CN112370451A - Maropritan citrate clathrate compound, injection and preparation method - Google Patents
Maropritan citrate clathrate compound, injection and preparation method Download PDFInfo
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- CN112370451A CN112370451A CN202011423422.1A CN202011423422A CN112370451A CN 112370451 A CN112370451 A CN 112370451A CN 202011423422 A CN202011423422 A CN 202011423422A CN 112370451 A CN112370451 A CN 112370451A
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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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
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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
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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
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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
- A61K9/08—Solutions
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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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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Abstract
The invention relates to the technical field of pharmacy, in particular to a citric acid maropritan inclusion compound, an injection and a preparation method thereof. The citric acid maropiptan clathrate takes sulfobutyl beta-cyclodextrin as an inclusion auxiliary material, has good water solubility, and can be further prepared into powder or injection for injection or other water-soluble preparations. The bioavailability of the inclusion compound is greatly improved, and the administration dosage of the citric acid maropiptan can be reduced. The preparation method provided by the invention determines the optimal inclusion condition of the citric acid malariptan and the sulfobutyl beta-cyclodextrin, greatly improves the inclusion rate, has simple operation and low cost, and obtains the product with stable quality.
Description
Technical Field
The invention relates to the technical field of pharmacy, in particular to a citric acid maropritan inclusion compound, an injection and a preparation method thereof.
Background
Maropritan citrate is a potent and selective type 1 neurokinin (NK-1) receptor antagonist, acting on the central nervous system by inhibiting substance P, a critical neurotransmitter responsible for emesis, and inhibiting peripheral and central emesis. It is the 1 st medicine for preventing and treating canine severe vomiting and motion sickness, is also the first approved medicine for treating canine motion sickness, and has good clinical application value and market prospect.
The acid, namely the malapidan citrate, is a hardly water-soluble drug, so that the bioavailability is greatly reduced, and the administration dosage is increased. At present, the citric acid maropiptan injection and the preparation process thereof are not available in China.
Disclosure of Invention
Aiming at the problems that the marzipan citrate is almost insoluble in water and no marzipan citrate injection and preparation process thereof exist at present, the invention provides a marzipan citrate clathrate compound, an injection and a preparation method thereof.
In order to achieve the purpose of the invention, the embodiment of the invention adopts the following technical scheme:
in a first aspect, the embodiment of the invention provides a citric acid malariptan clathrate compound, which comprises citric acid malariptan and sulfobutyl beta-cyclodextrin in a molar ratio of 1 (1-3).
The citric acid maropiptan clathrate compound provided by the invention has good water solubility, and can be further prepared into powder or injection for injection and other water-soluble preparations. The bioavailability of the inclusion compound is greatly improved, and the administration dosage of the citric acid maropiptan can be reduced. The inclusion compound takes sulfobutyl beta-cyclodextrin as an inclusion auxiliary material, and can obtain higher inclusion rate in the process of preparing the citric acid maropiptan inclusion compound.
Preferably, the molar ratio of the citric acid maropiptan to the sulfobutyl beta-cyclodextrin is 1: 2. Under the condition of the molar ratio, the obtained inclusion compound has the highest inclusion rate.
In a second aspect, an embodiment of the present invention provides a preparation method of the citric acid maropiptan clathrate, including the following operations: mixing the citric acid marzipan and sulfobutyl beta-cyclodextrin in water with the mass being 80-120 times that of the citric acid marzipan, stirring for 0.5-4 h under the condition that the temperature of feed liquid is kept at 45-65 ℃, naturally cooling to room temperature, and freeze-drying.
The preparation method determines the optimal inclusion condition of the citric acid maropiptan and the sulfobutyl beta-cyclodextrin, greatly improves the inclusion rate, has simple operation and low cost, and obtains products with stable quality. Experiments show that the inclusion rate of the inclusion compound does not have a linear relation with the temperature, and the inclusion compound can obtain higher inclusion rate when stirred for 0.5-4 hours at the temperature of 45-65 ℃.
When the above inclusion compound is used for preparing an injection, water for injection is selected, and filtration is performed with a 0.45 μm filter before freeze-drying, so as to remove impurities and most of bacterial microorganisms in the solution.
Preferably, the temperature of the feed liquid is 50-55 ℃ during stirring;
preferably, the stirring time is 1 h.
Preferably, the freeze-drying operation is: freezing at-30 deg.C for 12 hr, and freeze drying at-30 deg.C until water content is less than 2%.
In a third aspect, the embodiment of the invention also provides a citric acid marzipan injection, which comprises the citric acid marzipan clathrate compound, a preservative and water for injection.
