adding distil water filtering and washing is 2 times on filter, and 35 ℃～40 ℃ dryings get loose powder shape nifuroxazide clathrate.
3. the method for preparing of the clathrate of a kind of nifuroxazide beta-schardinger dextrin-or derivatives thereof according to claim 2; Its characteristic also comprises: adopt ultrasound wave to replace stirring means; Perhaps adopt Ginding process; The nifuroxazide solution that is about to contain 30 POVIDONE K 30 BP/USP 30 adds in the moisture cyclodextrin that grinds well, and grinds evenly, dry clathrate.
4. the clathrate of a kind of nifuroxazide beta-schardinger dextrin-or derivatives thereof according to claim 1, described nifuroxazide and 30 POVIDONE K 30 BP/USP 30 are 1 with the beta-schardinger dextrin-weight ratio: (0.125～0.25): (6～12).
5. the clathrate of a kind of nifuroxazide beta-schardinger dextrin-or derivatives thereof according to claim 1, described nifuroxazide and 30 POVIDONE K 30 BP/USP 30 are 1 with the beta-schardinger dextrin-weight ratio: (0.125～0.25): 8.
6. the clathrate of a kind of nifuroxazide beta-schardinger dextrin-or derivatives thereof according to claim 1, described nifuroxazide and 30 POVIDONE K 30 BP/USP 30 are 1 with the HP-weight ratio: (0.125～0.25): (4～8).
7. the clathrate of a kind of nifuroxazide beta-schardinger dextrin-or derivatives thereof according to claim 1, described nifuroxazide and 30 POVIDONE K 30 BP/USP 30 are 1 with the HP-weight ratio: (0.125～0.25): 5.
8. the clathrate of a kind of nifuroxazide beta-schardinger dextrin-or derivatives thereof according to claim 1, described nifuroxazide and 30 POVIDONE K 30 BP/USP 30 are 1 with SBE-beta-schardinger dextrin-weight ratio: (0.125～0.25): (3～6).
9. the clathrate of a kind of nifuroxazide beta-schardinger dextrin-or derivatives thereof according to claim 1, described nifuroxazide and 30 POVIDONE K 30 BP/USP 30 are 1 with SBE-beta-schardinger dextrin-weight ratio: (0.125～0.25): 4.
10. the clathrate of a kind of nifuroxazide beta-schardinger dextrin-or derivatives thereof according to claim 1 is characterized in that: its dosage form is tablet, capsule, granule, oral administration solution, small-volume injection, bulk capacity injection.
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