Antifungal gel pharmaceutical composition and method for its preparing

FIELD: medicine, dermatology, chemical-pharmaceutical industry, pharmacy.

SUBSTANCE: invention relates to an antifungal gel pharmaceutical composition based on ketoconazole and clotrimazole that are derivatives of imidazole. The composition comprises ketoconazole or clotrimazole as an active component, polyethylene glycol-400 (PEG-400) as a solvent, carboxyvinyl polymer as a gel-forming agent, polyethylene glycol as a gel stabilizing agent, organic amine or inorganic bas as a regulator of pH and water taken in the definite ratio of components. The composition is prepared by dissolving active component in PEG-400, dispersing carboxyvinyl polymer in water, successive addition to dispersion propylene glycol as a stabilizing agent and regulator of pH and combination of prepared solution and gel followed by stirring the mixture up to preparing the gel composition with pH 5-7. Invention provides preparing antifungal composition with reduced adverse effect.

EFFECT: improved preparing method, valuable medicinal properties of composition.

2 cl, 1 tbl, 11 ex

 

The invention relates to chemical-pharmaceutical industry and medicine, namely to antifungal gel pharmaceutical compositions based on derivatives of imidazole - ketoconazole and clotrimazole.

Clotrimazole (canesten) and ketoconazole (nizoral) has gotten the most publicity and the distribution of the entire group of imidazole antimycotics. Clotrimazole, or bis-phenyl-(2-chlorophenyl)-1-imidazolidin with the gross formula C22H17Cl2and molecular mass (MM) 344,8, was synthesized in 1967, the German company Bayer. The mechanism of action clotrimazole is the inhibition of the synthesis of nucleic acids, lipids and polysaccharides in the cells of the pathogenic fungus that causes damage to cell membranes, its dissolution, the increased permeability of phospholipid membranes of lysosomes [Cheglakov N, Rukavishnikov V. Imidazole drugs in Mycology//journal of dermatology and venereology. - 1984. No. 6. - P.51-57]. Clotrimazole has a broad antifungal spectrum. The drug is active against pathogenic dermatophytes, yeast fungi, pathogens multi-colored lichen, amitraz, some gram-positive (Staphylococcus, Streptococcus) and gram-negative bacteria, Trichomonas vaginalis. Dignity drugs clotrimazole is its good penetrating ability with the skin surface of the stratum corneum is the layer of the epidermis. Also, the positive side is the ability to clotrimazole to accumulate in the deeper layers of the epidermis, where its concentration can reach values above the minimum overwhelming concentration (MBC) for dermatophytes. When applying the product on the nail, clotrimazole can penetrate the layers of keratin [Register of medicines of Russia. Encyclopedia of drugs. Ed. 10-E. M., 2003].

Ketoconazole is a new drug of the group of imidazoles. Unlike clotrimazole drugs ketoconazole effectively applied not only locally, but also oral. An important feature of ketoconazole is its effect on superficial and systemic mycoses. This makes possible its use in the treatment of fungal infections [Mashkovsky PPM Medicines: a Guide to pharmacotherapy for physicians: 2 hours Part 1, s, M, LLC "New wave", 2002]. Ketoconazole or CIS-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(NH-imidazol-1-ylmethyl)-1,3-dioxolane-4-yl]methoxy]phenyl]-piperazine was synthesized in 1978 by the Belgian company “Jansen” in the form of water-soluble drug R-41400. Its formula is C26H28About4N4Cl2[Potekaev NS, Sosnin E.A. Nizoral. Perspectives of use and side effects//journal of dermatology and venereology. - 1987, No. 8, p.20-25]. Drugs ketoconazole is effective in the treatment of dermatomycosis, onychomycosis, mikoto the hair of the head, vaginal mycosis [Register of medicines of Russia. Encyclopedia of drugs. ISD-E. M., 2003, s]. Currently on sale there are many drugs clotrimazole and ketoconazole for topical application in the form of ointments, creams and solutions. The most widely manufactured by Pharma drugs in the form of alcoholic solutions and ointments. The disadvantage of liquid forms are the high turnover of the drug and the volatility of the solvent, resulting in the active component is not sufficiently fixed on the skin surface and does not penetrate inside, remaining on the surface in the form of a friable powder. Known [RF patent 2120305, IPC And 61 To 47/38, 1998] farmcampsite in the form of a cream containing clotrimazole or ketoconazole, the derived methyl cellulose, castor oil, preservative, stabilizer and additives target. The disadvantage of the composition is that the active substance is not dissolved, but in the form of dispersion, so not penetrate from the surface of the skin in its deep layers, which decreases therapeutic effect of the composition. In addition, castor oil is irritating effect on the mucous membranes, which limits the scope of application of the drug, for example, in the treatment of vaginal mycoses.