Preferably, the preservative is m-cresol.
Preferably, the dosage of the m-cresol is 3-4 mg/ml.
In a fourth aspect, the embodiment of the invention also provides a preparation method of the maririptan citrate injection, which comprises the following operations: mixing the citric acid malariptan and sulfobutyl beta-cyclodextrin in water for injection, wherein the mass of the citric acid malariptan is 80-120 times that of the citric acid malariptan, mixing for 0.5-4 hours at 45-65 ℃, naturally cooling to room temperature, filtering with a 0.45-micrometer filter membrane, freezing at-30 ℃ for 12 hours, and freeze-drying at-30 ℃ until the water content is less than 2% to obtain an inclusion compound solid; adding antiseptic and water for injection into the clathrate solid, dissolving, filtering with 0.45 μm filter membrane, packaging in nitrogen-filled ampoule, and sterilizing. The sterilization can be carried out at the temperature and time of conventional injection sterilization, such as 105 deg.C for 30min or 121 deg.C for 30 min.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Examples 1 to 3
Embodiments 1 to 3 of the invention respectively provide a citric acid marzipan clathrate compound, which comprises citric acid marzipan and sulfobutyl beta-cyclodextrin in molar ratios of 1:1, 1:2 and 1: 3. The preparation method comprises the following steps:
weighing 3 parts of 0.050g of malapidan citrate, putting the malapidan citrate, 0.121g of the malapidan citrate, 0.242g of the malapidan citrate, 0.363g of sulfobutyl beta-cyclodextrin and the malapidan citrate into a 50ml volumetric flask, adding 5ml of water, putting magnetons into the volumetric flask, fixing the volumetric flask in a heat collection type magnetic stirrer, and stirring the mixture for 1 hour at the temperature of 55 ℃. Stopping stirring, naturally cooling to room temperature, filtering with 0.45 μm filter membrane, freezing in refrigerator for 12 hr, and freeze drying (-30 deg.C for 7 hr) to obtain clathrate solid. Taking a proper amount of clathrate solid respectively for inclusion rate test.
Examples 4 to 8
Embodiments 4 to 8 of the invention respectively provide a citric acid maropiptan clathrate compound, which comprises the following components in a molar ratio of 1:2, citric acid, namely malapidan and sulfobutyl beta-cyclodextrin. The preparation method comprises the following steps:
putting 0.048-0.050 g of mallopitan citrate and 0.242g of sulfobutyl beta-cyclodextrin into a 50ml volumetric flask, adding 5ml of water, putting magnetons into the volumetric flask, fixing the volumetric flask in a heat collection type magnetic stirrer, and stirring for 1h at 45, 50, 55, 60 and 65 ℃ respectively. Stopping stirring, naturally cooling to room temperature, filtering with 0.45 μm filter membrane, freezing in refrigerator for 12 hr, and freeze drying (-30 deg.C for 7 hr) to obtain clathrate solid. Taking a proper amount of clathrate solid respectively for inclusion rate test.
Examples 9 to 12
Embodiments 9 to 12 of the present invention respectively provide a citric acid maropiptan clathrate, which includes a citric acid maropiptan clathrate compound with a molar ratio of 1:2, citric acid, namely malapidan and sulfobutyl beta-cyclodextrin. The preparation method comprises the following steps:
putting 0.050g of maropiptan citrate and 0.242g of sulfobutyl beta-cyclodextrin into a 50ml volumetric flask, adding 5ml of water, putting magnetons, fixing the volumetric flask into a heat collection type magnetic stirrer, and stirring for 0.5, 1, 2 and 4 hours at the temperature of 55 ℃. Stopping stirring, naturally cooling to room temperature, filtering with 0.45 μm filter membrane, freezing in refrigerator for 12 hr, and freeze drying (-30 deg.C for 7 hr) to obtain clathrate solid. Taking a proper amount of clathrate solid respectively for inclusion rate test.
Comparative example 1
The comparative example provides a citric acid maropiptan clathrate compound, which comprises citric acid maropiptan and beta-cyclodextrin in a molar ratio of 1: 2. The preparation method comprises the following steps:
weighing 3 parts of 0.050g of mallopitan citrate and 0.242g of beta-cyclodextrin, putting the mixture into a 50ml volumetric flask, adding 5ml of water, putting magnetons into the volumetric flask, fixing the volumetric flask into a heat collection type magnetic stirrer, and stirring the mixture for 1 hour at the temperature of 55 ℃. Stopping stirring, naturally cooling to room temperature, filtering with 0.45 μm filter membrane, freezing in refrigerator for 12 hr, and freeze drying (-30 deg.C for 7 hr) to obtain clathrate solid. Taking a proper amount of clathrate solid respectively for inclusion rate test.
