CN104399086B - Inclusion compound of aureomycin Zn complex and preparation method thereof - Google Patents
Inclusion compound of aureomycin Zn complex and preparation method thereof Download PDFInfo
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- CN104399086B CN104399086B CN201410737896.1A CN201410737896A CN104399086B CN 104399086 B CN104399086 B CN 104399086B CN 201410737896 A CN201410737896 A CN 201410737896A CN 104399086 B CN104399086 B CN 104399086B
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Abstract
The invention belongs to medicine preparing technical field, and in particular to inclusion compound of aureomycin Zn complex and preparation method thereof.The technical problem to be solved in the present invention is that aureomycin Zn complex dissolubility in water is poor, dissolution rate is small.The technical scheme is that the inclusion compound of aureomycin Zn complex, including inclusion material and aureomycin Zn complex, the weight ratio for including material and aureomycin Zn complex is 13 ︰ 1, and described inclusion material is cyclodextrin or cyclodextrine derivatives.Present invention also offers the oral formulations being prepared into by the inclusion compound.Present invention also offers the preparation method of the inclusion compound of aureomycin Zn complex.Aureomycin Zn complex dissolubility in water is good in inclusion compound of the present invention, dissolution rate is high, has the advantages that good water solubility, stability is strong, good effect, Small side effects.
Description
Technical field
The invention belongs to medicine preparing technical field, and in particular to the inclusion compound of aureomycin Zn complex and its preparation side
Method.
Background technology
Tetracyclines (Tetracyclines) is gained the name with the chemical constitution of aphthacene parent nucleus, and aureomycin
(Chlortetracycline, structure is shown in Fig. 1) belongs to one kind of Tetracyclines derivative also known as duomycin, and it mainly suppresses quick
Feel the protein synthesis of microorganism.Aureomycin has a broad antifungal spectrum, to gram positive bacteria, negative bacterium, conveyor screw, rickettsia, branch
Substance, Chlamydia, part protozoon etc. can suppress.Aureomycin is mainly combined with 30S small subunits A of microorganism, and then is disturbed
Amino phthalein tRNA is combined with 30S small subunits, prevents amino phthalein tRNA from entering on mRNA by position, it is suppressed that when protein synthesizes
The extension of skin chain；Aureomycin can also prevent the protein skin chain for having synthesized from discharging.Aureomycin to the effect of 70S ribosomes more
Be sensitivity, therefore, aureomycin can Selective depression sensitive microbial, with certain security performance.
Aureomycin Zn complex outward appearance is yellow powder or particle；Without mouldy, the odorless that lumps.Aureomycin Zn complex has
Growth promotion, the function of improving feed efficiency and bactericidal, make it play the role of in animal farming industry important.But it is golden at present
Mycin Zn complex can only be not high by gastrointestinal administration, absorptivity, therefore, to improve aureomycin Zn complex in animal body
In utilization rate, reduce gastric juice to aureomycin Zn complex destruction, it is necessary to further improve aureomycin Zn complex preparation
Technological level.
Inclusion technique refers to a kind of drug molecule wrapped be embedded in it is another be referred to as in the void structure of supramolecular materials, formed
The technology of inclusion compound.This supramolecular materials inclusion compound is made up of two kinds of components of host molecule and enclosed molecule.Supramolecular materials are just
It is so-called host molecule, it has larger void structure, it is sufficient to accommodate medicine enclosed molecule.Medicine is made after inclusion compound not only
The stability of medicine can be improved, moreover it is possible to increase the solubility of insoluble drugs, to reach the mesh of the bioavilability for improving medicine
's.