Known [U.S. patent 4267169, IPC And 61 To 31/74, 31/415, 1981] the pharmaceutical composition in the form of a gel, comprising clotrimazol is as an active ingredient. The composition contains as solvent crotamiton mixed with ethyl alcohol, carboxyvinyl polymer as a gelling agent, a pH regulator, an organic amine and propylene glycol as the water-bonding component. The disadvantage of the composition is the fact that one of its components - crotamiton has a side effect - causes severe skin irritation, is not suitable for children (under 12 years) [Register of medicines of Russia. Encyclopedia of drugs. ISD-E. M., 2003, p.472-473].

Closest to the claimed invention, the essential features is the composition in the form of a gel [patent EP 0186055, IPC a 61 K 31/415, 1986]. This composition contains (wt.%): as the active substance is clotrimazole or bifonazole - 0.5-3; as a gelling agent carboxyvinyl polymer is 0.1-3; as solvent - 1,3-butyleneglycol - 5-90 and, preferably, additional ethanol - 30; as the pH regulator is an organic amine and water. The disadvantage of gel on Pat. EP 0186055 is the presence of 1,3-butyleneglycol with irritant effect on skin and mucous membranes, which is an undesirable side effect of the drug [Harmful substances in industry. A Handbook for chemists, engineers and doctors. ISD-that is, Volume 1. Organic substances. Under re is. Professor Nuvasive, MD Anglewing. L., "Chemistry", 1976, s]. In addition, the gel typically contains ethanol, which, in turn, has tanning and irritant effect on skin and mucous membranes [Register of medicines of Russia. Encyclopedia of drugs. ISD-E. M., 2003, s]. Tanning action of ethyl alcohol leads to strengthening and thickening of the walls of the spores of the fungus, and thereby reduces therapeutic effect of the drug.

The task of the invention is to develop a gel pharmaceutical compositions on the basis of ketoconazole or clotrimazole with reduced side effects.

The problem is solved in that the antifungal gel pharmaceutical composition comprising the active ingredient is a derivative of imidazole, organic solvent, carboxyvinyl polymer as a gelling agent, a pH regulator and water, contains as the organic solvent is a glycol-400 (PEG-400), and as derived imidazole contains a substance selected from the group including ketoconazole and clotrimazole and additionally contains propylene glycol (PG) as a stabilizer of the gel in the following ratio of components (wt.%):

Clotrimazole or ketoconazole 0.5-3.0

The polyethylene glycol 400 15.0-70.0

Propylene glycol 1.0-70.0

Carboxyvinyl polymer .5-3 .0

The pH regulator 0.05-3.0

Water the rest

The inventive composition provides reduced side irritants through the use of an inert solvent is PEG-400, PEG-400 in combination with PG provides excellent consumer properties, namely: the application of the drug is aesthetic in appearance, does not spread through the use of stabilizing additives, does not stain clothing, easily removed and washed.

The authors first used in the gel composition ketoconazole. The composition has excellent therapeutic effect.

