WO2005004856A1 - Composition antifongique - Google Patents
Composition antifongique Download PDFInfo
- Publication number
- WO2005004856A1 WO2005004856A1 PCT/JP2004/009808 JP2004009808W WO2005004856A1 WO 2005004856 A1 WO2005004856 A1 WO 2005004856A1 JP 2004009808 W JP2004009808 W JP 2004009808W WO 2005004856 A1 WO2005004856 A1 WO 2005004856A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- antifungal
- composition
- terbinafine
- purified water
- pharmaceutical composition
- Prior art date
Links
- 239000012871 anti-fungal composition Substances 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 230000000843 anti-fungal effect Effects 0.000 claims abstract description 19
- 239000003899 bactericide agent Substances 0.000 claims abstract description 8
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 5
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 claims description 32
- 229940121375 antifungal agent Drugs 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 229960002722 terbinafine Drugs 0.000 claims description 12
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 claims description 12
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- 150000004982 aromatic amines Chemical class 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 10
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- 125000001453 quaternary ammonium group Chemical class 0.000 claims description 7
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- 150000003839 salts Chemical class 0.000 claims description 6
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- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 abstract 2
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- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- the present invention relates to an antifungal composition. More specifically, the present invention relates to an antifungal composition in which the antifungal activity of an arylamine antifungal agent is enhanced.
- Terbinafine is one of the currently widely used antifungal drugs in Japan and is classified as an allylaminine antifungal drug, which is different from conventional imidazoles, thiocarbamates, benzylamines, and morpholines Has a new structure. Its mechanism of action lies in the inhibition of the biosynthesis of fungal cell membrane ergosterol. Terbinafine selectively inhibits squalene epoxidase in fungal cells, resulting in squalene accumulation and reduced ergosterol content. As a result, a strong antifungal activity is exhibited (see Non-Patent Document 1).
- Terbinafine has a broad antibacterial spectrum against pathogenic fungi such as Trichophyton, Candida, Tareptococcus, Aspergillus and Penicillium. Particularly, it shows a very low MIC value against dermatophytes (see Non-Patent Document 2).
- compositions utilizing such excellent antifungal activity of terbinafine.
- One is a composition comprising terbinafine, an antihistamine, a terpene compound, and urea.
- the composition can enhance the skin permeability and skin retention of terbinafine (see Patent Document 1).
- a composition is known in which an additive such as methyl salicylate is added to terbinafine to promote penetration into the stratum corneum of the epidermis (see Patent Document 2).
- compositions do not improve the antifungal activity of terbinafine itself.
- Non-patent document 1 Hideyo Yamaro, "Pathogenic fungi and mycosis", Nanzando Co., Ltd., 84-85, 1999
- Non-patent document 2 Fungus Journal Vol. 32 No. 4 1991 323-332
- Patent Document 1 JP-A-2002-284702
- Patent Document 2 JP 08-20527 A
- An object of the present invention is to provide an antifungal agent composition having excellent efficacy, which enables treatment of athlete's foot and sickness with a short application.
- the present inventors have conducted various studies on antifungal drugs that are effective against Trichophyton, a causal fungus of athlete's foot and scabies. As a result, they have found that the combination of an arylamine antifungal and a quaternary ammonium salt-type bactericide exerts an excellent antifungal effect, thereby completing the present invention.
- a pharmaceutical composition comprising an arylamine antifungal and a quaternary ammonium salt-type bactericide.
- the pharmaceutical composition is one or two or more allybinamine antifungals selected from terbinafine and salts thereof.
- a pharmaceutical composition in which the quaternary ammonium salt-type bactericide is one or more compounds selected from the group consisting of benzalkonium chloride, benzethonium chloride, and decalinium chloride.
- the pharmaceutical composition of the present invention is a pharmaceutical composition that can be used as an antifungal composition. More preferably, the pharmaceutical composition of the present invention is a pharmaceutical composition that can be used as a therapeutic composition for athlete's foot or scabies.