The supramolecular materials of inclusion have cyclodextrin, urea, cholic acid, sephadex, cellulose, starch etc., in preparation
Usually using cyclodextrin and its derivative.Beta-schardinger dextrin (Cyclodextrin, abridge CD) is most important class supermolecule material
Material host molecule, can include or be embedded in formation Ultramicro Dispersion thing in its tubular structure, with anti-oxidant, fast light by drug molecule
According to, it is heat-resisting, sustained release property, so as to increased medicine stability, toxic and side effect is reduced, so the most commonly used.Beta-schardinger dextrin
Another conventional major reason is that beta-schardinger dextrin comes from natural material starch, inexpensive, nontoxic and can include various
Hydrophobic substrate, therefore research and application of the supramolecular techniques in terms of medicine at present focuses primarily upon beta-schardinger dextrin system, medicine
Cyclodextrin pharmaceutic adjuvant is also referred to as in thing application industry.But beta-schardinger dextrin solubility in water is low, with renal toxicity and haemolysis
Property, therefore, using beta-cyclodextrin inclusion compound taste masking, the inclusion compound water solubility for often being formed is low, have impact on the life of medicine guest molecule
Thing availability.
The content of the invention
The technical problem to be solved in the present invention is that aureomycin Zn complex dissolubility in water is poor, dissolution rate is small.
The technical scheme is that the inclusion compound of aureomycin Zn complex, including inclusion material and aureomycin zinc coordinate
The weight ratio of thing, inclusion material and aureomycin Zn complex is 1-3 ︰ 1, and described inclusion material is that cyclodextrin or cyclodextrin derive
Thing.
Specifically, described cyclodextrin is at least one in glucose group-beta-cyclodextrin and HP-β-CD.
Present invention also offers the oral formulations being prepared into by the inclusion compound.
Specifically, the oral formulations are tablet, soluble powder or oral liquid.
Specifically, aureomycin Zn complex content is 2.5~10% in soluble powder and oral administration solution, it is balance of medicinal dilute
Release at least one in agent, carrier, excipient, adhesive, lubricant, solubilizer, antioxidant or disintegrant.
Specifically, aureomycin Zn complex content is 2.5%, 5% or 10% in soluble powder and oral administration solution.
Specifically, aureomycin Zn complex content is 2.5~5mg, balance of medicinal diluent, carrier, figuration in tablet
At least one in agent, adhesive, lubricant, solubilizer, antioxidant or disintegrant.
Specifically, aureomycin Zn complex content is 2.5mg or 5mg in tablet.
Present invention also offers the preparation method of the inclusion compound of aureomycin Zn complex, comprise the following steps：By aureomycin
Zn complex is dissolved in organic solvent, and is kept for 45~65 DEG C, then is slowly dropped into the saturated aqueous solution for including material, is continuously stirred
Mixing yellowly solution, freeze-drying or spray drying, that is, obtain the inclusion compound of aureomycin Zn complex；It is described inclusion material and
The weight ratio of aureomycin Zn complex is 1~3 ︰ 1, and described inclusion material is cyclodextrin or cyclodextrine derivatives；Described has
Machine solvent is at least in methyl alcohol, ethanol, propyl alcohol, isopropanol, N,N-dimethylformamide, tetrahydrofuran or dimethyl sulfoxide (DMSO)
Kind.
Preferably, described organic solvent by following weight than into being grouped into：100~140 parts of methyl alcohol, dimethyl sulfoxide (DMSO)
100~140 parts, 2~5 parts of DMF, 2~5 parts of tetrahydrofuran.
Preferably, described organic solvent by following weight than into being grouped into：48 parts of methyl alcohol, 48 parts of dimethyl sulfoxide (DMSO),
2 parts of DMF, 2 parts of tetrahydrofuran.
In the present invention, glucose group-beta-cyclodextrin and HP-β-CD are beta-cyclodextrin derivative, can make
Solubility of the insoluble medicine in water is significantly lifted, and particularly HP-β-CD is in 50% ethanol and methyl alcohol
Can dissolving.The intra-molecular cyclic hydrogen bond of beta-schardinger dextrin has been broken in the introducing of glucityl and hydroxypropyl, is keeping cyclodextrin cavity
The major defect of beta-schardinger dextrin poorly water-soluble being overcome simultaneously, being that research is the most deep at present, most widely used cyclodextrin spreads out
One of biology.In medical industry, because apparent surface's activity and hemolytic activity are than relatively low and to muscle do not have excitant, so
They are a kind of preferable injection solubilizer and drug excipient, can not only improve the water solubility of insoluble drug, are increased
Medicine stability, raising drug bioavailability, make the curative effect of medicament increase or dose reduction, can also adjust or control medicine
The rate of release of thing, reduces poisonous side effect of medicine.(including nose is viscous to be commonly used to oral drugs, injection, mucoadhesive delivery system
Film, rectum, cornea etc.), Transdermal absorption delivery system, the carrier of lipophilicity targeted drug, can be used as the protective agent of protein
And stabilizer.
