CN110063934B - Liranaftate external solution for treating fungal infection of pets and preparation method thereof - Google Patents

Liranaftate external solution for treating fungal infection of pets and preparation method thereof Download PDF

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CN110063934B
CN110063934B CN201810060682.3A CN201810060682A CN110063934B CN 110063934 B CN110063934 B CN 110063934B CN 201810060682 A CN201810060682 A CN 201810060682A CN 110063934 B CN110063934 B CN 110063934B
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liranaftate
concentration
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skin
pets
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CN110063934A (en
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张许科
田朋飞
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Luoyang Huizhong Animal Medicine Co ltd
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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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • 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
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A61K9/0017—Non-human animal skin, e.g. pour-on, spot-on
    • 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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Abstract

The invention relates to a liranaftate solution for treating fungal infection of pets, which comprises the following components in part by weight: solvent glycerin fatty acid ester, cosolvent ethyl acetate, bacteriostatic agent lauric acid monoglyceride and liranaftate. The liranaftate solution can be directly applied to damaged skin, the acceptability is increased when the liranaftate solution is applied to pets, and the drug effect is equivalent to that of commercial products.

Description

Liranaftate external solution for treating fungal infection of pets and preparation method thereof
Technical Field
The invention relates to a pet dermatosis medicine, in particular to a solution for treating fungal infection of pets.
Background
The fungal infection of pets is one of the common diseases of pet skin diseases in China at present, and accounts for 41.75 percent of the skin diseases of pets. It not only seriously affects the health of pets, but also creates a favorable condition for other pathogens to invade the skin. In particular, the probability of infecting the microsporidian in the pet is high, and the pet can generate skin damage and pruritus symptoms after being infected, so that the animal can scratch continuously, thereby causing the skin and hair follicle damage of the animal and the rough and disordered animal skin, influencing the appearance of the animal and causing secondary infection of other fungi and bacteria.
Liranaftate is a novel third-generation thiocarbamic acid antifungal drug, is a novel chemical drug of three types, is a squalene epoxidase inhibitor which is jointly developed and developed by Tosoh corporation and zenyaku Kogyo corporation in Japan, is firstly marketed in Japan by Torrii corporation in 2000 for 8 months, inhibits the squalene epoxidation reaction of fungal cell membranes, inhibits the synthesis of ergosterol which is a constituent of the cell membranes, and causes the leakage of important substances in cells, thereby exerting antifungal activity. Compared with the existing medicines for clinically treating skin fungal infection such as tolnaftate, clotrimazole and miconazole ointment, the product has the characteristics of strong antibacterial activity, high curative effect, long curative effect, less administration times, less dosage, small adverse reaction and the like, is suitable for local treatment of skin fungal infection, and is particularly effective on floccus epidermophyton of trichophyton, microsporum and epidermophyton.
Currently, liranaftate is mainly used for human clinical administration, and no relevant use report exists for pets. At present, products for domestic and foreign people to use medicine on the market mainly comprise two dosage forms of cream and external solution. Since liranaftate is a granular crystalline powder and has extremely low solubility in water, there are few reports on the literature on a liranaftate external solution. Zefnart Solution 2% mainly permeates into sebum through the medicine to play the antifungal effect, but the product has certain skin irritation, particularly when the affected part is damaged due to scratching, the skin irritation is stronger, inconvenience is brought to a user, and the product has larger obstacle when being popularized as a pet medicine.
Disclosure of Invention
In order to solve the problems of the prior art, the present invention provides a safer solution for external use that improves skin irritation.
The invention relates to a liranaftate solution for treating fungal infection of pets, which comprises the following components in part by weight: solvent glycerin fatty acid ester, cosolvent ethyl acetate, bacteriostatic agent lauric acid monoglyceride and liranaftate.
The liranaftate solution of the present invention can be applied directly to damaged skin, and is more acceptable to users, particularly when the user is a pet.
In one embodiment of the invention, the concentration of liranaftate is 5-50 g/L.
The liranaftate solution of the present invention has the same therapeutic effect as the products of the prior art.
As an embodiment of the present invention, the liranaftate solution further contains: antioxidants, emollients, and flavorants.
As a preferred embodiment of the present invention, the antioxidant is one or both of BHT and citric acid; the emollient is isopropyl palmitate; the flavoring agent is diethyl sebacate.
As an embodiment of the present invention, the liranaftate solution is in the form of liniment, spray, liniment, lotion, drops, or pour-on.
The liranaftate external solution can be one of liniment, dipping lotion, spray, drops and pour-on agent, and is stable, easy to apply and spreadable.
In one embodiment of the present invention, the concentration of the cosolvent is in the range of 1% to 40% (v/v), and the concentration of the solvent is in the range of 40% to 90% (v/v); the concentration range of the bacteriostatic agent is 0.1-200 g/L.
