CA1209920A - Antimycotic agents in gel form for the treatment of fungal infections of the oral cavity - Google Patents
Antimycotic agents in gel form for the treatment of fungal infections of the oral cavityInfo
- Publication number
- CA1209920A CA1209920A CA000441740A CA441740A CA1209920A CA 1209920 A CA1209920 A CA 1209920A CA 000441740 A CA000441740 A CA 000441740A CA 441740 A CA441740 A CA 441740A CA 1209920 A CA1209920 A CA 1209920A
- Authority
- CA
- Canada
- Prior art keywords
- antimycotic
- gel
- azole compound
- forming agent
- oral cavity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
-
- 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
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Communicable Diseases (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Cosmetics (AREA)
- Orthopedics, Nursing, And Contraception (AREA)
Abstract
Antimycotic agents in gel form for the treatment of fungal infections of the oral cavity ABSTRACT OF THE DISCLOSURE
The invention provides for novel antimycotic agents in gel form for the treatment of fungal infections of the oral cavity. The gel form of the invention provides a depot effect, good adhesion properties and relatively high bioavailability of the active compounds. The gels of the invention makes possible the use of short term therapy.
The invention provides for novel antimycotic agents in gel form for the treatment of fungal infections of the oral cavity. The gel form of the invention provides a depot effect, good adhesion properties and relatively high bioavailability of the active compounds. The gels of the invention makes possible the use of short term therapy.
Description
'" 1~09~0 The present invention reLates to novel antimycotic agents in gel form, for the treatment of fungal infections of the oral cavity, having a depot effect, good adhesion properties and a relatively high bioavailabil;ty of the active compounds and thus they make short-term therapy possible.
Formulations of antimycotic compounds have already been disclosed for the treatment of infections, primarily by blastomycetes, sf the oral cavity. Using these formu-lations, a 10 to 21-day therapy period is neGessary for complete heal;ng.
In order to ach;eve a shortening of the durat;on of therapy, a certain depot effect and a relatively high bioavailability of the active compounds are necessary especially in order to eliminate the organisms and achieve mycolog;cal healing. The known formulations have only restricted suitability for this purpose. ~f it is now desired to achieve a shorten;ng of the duration of therapy without a further increase in the concentration of the Z0 active compound, care must ~e taken that the bioavailabil-ity of the active compound is optimal.
Thus, formulations which~ on the one hand, have an adequate adhesion after application to the oral mucosa and, on the other hand, are able adequately to release ~he active compound conta;ned in the formulat;on, even dis-solved in saliva~ were requ;red.
It has now been found that formulations of anti-mycotic active compounds which contain as the gel-forming agent a celluLose ether, in particuiar hydroxypropylcel-lulose, sodium alginate or propylene glycol alginate, andalso contain the customary formulating aux;liaries, pro-duce optimal adhesion propert;es and optimal release of the active compound and thus shorten the duration of ther-apy because fung;cidal concentrations of the act;ve Le ~ 22 023 q~
- ` ~21i 9~2~
compound are reached. This effect is achieved by increasing th~e bioavail-ability of the active compounds contained in the formulations, due to the adhesion properties, and thus the release of the active compound into the sal-iva can be increased.
In particular, it has been found that formulations of antimycotic derivatives which contain the abovementioned gel-forming agents in addition to linear high-molecular weight polysaccharides as stabilising gel-forming agents significantly improve the stability of the formulations to heat and thus the long-term storage stability. Formulations without the addition of high-molecular weight polysaccharides are only stable up to 30C, phase separa-tion occurring after a short time at above 30C, that is to say the gel structure is irreversibly destroyed. Formulations which, in addition to the gel-forming agents, also contain small amounts of a linear high-molecular weight polysaccharide are stable up 50C and thus the storage stability of formulations of this type is significantly increased.
The agents thus prepared also possess other unusual properties:
The viscosity is hardly affected by variations in temperature;
the adhesion properties of the formulation are improved.
The development of the flavour is improved and a pleasant sensa-tion in the mouth is achieved.
Thus the present invention provides an antimycotic agent in gel form for the treatment of fungal infections of the oral cavi~y, containing an antimycotic azole compound and customary formulating auxiliaries, charac-terised in that it contains 2.5% - 17.5% of a cellulose ether, sodium alginate, propylene glycol alginate, polyacrylic acid or a salt thereof, polymeth-acrylic acid or a salt thereof sodium amylopectin semiglycolate J gum arabic, Le A 22 023 ~209~
- 2a -guar gum or a protein derivative as gel-forming agent and 0.1 - 1.5% of a biopolysaccharide as stabiliser and/or gel-forming agent.