In the present invention, because aureomycin metal complex is water insoluble, atomic to be dissolved in methyl alcohol, ethanol, propyl alcohol etc. organic molten
Agent, therefore be difficult to be dissolved into aureomycin metal complex in the middle of solvent, and in inclusion technique, it is necessary to by enclosed molecule, (gold is mould
Doxycycline metal complex) it is dissolved in solvent, can just be included.However, current both at home and abroad not to the inclusion of tetracycline medication
Thing carried out report.Inventor is optimized by test of many times to organic solvent formula, finally can be by aureomycin metal combination
Thing is preferably dissolved in the organic solvent, possesses the precondition that aureomycin metal complex is carried out inclusion reaction.
Beneficial effects of the present invention：The present invention has carried out cyclodextrin inclusion technique treatment to tetracycline medication first, solves
Current aureomycin Zn complex dissolubility in water of having determined is poor, the problem that dissolution rate is small, and this treatment technology is molecule
In level.The principle of cyclodextrin inclusion technique is that the inclusion compound to be formed completely or partially is wrapped in a kind of space structure of molecule
Enter another molecule to form, the outer layer molecule with clathration is referred to as host molecule, included small point in host molecule space
Sub- material, referred to as enclosed molecule.When host molecule and enclosed molecule carry out clathration, do not chemically react each other, do not exist
The effect of the chemical bonds such as ionic bond, covalent bond or coordinate bond, is a kind of physical process in molecular level.Inclusion compound of the present invention
Middle aureomycin Zn complex dissolubility in water is good, dissolution rate is high, with good water solubility, strong stability, good effect, side effect
Small the advantages of.Preparation method simple possible of the present invention, it is with low cost, it is with a wide range of applications.
Brief description of the drawings
Fig. 1 aureomycin molecular structures
The water solubility of Fig. 2 aureomycin Zn complex and its inclusion compound compares
The stability of Fig. 3 aureomycin Zn complex and its inclusion compound compares
Specific embodiment
The preparation of the inclusion compound of the present invention of embodiment 1
10 grams of aureomycin Zn complex is weighed, 48 milliliters of methyl alcohol, 48 milliliters of dimethyl sulfoxide (DMSO), N, N- dimethyl formyl is added
2 milliliters of amine, in the mixed organic solvents that 2 milliliters of tetrahydrofuran, and is completely dissolved it, keep 55 DEG C, instill containing hydroxy propyl-Beta-
The saturated aqueous solution that 14 grams of cyclodextrin, 55 DEG C are stirred 2 hours, stop heating, are further continued for stirring to room temperature, obtain yellow solution,
It is spray-dried after filtering, as the inclusion compound of aureomycin Zn complex.
The preparation of the inclusion compound of the present invention of embodiment 2
10 grams of aureomycin Zn complex is weighed, 48 milliliters of methyl alcohol, 48 milliliters of dimethyl sulfoxide (DMSO), N, N- dimethyl formyl is added
2 milliliters of amine, in the mixed organic solvents that 2 milliliters of tetrahydrofuran, and is completely dissolved it, keep 60 DEG C, instill containing hydroxy propyl-Beta-
The saturated aqueous solution that 28 grams of cyclodextrin, continues to stir 30 minutes, stops heating, is further continued for stirring to room temperature, obtains yellow solution,
Freeze-drying after filtering, the as inclusion compound of aureomycin Zn complex.