- a step of administering an effective amount of a composition comprising an arylamine antifungal and a quaternary ammonium salt-type bactericide to a site infected with a fungus of a mammal including humans.
- a method for treating mycosis and a method for treating athlete's foot or scabies, including Law is provided.
- an arylamine antifungal agent and a quaternary ammonium salt for producing a composition for treating mycosis, a composition for treating athlete's foot, or a composition for treating scabies.
- the use of a composition incorporating a salt-type fungicide is provided. The invention's effect
- the antifungal activity of an arylamine antifungal agent can be further enhanced, and therefore, it has become possible to provide an antifungal agent composition that is extremely effective against dermatophytes. .
- the antifungal agent composition of the present invention is used, a therapeutic agent for athlete's foot and sickness that can be treated with a short-term application can be obtained.
- the arylamine antifungal agent to be blended in the present invention may be any one having an arylamine skeleton in its chemical structure, but terbinafine is preferred.
- Any salt can be used without particular limitation as long as it forms a salt with the substituted amino acid group bonded to the naphthalene ring, and examples thereof include mineral salts such as hydrochloride, nitrate and sulfate, and quinone.
- Organic acid salts such as acid salts, oxalates, and succinates are preferred, and hydrochlorides are particularly preferred.
- the quaternary ammonium-type bactericide is preferably a cationic surfactant belonging to quaternary ammonium salt, and particularly preferably benzalkonium chloride, benzethonium chloride, decalinium chloride and the like.
- the arylamine antifungal agent to be blended in the present invention may be any effective amount capable of obtaining an antifungal effect.
- the content is 0.2 to 2% by mass, preferably 0.5 to 1.5% by mass in the whole composition (in the case of azole, in a stock solution).
- the amount of the quaternary ammonium fungicide differs depending on the component and the antifungal to be mixed. For example, when terbinafine hydrochloride is compounded in the above range as an antifungal, the amount of benzalkonium chloride is adjusted. Is 0.01-1% by mass, preferably 0.02-0.5% by mass, and the blending amount of benzenium chloride is 0.05-2% by mass, preferably 0.1-1% by mass, and decalinium chloride. Is 0.05 to 2% by mass, preferably 0.1 to 1% by mass.
- composition of the present invention may be mixed with an additive usually used as an external preparation, if necessary, and mixed in a usual manner with a liquid, lotion, emulsion, tincture, ointment, cream, aqueous gel.
- external preparations such as oily gels, aerosols and powders.
- Components that can be blended in the present invention include water-soluble components such as propylene glycol, 1,3-butylendalcol, glycerin, ethanol, macrogol, diisopropyl adipate, stearyl alcohol, cetanol, squalane, and medium-chain triglyceride.
- water-soluble components such as propylene glycol, 1,3-butylendalcol, glycerin, ethanol, macrogol, diisopropyl adipate, stearyl alcohol, cetanol, squalane, and medium-chain triglyceride.
- Oily components such as carboxyvinyl polymer, polymers such as methylcellulose and ethylcellulose, pH adjusters such as citric acid, sodium hydroxide and diisopropanolamine, dibutylhydroxytoluene (BHT), butylhydroxydisole (BHA), anti-oxidants such as heart tocopherol, erythorbic acid, sodium pyrosulfite, polyoxyethylene hardened castor oil, sorbitan monostearate, sorbitan monopalmitate, glycerin monostearate, sorbitan Noraureto, polyoxyethylene polyoxypropylene block Kukoporima, polysorbates, sodium lauryl sulfate, sucrose fatty acid esters, surfactants such as Residencial Chin, stabilizers such EDTA_2Na the like. It should be noted that there is no particular limitation on the soybean pastes described so far.
- Aqueous phase components (1,3-butylene glycol, decalinium chloride, EDTA_2Na, dipotassium glycyrrhizinate, purified water) and oil phase components (terbinafine hydrochloride, lidocaine, 1_menthol, sorbitan monostearate, polysonole) Bate 60, medium-chain fatty acid triglyceride, daliserine monostearate) were mixed after heating, respectively, to produce a cream by the usual method.