Gel composition according to patent EP 0186055 obtained by mixing the active component - clotrimazole or bifonazole with an organic solvent, heated to 65-75°, 1,3-butyleneglycol and ethyl alcohol, a gelling agent, an organic amine and water. The disadvantage of this method is the use of 1,3-butyleneglycol, which has a relatively low flash point (121°C), is very hygroscopic, under normal conditions, is easily oxidized in the air, which require special conditions of storage and handling. 1,3-butyleneglycol has no status pharmacopoeial product.

The present invention is to develop a simple, safe, technologically advanced way to obtain gel.

The problem is solved in that in the method of obtaining PR is telegraphos gel farbkomposition, including mixing the active component - imidazole derivative with an organic solvent, a gelling agent carboxyvinyl polymer, a pH regulator and water, as an active ingredient use ketoconazole or clotrimazole, the solvent is PEG-400 and impose additional stabilizer gel - PG, and the active ingredient is dissolved in PEG-400 when heated, carboxyvinyl polymer is dispersed in water, the dispersion is sequentially mixed with PG and pH regulator, and the resulting mass is combined with a solution of the active component under stirring to obtain a gel with a pH of 5-7.

The advantage of the proposed method is that it provides a simple and safe process for the production of the gel due to the use of PEG-400 as solvent, does not require special conditions of production and can be performed on conventional manufacturing equipment for the production of soft medicinal forms. PEG with molecular weight of 400 is inert, non-toxic solvent, recommended for use in the pharmaceutical industry. In a production environment toxic effect of PEG-400 was not detected [Harmful substances in industry. A Handbook for chemists, engineers and doctors. ISD-that is, Volume 1. Organic substances. Edited by Prof. NFL is AREVA, MD Anglewing. L., "Chemistry", 1976, s]. PEG-400 has the status of a pharmaceutical product [FS 42-1242-96] and is widely used as excipients for the production of many medicines, including soft medicinal forms.

The inventive composition and method of reception ensure the creation of new antifungal gel drug with excellent medicinal properties, with reduced side effects, as well as simple and safe production technology.

For the production of the inventive anti-fungal gel pharmaceutical composition can be used with a wide range of redkostej carboxyvinyl polymers based on acrylic acid. During the development of the claimed composition, we used carboxyvinyl polymers grades of Carbopol 974P NF and Carbopol 934P NF Belgian company BF Goodrich.

As the pH regulator may be used organic amines or inorganic bases. As organic amines can be used mono-, di - or trialkanolamines, mono-, di - or trialkylamine; as inorganic bases can be used sodium hydroxide or potassium. During the development of the claimed composition we used diethylamine (deja) THE 6-09-68-89, triethanolamine (tea) THE 6-09-982-96 and NaOH in the form of a 10% solution.

During the development of the claimed composition and the pic is her BA get used substance of clotrimazole ND 42-9851-99 Chinese manufacturer "tai yuan pharmaceutical, Factory and substance ketoconazole ND 42-10696-00 Indian firms "global Balk " & Fayne chemicals LTD.". In the manufacture of the claimed antifungal gel pharmaceutical composition can be used all registered in the Russian Federation substance of ketoconazole and clotrimazole. Were also used GHG VFS 42-1594-86 and PEG-400 FS 42-1242-96.

The invention is illustrated by the following examples.

Example 1.

The substance of clotrimazole (1 g) is mixed with PEG-400 (15 g), heated to 65-75°C and stirred until complete dissolution of clotrimazole, cooled to room temperature. The carbopol R NF (1 g) was dispersed in water (19 g) before the formation of mass without lumps. In the resulting mass is injected GHG (63.6 g) and tea (0.4 g) and stirred until homogeneous, transparent gel. In the resulting mass is injected solution clotrimazole in PEG-400. Mix until a homogeneous mass. Got a gel with a pH 6.09.

Examples 2-11.

Composition was prepared as described in example 1. The composition and properties of the resulting gels are shown in table 1.

The authors found the optimal values of the concentration of PEG-400, providing the necessary level of solubility of clotrimazole and ketoconazole, and hence the level of specific activity of the drug. The claimed values carboxy-vinyl polymer provide an effective release of the active substance.