In another aspect the invention provides a process for the pro-duction of an antimycotic agent in gel form for the treatment of fungal in-fections of the oral cavity, wherein there is added to a 1% solution of benzyl alcohol in demineralised waterJ at about 60C under vigorous stirring, 2.5 -17.5 % of a cellulose etherJ sodium alginate, propylene glycol alginate, polyacrylic acid or a salt thereof, polymethacrylic acid or a salt thereof, sodium a~ opectin semiglycolate, gum arabic, guar gum or a protein derivative as gel-forming agent and 0.1 - 1.5% of a biopolysaccharide, the mixture is cooled to about 30C, there is added 0.05 - 1% of an antimycotic azole com-pound and the mixture cooled to room temperature.
The demineralised water can contain the usual formulation auxi-liaries.
Active compounds which can be formulated in this manner are any compounds having antimycotic activity, in particular imidazole and triazole derivatives. They are present in the agents according to the invention in amounts pref~rably of 0.05 - 1%, most preferably 0.1 1%.
The comp~ ds of the formulae below may be mentioned as examples:
Le A 22 023 09~
Cl~trimazole ~ l~ Cl II ~--CP. ~3 II Bi f onazo le L~1 ~ I C1 Lomb a zoL e Le A 22 023 ___ ~o9~z~
Nu~erous other azole clerivatives having antimycotic activity are disclosed in DE-OS (German Published Specifi-cation~ 2~430,039. They can likewise be used as active compounds ;n the agents according to the invention.
Suitable gel-forming agents are those macromolecular compounds which can dissolve or swell both in water and in organic solvents.
In this context, cellulose ethers, p.e. hydroxypropylcellulose, may be particularly mentioned, 2.5 to 17.5 % of these being re~uired. Especially suitable is hydroxypropylcellulose, having 1~ a molecular weight from 60 000 to 1000 000. Foll~wing a classi-fication of macromolecul~ auxiliaries (Keipert et al., Die Pharmazie 28, 145-183 (1973)), in particular, ionic macromolecules in the form of their salts are used. These are, inter alia, sodium carboxymethylcellulose, polyacrylic acid, polymethacrylic acids and their salts, sodium amylopectin semiglycolate, alginic acid and propylene glycol alginate as the sodium salt, gum arabic and guar gum.
Amphoter;c macromolecules, such as protein deriva-tives, for example gelatin, are just as suitable as non-;onic polymers, for example methylcellulose, hydroxypropyl-cellulose and solubLe starches, ~hich fulfil the above requirements.
Suitable gel-forming agents ~hich also have a stabilising effect are long-chain linear high-molecular ~e;ght polysacchar;des having a molecular ~eight of more than one mill;on. 0.1 - 1.5X of stab;lisers of this type are requ;red.
Suitable solvents are water and all solvents mis-cible with ~ater. Examples of suitable solvents are alka-nols, such as ethanol and isopropyl alcohol, benzyl alco-hol, propylene glycol etc~.
Gel comb;nation bases which have been found to be particularly stable are those macromolecular compounds, such as, for example, hydroxypropylcellulose ~molecular weight 60,000 - 1,00U,000), with a linear high-molecular weight polysaccharide tmolecular weight probably 2,000,000).
Le A 22 023
Formulations of antimycotic compounds have already been disclosed for the treatment of infections, primarily by blastomycetes, sf the oral cavity. Using these formu-lations, a 10 to 21-day therapy period is neGessary for complete heal;ng.
In order to ach;eve a shortening of the durat;on of therapy, a certain depot effect and a relatively high bioavailability of the active compounds are necessary especially in order to eliminate the organisms and achieve mycolog;cal healing. The known formulations have only restricted suitability for this purpose. ~f it is now desired to achieve a shorten;ng of the duration of therapy without a further increase in the concentration of the Z0 active compound, care must ~e taken that the bioavailabil-ity of the active compound is optimal.
Thus, formulations which~ on the one hand, have an adequate adhesion after application to the oral mucosa and, on the other hand, are able adequately to release ~he active compound conta;ned in the formulat;on, even dis-solved in saliva~ were requ;red.