As a preferred embodiment of the invention, the concentration range of the antioxidant is 0.2-50 g/L; the concentration range of the emollient is 0.1-5% (v/v); the concentration range of the flavoring agent is 0.1-10% (v/v).
In a more preferred embodiment of the present invention, the liranaftate solution comprises liranaftate at a concentration of 20g/L, ethyl acetate at a concentration of 20% (v/v), lauric monoglyceride at a concentration of 0.5g/L, BHT at a concentration of 1.0g/L, isopropyl palmitate at a concentration of 3% (v/v), diethyl sebacate at a concentration of 6% (v/v), and the balance of glycerin fatty acid ester.
The invention also relates to a method for preparing the liranaftate solution, which is characterized by comprising the following steps: respectively putting other weighed liquid components and part of solvent into a container at the temperature of 20-30 ℃ and stirring, and then adding the weighed liranaftate and other solid components into the container containing the solvent and stirring until all the liranaftate and the other solid components are dissolved; and (2) adding a solvent to a constant volume, and filtering the prepared solution.
The preparation method of the liranaftate solution has simple process and is easy for large-scale industrial preparation.
As an embodiment of the invention, in the step (1), the temperature is 25 ℃, the stirring speed is 500-1500 rpm/min, and the stirring time is 5-60 min; the aperture of the filter membrane in the step (2) is 0.45 μm.
The invention also relates to application of the liranaftate solution in preparing a medicine for treating fungal infection of pets.
The liranaftate solution can be prepared into various external preparations, can effectively treat fungal infection of pets, and can be directly applied to damaged skin.
Detailed Description
Hereinafter, embodiments of the present invention will be described.
The chemicals used in the examples of the present invention, unless otherwise specified, were all analytical grade and were all commercially available.
Comparative example 1: comparative preparation with liranaftate solution
The components are as follows:
Figure BDA0001555217080000031
Figure BDA0001555217080000041
the preparation method comprises the following steps: and step A, at room temperature of 25 ℃, sequentially putting weighed liranaftate, BHT and citric acid into a stirring tank with weighed ethyl acetate, a proper amount of glycerin fatty acid ester, ethanol and isopropyl palmitate, stirring at the stirring speed of 1000rpm/min for 30min until the liranaftate and the glycerin fatty acid ester are completely dissolved, adding the rest glycerin fatty acid ester to a constant volume, and filtering by using a 0.45-micrometer nylon filter membrane to obtain a semi-finished product.
And step B, taking the semi-finished product, filling and packaging to obtain the finished product.
Preparation example 2: preparation of liranaftate solution
The components are as follows:
Figure BDA0001555217080000042
the preparation method comprises the following steps: and step A, at room temperature of 25 ℃, sequentially putting weighed liranaftate, BHT and BHA into a stirring tank of weighed ethyl acetate, diethyl sebacate, a proper amount of glycerin fatty acid ester and isopropyl palmitate, stirring at the stirring speed of 1000rpm/min for 30min until the materials are completely dissolved, adding the rest glycerin fatty acid ester to a constant volume, and filtering by using a 0.45-micrometer nylon filtering membrane to obtain a semi-finished product.
And step B, taking the semi-finished product, filling and packaging to obtain the finished product.
Example 3 skin irritation study of unbroken skin:
3.1 test article
Test drugs:
prepared by Luoyang Hui Chinese veterinary drug Co Ltd; the liranaftate external solution prepared in the embodiment 1 of the invention; the liranaftate external solution prepared in the embodiment 2 of the invention; japanese product ZEFNARTSOLUTION 2%.
Test animals:
10 New Zealand white rabbits, 2.5-3kg weight, female and male half.
3.2 operating procedure
Preparation of rabbit skin
The two sides of the spine of the rabbit are shaved 24 hours before administration, the shaving area of each side is about 3cm multiplied by 3cm, whether the dehaired skin is damaged due to dehairing or not is checked before administration, and 8 dehaired rabbits without skin damage are selected for test.
Method of administration
Selecting 8 shaved rabbits with intact skin, directly applying 0.5 mL/rabbit to the left depilated skin, covering with two layers of gauze (2.5 cm. times.2.5 cm) and a layer of non-irritating plastic film, fixing with non-irritating adhesive tape, and applying excipient (0.9% physiological saline) to the right depilated skin of rabbits as control. After 4 hours of application, the test substance was removed and the administration site was cleaned with warm water. The same method is adopted to continuously administer the medicine to the same part for 1 week (7 times), and the administration time is the same for each time. After 4h of application, the residual test substance was removed with warm water, and the skin at the site of hair removal was observed for erythema, edema and other abnormal manifestations 1h after each removal of the drug and before reapplication, and the skin local reactions at the site of hair removal were visually observed 1h, 24h, 48h and 72h after the last administration, and the irritation response was scored. The skin irritation response scores and skin irritation intensity grading criteria are detailed in tables 1 and 2.
TABLE 1 skin irritation response Scoring criteria
Figure BDA0001555217080000051
Figure BDA0001555217080000061
TABLE 2 evaluation criteria for skin irritation intensity
Score (A + B) Evaluation of
0-0.49 Has no irritation
0.5-2.99 Mild irritation
3.0-5.99 Moderate irritation
6.0-8.0 Strong irritation
Statistical analysis was performed on the test data and the results are shown in tables 3, 4 and 5.
TABLE 3 skin irritation results of Japanese product ZEFNART SOLUTION 2% on non-lesioned skin rabbits
Figure BDA0001555217080000062
Figure BDA0001555217080000071
Figure BDA0001555217080000081
