CA2747845A1 - Compositions and methods for dermally treating pain - Google Patents
Compositions and methods for dermally treating pain Download PDFInfo
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- CA2747845A1 CA2747845A1 CA2747845A CA2747845A CA2747845A1 CA 2747845 A1 CA2747845 A1 CA 2747845A1 CA 2747845 A CA2747845 A CA 2747845A CA 2747845 A CA2747845 A CA 2747845A CA 2747845 A1 CA2747845 A1 CA 2747845A1
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Abstract
The present invention is drawn to solidifying formulations for dermal delivery of a drug for treating pain, such as musculoskeletal pain, inflammation, joint pain, or neuropathic pain. The formulation can include a drug selected from certain drug classes, a solvent vehicle, and a solidifying agent. The solvent vehicle can include a volatile solvent system comprising at least one volatile solvent, and a non-volatile solvent system comprising at least one non-volatile solvent, wherein the evaporation of at least some of the volatile solvent converts the formulation on the skin into a solidified layer and the non-volatile solvent system is capable of facilitating the topical delivery of the drug(s) at therapeutically effective rates over a sustained period of time.
Claims (72)
1. A pharmaceutical formulation for topical delivery of an antiviral agent, comprising:
a) a drug comprising an antiviral agent;
b) a solvent vehicle, comprising:
i) a volatile solvent system including at least one volatile solvent, and ii) a non-volatile solvent system including at least one non-volatile solvent, wherein the volatile solvent system comprises one or more solvents consisting of water or a solvent more volatile than water; and c) a solidifying agent;
wherein the formulation has a viscosity suitable for application and adhesion to a skin surface as a layer prior to evaporation of the volatile solvent system, the layer applied to the skin surface forms a solidified layer after at least partial evaporation of the volatile solvent system, and the drug continues to be dermally delivered at a therapeutically effective rate after the volatile solvent system is evaporated, wherein the solidified layer, upon formation, is a soft, coherent solid that can be peeled from a skin surface as a single piece or as only a few large pieces relative to the application size.
a) a drug comprising an antiviral agent;
b) a solvent vehicle, comprising:
i) a volatile solvent system including at least one volatile solvent, and ii) a non-volatile solvent system including at least one non-volatile solvent, wherein the volatile solvent system comprises one or more solvents consisting of water or a solvent more volatile than water; and c) a solidifying agent;
wherein the formulation has a viscosity suitable for application and adhesion to a skin surface as a layer prior to evaporation of the volatile solvent system, the layer applied to the skin surface forms a solidified layer after at least partial evaporation of the volatile solvent system, and the drug continues to be dermally delivered at a therapeutically effective rate after the volatile solvent system is evaporated, wherein the solidified layer, upon formation, is a soft, coherent solid that can be peeled from a skin surface as a single piece or as only a few large pieces relative to the application size.
2. A formulation as in claim 1, wherein the non-volatile solvent system acts as a plasticizer for the solidifying agent.
3. A formulation as in claim 1, wherein the non-volatile solvent system facilitates transdermal delivery of the drug at a therapeutically effective rate over a sustained period of time.
4. A formulation as in claim 1, wherein the non-volatile solvent system is flux-enabling for the drug.
5. A formulation as in claim 1, wherein the formulation further comprises a pH
modifying agent.
modifying agent.
6. A formulation as in claim 1, wherein the formulation further comprises an additional agent which is added to increase adhesion of the formulation when applied to the skin surface.
7. A formulation as in claim 6, wherein the additional agent comprises a copolymer of methylvinyl ether and maleic anhydride, a copolymer of polyethylene glycol and polyvinyl pyrrolidone, gelatin, a low molecular weight polyisobutylene rubber, a copolymer of acrylsan alkyl/octylacrylamido, an aliphatic resin, or an aromatic resin, or a combination thereof.
8. A formulation as in claim 1, wherein the volatile solvent system is substantially free of water.
9. A formulation as in claim 1, wherein the solidifying agent is present in the solidified layer at least at 20% by weight after all of the volatile solvent system has evaporated.