It has now been found that formulations of anti-mycotic active compounds which contain as the gel-forming agent a celluLose ether, in particuiar hydroxypropylcel-lulose, sodium alginate or propylene glycol alginate, andalso contain the customary formulating aux;liaries, pro-duce optimal adhesion propert;es and optimal release of the active compound and thus shorten the duration of ther-apy because fung;cidal concentrations of the act;ve Le ~ 22 023 q~
- ` ~21i 9~2~
compound are reached. This effect is achieved by increasing th~e bioavail-ability of the active compounds contained in the formulations, due to the adhesion properties, and thus the release of the active compound into the sal-iva can be increased.
In particular, it has been found that formulations of antimycotic derivatives which contain the abovementioned gel-forming agents in addition to linear high-molecular weight polysaccharides as stabilising gel-forming agents significantly improve the stability of the formulations to heat and thus the long-term storage stability. Formulations without the addition of high-molecular weight polysaccharides are only stable up to 30C, phase separa-tion occurring after a short time at above 30C, that is to say the gel structure is irreversibly destroyed. Formulations which, in addition to the gel-forming agents, also contain small amounts of a linear high-molecular weight polysaccharide are stable up 50C and thus the storage stability of formulations of this type is significantly increased.
The agents thus prepared also possess other unusual properties:
The viscosity is hardly affected by variations in temperature;
the adhesion properties of the formulation are improved.
The development of the flavour is improved and a pleasant sensa-tion in the mouth is achieved.
Thus the present invention provides an antimycotic agent in gel form for the treatment of fungal infections of the oral cavi~y, containing an antimycotic azole compound and customary formulating auxiliaries, charac-terised in that it contains 2.5% - 17.5% of a cellulose ether, sodium alginate, propylene glycol alginate, polyacrylic acid or a salt thereof, polymeth-acrylic acid or a salt thereof sodium amylopectin semiglycolate J gum arabic, Le A 22 023 ~209~
- 2a -guar gum or a protein derivative as gel-forming agent and 0.1 - 1.5% of a biopolysaccharide as stabiliser and/or gel-forming agent.
In another aspect the invention provides a process for the pro-duction of an antimycotic agent in gel form for the treatment of fungal in-fections of the oral cavity, wherein there is added to a 1% solution of benzyl alcohol in demineralised waterJ at about 60C under vigorous stirring, 2.5 -17.5 % of a cellulose etherJ sodium alginate, propylene glycol alginate, polyacrylic acid or a salt thereof, polymethacrylic acid or a salt thereof, sodium a~ opectin semiglycolate, gum arabic, guar gum or a protein derivative as gel-forming agent and 0.1 - 1.5% of a biopolysaccharide, the mixture is cooled to about 30C, there is added 0.05 - 1% of an antimycotic azole com-pound and the mixture cooled to room temperature.
The demineralised water can contain the usual formulation auxi-liaries.
Active compounds which can be formulated in this manner are any compounds having antimycotic activity, in particular imidazole and triazole derivatives. They are present in the agents according to the invention in amounts pref~rably of 0.05 - 1%, most preferably 0.1 1%.
The comp~ ds of the formulae below may be mentioned as examples:
Le A 22 023 09~
Cl~trimazole ~ l~ Cl II ~--CP. ~3 II Bi f onazo le L~1 ~ I C1 Lomb a zoL e Le A 22 023 ___ ~o9~z~
Nu~erous other azole clerivatives having antimycotic activity are disclosed in DE-OS (German Published Specifi-cation~ 2~430,039. They can likewise be used as active compounds ;n the agents according to the invention.
Suitable gel-forming agents are those macromolecular compounds which can dissolve or swell both in water and in organic solvents.
In this context, cellulose ethers, p.e. hydroxypropylcellulose, may be particularly mentioned, 2.5 to 17.5 % of these being re~uired. Especially suitable is hydroxypropylcellulose, having 1~ a molecular weight from 60 000 to 1000 000. Foll~wing a classi-fication of macromolecul~ auxiliaries (Keipert et al., Die Pharmazie 28, 145-183 (1973)), in particular, ionic macromolecules in the form of their salts are used. These are, inter alia, sodium carboxymethylcellulose, polyacrylic acid, polymethacrylic acids and their salts, sodium amylopectin semiglycolate, alginic acid and propylene glycol alginate as the sodium salt, gum arabic and guar gum.
Amphoter;c macromolecules, such as protein deriva-tives, for example gelatin, are just as suitable as non-;onic polymers, for example methylcellulose, hydroxypropyl-cellulose and solubLe starches, ~hich fulfil the above requirements.