Comparative example 2
The comparative example provides a citric acid marzipan inclusion compound, which comprises citric acid marzipan and hydroxypropyl beta cyclodextrin in a molar ratio of 1: 2. The preparation method comprises the following steps:
weighing 3 parts of 0.050g of mallopitan citrate and 0.305g of hydroxypropyl beta cyclodextrin, putting the mixture into a 50ml volumetric flask, adding 5ml of water, putting magnetons into the volumetric flask, fixing the volumetric flask in a heat collection type magnetic stirrer, and stirring the mixture for 1 hour at the temperature of 55 ℃. Stopping stirring, naturally cooling to room temperature, filtering with 0.45 μm filter membrane, freezing in refrigerator for 12 hr, and freeze drying (-30 deg.C for 7 hr) to obtain clathrate solid. Taking a proper amount of clathrate solid respectively for inclusion rate test.
Comparative example 3
The comparative example provides a citric acid malaitan clathrate compound, which comprises citric acid malaitan and sulfobutyl beta-cyclodextrin in a molar ratio of 1: 2. The preparation method comprises the following steps:
weighing 3 parts of 0.050g of maropiptan citrate and 0.242g of sulfobutyl beta-cyclodextrin, putting the maropiptan citrate and the sulfobutyl beta-cyclodextrin into a 50ml volumetric flask, adding 5ml of water, putting magnetons into the volumetric flask, fixing the volumetric flask in a heat collection type magnetic stirrer, and stirring for 1 hour at the temperature of 35 ℃. Stopping stirring, naturally cooling to room temperature, filtering with 0.45 μm filter membrane, freezing in refrigerator for 12 hr, and freeze drying (-30 deg.C for 7 hr) to obtain clathrate solid. Taking a proper amount of clathrate solid respectively for inclusion rate test.
Comparative example 4
The comparative example provides a citric acid malaitan clathrate compound, which comprises citric acid malaitan and sulfobutyl beta-cyclodextrin in a molar ratio of 1: 2. The preparation method comprises the following steps:
weighing 3 parts of 0.050g of maropiptan citrate and 0.242g of sulfobutyl beta-cyclodextrin, putting the maropiptan citrate and the sulfobutyl beta-cyclodextrin into a 50ml volumetric flask, adding 5ml of water, putting magnetons into the volumetric flask, fixing the volumetric flask in a heat collection type magnetic stirrer, and stirring for 1 hour at the temperature of 75 ℃. Stopping stirring, naturally cooling to room temperature, filtering with 0.45 μm filter membrane, freezing in refrigerator for 12 hr, and freeze drying (-30 deg.C for 7 hr) to obtain clathrate solid. Taking a proper amount of clathrate solid respectively for inclusion rate test.
The amounts of the maropiptan citrate and the inclusion excipients, the reaction temperature and the reaction time in the above examples 1 to 12 and comparative examples 1 to 4 are detailed in table 1.
Test example 1
Taking a proper amount of the inclusion compound for inclusion rate test in examples 1-12 (namely, placing the inclusion compound in a refrigerator for freezing for 12 hours, and then freeze-drying to obtain a solid inclusion compound), fixing the volume with water, shaking, filtering with 0.45 mu m microporous filter membranes respectively, measuring the absorbance of the solution respectively, and calculating the inclusion rate respectively, wherein the results are shown in Table 1.
TABLE 1
Example 13
The embodiment provides a citric acid marziptan injection, and each 100ml of the citric acid marziptan injection contains 1g of citric acid marziptan, 6.3g of sulfobutyl beta-cyclodextrin, 0.34g of m-cresol and the balance of water for injection. The preparation method comprises the following steps:
(1) adding 1g of maropiptan citrate and 6.3g of sulfobutyl beta-cyclodextrin into a preparation container according to the molar ratio of 1:2, adding 80ml of water for injection, putting magnetons into the container, fixing the preparation container on a heat collection type magnetic stirrer, and starting stirring for 1h at 55 ℃;
(2) placing the solution obtained in the step (1) at room temperature, filtering with a 0.45 μm filter membrane, freezing the filtrate in a refrigerator for 12h, and freeze-drying at-30 deg.C for 8h to obtain clathrate solid with water content of 1.2%;
(3) adding 0.34g of m-cresol into the clathrate solid obtained in the step (2), adding water for injection to 100ml, and stirring uniformly;
(4) filtering the solution obtained in the step (3) by using a 0.45-micron filter membrane;
(5) and (4) encapsulating, introducing nitrogen into the ampoule during encapsulation, and sterilizing at 105 ℃ for 30 minutes after encapsulation.