Study of biological activity of C which show the means were compared with standard samples clotrimazole and ketoconazole dissolved in an inert carrier - PEG-400. Was used trehgogny method of diffusion in agar (hole modification of Petri-dish) [State Pharmacopoeia of the USSR, XI edition, issue 2, M, "Medicine", 1990, s-225]. As the test cultures were selected Candida albicans and Staphylococcus aureus. Petri dishes after drug application and standard solutions were cultivated under standard conditions (Candida albicans - 24 hours at T=24°; Staphylococcus aureus - 4 hours at 26°). After the time of cultivation were obtained a clear zone of growth inhibition of the test organisms. The most pronounced effect of the drugs possessed against Candida albicans (with a standard load of microorganism), and to a lesser extent against Staphylococcus aureus. In all cases, the diameter of the zones of growth inhibition of the test cultures when making preparations were comparable to zones when making standard samples relatives concentrations, and in some cases exceeded them. This suggests that the release of the active substance in vitro of drug is equal or greater extent in comparison with an inert carrier.

The proposed tool has been tested in vivo in acute, subacute and chronic toxicity and local irritation. The experiments were performed on white nonlinear mice and rats. It is shown that in conditions of long-term (30 days of continuous use (application on an exposed surface) the composition does not cause violations of biochemical parameters of blood, no adverse effects on internal organs, does not cause local irritation.

The components of the composition are widespread industrial products, method of its manufacture is simple and safe and can be performed on standard equipment.

TABLE 1

Variants of the claimed composition and its properties.
ExamplesThe composition, wt.%Properties of composition
ClotrimazoleKetoconazolePEG-400Propylene glycolGelling agentThe pH regulatorWaterpHDescription
The carbopol R NFThe carbopol R NFThe teaDeja10% NaOH aq
12345678910111213
1.1,00-15,0063,601,00- 0,40--19,006,09Colorless, transparent

gel
2.0,50-15,0064,101,00-0,40--19,006,00Too
3.2,00-15,0062,601,00-0,40--19,006,20Too
4.1,00-15,0060,00-3,00--2,3518,655,00Too
5.1,00-15,0070,000,50--0,05-13,456,28Too
6.1,00-15,0060,003,00---3,0018,005,20Too
7.1,00-15,0063,601,00 -0,87--18,537,00Too
8. 2,0067,0010,001,00-0,08--19,926,22Colorless, transparent gel when stored Pets pink coloration.
9.-1,0070,0010,001,00-0,08--17,925,70Too

12345678910111213
10.-3,0067,0010,001,00-0,08--18,926,36Colorless, transparent gel when stored Pets pink coloration.
11.1,00-70,001,001,00-0,40-- 26,606,40Colorless, transparent gel

1. Antifungal gel pharmaceutical composition comprising the active substance is a derivative of imidazole, organic solvent, carboxyvinyl polymer as a gelling agent, a pH regulator and water, characterized in that it contains as a solvent of the glycol, and as active substances it contains a substance selected from the group comprising ketoconazole or clotrimazole and additionally contains propylene glycol as a stabilizer of the gel in the following ratios, wt.%:

Ketoconazole or clotrimazole 0.5-3.0

The glycol 15.0-70.0

Propylene glycol 1.0-70.0

Carboxyvinyl polymer is 0.5 to 3.0

The pH regulator 0.05-3.0

Water the Rest

2. The method of obtaining antifungal gel pharmaceutical composition according to claim 1, comprising mixing the active ingredient with a gelling agent carboxyvinyl polymer, organic solvent, pH regulator and water, characterized in that the solvent used PEG-400, propylene glycol - as a stabilizing additive, the active ingredient is dissolved in PEG-400 when heated, carboxyvinyl polymer is dispersed in water, the dispersion is consistently mesilat with propylene glycol and pH regulator, the obtained gel is combined with a solution of the active ingredient and mix until a homogeneous gel composition with a pH from 5 to 7.



 

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