Suitable gel-forming agents ~hich also have a stabilising effect are long-chain linear high-molecular ~e;ght polysacchar;des having a molecular ~eight of more than one mill;on. 0.1 - 1.5X of stab;lisers of this type are requ;red.
Suitable solvents are water and all solvents mis-cible with ~ater. Examples of suitable solvents are alka-nols, such as ethanol and isopropyl alcohol, benzyl alco-hol, propylene glycol etc~.
Gel comb;nation bases which have been found to be particularly stable are those macromolecular compounds, such as, for example, hydroxypropylcellulose ~molecular weight 60,000 - 1,00U,000), with a linear high-molecular weight polysaccharide tmolecular weight probably 2,000,000).
Le A 22 023
2~
A suitable biopolysaccharide in Xanthan Gum (Keltron, Kelza of the firm Kelco.) It is th~ high molecular aarbo-hydrate of the formula CH,OH CH.Otl _ OHo ~ n c~orcH~ I
~1 ~0~
COOCM3 ~ .~ N
COO~M~O Cl-, ~
CH, \~
which is formed during the fermentation of Xanthomonas campestris.
The gels according to the invention are prepaxed in that to a 1 ~ solution of benzyl alcohol in demineralised water, which contains the usual formulation auxiliaries, there is added at 60 C under vigorous stirring 2.5 - 17.5 % cellulose ether as gel forming agent and 0.1 - 1.5 % biopolysaccharide, ~he mixture is cooled down to 30 C, there is added 0.05 -1 %, preferably 0.1 - 1~ azole deriva~ive and the mixture cooled down to room temperature.
1 kg benzyl alcohol, 0.1 kg saccharin and 0.01 kg prim.
sodium citrate are dissolved in 94.89 kg dimineralised water and the solution warmed to 60 C.
Le A 22 023 ``` ~2~9~
Under vigorous stirring 2.5 kg hydroxypropylcellulose (m.w. 1 OOO OOO) and O.S kg biopolysaccharide are added and the mixture cooled down to 30 C. 1 kg clotrimazole is added under vigorous stirring and the mixtuxe cooled down to room temperature.
In an analogous manner the gels of the following examples are prep~red.
Example 2 ~ifonazole active compound, micron. 1.00 10 Benzyl alcohol 1.00 Hydroxypropylcellulose (M.~. about 1,000,000) 2.5 Biopolysaccharide (M.W. about 2,000,000) 0.5 Sweetener 0.1 Aroma 0.2 15 Demieralised water ad 100 Example_ Lombazole active compound, micron. 1.00 6enzal aLcohol 1.00 Hydroxypropylcellulose ~M.W. 1,000,000) 2.5 20 Biopolysaccharide (M.W. about 2,000,000) 0.5 Sweetener 0.1 Aroma 0.25 Demineralised ~ater ad 100 Example 4 25 Clotrimazole act;ve compound, micron.1.00 8enzyl alcohol 1.00 Hydroxypropylcellulose ~M.W. 60,000)17.50 Biopolysaccharide (M.W. about 2,00D,000) 0.50 Sweetener 0~20 30 Demineralised ~ater ad 100 Le A 22 023
A suitable biopolysaccharide in Xanthan Gum (Keltron, Kelza of the firm Kelco.) It is th~ high molecular aarbo-hydrate of the formula CH,OH CH.Otl _ OHo ~ n c~orcH~ I
~1 ~0~
COOCM3 ~ .~ N
COO~M~O Cl-, ~
CH, \~
which is formed during the fermentation of Xanthomonas campestris.
The gels according to the invention are prepaxed in that to a 1 ~ solution of benzyl alcohol in demineralised water, which contains the usual formulation auxiliaries, there is added at 60 C under vigorous stirring 2.5 - 17.5 % cellulose ether as gel forming agent and 0.1 - 1.5 % biopolysaccharide, ~he mixture is cooled down to 30 C, there is added 0.05 -1 %, preferably 0.1 - 1~ azole deriva~ive and the mixture cooled down to room temperature.
1 kg benzyl alcohol, 0.1 kg saccharin and 0.01 kg prim.
sodium citrate are dissolved in 94.89 kg dimineralised water and the solution warmed to 60 C.
Le A 22 023 ``` ~2~9~
Under vigorous stirring 2.5 kg hydroxypropylcellulose (m.w. 1 OOO OOO) and O.S kg biopolysaccharide are added and the mixture cooled down to 30 C. 1 kg clotrimazole is added under vigorous stirring and the mixtuxe cooled down to room temperature.