Example 14
The embodiment provides a citric acid marziptan injection, and each 100ml of the citric acid marziptan injection contains 1g of citric acid marziptan, 6.3g of sulfobutyl beta-cyclodextrin, 0.34g of m-cresol and the balance of water for injection. The preparation method comprises the following steps:
(1) adding 1g of maropiptan citrate and 6.3g of sulfobutyl beta-cyclodextrin into a preparation container according to the molar ratio of 1:2, adding 80ml of water for injection, putting magnetons into the container, fixing the preparation container on a heat collection type magnetic stirrer, and starting stirring for 1h at 55 ℃;
(2) placing the solution obtained in the step (1) at room temperature, filtering with a 0.45 μm filter membrane, freezing in a refrigerator for 12h, and freeze-drying at-30 deg.C for 8h to obtain clathrate solid with water content of 1.3%;
(3) adding 0.34g of m-cresol into the clathrate solid obtained in the step (2), adding water for injection to 100ml, and stirring uniformly;
(4) filtering the solution obtained in the step (3) by using a 0.45-micron filter membrane;
(5) and (4) encapsulating, introducing nitrogen into the ampoule during encapsulation, and sterilizing at 121 ℃ for 30 minutes after encapsulation.
Test example 2
3 batches of the Marropinan citrate injection prepared by the method of example 13 were placed in a constant temperature and humidity cabinet at 60 ℃, and sampled on the 5 th day and the 10 th day, and the appearance, clarity, pH value and content of the Marropinan injection were checked, and the results are shown in tables 2 and 3.
TABLE 2 day 5 sampling (60 ℃ constant temperature and humidity box)
TABLE 3 day 10 sampling (60 ℃ constant temperature and humidity box)
Test example 3
3 batches of the Marropinan citrate injection prepared by the method of example 13 were cultured in a light incubator with a fluorescent lamp under the condition of 4500 + -500 Lx for 10 days, and samples were taken at day 5 and day 10 respectively to examine the appearance, clarity, pH and content of the Marropinan injection, and the results are shown in tables 4 and 5.
TABLE 4 day 5 sampling (light incubator)
TABLE 5 day 10 sampling (light incubator)
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (9)
1. The citric acid maropritan clathrate compound is characterized by comprising the following components in a molar ratio of 1: (1-3) acid citrate malariptan and sulfobutyl beta-cyclodextrin.
2. The citric acid marzipan clathrate compound according to claim 1, wherein the molar ratio of citric acid marzipan to sulfobutyl β -cyclodextrin is 1: 2.
3. The preparation method of the citric acid marzipan clathrate compound in claim 1 or 2, which is characterized by comprising the following operations: mixing the citric acid marzipan and sulfobutyl beta-cyclodextrin in water with the mass being 80-120 times that of the citric acid marzipan, stirring for 0.5-4 h under the condition that the temperature of feed liquid is kept at 45-65 ℃, naturally cooling to room temperature, and freeze-drying.
4. The preparation method of the citric acid marzipan clathrate compound according to claim 3, wherein the temperature of feed liquid is 50-55 ℃ during stirring; and/or
The stirring time was 1 h.
5. The preparation method of the citric acid marzipan clathrate compound, according to claim 3, wherein the freeze-drying operation comprises: freezing at-30 deg.C for 12 hr, and freeze drying at-30 deg.C until water content is less than 2%.
6. An Marospitan citrate injection, which is characterized by comprising the Marospitan citrate clathrate compound as claimed in claim 1 or 2, a preservative and water for injection.
7. The Marropinitant citrate injection according to claim 6, wherein the preservative is m-cresol.
8. The maririptan citrate injection according to claim 7, wherein the amount of m-cresol is 3-4 mg/ml.
9. The preparation method of the citric acid maropiptan injection according to any one of claims 6 to 8, which is characterized by comprising the following operations:
mixing the citric acid maladaptan and sulfobutyl beta-cyclodextrin in water for injection, wherein the mass of the citric acid maladaptan is 80-120 times that of the citric acid maladaptan, mixing for 0.5-4 h at 45-65 ℃, naturally cooling to room temperature, filtering with a 0.45-micrometer filter membrane, freezing for 12h at-30 ℃, and freeze-drying at-30 ℃ until the water content is less than 2% to obtain an inclusion compound solid; adding antiseptic and water for injection into the clathrate solid, dissolving, filtering with 0.45 μm filter membrane, packaging in nitrogen-filled ampoule, and sterilizing.
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2020
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