- the carboxybutyl polymer was dissolved in purified water, and the carboxybutyl polymer was swollen and then heated.
- the oil phase components (terbinafine hydrochloride, lidocaine, polysorbate 80, medium-chain fatty acid triglyceride, stearyl alcohol, cetanol, 1_ menthol) are heated and mixed, added to the previously prepared swelling solution of carboxybutyl polymer, and dissolved in purified water. did
- the aqueous phase components (benzalkonium chloride, dipotassium glycyrrhizinate, EDTA_2Na) and 1,3-butylene glycol were added and emulsified.
- a neutralizing agent diisopropanolanolamine
- the carboxyvinyl polymer was dissolved in purified water, and the carboxyvinyl polymer was swollen and then heated.
- the oil phase components (terbinafine hydrochloride, lidocaine, polysorbate 80, medium-chain fatty acid triglyceride, stearyl alcohol, cetanol, 1-menthol, squalane) are heated and mixed, added to the previously prepared carboxybutyl polymer swelling liquid, and purified water is added thereto.
- the aqueous phase components Benzalkonidium benzil, dipotassium glycyrrhizinate, EDTA-2 Na
- aqueous phase components Benzalkonidium benzil, dipotassium glycyrrhizinate, EDTA-2 Na
- the carboxyvinyl polymer was dissolved in purified water, and the carboxyvinyl polymer was swollen and then heated. Oil phase components (terbinafine hydrochloride, lidocaine, polysorbate 80, medium-chain fatty acid triglyceride, stearyl alcohol, cetanol, 1-menthol, dimethylpolysiloxane, otatyl dodecyl myristate) are heated and mixed, and the carboxybutyl polymer prepared earlier is swelled.
- Oil phase components terbinafine hydrochloride, lidocaine, polysorbate 80, medium-chain fatty acid triglyceride, stearyl alcohol, cetanol, 1-menthol, dimethylpolysiloxane, otatyl dodecyl myristate
- Aqueous phase components (benzalcodium chloride, dipotassium glycyrrhizinate, EDTA_2Na) dissolved in purified water were added to the solution, and the mixture was emulsified and cooled to produce a gel tarme.
- the carboxybutyl polymer was dissolved in purified water to swell the carboxybutyl polymer, and then heated.
- the oil phase components terbinafine hydrochloride, lidocaine, polyethylene glycol monostearate, medium-chain fatty acid triglyceride, stearyl alcohol, cetanol, 1-menthol, dimethylpolysiloxane
- the oil phase components are heated and mixed, and the carboxybutyl polymer previously prepared is swollen.
- an aqueous phase component (Shiiro Benzanoreconidum, dipotassium dalicyrrhizinate, EDTA_2Na) dissolved in purified water was emulsified with Kadone and cooled to produce a gel cream.
- a stock solution was prepared by dissolving other stock solution components in a base of ethanol and purified water. After filling the container, a valve was attached and the propellant was filled to produce an aerosol.
- Specimen 1 Benzalkonium chloride
- the susceptibility test was performed by the microfluidic dilution method proposed by the Japanese Society for Medical Mycology (Standardization Committee). 0.165M MOPS-RPMI1640 was used as a sensitivity measurement medium.
- agents inoculated solution was adjusted to about 10 5 conidia / mL in medium containing, they were cultured for up to 4 days at 27 ° C,. Antibacterial activity was determined visually when the growth control clearly turned red.
- the MIC value minimum inhibitory concentration, / ig / mL was defined as the minimum concentration of the blue well similar to the negative control.
- the FIC index Fractional Inhibitory and oncentration index was calculated using the checkerboard method.
- the combination effect was judged as an antagonistic effect when the value was 2 or more, an additive effect when the value was 2 or less and 1 or more, and a synergistic effect when the value was 1 or less.
- the present invention is an antifungal composition exhibiting an excellent antifungal effect, obtained by blending a quaternary ammonium salt fungicide with an arylamine antifungal.