10. A formulation as in claim 1, wherein the non-volatile solvent system is present in the solidified layer at least at 20% by weight after all of the volatile solvent system has evaporated.
11. A formulation as in claim 1, wherein the volatile solvent system comprises ethanol, isopropyl alcohol, water, dimethyl ether, diethyl ether, butane, propane, isobutene, 1,1, difluoroethane, 1,1,1,2 tetrafluorethane, 1,1,1,2,3,3,3-heptafluoropropane, 1,1,1,3,3,3 hexafluoropropane, ethyl acetate, acetone, denatured alcohol, methanol, propanol, isobutene, pentane, hexane, cytopentasiloxane, cyclomethicone, or methyl ethyl ketone, or a combination thereof.
12. A formulation as in claim 1, wherein the non-volatile solvent system includes multiple non-volatile solvents admixed together which, along with other ingredients in the formula-tion, forms a formulation which solidifies onto the skin and delivers the drug at therapeutical-ly effective rates over a sustained period of time.
13. A formulation as in claim 1, wherein the non-volatile solvent system comprises glycerol, propylene glycol, isostearic acid, oleic acid, propylene glycol, trolamine, tromethamine, triacetin, sorbitan monolaurate, sorbitan monooleate, sorbitan monopalmitate, butanol, benzoic acid, dibutyl sebecate, a diglyceride, dipropylene glycol, eugenol, a fatty acid, isopropyl myristate, mineral oil, oleyl alcohol, vitamin E, a triglyceride, a sorbitan fatty acid surfactant, triethyl citrate, 1,2,6-hexanetriol, an alkyltriol, an alkyldiol, tocopherol, p-propenylanisole, anise oil, apricot oil, dimethyl isosorbide, alkyl glucoside, benzyl alcohol, bees wax, benzyl benzoate, butylene glycol, caprylic/capric triglyceride, caramel, cassia oil, castor oil, cinnamaldehyde, cinnamon oil, clove oil, coconut oil, cocoa butter, a cocoglyceride, coriander oil, corn oil, corn syrup, cottonseed oil, cresol, diacetin, a diacetylated monoglyceride, diethanolamine, ethylene glycol, eucalyptus oil, fat, a fatty alcohol, a flavoring, a liquid sugar, ginger extract, glycerin, high fructose corn syrup, hydrogenated castor oil, IP palmitate, lemon oil, lime oil, limonene, monoacetin, a mono-glyceride, nutmeg oil, octyldodecanol, orange oil, palm oil, peanut oil, PEG
vegetable oil, peppermint oil, petrolatum, phenol, pine needle oil, polypropylene glycol, sesame oil, spearmint oil, soybean oil, vegetable oil, vegetable shortening, wax, 2-(2-(octa-decyloxy)ethoxy)ethanol, benzyl benzoate, butylated hydroxyanisole, candelilla wax, carnauba wax, ceteareth-20, cetyl alcohol, polyglyceryl, dipolyhydroxy stearate, PEG-7 hydrogenated castor oil, diethyl phthalate, diethyl sebacate, dimethicone, dimethyl phthalate, a PEG fatty acid ester, PEG- stearate, PEG-oleate, PEG laurate, a PEG fatty acid diester, PEG- dioleate, PEG-distearate, PEG-castor oil, glyceryl behenate, a PEG
glycerol fatty acid ester, PEG glyceryl laurate, PEG glyceryl stearate, PEG
glyceryl oleate, lanolin, lauric diethanolamide, lauryl lactate, lauryl sulfate, medronic acid, multisterol extract, myristyl alcohol, neutral oil, PEG-octyl phenyl ether, PEG-alkyl ethers, PEG-cetyl ether, PEG-stearyl ether, PEG-sorbitan fatty acid esters, PEG-sorbitan diisosterate, PEG-sorbitan monostearate, a propylene glycol fatty acid ester, propylene glycol stearate, propylene glycol, caprylate/caprate, sodium pyrrolidone carboxylate, sorbitol, squalene, stear-o-wet, an alkyl aryl polyether alcohol, a polyoxyethylene derivative of a sorbitan-ether, a saturated polyglycolyzed C8-C10 glyceride, N-methyl pyrrolidone, honey, a polyoxyethylated glyceride, dimethyl sulfoxide, an azone or a related compound, dimethylformamide, N-methyl formamaide, a fatty acid ester, a fatty alcohol ether, an alkyl-amide (N,N-dimethylalkylamide), an N-methyl pyrrolidone related compound, ethyl oleate, a polyglycerized fatty acid, glycerol monooleate, glyceryl monomyristate, a glycerol ester of a fatty acid, a silk amino acid, PPG-3 benzyl ether myristate, Di-PPG2 myreth 10-adipate, honeyquat, sodium pyroglutamic acid, abyssinica oil, dimethicone, macadamia nut oil, limnanthes alba seed oil, cetearyl alcohol, PEG-50 shea butter, shea butter, aloe vera juice, phenyl trimethicone, or hydrolyzed wheat protein, or a combination thereof.
vegetable oil, peppermint oil, petrolatum, phenol, pine needle oil, polypropylene glycol, sesame oil, spearmint oil, soybean oil, vegetable oil, vegetable shortening, wax, 2-(2-(octa-decyloxy)ethoxy)ethanol, benzyl benzoate, butylated hydroxyanisole, candelilla wax, carnauba wax, ceteareth-20, cetyl alcohol, polyglyceryl, dipolyhydroxy stearate, PEG-7 hydrogenated castor oil, diethyl phthalate, diethyl sebacate, dimethicone, dimethyl phthalate, a PEG fatty acid ester, PEG- stearate, PEG-oleate, PEG laurate, a PEG fatty acid diester, PEG- dioleate, PEG-distearate, PEG-castor oil, glyceryl behenate, a PEG
glycerol fatty acid ester, PEG glyceryl laurate, PEG glyceryl stearate, PEG
glyceryl oleate, lanolin, lauric diethanolamide, lauryl lactate, lauryl sulfate, medronic acid, multisterol extract, myristyl alcohol, neutral oil, PEG-octyl phenyl ether, PEG-alkyl ethers, PEG-cetyl ether, PEG-stearyl ether, PEG-sorbitan fatty acid esters, PEG-sorbitan diisosterate, PEG-sorbitan monostearate, a propylene glycol fatty acid ester, propylene glycol stearate, propylene glycol, caprylate/caprate, sodium pyrrolidone carboxylate, sorbitol, squalene, stear-o-wet, an alkyl aryl polyether alcohol, a polyoxyethylene derivative of a sorbitan-ether, a saturated polyglycolyzed C8-C10 glyceride, N-methyl pyrrolidone, honey, a polyoxyethylated glyceride, dimethyl sulfoxide, an azone or a related compound, dimethylformamide, N-methyl formamaide, a fatty acid ester, a fatty alcohol ether, an alkyl-amide (N,N-dimethylalkylamide), an N-methyl pyrrolidone related compound, ethyl oleate, a polyglycerized fatty acid, glycerol monooleate, glyceryl monomyristate, a glycerol ester of a fatty acid, a silk amino acid, PPG-3 benzyl ether myristate, Di-PPG2 myreth 10-adipate, honeyquat, sodium pyroglutamic acid, abyssinica oil, dimethicone, macadamia nut oil, limnanthes alba seed oil, cetearyl alcohol, PEG-50 shea butter, shea butter, aloe vera juice, phenyl trimethicone, or hydrolyzed wheat protein, or a combination thereof.
14. The formulation of any one of claims 1-13 wherein the antiviral agent comprises acyclovir, penciclovir, famciclovir, or valacyclovir.
15. A formulation as in claim 1, wherein the solidifying agent comprises a polyvinyl alcohol, an ester of polyvinylmethylether/maleic anhydride copolymer, a neutral copolymer of butyl methacrylate and methyl methacrylate, a dimethylaminoethyl methacrylate-butyl methacrylate-methyl methacrylate copolymer, a ethyl acrylate-methyl methacrylate-trimethylammonioethyl methacrylate chloride copolymer, prolamine (Zein), pregelatinized starch, ethyl cellulose, fish gelatin, gelatin, an acrylate/octylacrylamide copolymer, ethyl cellulose, hydroxy ethyl cellulose, hydroxy methyl cellulose, hydroxy propyl cellulose, hydroxypropyl methyl cellulose, carboxymethyl cellulose, methyl cellulose, a polyether amide, corn starch, pregelatinized corn starch,a polyether amide, shellac, polyvinyl pyrrolidone, polyisobutylene rubber, polyvinyl acetate phthalate, ammonia methacrylate, carrageenan, cellulose acetate phthalate aqueous, carboxy polymethylene, cellulose acetate (microcrystalline), a cellulose polymer, divinyl benzene styrene, ethylene vinyl acetate, silicone, guar gum, guar rosin, gluten, casein, calcium caseinate, ammonium caseinate, sodium caseinate, potassium caseinate, methyl acrylate, microcrystalline wax, polyvinyl acetate, PVP ethyl cellulose, acrylate, PEG/PVP, xantham gum, a trimethyl siloxysilicate, a maleic acid/anhydride colymer, polacrilin, poloxamer, polyethylene oxide, poly glactic acid/poly-l-lactic acid, turpene resin, locust bean gum, an acrylic copolymer, a polyurethane dispersion, dextrin, a polyvinyl alcohol-polyethylene glycol co-polymer, a methyacrylic acid-ethyl acrylate copolymer, methacrylic acid, or a methacrylate based polymer, or a combination thereof.
16. A formulation as in claim 1, wherein the drug includes multiple pharmaceutically active agents.
17. A formulation as in claim 1, wherein the solidified layer is sufficiently flexible and adhesive to the skin such that when applied to the skin at a human joint, the solidified layer will remain intact on the skin upon bending of the joint.
18. A formulation as in claim 1, wherein the volatile solvent system comprises a volatile solvent whose boiling point is below 20°C.
19. A formulation as in claim 18, wherein the volatile solvent with the boiling point below
20°C is completely dissolved in the formulation.
20. A formulation as in claim 18, wherein the volatile solvent with the boiling point below 20°C is included in the formulation as a propellant for pressurized spray-on application.
20. A formulation as in claim 18, wherein the volatile solvent with the boiling point below 20°C is included in the formulation as a propellant for pressurized spray-on application.
21. A formulation as in claim 18, wherein the volatile solvent with the boiling point below 20°C is a hydrofluorocarbon.
22. The formulation of claim 18, wherein the volatile solvent whose boiling point is below 20°C comprises dimethyl ether, butane, 1,1, difluoroethane, 1,1,1,2 tetrafluorethane, 1,1,1,2,3,3,3-heptafluoropropane, or 1,1,1,3,3,3 hexafluoropropane, or a combination thereof.
23. A formulation as in claim 1, wherein the formulation is formulated to deliver the drug at a therapeutically effective rate for at least 2 hours following the formation of the solidified layer.
24. A formulation as in claim 1, wherein the formulation is formulated to deliver the drug at a therapeutically effective rate for at least 4 hours following the formation of the solidified layer.
25. A formulation as in claim 1, wherein the formulation is formulated to deliver the drug at a therapeutically effective rate for at least 8 hours following the formation of the solidified layer.
26. A formulation as in claim 1, wherein the formulation is formulated to deliver the drug at a therapeutically effective rate for at least 12 hours following the formation of the solidified layer.
27. A formulation as in claim 1, wherein the solidifying agent is dispersed in the solvent vehicle.
28. A formulation as in claim 1, wherein the solidifying agent is solvated in the solvent vehicle.
29. A formulation as in claim 1, wherein the weight ratio of the non-volatile solvent system to the solidifying agent is from about 0.1:1 to about 10:1.
30. A formulation as in claim 1, wherein the weight ratio of the non-volatile solvent system to the solidifying agent is from about 0.5:1 to about 2:1.
31. A formulation as in claim 1, wherein the non-volatile solvent system is capable of causing human skin irritation and at least one non-volatile solvent of the non-volatile solvent system is capable of reducing the skin irritation.
32. A formulation as in claim 31, wherein the non-volatile solvent capable of reducing skin irritation comprises glycerin, propylene glycol, or honey, or a combination thereof.
33. A formulation as in claim 1, wherein the solidified layer is formed within about 15 minutes of application to the skin surface under standard skin and ambient conditions.
34. A formulation as in claim 1, wherein the solidified layer is formed within 4 minutes of the application to the skin surface under standard skin and ambient conditions.
35. A formulation as in claim 1, wherein the formulation has an initial viscosity prior to skin application from about 100 cP to about 3,000,000 cP.
36. A formulation as in claim 1, wherein the formulation has an initial viscosity prior to skin application from about 1,000 cP to about 1,000,000 cP.
37. A formulation as in claim 1, wherein the weight percentage of the volatile solvent system is from about 10 wt% to about 85 wt%.
38. A formulation as in claim 1, wherein the weight percentage of the volatile solvent system is from about 20 wt% to about 50 wt%.
39. A formulation as in claim 1, wherein the non-volatile solvent system includes multiple non-volatile solvents, and at least one of the non-volatile solvents improves the compatibility of the non-volatile solvent system with the solidifying agent.
40. A formulation as in claim 1, wherein the non-volatile solvent system includes at least two non-volatile solvents, and wherein one of the at least two non-volatile solvents is included to improve compatibility with the solidifying agent.
41. A formulation as in claim 1, wherein the solidified layer is coherent, flexible, and continuous.
42. A formulation as in claim 1, wherein the solidified layer is formulated to deliver the drug transdermally.
43. A placebo formulation for dermal application, said formulation comprising:
a) a solvent vehicle, comprising:
i) a volatile solvent system including at least one volatile solvent, and ii) a non-volatile solvent system including at least one non-volatile solvent, wherein the volatile solvent system comprises one or more solvents consisting of water or a solvent more volatile than water, and b) a solidifying agent, wherein the formulation has a viscosity suitable for application and adhesion to a skin surface as a layer prior to evaporation of the volatile solvent system, the layer applied to the skin surface forms a solidified layer after at least partial evaporation of the volatile solvent system, wherein the solidified layer, upon formation, is a soft, coherent solid that can be peeled from a skin surface as a single piece or as only a few large pieces relative to the application size.
a) a solvent vehicle, comprising:
i) a volatile solvent system including at least one volatile solvent, and ii) a non-volatile solvent system including at least one non-volatile solvent, wherein the volatile solvent system comprises one or more solvents consisting of water or a solvent more volatile than water, and b) a solidifying agent, wherein the formulation has a viscosity suitable for application and adhesion to a skin surface as a layer prior to evaporation of the volatile solvent system, the layer applied to the skin surface forms a solidified layer after at least partial evaporation of the volatile solvent system, wherein the solidified layer, upon formation, is a soft, coherent solid that can be peeled from a skin surface as a single piece or as only a few large pieces relative to the application size.
44. The placebo formulation of claim 43 wherein said volatile solvent system, said non-volatile solvent system, said formulation or said solidifying agent or layer are as described in any one of claims 2, 5-13, 15, 17-22 or 27-41.
45. A use of the formulation of any one of claims 1-42 for dermally delivering a drug, wherein said formulation forms a solidified layer on the skin surface by at least partial evaporation of the volatile solvent system.
46. A use as in claim 45, for delivery to a skin area over a wrist, ankle, elbow, or knee.
47. A use as in claim 45, for delivery to a skin area over a finger or toe joint.
48. A use as in claim 45, for delivery to a skin area over a back.
49. A use as in claim 45, for delivery to a skin area over a neck.
50. A use as in claim 45, wherein said use comprises applying the formulation at a thickness from about 0.01 mm to about 3 mm.
