MX2008004132A - Antifungal composition - Google Patents
Antifungal compositionInfo
- Publication number
- MX2008004132A MX2008004132A MXMX/A/2008/004132A MX2008004132A MX2008004132A MX 2008004132 A MX2008004132 A MX 2008004132A MX 2008004132 A MX2008004132 A MX 2008004132A MX 2008004132 A MX2008004132 A MX 2008004132A
- Authority
- MX
- Mexico
- Prior art keywords
- composition
- film
- skin
- agent
- group
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 230000000843 anti-fungal Effects 0.000 title claims abstract description 13
- 210000003491 Skin Anatomy 0.000 claims abstract description 40
- 239000002904 solvent Substances 0.000 claims abstract description 26
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 239000003429 antifungal agent Substances 0.000 claims abstract description 17
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 230000000699 topical Effects 0.000 claims abstract description 6
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- 229960002722 terbinafine Drugs 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 239000011780 sodium chloride Substances 0.000 claims description 10
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- XAPRFLSJBSXESP-UHFFFAOYSA-N Oxycinchophen Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=C(O)C=1C1=CC=CC=C1 XAPRFLSJBSXESP-UHFFFAOYSA-N 0.000 claims description 7
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- 150000003852 triazoles Chemical class 0.000 claims description 6
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
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- OZGNYLLQHRPOBR-DHZHZOJOSA-N naftifine Chemical compound C=1C=CC2=CC=CC=C2C=1CN(C)C\C=C\C1=CC=CC=C1 OZGNYLLQHRPOBR-DHZHZOJOSA-N 0.000 claims description 4
- 229960004313 naftifine Drugs 0.000 claims description 4
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- ABJKWBDEJIDSJZ-UHFFFAOYSA-N Butenafine Chemical compound C=1C=CC2=CC=CC=C2C=1CN(C)CC1=CC=C(C(C)(C)C)C=C1 ABJKWBDEJIDSJZ-UHFFFAOYSA-N 0.000 claims 3
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- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
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- 238000001035 drying Methods 0.000 claims 1
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- 229920000642 polymer Polymers 0.000 description 8
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- 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 description 3
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- 241000196324 Embryophyta Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
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- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 2
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- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 2
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- 235000014113 dietary fatty acids Nutrition 0.000 description 2
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- 239000003960 organic solvent Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000000275 pharmacokinetic Effects 0.000 description 2
- 125000005498 phthalate group Chemical class 0.000 description 2
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- MPIPASJGOJYODL-SFHVURJKSA-N (R)-isoconazole Chemical compound ClC1=CC(Cl)=CC=C1[C@@H](OCC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 MPIPASJGOJYODL-SFHVURJKSA-N 0.000 description 1
- AFNXATANNDIXLG-SFHVURJKSA-N 1-[(2R)-2-[(4-chlorophenyl)methylsulfanyl]-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound C1=CC(Cl)=CC=C1CS[C@H](C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 AFNXATANNDIXLG-SFHVURJKSA-N 0.000 description 1
- VHVPQPYKVGDNFY-TUJWMRSMSA-N 2-[(2S)-butan-2-yl]-4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-TUJWMRSMSA-N 0.000 description 1
- VUKAUDKDFVSVFT-UHFFFAOYSA-N 2-[6-[4,5-bis(2-hydroxypropoxy)-2-(2-hydroxypropoxymethyl)-6-methoxyoxan-3-yl]oxy-4,5-dimethoxy-2-(methoxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)-5-methoxyoxane-3,4-diol Chemical compound COC1C(OC)C(OC2C(C(O)C(OC)C(CO)O2)O)C(COC)OC1OC1C(COCC(C)O)OC(OC)C(OCC(C)O)C1OCC(C)O VUKAUDKDFVSVFT-UHFFFAOYSA-N 0.000 description 1
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- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
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- 229960003957 Dexamethasone Drugs 0.000 description 1
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- RAGOYPUPXAKGKH-XAKZXMRKSA-N posaconazole Chemical compound O=C1N([C@H]([C@H](C)O)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@H]3C[C@@](CN4N=CN=C4)(OC3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 RAGOYPUPXAKGKH-XAKZXMRKSA-N 0.000 description 1
- 229960001589 posaconazole Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 230000001737 promoting Effects 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 230000000306 recurrent Effects 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 229960005429 sertaconazole Drugs 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229960002607 sulconazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
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Abstract
The invention provides a topical liquid antifungal composition containing an antifungal agent, a film-forming agent and a solvent. The composition is applied on the infected skin area to form a film that delivers the active agent. The invention also provides a method for treating a fungal infection on the skin by applying the topical antifungal composition that forms a film on the skin.