In an analogous manner the gels of the following examples are prep~red.
Example 2 ~ifonazole active compound, micron. 1.00 10 Benzyl alcohol 1.00 Hydroxypropylcellulose (M.~. about 1,000,000) 2.5 Biopolysaccharide (M.W. about 2,000,000) 0.5 Sweetener 0.1 Aroma 0.2 15 Demieralised water ad 100 Example_ Lombazole active compound, micron. 1.00 6enzal aLcohol 1.00 Hydroxypropylcellulose ~M.W. 1,000,000) 2.5 20 Biopolysaccharide (M.W. about 2,000,000) 0.5 Sweetener 0.1 Aroma 0.25 Demineralised ~ater ad 100 Example 4 25 Clotrimazole act;ve compound, micron.1.00 8enzyl alcohol 1.00 Hydroxypropylcellulose ~M.W. 60,000)17.50 Biopolysaccharide (M.W. about 2,00D,000) 0.50 Sweetener 0~20 30 Demineralised ~ater ad 100 Le A 22 023
Claims (13)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. An antimycotic agent in gel form for the treatment of fungal infections of the oral cavity, containing an antimycotic azole compound and customary formulating auxiliaries, characterised in that it contains 2.5% -17.5% of a cellulose ether, sodium alginate, propylene glycol alginate, poly-acrylic acid or a salt thereof, polymethacrylic acid or a salt thereof, sodium amylopectin semiglycolate, gum arabic, guar gum or a protein derivative as gel forming agent and 0.1 - 1.5% of a biopolysaccharide as stabiliser and/or gel-forming agent.
2. An antimycotic gel according to Claim 1, characterised in that it contains, as the active compound, clotrimazole of the formula
3. An antimycotic gel according to Claim 1, characterised in that it contains, as the active compound, bifonazole of the formula
4. An antimycotic gel according to Claim 1, characterised in that it contains, as the active compound, lombazole of the formula
5. An antimycotic gel according to Claim 1, 2 or 3 characterised in that it contains an antimycotic azole compound in an amount of 0.05 - 1%.
6. An antimycotic gel according to Claim 1, 2 or 3 characterised in that it contains an antimycotic azole compound in an amount of 0.1 - 1%.
7. An antimycotic gel according to Claim 1, 2 or 3 characterised in that it contains hydroxypropylcellulose as the gel-forming agent.
8. A process for the preparation of an antimycotic agent in gel form for the treatment of fungal infections of the oral cavity, sherein there is added to a 1% solution of benzyl alcohol in demineralised water, at about 60°C under vigorous stirring, 2.5 17.5% of a cellulose ether, sodium alginate, propylene glycol alginate, polyacrylic acid or a salt thereof, polymethacrylic acid or a salt thereof, sodium amylopectin semiglycolate, gum arabic, guar gum or a protein derivative as gel-forming agent and 0.1 - 1.5% of a biopoly-saccharide, the mixture is cooled to about 30°C, there is added 0.05 - 1% of an antimycotic azole compound and the mixture cooled to room temperature.