51. A use as in claim 45, wherein said use comprises applying the formulation at a thickness from about 0.05 mm to about 1 mm.
52. A use as in claim 45, wherein said use comprises the formulation being sprayed on the skin.
53. A use as in claim 45, wherein said use comprises the formulation being applied on the skin using a manual pump.
54. A use of the formulation of claim 43, wherein said placebo formulation is for comparative testing against a preparation which comprises a drug for dermal delivery.
55. A use of the formulation of claim 43, wherein said placebo formulation is formulated for addition of a drug.
56. A solidified layer for topical delivery of an antiviral agent, comprising:
a) a drug comprising an antiviral agent, b) a non-volatile solvent system including at least one non-volatile solvent, and c) a solidifying agent, wherein the solidified layer is capable of adhering to a skin surface and delivering the drug across the skin surface at therapeutically effective rates over a sustained period of time and wherein the solidified layer is a soft, coherent solid that can be peeled from a skin surface as a single piece or as only a few large pieces relative to the application size.
a) a drug comprising an antiviral agent, b) a non-volatile solvent system including at least one non-volatile solvent, and c) a solidifying agent, wherein the solidified layer is capable of adhering to a skin surface and delivering the drug across the skin surface at therapeutically effective rates over a sustained period of time and wherein the solidified layer is a soft, coherent solid that can be peeled from a skin surface as a single piece or as only a few large pieces relative to the application size.
57. A solidified layer as in claim 56, wherein the solidified layer is formulated to be applied to a skin surface over a wrist, ankle, elbow, or knee.
58. A solidified layer as in claim 56, wherein the solidified layer is formulated to be applied to the skin surface over a finger or toe joint.
59. A solidified layer as in claim 56, wherein the solidified layer is formulated to be applied to the skin surface over a back, neck, shoulder, or hip.
60. A solidified layer as in claim 56, wherein the solidified layer has a thickness from about 0.01 mm to about 3 mm.
61. A solidified layer as in claim 56, wherein the solidified layer is sufficiently flexible and adhesive to the skin such that when applied to the skin at a human joint, the solidified layer will remain intact on the skin upon bending of the joint.
62. A solidified layer as in claim 56, wherein the solidified layer is formulated to deliver the drug at a therapeutically effective rate for at least 2 hours.
63. A solidified layer as in claim 56, wherein the formulation is formulated to deliver the drug at a therapeutically effective rate for at least 12 hours.
64. A solidified layer as in claim 56, wherein the weight ratio of the non-volatile solvent system to the solidifying agent is from about 0.5:1 to about 2.1.
65. A solidified layer as in claim 56, wherein the solidified layer is a soft, coherent solid layer that is peelable from a skin surface as a single piece or as only a few large pieces relative to the application size.
66. A solidified layer as in claim 56, wherein the solidified layer is a soft, coherent solid layer that is removable by washing.
67. A solidified layer as in claim 56, wherein the solidified layer contains no more than wt% of water and solvents more volatile than water.
68. A solidified layer as in claim 56, wherein the solidified layer contains no more than wt% of water and solvents more volatile than water.
69. A solidified layer as in claim 56, wherein the solidified layer is adhesive to the skin surface on one surface, and is non-adhesive on an opposing surface.
70. A solidified layer as in claim 56, wherein the solidified layer is flux-enabling for the drug.
71. The solidified layer of any one of claims 56-70 wherein said antiviral agent comprises acyclovir, penciclovir, famciclovir, or valacyclovir.
72. A solidified layer of a placebo formulation, said layer comprising:
a) a non-volatile solvent system including at least one non-volatile solvent, and b) a solidifying agent, wherein the solidified layer is capable of adhering to a skin surface, and wherein the solidified layer is a soft, coherent solid that can be peeled from a skin surface as a single piece or as only a few large pieces relative to the application size.
a) a non-volatile solvent system including at least one non-volatile solvent, and b) a solidifying agent, wherein the solidified layer is capable of adhering to a skin surface, and wherein the solidified layer is a soft, coherent solid that can be peeled from a skin surface as a single piece or as only a few large pieces relative to the application size.