Description
ANTIFUNGAL COMPOSITION The invention relates to a topical pharmaceutical composition with antifungal activities and to a method for treating fungal infections. Dermatophytes are fungi that can cause skin infections. Organisms colonize keratotic tissues and produce fungal infections. Symptoms of dermatophyte infections, such as dermatophytosis of the foot, are characterized by lesions between the fingers, with possible extension to the lateral surfaces and to the plants. Burning, itching and peeling are the most common symptoms and signs of the infected area, and the infection is contagious and may be recurrent. The organisms are transmitted either by direct contact with the infected host (human or animal) or by direct or indirect contact with, for example, the infected exfoliate or hair combs, hair brushes, clothing, furniture, towels and changing rooms floors. There is an increased susceptibility to infection when there is a preexisting skin injury such as scars, burns, marks, excessive temperature and humidity. There are topical pharmaceutical compositions that are designed to treat dermatophytic infections. These topical compositions are commercially available, by
example, in cream, ointment, powder, dissolving and spraying forms, and applied once or twice a day for a week to four weeks or more to treat the infection. Since these compositions require a treatment regimen for one to several weeks, it is difficult to completely comply with the regimen for satisfactory treatment is difficult and premature terminations of treatment are common. Another way of administering a pharmaceutically active agent is a liquid film-forming composition. Compositions for removing warts and compositions for liquid nail polish for treating onychomycosis are examples of such compositions. These compositions are applied on the affected area repeatedly to treat the problem. For example, such a composition for the treatment of onychomycosis should be applied over the infected zone and then removed before the composition can be applied again. The application and elimination procedures are repeated periodically for a prolonged period of time to treat onychomycosis. Although it may not be necessary to apply these film-forming compositions on a daily basis, the application regime is not simple to comply with.
It is highly desirable to have an antifungal composition that is highly effective and has a simple application regime that can be easily met.
SUMMARY OF THE INVENTION The present invention provides a topical liquid antifungal composition containing an antifungal agent, a film forming agent and a solvent. The composition is applied to the infected skin to form a film and has a mycological cure rate of at least 50% with an application in the infected area. The invention also provides a method for treating a fungal infection on the skin by applying the topical antifungal composition which forms a film on the skin and allowing the film to remain on the skin for at least 48 hours. More specifically, the invention provides a method for treating a fungal infection of the skin, which presents the step of topically applying a film-forming composition to form a film on the infected area of the skin. The composition contains an antifungal agent selected from imidazole, triazole or allylamine, a film-forming polymer selected from the group consisting of acrylate polymers, acrylate copolymers, alkyl-olefinic acid,
copolymers of alkyl-olefinic acid ester, olefinic acid / amide, olefinic acid / amide copolymers, pol (vmyl acetate), polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymer, hydroxyalkylcellulose and alkylcellulose, and a solvent selected from ethanol, isopropanol, acetone, ethyl acetate, and a mixture of water and one or more of the solvents. The composition of the present invention is highly effective and normally requires only one application to treat a fungal infection on the skin, such as foot tub, body tub, crural tub and scalp tub. Although the composition is effective with only one application, it can be applied more than once to the infected area of the skin. The term "skin" as used herein indicates the external surface of the body other than the nail and the cornea. of mycological cure as used herein indicates the percentage of samples that do not present any visual evidence of mycology examined under a microscope
DETAILED DESCRIPTION OF THE INVENTION The invention provides a single dose application composition for treating dermatophytic infections, making the treatment simple. In addition, the composition is