9. A process according to claim 8 wherein the antimycotic azole compound is present in an amount of from 0.1 - 1%.
10. A process according to claim 8 wherein the gel-forming agent is hydroxypropylcellulose.
11. A process according to claim 8, 9 or 10 wherein the antimycotic azole compound is clotrimazole.
12. A process according to claim 8, 9 or 10 wherein the antimycotic azole compound is bifonazole.
13. A process according to claim 8, 9 or 10 wherein the antimycotic azole compound is lombazole.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3243546.0 | 1982-11-25 | ||
| DE19823243546 DE3243546A1 (en) | 1982-11-25 | 1982-11-25 | ANTIMYCOTIC AGENTS IN GEL FOR TREATING FUNGAL INFECTIONS OF THE ORAL CAVES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1209920A true CA1209920A (en) | 1986-08-19 |
Family
ID=6178958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000441740A Expired CA1209920A (en) | 1982-11-25 | 1983-11-23 | Antimycotic agents in gel form for the treatment of fungal infections of the oral cavity |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0112485B1 (en) |
| JP (1) | JPS59108712A (en) |
| KR (1) | KR840006766A (en) |
| AT (1) | ATE33759T1 (en) |
| CA (1) | CA1209920A (en) |
| DE (2) | DE3243546A1 (en) |
| DK (1) | DK538683A (en) |
| ES (1) | ES527514A0 (en) |
| GR (1) | GR79726B (en) |
| IL (1) | IL70290A (en) |
| NO (1) | NO834160L (en) |
| ZA (1) | ZA838774B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4542020A (en) * | 1984-08-17 | 1985-09-17 | E. R. Squibb & Sons, Inc. | Long-lasting adhesive antifungal suppositories |
| JPS61151117A (en) * | 1984-12-25 | 1986-07-09 | Bayer Yakuhin Kk | Gelatinous antimycotic preparation |
| DE3614095A1 (en) * | 1986-04-25 | 1987-10-29 | Goedecke Ag | OXYALKYLCELLULOSE CONTAINING GEL PREPARATION |
| US5093133A (en) * | 1990-01-24 | 1992-03-03 | Mcneil-Ppc, Inc. | Method for percutaneous delivery of ibuprofen using hydroalcoholic gel |
| JP2005097271A (en) * | 2003-08-20 | 2005-04-14 | Matsumoto Shika Univ | Composition for antifungal agent |
| US20050054583A1 (en) * | 2003-08-20 | 2005-03-10 | Matsumoto Dental University | Composition for an antifungal agent for suppressing fungal growth in an oral cavity |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL287272A (en) * | 1962-04-26 | |||
| US4056611A (en) * | 1973-04-16 | 1977-11-01 | Stiefel Laboratories, Inc. | Therapeutic composition |
| US4313765A (en) * | 1980-09-24 | 1982-02-02 | Merck & Co., Inc. | Synergistic blends of cellulase-free xanthan gum and cellulosics |
| DE3045915A1 (en) * | 1980-12-05 | 1982-07-08 | Bayer Ag, 5090 Leverkusen | ANTIMYCOTIC AGENTS WITH HIGH ACTIVE SUBSTANCE RELEASE IN THE FORM OF ELASTIC LIQUID PLASTERS |
| JPS57120576A (en) * | 1981-01-20 | 1982-07-27 | Sumitomo Chem Co Ltd | Novel imidazole ester |
| DE3106635A1 (en) * | 1981-02-23 | 1982-09-09 | Bayer Ag | ANTIMYCOTIC AGENT WITH HIGH ACTIVE SUBSTANCE RELEASE IN THE FORM OF PEN |
-
1982
- 1982-11-25 DE DE19823243546 patent/DE3243546A1/en not_active Withdrawn
-
1983
- 1983-11-14 NO NO834160A patent/NO834160L/en unknown
- 1983-11-17 DE DE8383111479T patent/DE3376386D1/en not_active Expired
- 1983-11-17 AT AT83111479T patent/ATE33759T1/en not_active IP Right Cessation
- 1983-11-17 EP EP83111479A patent/EP0112485B1/en not_active Expired
- 1983-11-22 IL IL70290A patent/IL70290A/en unknown
- 1983-11-22 JP JP58218838A patent/JPS59108712A/en active Pending
- 1983-11-23 GR GR73047A patent/GR79726B/el unknown
- 1983-11-23 CA CA000441740A patent/CA1209920A/en not_active Expired
- 1983-11-24 ZA ZA838774A patent/ZA838774B/en unknown
- 1983-11-24 DK DK538683A patent/DK538683A/en not_active Application Discontinuation
- 1983-11-24 ES ES527514A patent/ES527514A0/en active Granted
- 1983-11-24 KR KR1019830005566A patent/KR840006766A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA838774B (en) | 1984-07-25 |
| DE3243546A1 (en) | 1984-05-30 |
| EP0112485B1 (en) | 1988-04-27 |
| GR79726B (en) | 1984-10-31 |
| DE3376386D1 (en) | 1988-06-01 |
| DK538683A (en) | 1984-05-26 |
| NO834160L (en) | 1984-05-28 |
| IL70290A (en) | 1988-01-31 |
| DK538683D0 (en) | 1983-11-24 |
| IL70290A0 (en) | 1984-02-29 |
| ES8502337A1 (en) | 1985-01-01 |
| KR840006766A (en) | 1984-12-03 |
| ATE33759T1 (en) | 1988-05-15 |
| EP0112485A2 (en) | 1984-07-04 |
| ES527514A0 (en) | 1985-01-01 |
| EP0112485A3 (en) | 1985-10-23 |
| JPS59108712A (en) | 1984-06-23 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |