CN109453390A - A kind of Enrofloxacin hydroxypropyl cyclodextrin inclusion and its preparation method and application - Google Patents
A kind of Enrofloxacin hydroxypropyl cyclodextrin inclusion and its preparation method and application Download PDFInfo
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- CN109453390A CN109453390A CN201811454860.7A CN201811454860A CN109453390A CN 109453390 A CN109453390 A CN 109453390A CN 201811454860 A CN201811454860 A CN 201811454860A CN 109453390 A CN109453390 A CN 109453390A
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- enrofloxacin
- hydroxypropyl cyclodextrin
- inclusion
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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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene
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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
Abstract
The invention discloses a kind of preparation methods of Enrofloxacin hydroxypropyl cyclodextrin inclusion, using the high hydroxypropyl cyclodextrin of dissolubility, insoluble,practically Enrofloxacin in water is included to form the stable inclusion compound of quality, dissolubility of the Enrofloxacin hydroxypropyl cyclodextrin inclusion obtained in water phase is obviously improved, dissolution rate with higher, inclusion rate is high, and yield is also greatly improved, with the drug dissolution rates raising into Enrofloxacin hydroxypropyl cyclodextrin inclusion, release is faster, and it can increase organism absorption of drugs, be conducive to improve the bioavilability of drug；After hydroxypropyl cyclodextrin includes Enrofloxacin, so that Enrofloxacin enters in hole, drug volatilization, distillation can be prevented, aoxidizes and decomposes in light；Drug also be can significantly reduce to the toxicity and irritation of human body.Preparation method of the invention is easy to operate, high-efficient, is suitble to large-scale production, can be used in animal bacteria disease prevention and cure.
Description
Technical field
The invention belongs to pharmaceutical technology fields, and in particular to a kind of Enrofloxacin hydroxypropyl cyclodextrin inclusion and its preparation
Methods and applications.
Background technique
Enrofloxacin (Enrofloxacin) is chemically synthesized carbostyril family antibacterial drugs also known as ethyl ring Ciprofloxacin
Acid, Ethyl Ciprofloxacin.Enrofloxacin is animal specific medicine, includes skin infection, urinary tract infections, respiratory tract infection for treating
And wound infection.Its structure is as follows:
Enrofloxacin appearance is yellowish or greenish orange yellow crystalline powder；It is odorless, bitter；Meet it is photochromic become orange red,
It is readily soluble in chloroform, slightly molten in dimethylformamide, in methyl alcohol slightly soluble, but is practically insoluble in water；It is tried in sodium hydroxide
It is readily soluble in the organic solvents such as liquid, methanol and cyanogen methane, 221~226 DEG C of fusing point, easy moisture absorption agglomeration in air.
The broad-spectrum antiseptic of Enrofloxacin and unique same bactericidal function, to Escherichia coli, klebsiella bacillus, Salmonella
Bacterium, proteus, Pseudomonas aeruginosa, haemophilus, pasteurella multocida, pasteurella haemolytica, S. aureus L-forms, streptococcus etc. are all
There is sterilization effectiveness.It can be used as animal-use drug product, long half time in animal body has good tissue distribution, belongs to wide effect
Property bacteriostatic agent, for gram-positive bacteria, negative bacterium and mould slurry have bacteriostasis.But since Enrofloxacin dissolution rate is low,
The enrofloxacin preparation process of high concentration is relatively difficult, and stable product quality can not be guaranteed, and low concentration
Enrofloxacin drug effect necessarily weakens, and therefore, needs to seek a kind of new preparation method, a kind of En Nuosha of high-dissolution is made
Star hydroxypropyl cyclodextrin inclusion.
Summary of the invention
The purpose of the present invention is to provide a kind of Enrofloxacin hydroxypropyl cyclodextrin inclusion and its preparation method and application,
Enrofloxacin hydroxypropyl cyclodextrin inclusion dissolution rate with higher obtained, can effectively solve the above problems and defect.
The technical solution used in the present invention is:
A kind of preparation method of Enrofloxacin hydroxypropyl cyclodextrin inclusion, includes the following steps:
S1. solvent is added into hydroxypropyl cyclodextrin, dissolves by heating, suitable maltol and grape is added toward solution the inside
It is spare to obtain mixed solution A for sugar；
S2. a small amount of solvent is added into Enrofloxacin, is prepared into solution B, it is spare；
S3. solution A is placed on magnetic stirring apparatus, under the conditions of 50 DEG C of -65 DEG C of heated at constant temperature, is slowly dropped into solution B, into
Row inclusion reaction obtains inclusion liquid；
S4. the inclusion liquid of S3 is persistently stirred into 2h~4h, stops heating, stirring to room temperature；
S4. it refrigerates and is freeze-dried afterwards for 24 hours to get Enrofloxacin hydroxypropyl cyclodextrin inclusion.