highly effective in curing or treating fungal infections on the skin. The convenient single dose regimen and the high efficacy of the composition make the treatment of the infectious disease simple to comply with. The composition, which contains a film-forming agent, an antifungal agent and a solvent, is formulated to adhere to and remain on the skin for at least 48 hours, preferably at least 60 hours, more preferably at least 72 hours, although they can be removed or eroding minority portions of the movie during that time. It has been found that an application of the composition of the invention provides a treatment efficacy that is equivalent to or better than the treatment result of strictly following the regimens of repeated application of non-prescription antifungal pharmaceutical products currently available for a period of one year. at four weeks Antifungal agents suitable for the invention include imidazoles, tpazoles, allylammas and mixtures thereof. Suitable imidazoles include miconazole, ketoconazole, clotpmazole, econazole, mebendazole, bifonazole, butoconazole, fenticonazole, isoconazole, oxiconazole, sertaconazole, sulconazole, thiabendazole and thiaconazole. Miconazole, ketoconazole and clotrimazole are preferred, and clotrimazole is more preferred. Suitable triazoles include
fluconazole, itraconazole, ravuconazole and posaconazole. Suitable allylams include terbmafma, amorolfma, naftifine and butenafma. Of these, terbmaphine and butenafma are preferred, and more terbmaphine is preferred. All of these antifungal agents can be in the pharmaceutically active salt form. Examples of suitable salt forms are the hydrochloride, lactate and ascorbate forms. Particularly preferred antifungal agents are ali] amines and salts thereof, and more particularly preferred are terbmaphine and terbmaphine hydrochloride. The composition contains between 0.5% w / w and 30% w / w of an antifungal agent, preferably between 0% , 75% w / w and 20% w / w, more preferably between 0.9% w / w and 15% w / w, most preferably between 1% w / w and 10% w / w. A particularly desirable embodiment of the invention contains between 0.9% w / w and 1.2% w / w, preferably between 0.95% w / w and 1.15% w / w, more preferably between 0 , 97% w / w and 1.125% w / w, and most preferably 1% w / w, of terbinafma. Film forming agents suitable for the invention include hydrophilic and hydrophobic film-forming polymers that form a film when applied to the skin. The composition contains a sufficient amount of a film forming polymer to form a film layer when applied to the p,
and may contain up to 50% w / w of a film-forming polymer. Desirably, the film-forming polymers form a film on the skin, which adheres solidly to the skin, so that the film remains on the skin for a required period of time even when exposed to typical cycles of hygienic cleaning. In general, the film-forming agent is applied with a solvent on the skin, and when the solvent evaporates, the agent forms a film on the skin. Suitable hydrophobic polymers include acrylic polymers, acrylic copolymers, alkyl-olefinic acid , copolymers of alkyl-olefinic acid ester, olefinic acid / amide, copolymers of olefinic acid / amide and polyvinyl acetate. Preferred hydrophobic polymers include octylacplamide, acrylic-octylacplamide copolymer, acrylate-octylpropenamide copolymer, methacrylate-ammoalkyl copolymer, methacrylate-ammonium copolymer, poly (vinyl acetate), and methyl methacrylate-alkyl acrylate copolymer. Suitable hydrophilic polymers include polyvinylpyrrolidone, vimlpyrrolidone-vmyl acetate copolymer, hydroxyalkylcellulose and alkylcellulose. Preferred hydrophilic polymers include hydroxypropylcellulose, hydroxypropylmethylcellulose and polyvinylpyrrolidone. It is desirable to have polymers both
hydrophilic as hydrophobic in the composition. As a preferred embodiment, the hydrophilic polymer is present in an amount between 0.05% w / w and 30% w / w of the composition, preferably between 0.5% w / w and 10% w / w and more preferably between 1% w / w and 5% w / w, and the hydrophobic polymer is present in an amount between 0.05% w / w and 30% w / w of the composition, preferably between 1% w / w 10% w / w and more preferably between 3% w / w and 7% w / w A desirable composition by way of example has between 4% w / w and 6% w / w acrylate-octylacrylamide copolymer and between 2% w / w and 3% w / w hydroxypropylcellulose. The octylacplamide acrylate copolymer is commercially available, for example, under the tradename DERMACRYL, and hydroxypropylcellulose is available, for example, under the tradename KLUCEL. The composition additionally contains a solvent. A suitable solvent can be an aqueous solvent, an organic solvent, or a mixture thereof. Organic solvents are those which are physiologically acceptable and compatible with the active ingredient and the other components of the composition including the film-for polymer. Suitable solvents include ethanol, isopropanol, acetone and ethyl acetate. Preferred solvents are ethanol and a mixture of ethanol and