The results showed that 2% of the Japanese product ZEFNART SOLUTION had mild skin irritation 72 hours before application.
Table 4 results of skin irritation of comparative liranaftate solutions prepared in example 1 to rabbits with unbroken skin
Figure BDA0001555217080000091
Figure BDA0001555217080000101
Figure BDA0001555217080000111
The results show that the liranaftate solutions of the comparative example of example 1 are all non-damaging to rabbit skin and non-irritating to the skin after application.
Table 5 results of skin irritation of non-lesioned skin rabbits by liranaftate solution of the invention prepared in example 2
Figure BDA0001555217080000112
Figure BDA0001555217080000121
Figure BDA0001555217080000131
The results show that the liranaftate solutions of the present invention prepared in example 2 were non-damaging to rabbit skin and non-irritating to rabbit skin after application.
Example 4 study of damaged skin irritation:
4.1 test article
Test drugs:
luoyanghui veterinary drug ltd; the liranaftate external solution prepared in the embodiment 1 of the invention; the liranaftate external solution prepared in the embodiment 2 of the invention; japanese product ZEFNARTSOLUTION 2%.
Test animals:
10 New Zealand white rabbits, 2.5-3kg weight, female and male half.
4.2 test procedure
Preparation of rabbit skin
The two side hairs of the spine of the rabbit are shaved 24 hours before administration, the shaving area of each side is about 3cm multiplied by 3cm, the medicine application part of the damaged skin group is marked with a Chinese character 'jing', and 8 dehaired rabbits with damaged skin are selected for experiment by taking exudation as the degree.
Method of administration
Selecting 8 shaved rabbits with damaged skin, directly applying 0.5 mL/rabbit to the left depilated skin, covering with two layers of gauze (2.5 cm. times.2.5 cm) and a non-irritating plastic film, fixing with non-irritating adhesive tape, coating excipient (0.9% physiological saline as control), applying for 4 hr, removing the test substance, and cleaning the application site with warm water, continuously applying to the same site for 1 week (7 times) with the same method, removing residual test substance with warm water 4 hr after application, observing the skin at the depilated site for erythema, edema and other abnormal manifestations 1 hr after removing the medicine and before applying again, and observing the skin local reactions at the depilated site with naked eyes 1 hr, 24 hr, 48 hr and 72 hr after the last application, and performing irritation grading standards for skin irritation reaction and skin irritation strength, which are detailed in tables 1 and 2, statistical analysis was performed on the test data and the results are shown in tables 6, 7 and 8.
TABLE 6 skin irritation results of Japanese product ZEFNART SOLUTION 2% on rabbits with damaged skin
Figure BDA0001555217080000141
Figure BDA0001555217080000151
Figure BDA0001555217080000161
Figure BDA0001555217080000171
The results show that 2% of the Japanese product ZEFNART SOLUTION has moderate skin irritation to the rabbits with damaged skin up to 72 hours after application.
Table 7 results of skin irritation of rabbit with damaged skin by comparative liranaftate solution prepared in example 1
Figure BDA0001555217080000172
Figure BDA0001555217080000181
Figure BDA0001555217080000191
The results show that the liranaftate solution of comparative example 1 has a slight skin irritation on the damaged skin of rabbits up to 72 hours after application.
Table 8 results of skin irritation of damaged skin rabbits with liranaftate solution prepared in example 2
Figure BDA0001555217080000192
Figure BDA0001555217080000201
Figure BDA0001555217080000211
The results show that the liranaftate solutions of the present invention of example 2 are all non-skin irritating to the damaged rabbit skin after application.
EXAMPLE 5 liranaftate solution efficacy test of the invention
5.1 test article
Test drugs:
the liranaftate external solution prepared in the embodiment 2 of the invention; japanese product ZEFNARTSOLUTION 2%.
Test animals:
120 beagle dogs with the age of 10 months are selected from a certain dog breeding base in Yibin region of Luoyang city, Henan province. The clinical manifestations are psoriasis, alopecia, scurf and the like, and the infection of dog microspore is detected by a microscope.
5.2 test procedure
120 cases of naturally infected dogs are divided into 2 groups of 60 dogs, the group 1 is externally applied with the medicine prepared in the embodiment 2, the medicine is smeared on the affected part for 1 time/day, and the medicine is applied for 7 days; group 2 is applied topically with ZEFNART SOLUTION 2%, and the medicine is applied to affected part for 1 time/day for 7 days;
the judgment standard of the curative effect is as follows:
after the medicine is taken for curing, the separation negative conversion rate of pathogenic bacteria of the skin is more than or equal to 80 percent, simultaneously, the skin pruritus symptom disappears, and the scurf obviously disappears.
After the medicine is effectively applied, the separation negative conversion rate of pathogenic bacteria of the skin is more than or equal to 60 percent, and meanwhile, the skin pruritus symptom is relieved, and the scurf is reduced.
After the drug is taken inefficiently, the separation negative conversion rate of pathogenic bacteria of the skin is less than 60 percent, obvious pruritus symptom still exists, and no reduction of scurf is seen.
Statistical analysis was performed on the test data and the results are shown in table 9.
TABLE 9 therapeutic Effect of the drugs obtained in the present invention on Microsporum canis
Figure BDA0001555217080000221
The results show that the liranaftate SOLUTION prepared in example 2 and ZEFNART SOLUTION 2% effective rate of the drug for treating the microsporum canis infection are both 100%, and the total cure rates are 93.3% and 90.0% respectively, and have no significant difference. The liranaftate SOLUTION of the invention is shown to have 2 percent of drug effect equivalent to ZEFNART SOLUTION.
Although the present invention has been described with reference to the preferred embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.