As a further improvement of the foregoing solution, solvent described in step S1 includes water, alcohols solvent or their mixing
Object.
As a further improvement of the foregoing solution, solvent described in step S2 is selected from acetic acid, sodium hydroxide solution, dilute hydrochloric acid
One of solution, methanol solution or ethanol solution.
As a further improvement of the foregoing solution, the molar ratio of Enrofloxacin and hydroxypropyl cyclodextrin is (1~3): 1.
As a further improvement of the foregoing solution, revolving speed when being stirred in step S3 and S4 be 400r/min~
600r/min。
As a further improvement of the foregoing solution, stirring described in step S4 is to carry out in a water bath to room temperature.
A kind of Enrofloxacin hydroxypropyl cyclodextrin inclusion, the Enrofloxacin hydroxypropyl cyclodextrin inclusion are such as taken up an official post
The item preparation method of anticipating is made.
A kind of application of Enrofloxacin hydroxypropyl cyclodextrin inclusion, by Enrofloxacin hydroxypropyl cyclodextrin as described above
Inclusion compound is applied in animal bacteria disease prevention and cure.
The beneficial effects of the present invention are: the present invention provides a kind of preparation side of Enrofloxacin hydroxypropyl cyclodextrin inclusion
Method includes insoluble,practically Enrofloxacin in water to form the stable packet of quality using the high hydroxypropyl cyclodextrin of dissolubility
Object is closed, dissolubility of the Enrofloxacin hydroxypropyl cyclodextrin inclusion obtained in water phase is obviously improved, dissolution with higher
Degree, inclusion rate is high, and yield is also greatly improved, while the drug dissolution rates of Enrofloxacin hydroxypropyl cyclodextrin inclusion
It improves, release faster, and can increase organism absorption of drugs, be conducive to the bioavilability for improving drug；Hydroxypropyl basic ring
After dextrin includes Enrofloxacin, so that Enrofloxacin enters in hole, drug volatilization, distillation can be prevented, aoxidizes and sees
Photodegradation；Drug also be can significantly reduce to the toxicity and irritation of human body.Preparation method of the invention is easy to operate, high-efficient,
It is suitble to large-scale production, suitable for animal bacteria disease prevention and cure.
Detailed description of the invention
Fig. 1 is the high-efficient liquid phase chromatogram of hydroxypropyl cyclodextrin；
Fig. 2 is the high-efficient liquid phase chromatogram of Enrofloxacin standard items；
Fig. 3 is the high-efficient liquid phase chromatogram of Enrofloxacin hydroxypropyl cyclodextrin inclusion；
Fig. 4 is that the SEM of hydroxypropyl cyclodextrin schemes；
Fig. 5 is that the SEM of Enrofloxacin schemes；
Fig. 6 is that the SEM of Enrofloxacin hydroxypropyl cyclodextrin mixture schemes；
Fig. 7 is that the SEM of Enrofloxacin hydroxypropyl cyclodextrin inclusion schemes；
Fig. 8 is the infared spectrum of hydroxypropyl cyclodextrin；
Fig. 9 is the infared spectrum of Enrofloxacin；
Figure 10 is the infared spectrum of Enrofloxacin hydroxypropyl cyclodextrin mixture；
Figure 11 is the infared spectrum of Enrofloxacin hydroxypropyl cyclodextrin inclusion；
Figure 12 is the canonical plotting of Enrofloxacin；
Figure 13 is the Dissolution profiles figure of all kinds of samples in embodiment 11.
Specific embodiment
The present invention is specifically described below with reference to embodiment, in order to technical field personnel to of the invention
Understand.It is necessary to it is emphasized that embodiment is only intended to, the present invention will be further described herein, should not be understood as to this
The limitation of invention protection scope, fields person skilled in the art, the non-intrinsically safe that the present invention is made according to foregoing invention content
The modifications and adaptations of property, should still fall within protection scope of the present invention.Mentioned raw materials following simultaneously are unspecified, are
Commercial product；The processing step or preparation method not referred in detail be processing step known to a person skilled in the art or
Preparation method.
Using L9 (34) four factors, three horizontal quadrature test method, the preparation to Enrofloxacin hydroxypropyl cyclodextrin inclusion
4 influence factors in method are combined, and are obtained such as 9 kinds of combination (i.e. such as the embodiment 1-9 in the following table 1) institutes in the following table 1
Show.