- an antifungal agent composition of the present invention it is possible to treat athlete's foot and sickness with a shorter application time than before.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Priority Applications (1)
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JP2005511534A JP4692280B2 (ja) | 2003-07-11 | 2004-07-09 | 抗真菌剤組成物 |
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JP2003-196089 | 2003-07-11 | ||
JP2003196089A JP2005029502A (ja) | 2003-07-11 | 2003-07-11 | 抗真菌剤組成物 |
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WO2005004856A1 true WO2005004856A1 (fr) | 2005-01-20 |
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PCT/JP2004/009808 WO2005004856A1 (fr) | 2003-07-11 | 2004-07-09 | Composition antifongique |
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JP (2) | JP2005029502A (fr) |
WO (1) | WO2005004856A1 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010501612A (ja) * | 2006-08-31 | 2010-01-21 | ノバルティス アクチエンゲゼルシャフト | 真菌感染の処置用医薬組成物 |
US7799056B2 (en) | 2007-12-31 | 2010-09-21 | Warsaw Orthopedic, Inc. | Bone fusion device and methods |
CN101467960B (zh) * | 2007-12-29 | 2012-11-28 | 浙江康恩贝制药股份有限公司 | 一种盐酸特比萘芬乳膏及其制备方法 |
WO2015102850A3 (fr) * | 2014-01-02 | 2015-12-17 | Cook Medical Technologies Llc | Compositions, dispositifs et méthodes de traitement d'infections |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5559449B2 (ja) * | 2006-06-05 | 2014-07-23 | 小林製薬株式会社 | 抗真菌組成物 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09110690A (ja) * | 1995-06-07 | 1997-04-28 | Taisho Pharmaceut Co Ltd | 抗真菌剤 |
JP2002053462A (ja) * | 2000-08-10 | 2002-02-19 | Pola Chem Ind Inc | 抗真菌医薬組成物 |
JP2002114680A (ja) * | 2000-07-31 | 2002-04-16 | Nippon Nohyaku Co Ltd | 抗真菌剤 |
JP2003055205A (ja) * | 2001-08-09 | 2003-02-26 | Taisho Pharmaceut Co Ltd | 抗真菌病組成物 |
-
2003
- 2003-07-11 JP JP2003196089A patent/JP2005029502A/ja active Pending
-
2004
- 2004-07-09 JP JP2005511534A patent/JP4692280B2/ja not_active Expired - Fee Related
- 2004-07-09 WO PCT/JP2004/009808 patent/WO2005004856A1/fr active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09110690A (ja) * | 1995-06-07 | 1997-04-28 | Taisho Pharmaceut Co Ltd | 抗真菌剤 |
JP2002114680A (ja) * | 2000-07-31 | 2002-04-16 | Nippon Nohyaku Co Ltd | 抗真菌剤 |
JP2002053462A (ja) * | 2000-08-10 | 2002-02-19 | Pola Chem Ind Inc | 抗真菌医薬組成物 |
JP2003055205A (ja) * | 2001-08-09 | 2003-02-26 | Taisho Pharmaceut Co Ltd | 抗真菌病組成物 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010501612A (ja) * | 2006-08-31 | 2010-01-21 | ノバルティス アクチエンゲゼルシャフト | 真菌感染の処置用医薬組成物 |
CN101467960B (zh) * | 2007-12-29 | 2012-11-28 | 浙江康恩贝制药股份有限公司 | 一种盐酸特比萘芬乳膏及其制备方法 |
US7799056B2 (en) | 2007-12-31 | 2010-09-21 | Warsaw Orthopedic, Inc. | Bone fusion device and methods |
US8177812B2 (en) | 2007-12-31 | 2012-05-15 | Kyphon Sarl | Bone fusion device and methods |
WO2015102850A3 (fr) * | 2014-01-02 | 2015-12-17 | Cook Medical Technologies Llc | Compositions, dispositifs et méthodes de traitement d'infections |
Also Published As
Publication number | Publication date |
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JPWO2005004856A1 (ja) | 2006-10-26 |
JP2005029502A (ja) | 2005-02-03 |
JP4692280B2 (ja) | 2011-06-01 |
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