The preparation of the inclusion compound of the present invention of embodiment 3
10 grams of aureomycin Zn complex is weighed, 48 milliliters of methyl alcohol, 48 milliliters of dimethyl sulfoxide (DMSO), N, N- dimethyl formyl is added
2 milliliters of amine, in the mixed organic solvents that 2 milliliters of tetrahydrofuran, and is completely dissolved it, keep 60 DEG C, instill containing hydroxy propyl-Beta-
The saturated aqueous solution that 28 grams of cyclodextrin, ultrasound 30 minutes at 65 DEG C, after 0.45 μm of membrane filtration, the solution of gained is sprayed
Mist is dried, as the inclusion compound of aureomycin Zn complex.
Embodiment 4 prepares dispersible tablet
Take 315 milligrams of inclusion compound, 100 milligrams of amylum pregelatinisatum, 100 milligrams of mannitol, the PVP powder of aureomycin Zn complex
100 milligrams of end, 15 milligrams of magnesium stearate, 200 milligrams of talcum powder are well mixed, and Control granularity is in 35-85 μ ms, dry method
Direct tablet compressing, its main ingredient aureomycin Zn complex content is 2.5 millis gram/piece, obtains final product dispersible tablet of the invention.
Embodiment 5 prepares rapidly dissolving tablet
Take 514 milligrams of inclusion compound, 200 milligrams of lactose, 20 milligrams of PEG6000 powder, the dodecyl of aureomycin Zn complex
30 milligrams of sodium sulphate, 5 milligrams of magnesium stearate, 63 milligrams of sodium thiosulfate, 30 milligrams of carboxymethylcellulose calcium, are well mixed, by straight
Platen press carries out compressing tablet, and its main ingredient aureomycin Zn complex content is 5 millis gram/piece, obtains final product rapidly dissolving tablet of the invention.
Embodiment 6 prepares oral administration solution
45.2 grams of inclusion compound for taking aureomycin Zn complex is dissolved in water for injection, adds 25 grams of glucose and 2 grams of activity
Charcoal, is stirred 30 minutes, and pH to 11-13 is adjusted with alkali, after depyrogenation, filters decarburization, with 0.22 μm of membrane filtration, then with note
Penetrate after being adjusted to ormal weight with water, obtain the inclusion compound oral administration solution of aureomycin Zn complex.
Embodiment 7 prepares soluble powder
51.4 grams of the inclusion compound of aureomycin Zn complex is taken, adds 25 grams of DEXTROSE ANHYDROUSs, three-dimensional mixer to be well mixed,
Obtain the inclusion compound soluble powder of aureomycin Zn complex.
The water-soluble experiment of embodiment 8
The inclusion compound 150mg of aureomycin Zn complex 150mg and aureomycin Zn complex is separately added into 500ml water,
In 30 DEG C of temperature environments, its solubility property in water is determined respectively in 5,10,15,30,60,120,180,240min.From
Experimental result can be seen that (be shown in Table 1 and Fig. 2), and the dissolubility of the inclusion compound of aureomycin Zn complex in water is mould apparently higher than gold
Plain Zn complex.
The water solubility of table 1 compares
| Time (min) | Aureomycin Zn complex (mg) | The inclusion compound (mg) of aureomycin Zn complex |
| 5 | 0.1015 | 44.35 |
| 10 | 0.07225 | 76.78 |
| 15 | 0.276 | 130.32 |
| 30 | 0.416 | 143.65 |
| 60 | 0.44 | 140.17 |
| 120 | 0.5 | 138.48 |
| 180 | 0.7424 | 142.23 |
| 240 | 0.654 | 140.41 |
The stability test of embodiment 9
It is the water-soluble of 20 μ g/ml that the inclusion compound of aureomycin Zn complex and aureomycin Zn complex is each configured into concentration
Liquid, is placed 15 days under the conditions of 60 DEG C, and its content in aqueous was determined respectively with high-efficient liquid phase technique in 0,5,10,15 days.