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US75063705P | 2005-12-14 | 2005-12-14 | |
US75051905P | 2005-12-14 | 2005-12-14 | |
US75068305P | 2005-12-14 | 2005-12-14 | |
US60/750,683 | 2005-12-14 | ||
US60/750,519 | 2005-12-14 | ||
US60/750,637 | 2005-12-14 | ||
CA2633515A CA2633515C (en) | 2005-12-14 | 2006-12-14 | Compositions and methods for dermally treating pain |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA2633515A Division CA2633515C (en) | 2005-12-14 | 2006-12-14 | Compositions and methods for dermally treating pain |
Publications (2)
Publication Number | Publication Date |
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CA2747845A1 true CA2747845A1 (en) | 2007-06-21 |
CA2747845C CA2747845C (en) | 2012-10-09 |
Family
ID=40925298
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA2747845A Expired - Fee Related CA2747845C (en) | 2005-12-14 | 2006-12-14 | Compositions and methods for dermally treating pain |
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CN (1) | CN101494976B (en) |
CA (1) | CA2747845C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111067919A (en) * | 2019-12-23 | 2020-04-28 | 李益谦 | Spray analgesic |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102846610A (en) * | 2012-09-19 | 2013-01-02 | 中国人民解放军第二军医大学 | Local externally-applied antalgic compound preparation composition for skin and preparation method thereof |
US20140113970A1 (en) * | 2012-10-22 | 2014-04-24 | Mallinckrodt LLC Covidien | Dispensing system |
EP3319598A4 (en) * | 2015-07-08 | 2019-02-27 | Elliptical Therapeutics, LLC | Improved topical ketoprofen formulations |
CN106377793A (en) * | 2016-11-16 | 2017-02-08 | 广东泰宝医疗科技股份有限公司 | Compound liquid dressing and preparation method thereof |
TWI688405B (en) * | 2018-03-19 | 2020-03-21 | 國立臺北科技大學 | Biodegradable microneedle array |
FR3080770B1 (en) * | 2018-05-04 | 2020-09-18 | Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic | TOPICAL USE OF OIL FROM SEEDS OF AT LEAST ONE OMBELLIFIER PLANT FOR A SOOTHING EFFECT ON REACTIVE SKIN |
WO2022063294A1 (en) * | 2020-09-28 | 2022-03-31 | 江苏恒瑞医药股份有限公司 | Percutaneously absorbable pharmaceutical composition containing amide local anaesthetics, preparation method therefor, and use thereof |
WO2023242417A1 (en) * | 2022-06-17 | 2023-12-21 | Bertie International Ab | Long-lasting anaesthetic formulation |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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EP1021204B1 (en) * | 1997-09-26 | 2005-12-28 | Noven Pharmaceuticals, Inc. | Bioadhesive compositions and methods for topical administration of active agents |
AUPQ419099A0 (en) * | 1999-11-23 | 1999-12-16 | Ko, Thomas Sai Ying | Novel compositions and methods |
US6432415B1 (en) * | 1999-12-17 | 2002-08-13 | Axrix Laboratories, Inc. | Pharmaceutical gel and aerosol formulations and methods to administer the same to skin and mucosal surfaces |
-
2006
- 2006-12-14 CA CA2747845A patent/CA2747845C/en not_active Expired - Fee Related
- 2006-12-14 CN CN200680051992.4A patent/CN101494976B/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN111067919A (en) * | 2019-12-23 | 2020-04-28 | 李益谦 | Spray analgesic |
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Publication number | Publication date |
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CN101494976B (en) | 2013-12-18 |
CN101494976A (en) | 2009-07-29 |
CA2747845C (en) | 2012-10-09 |
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