A kind of preparation method of Enrofloxacin hydroxypropyl cyclodextrin inclusion, includes the following steps: to take 0.1mol hydroxypropyl
Cyclodextrin is added distilled water, saturated solution A is made after heating for dissolving, spare；
S2. the Enrofloxacin of 0.1mol is taken, and acetic acid is added, is prepared into solution B, it is spare；
S3. solution B is placed on magnetic stirring apparatus, under the conditions of 55 DEG C of heated at constant temperature, the revolving speed of magnetic stirring apparatus is set as
400r/min is slowly dropped into solution A, carries out inclusion reaction, obtains inclusion liquid；
S4. the inclusion liquid of S3 is persistently stirred into 2h, stops heating, is placed in stirred in water bath to room temperature；
S4. it refrigerates and is freeze-dried afterwards for 24 hours to get Enrofloxacin hydroxypropyl cyclodextrin inclusion finished product is arrived；
Wherein, the molar ratio of Enrofloxacin and hydroxypropyl cyclodextrin is (1~3): 1.
The molar ratio of Enrofloxacin hydroxyl and propyl cyclodextrin is denoted as a, the temperature of heated at constant temperature is denoted as b in S3, will in S4
Inclusion liquid continues stirring until the stirring duration for stopping heating and is denoted as c, and the stirring rate in preparation process is denoted as d.
Experiment process:
The molar ratio (a factor) of Enrofloxacin hydroxyl and propyl cyclodextrin: 1 (a1), 2 (a2), 3 (a3)；
The temperature (b factor) of heated at constant temperature in S3: 55 DEG C (b1), 60 DEG C (b2), 65 DEG C (b3)；
Liquid will be included in S4 continues stirring until the stirring duration (c factor) for stopping heating: 2h (c1), 3h (c2), 4h (c3)；
Stirring rate (d factor) in preparation process: 400r/min (d1), 500r/min (d2), 600r/min (d3).
1 L of table9(34) orthogonal test table
Embodiment 10
Finished product detection
It the use of chromatographic condition and system suitability with octadecylsilane chemically bonded silica is filler；With
0.025mo1/L phosphoric acid solution (adjusting pH value to 3.0 with triethylamine) second eyeball (83:17) is mobile phase；Detection wavelength is
278nm.Number of theoretical plate is calculated by Enrofloxacin peak is not less than 2500.
Measuring method: the resulting finished product 1-9 of Example 1-9 is appropriate (identical amount) respectively, accurately weighed, adds mobile phase
In right amount, it after ultrasonic dissolution, is made in every 1ml with flowing phase dilution containing about the solution of 50 μ g finished products, is shaken up；Precision measures 10 μ l,
Liquid chromatograph is injected, chromatogram is recorded；Enrofloxacin reference substance separately is taken, is measured in the same method, is denoted as the 10th group, and as control
Group.By external standard method with calculated by peak area to get data as shown in table 2.
Wherein,
2 orthogonal experiments of table
As shown in Table 2, using the average value of yield and inclusion rate as evaluation criterion, Enrofloxacin hydroxyl and propyl cyclodextrin rub
You are than being 1:1, and the temperature of heated at constant temperature is 55 DEG C in S3, will be included in S4 liquid continue stirring until it is a length of when the stirring for stopping heating
4h, when the stirring rate in preparation process is 500r/min, the yield of Enrofloxacin hydroxypropyl cyclodextrin inclusion obtained and
Inclusion rate reaches best, it is seen that the factors such as the proportion of Enrofloxacin hydroxyl and propyl cyclodextrin, technique and technological parameter will affect
The effect of Enrofloxacin hydroxypropyl cyclodextrin inclusion finished product, only each factor complement each other, and are rationally arranged, can be produced
Rate and inclusion rate reach optimal Enrofloxacin hydroxypropyl cyclodextrin inclusion finished product simultaneously.
Fig. 1-Fig. 3 is respectively hydroxypropyl cyclodextrin, Enrofloxacin standard items, Enrofloxacin hydroxypropyl cyclodextrin inclusion
High-efficient liquid phase chromatogram, observation Fig. 1-Fig. 3 can have found that cyclodextrin does not absorb under the high efficiency condition specified according to pharmacopeia
Peak, it was demonstrated that the detection of Enrofloxacin will not be impacted in the high performance liquid chromatography detection of cyclodextrin with this condition；En Nuo
For husky star standard items under the conditions of 278nm, there is absorption peak in when 10.328min；And the Enrofloxacin clathrate compound of cyclodextrin is water-soluble
Liquid is also separating existing absorption peak 10.328 under the conditions of 278nm, identical efficient liquid phase, it was demonstrated that includes successfully.