Claims (8)

1. A liranaftate solution for the treatment of fungal infections in pets, comprising: solvent glycerin fatty acid ester, cosolvent ethyl acetate, bacteriostatic agent lauric acid monoglyceride, liranaftate, antioxidant BHT, emollient isopropyl palmitate, and flavoring agent diethyl sebacate.
2. The liranaftate solution according to claim 1, wherein the concentration of liranaftate is 5-50 g/L.
3. The liranaftate solution according to claim 1, wherein the liranaftate solution is in the form of a liniment, a spray, a liniment, a lotion, drops, or a pour-on.
4. The liranaftate solution according to claim 1, wherein the concentration of the cosolvent is in the range of 1% to 40% (v/v), and the concentration of the solvent is in the range of 40% to 90% (v/v); the concentration range of the bacteriostatic agent is 0.1-200 g/L.
5. The liranaftate solution according to claim 1, wherein the concentration of the antioxidant is in the range of 0.2-50 g/L; the concentration range of the emollient is 0.1-5% (v/v); the concentration range of the flavoring agent is 0.1-10% (v/v).
6. The liranaftate solution according to claim 5, wherein the liranaftate solution comprises liranaftate at a concentration of 20g/L, ethyl acetate at a concentration of 20% (v/v), lauric monoglyceride at a concentration of 0.5g/L, BHT at a concentration of 1.0g/L, isopropyl palmitate at a concentration of 3% (v/v), diethyl sebacate at a concentration of 6% (v/v), and the balance of glycerin fatty acid ester.
7. A method of preparing the liranaftate solution of claim 1, wherein the preparation method comprises:
respectively putting other weighed liquid components and part of solvent into a container at the temperature of 20-30 ℃ and stirring, and then adding the weighed liranaftate and other solid components into the container containing the solvent and stirring until all the liranaftate and the other solid components are dissolved;
adding a solvent to a constant volume, and filtering the prepared solution;
preferably, in the step (1), the temperature is 25 ℃, the stirring speed ranges from 500rpm/min to 1500rpm/min, and the stirring time ranges from 5 min to 60 min;
the aperture of the filter membrane in the step (2) is 0.45 μm.
8. Use of a liranaftate solution according to any one of claims 1 to 6 in the manufacture of a medicament for the treatment of fungal infections in pets.
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Publication number Priority date Publication date Assignee Title
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CN101433537A (en) * 2007-11-12 2009-05-20 浙江万马药业有限公司 External-use spray for resisting mycotic infection of superficial part and preparation method thereof
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Title
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"药物治疗犬真菌性皮肤病的最新研究进展";冯秀娟等;《中国工作犬业》;20141231;第20-23页 *
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鸟居药品株式会社.zefnart cream 2% & solution 2% 说明书.《zefnart cream 2% & solution 2% 说明书》.2015,第1-2页. *

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