Water. The amount of water is in most cases less than the amount of the solvent. Typical water / solvent ratios are less than 1: 3. However, in some cases the amount of water may exceed that of the solvent. Then it can be up to 2.5: 1. The solvent is used to solubilize or suspend the components of the composition, and when the composition is applied to the skin, the solvent evaporates and the composition forms a film adhering to the skin. The composition of the invention may contain additional components to improve the composition. Such ingredients include plasticizers, film modifiers, surfactants, penetration enhancers, coloring agents, antioxidants, prior complexing agents and UV absorbers. Suitable plasticizers include dialkyl phthalates, for example dibutyl phthalate, hydroxy fatty acid oils, for example castor oil, silicon oils and triglycerides. Film modifiers that change the properties of the film-for polymer, in particular, improve their application properties, for example hardness after evaporation of the solvent or flexibility on the skin. Suitable film modifiers include acrylic esters, arylsulfonamide-formaldehyde, cellulose derivatives or polyamides. The surfactants
Suitable, which aid solubilization of the components, include polyethylene glycol alkyl ethers (for example, such as that available under the tradename BRIJ). Suitable penetration enhancers include azole, dimethyl sulfoxide, more saturated fatty alcohols, surfactants and propylene glycol. The composition may additionally contain additional pharmaceutically active agents, including anti-inflammatory agents. Suitable anti-inflammatory agents include spheroids, for example, hydrocortisone, cortisone, dexamethasone, fluocinolone, triamcmolone. , medrisona, prednisolona, flurandrenolida, prednisona, falcmonida, methylprednisolona, fludrocortisona, corticosterona, parametasona and betamethasone; and non-steroidal anti-inflammatory drugs, for example, ibuprofen, diclofenac, naproxen, fenoprofen, fenbufen, flurbiprofen, mdoprofen, ketoprofen, suprofen, mdometacin, sulfasalazma, piroxicam and aspirin. Of these, hydrocortisone and diclofenac, mdometacin and salts thereof are particularly suitable. The addition of the anti-inflammatory agent improves and cures more quickly the symptoms that accompany mycoses, such as itching, erythema, blistering, burning or fissures. Another embodiment of the invention is characterized by pharmaceutical compositions comprising between 0.75%
p / p and 20% w / w of terbinafine or a pharmaceutically active salt thereof, between 0.05% w / w and 30% w / w of hydroxypropylcellulose, between 1% w / w and 10% w / w p of acrylate-octylacrylamide copolymer and a solvent selected from the group consisting of ethanol, isopropanol, acetone and ethyl acetate. Especially preferred among these are pharmaceutical compositions, which further comprise a plasticizer selected from the group consisting of dialkyl phthalates, hydroxyl fatty acid oils, silicon oils and triglycerides. The composition is applied on the area of skin infected with fungi to treat the infection. The composition is highly effective for treating fungal infections of the skin including foot tub, body tub, crural tub and scalp tub. The composition is applied to the infected area of the skin and the solvent of the composition is allowed to evaporate. As the solvent evaporates, the composition forms a film on the skin, making close contact with the skin to deliver the active agent directly. to the area of infection. The composition has a mycological cure rate of at least 50% with a single dose treatment, preferably at least 60%, more preferably at least 70% and most preferably at least 80%. The mycological cure rate is determined by defining the
Curing as a negative culture and microscopy of the infected area of the skin six weeks after treatment.
The composition of the invention is further illustrated with the following examples.