It can be seen that by the scanning electron microscope (SEM) photograph map of Fig. 4-Fig. 7, before inclusion, the hydroxypropyl cyclodextrin under scanning electron microscope is capsule
Shape, Enrofloxacin are graininess；After the two is mixed, and not formed inclusion compound, and only simple physical mixed；But occurring
After inclusion, then spherical inclusion compound is formd, at this point, i.e. Enrofloxacin hydroxypropyl cyclodextrin inclusion has been formed.
The infared spectrum of Fig. 8-Figure 11 can be seen that the infrared signature peak of Enrofloxacin is in 1737cm-1And 1629cm-1Place,
After tentatively mixing with hydroxypropyl cyclodextrin, the characteristic peak of Enrofloxacin does not disappear, but after forming inclusion compound, two characteristic peaks disappear
It loses, it was demonstrated that form Enrofloxacin hydroxypropyl cyclodextrin inclusion.
Embodiment 11
Dissolution rate detection is carried out to Enrofloxacin hydroxypropyl cyclodextrin inclusion
Take Enrofloxacin, any finished product and Enrofloxacin in Enrofloxacin hydroxypropyl cyclodextrin inclusion finished product 1-9
Hydroxypropyl cyclodextrin mixture (being equivalent to Enrofloxacin 100mg) is detected as sample, presses " People's Republic of China's veterinary drug
Allusion quotation " 2015 years first annex of version 160 second method (paddle method) testing drug dissolution rates.Dissolution medium be degassed processing go from
Sub- water 900mL temperature (37 scholar 0.3) DEG C, revolving speed 100r/min, respectively at 2min, 5min, 10min, 15min, 20min,
30min, 45min and 60min quantitative sampling 5mL, while supplementing equivalent equality of temperature medium 5mL, through 0.22 μm of filtering with microporous membrane, with
Deionized water is blank, using the Enrofloxacin in the detection each sample of HPLC method described in embodiment 10, and result is substituted into and is marked
In directrix curve regression equation, dissolution rate is calculated.Wherein, it measures 3 times, is averaged with batch sample.
Enrofloxacin standard curve is as shown in figure 12；The Dissolution profiles of each sample are as shown in figure 13.As seen from Figure 13,
For Enrofloxacin and Enrofloxacin hydroxypropyl cyclodextrin mixture, Enrofloxacin hydroxypropyl cyclodextrin inclusion obviously has very
Good dissolution rate.After measured, Enrofloxacin solubility is 0.24g/L, the Enrofloxacin solubility in inclusion compound is 180~
192g/L, the solubility of inclusion compound increase 750~800 times.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (8)
1. a kind of preparation method of Enrofloxacin hydroxypropyl cyclodextrin inclusion, which comprises the following steps:
S1. solvent is added into hydroxypropyl cyclodextrin, dissolves by heating and be configured to the solution of saturation, and suitable toward addition inside solution
The maltol and glucose of amount, it is spare to obtain solution A；
S2. a small amount of solvent is added into Enrofloxacin, obtains solution B, it is spare；
S3. solution B is placed in heated at constant temperature and stirring at 50 DEG C -65 DEG C, while is slowly added to solution A, carried out inclusion reaction, obtain
To inclusion liquid；
S4. the inclusion liquid of S3 is persistently stirred into 2h~4h, stops heating, continue stirring to room temperature；
S5. it refrigerates and is freeze-dried afterwards for 24 hours to get Enrofloxacin hydroxypropyl cyclodextrin inclusion.
2. preparation method according to claim 1, which is characterized in that solvent described in step S1 includes water, alcohols solvent
Or their mixture.
3. preparation method according to claim 1, which is characterized in that solvent described in step S2 is selected from acetic acid, hydroxide
One of sodium solution, dilute hydrochloric acid solution, methanol solution or ethanol solution.
4. preparation method according to claim 1, which is characterized in that the molar ratio of Enrofloxacin and hydroxypropyl cyclodextrin is
(1~3): 1.
5. preparation method according to claim 1, which is characterized in that revolving speed when being stirred in step S3 and S4 is
400r/min~600r/min.
6. preparation method according to claim 1, which is characterized in that stirring to room temperature is in a water bath described in step S4
It carries out.
7. a kind of Enrofloxacin hydroxypropyl cyclodextrin inclusion, which is characterized in that the Enrofloxacin hydroxypropyl cyclodextrin inclusion
Object is made through preparation method described in claim 1-6 Arbitrary Term.
8. a kind of application of Enrofloxacin hydroxypropyl cyclodextrin inclusion, which is characterized in that by En Nuosha as claimed in claim 7
Star hydroxypropyl cyclodextrin inclusion is applied in animal bacteria disease prevention and cure.
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| CN113288866A (en) * | 2021-07-12 | 2021-08-24 | 山东诺明康药物研究院有限公司 | Antibacterial eye drops and preparation method thereof |
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