From experimental result it can be seen that (being shown in Table 2 and Fig. 3), the degradation rate of the inclusion compound of aureomycin Zn complex is substantially mould less than gold
The degradation rate of plain Zn complex, illustrates that the stability of aureomycin Zn complex is better than aureomycin Zn complex.
The stability test result of table 2
| Time | Aureomycin Zn complex content (%) | The inclusion compound content (%) of aureomycin Zn complex |
| 0 day | 93.73 | 70.32 |
| 5 days | 76.56 | 65.46 |
| 10 days | 65.52 | 63.89 |
| 15 days | 50.38 | 61.42 |
Claims (6)
1. the inclusion compound of aureomycin Zn complex, it is characterised in that：Including inclusion material and aureomycin Zn complex, material is included
It is 1-3 ︰ 1 with the weight ratio of aureomycin Zn complex, described inclusion material is cyclodextrin or cyclodextrine derivatives；The inclusion
The preparation method of thing, comprises the following steps：Aureomycin Zn complex is dissolved in organic solvent, and 45 DEG C~65 DEG C of holding,
The saturated aqueous solution of inclusion material being slowly dropped into again, being continuously stirred and is made yellow solution, freeze-drying or spray drying obtain
The inclusion compound of aureomycin Zn complex；Described organic solvent by following weight than into being grouped into：48 parts of methyl alcohol, dimethyl is sub-
48 parts of sulfone, 2 parts of DMF, 2 parts of tetrahydrofuran.
2. the inclusion compound of aureomycin Zn complex as claimed in claim 1, it is characterised in that：Described cyclodextrine derivatives are
At least one in glucose group-beta-cyclodextrin and HP-β-CD.
3. the oral formulations that the inclusion compound as described in claim 1 or 2 is prepared into.
4. oral formulations as claimed in claim 3, it is characterised in that：The oral formulations are tablet, soluble powder or oral
Liquid.
5. oral formulations as claimed in claim 4, it is characterised in that：Aureomycin Zn complex in soluble powder and oral administration solution
Weight content is 2.5~10%, in balance of medicinal diluent, adhesive, lubricant, solubilizer, antioxidant or disintegrant
It is at least one.
6. oral formulations as claimed in claim 4, it is characterised in that：In tablet aureomycin Zn complex content be 2.5mg or
5mg, at least one in balance of medicinal diluent, adhesive, lubricant, solubilizer, antioxidant or disintegrant.
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105524082A (en) * | 2015-12-01 | 2016-04-27 | 齐鲁工业大学 | Synthesis and antibacterial activity of zinc voriconazole complex |
| CN107951843B (en) * | 2017-12-29 | 2020-09-29 | 浦城正大生化有限公司 | Chlortetracycline hydrochloride soluble powder and preparation method thereof |
| CN112957481A (en) * | 2021-04-26 | 2021-06-15 | 佛山市南海东方澳龙制药有限公司 | Insoluble drug inclusion compound, inclusion method and chlortetracycline hydrochloride soluble powder |
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| CN1788558A (en) * | 2004-12-15 | 2006-06-21 | 利统股份有限公司 | Instant complex composition |
| CN101128206A (en) * | 2005-01-21 | 2008-02-20 | 沃纳奇尔科特公司 | Tetracycline metal complex in a solid dosage form |
| CN102921018A (en) * | 2012-11-27 | 2013-02-13 | 重庆市畜牧科学院 | Enrofloxacin/sulfobutylether-beta-cyclodextrin inclusion compound, preparation method and medicinal preparation thereof |
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2014
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Patent Citations (3)
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|---|---|---|---|---|
| CN1788558A (en) * | 2004-12-15 | 2006-06-21 | 利统股份有限公司 | Instant complex composition |
| CN101128206A (en) * | 2005-01-21 | 2008-02-20 | 沃纳奇尔科特公司 | Tetracycline metal complex in a solid dosage form |
| CN102921018A (en) * | 2012-11-27 | 2013-02-13 | 重庆市畜牧科学院 | Enrofloxacin/sulfobutylether-beta-cyclodextrin inclusion compound, preparation method and medicinal preparation thereof |
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