Example 1 A liquid composition containing 1% of terbinafine is prepared by combining 1.13% (w / w) of terbinafine hydrochloride salt, 5% of acrylate-octyl acrylamide copolymer (Dermacryl 79), 5% triglyceride medium chain (Miglycol 812) and 2.5% hydroxypropylcellulose (Klucel MF) and 86.37% 96% ethanol. A composition of 5% terbinafine and a composition of 10% terbinafine is prepared by increasing the content of terbinafine and decreasing the ethanol content proportionally. A placebo is also prepared without the active agent by proportionally increasing the other components of the composition. Patients with interdigital foot tub are included and divided into four groups - 107 patients for the composition group of 1%, 99 patients for the group of 5%, 93 patients for the group of 10% and 45 patients for the group of placebo. Mycological species identified in the cultures of the patients include T. rubrum, T. mentagrophytes and E. floccosum. Each patient is treated
once with one of the four previous compositions by applying the composition to cover the four interdigital spaces, the plant and the lateral surfaces up to approximately 1.5 cm. 6 weeks after treatment, the infected skin areas of the patients are examined by direct microscopy, culture and clinical signs and symptoms. Symptoms that include erythema, scaling, pruritus, pustules, vesiculation and embedding are scored by the investigator using a 4-point scale. The efficacy endpoint is the effective treatment rate in week 6, defined as negative culture and microscopy. Mycological cure is defined as negative culture and microscopy.
The mycological cure rates at week 6 are very high in the three groups treated with the terbinafine compositions and significantly higher than the rate in the placebo group, as can be seen from table 1.
Table 1
Success rate (%) Composition 1% 5% 10% Placebo Cultivation ~ 9 ~? 88 97 33 negative Microscopy 87 83 83 42 negative Healing 84 80 83 27 mycological
The result of the success rate indicated in table 1 demonstrates the high curing efficiency of the present composition, even with the composition containing a low concentration of the active antifungal ingredient. The mycological cure rate for the compositions ranges from 80% to 83% with only one application. The cure rate of the present compositions is similar to the cure rate obtained by commercial nonprescription antifungal products currently available when these products are administered in strict compliance with the required regimen of one or two daily applications for one to four weeks. The ease of
administration and dosage of the present composition encourages infected individuals to undertake the treatment, promoting high compliance results and reducing the spread of infection.
Example 2 A liquid composition of 1% terbinafine according to Example 1 is prepared. Patients are treated with interdigital foot tub with the liquid composition once and examined to determine the efficacy of the treatment in week 6. Effective treatment is it defines as negative mycological presence and minimal signs of symptoms (ie, erythema, scaling, pruritus, pustules, vesiculation, and incrustation). The culture of patients treated effectively in week 12 to re-infection is re-examined. Only one in eight of the treated patients has a positive culture at week 12, indicating reinfection. This result is similar to the reinfection rate observed in a study with a commercial cream product of 1% of terbinafine, Lamisil "cream, applied twice a day for seven days.The product Lamisil is used as a comparison product put that the product presents the simplest treatment regime requirement among the antifungal product currently
available in the market without a prescription, that is, once a day for only seven days. The result shows that the present film-forming composition, which only requires one application of the treatment, is an effective and convenient treatment for fungal infections of the skin.
EXAMPLE 3 A liquid composition of 5% terbinafine according to example 1 is prepared. The composition is applied to form areas of adherent film on the backs of patients, providing a single dose of 250 μg per cm 2 of terbinafine per zone of treatment. The patients are divided into three groups. For a group the applied film is removed by washing carefully with a sponge impregnated with soapy water at 2 hours after application. For another group, the applied film is removed 12 hours after the application. The patient's corneal layers are investigated to determine the pharmacokinetics of absorption. The pharmacokinetic study indicates that approximately 30% of terbinafine reaches the corneous layers in the first two hours, approximately 31% in the next two to twelve hours and approximately 39% after twelve hours.
Additionally, Cmax is observed as soon as in one hour among the treated patients.
EXAMPLE 4 A liquid composition of 1% terbinafine according to Example 1 is prepared. The composition is applied to form areas of adherent film on the backs of a group of patients, providing a single dose of 50 μg per cm 2 per area of treatment. To another group of patients, a commercial cream product of 1% of termama, Lamisil cream, is applied in the same manner and concentration as the film composition, except that the cream is applied daily for seven days. The treated corneal layers of both groups of patients are tested to determine the concentration of terbinafine at 13 days from the initial treatment. Pharmacokinetic analyzes indicate that the terbinafine average concentrations of terbinafine of the two groups are at a similar level, indicating that an application of the film composition is as effective as the cream treatment applied for seven days. The present composition is a highly effective composition for treating fungal infections of the skin. Normally it requires only one application to treat the fungal infection, making it highly convenient and easy
so that patients comply with the treatment regimen for a satisfactory cure of the infection.
Claims (16)
- CLAIMS Topical antifungal composition adapted to treat a fungal infection of the skin, comprising a) an antifungal agent selected from the group consisting of imidazoles, triazoles and allylamines, b) a film forming agent, and c) a solvent, wherein said composition is adapted to be applied to the skin and provides a mycological cure rate of at least 50% with one application.
- Composition according to claim 1, wherein said antifungal agent is terbinafine, amorolfine, naftifine, butenafine or a salt thereof.
- Composition according to claim 1, wherein said film-forming agent is selected from the group consisting of acrylate polymers, acrylate copolymers, alkyl-olefinic acid, alkyl-olefinic acid ester copolymers, olefinic acid / amide copolymers of olefinic acid / amide, polyvinyl acetate, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymer, hydroxyalkylcellulose and alkylcellulose.
- Composition according to claim 1, wherein said composition further comprises an anti-inflammatory agent.
- Method for treating a dermatophyte infection of the skin, comprising the step of topically applying a film-forming composition comprising a) an antifungal agent selected from the group consisting of imidazoles, triazoles and allylamines, b) an agent of film formation, and c) a solvent, wherein said treatment applies an application of said composition.
- The method according to claim 5, wherein said antifungal agent is terbinafine, amorolfine, naftifine, butenafine or a salt thereof.
- The method according to claim 5, wherein said film-forming agent is selected from the group consisting of acrylate polymers, acrylate copolymers, alkyl-olefinic acid, alkyl-olefinic acid ester copolymers, olefinic acid / amide, copolymers of olefinic acid / amide, polyvinyl acetate, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymer, hydroxyalkylcellulose and alkylcellulose.
- The method according to claim 5, wherein said antifungal agent is terbinafine or a salt thereof, said film-forming agent is a mixture of a hydroxyalkyl cellulose and an acrylate copolymer.
- The method according to claim 5, wherein said composition comprises between 0.75% w / w and 20% w / w of terbinafine or a salt thereof, between 0.05% w / w and 30% w / w p of a mixture of acrylate-octylacrylamide copolymer and hydroxypropylcellulose, and a solvent selected from the group consisting of ethanol, isopropanol, acetone and ethyl acetate.
- Method for treating a fungal infection of the skin, comprising the steps of topically applying a liquid film-forming composition to the skin, drying the liquid composition to form a film on the skin, letting the film remain on the skin for at least 48 hours, wherein said composition comprises a) an antifungal agent selected from the group consisting of imidazoles, triazoles and allylamines, b) a film-forming agent, and c) a solvent.
- The method according to claim 10, wherein said antifungal agent is terbinafine, amorolfine, naftifine, butenafine or a salt thereof.
- The method according to claim 10, wherein said film-forming agent is selected from the group consisting of acrylate polymers, acrylate copolymers, alkyl-olefinic acid, alkyl-olefinic acid ester copolymers, acid - > - > olefinic / amide, olefinic acid / amide copolymers, polyvinyl acetate, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymer, hydroxyalkylcellulose and alkylcellulose.
- The method of claim 10, wherein said antifungal agent is terbinafine or a salt thereof, said film-forming agent is a mixture of a hydroxyalkyl cellulose and an acrylate copolymer.
- 14. Method according to claim 10, wherein said composition comprises between 0.75% w / w and 20% w / w of terbinafine or a salt thereof, between 0.05% w / w and 30% w / w of a mixture of acrylate-octylacrylamide copolymer and hydroxypropylcellulose, and a solvent selected from the group consisting of ethanol, isopropanol, acetone and ethyl acetate.
- The method according to claim 10, wherein said composition further comprises an anti-inflammatory agent.
- 16. Process for the manufacture of a topical pharmaceutical composition comprising a) an antifungal agent selected from the group consisting of imidazoles, triazoles and allylamines, b) a film forming agent, and c) a solvent, for the treatment of a fungal infection of the skin with only one application.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US60/722,625 | 2005-09-29 | ||
US60/723,163 | 2005-10-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
MX2008004132A true MX2008004132A (en) | 2008-09-02 |
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