CA2471041A1 - Compositions and methods for enhancing corticosteriod delivery - Google Patents

Compositions and methods for enhancing corticosteriod delivery Download PDF

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Publication number
CA2471041A1
CA2471041A1 CA002471041A CA2471041A CA2471041A1 CA 2471041 A1 CA2471041 A1 CA 2471041A1 CA 002471041 A CA002471041 A CA 002471041A CA 2471041 A CA2471041 A CA 2471041A CA 2471041 A1 CA2471041 A1 CA 2471041A1
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composition
stearate
corticosteroid
present
propylene glycol
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CA002471041A
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French (fr)
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CA2471041C (en
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Eugene H. Gans
Mitchell S. Wortzman
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Medicis Pharmaceutical Corp
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    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • 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
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • 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
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • 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
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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
    • 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
    • A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
    • 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
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • 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
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11C—STATIC STORES
    • G11C16/00—Erasable programmable read-only memories
    • G11C16/02—Erasable programmable read-only memories electrically programmable
    • G11C16/04—Erasable programmable read-only memories electrically programmable using variable threshold transistors, e.g. FAMOS
    • G11C16/0408—Erasable programmable read-only memories electrically programmable using variable threshold transistors, e.g. FAMOS comprising cells containing floating gate transistors
    • G11C16/0433—Erasable programmable read-only memories electrically programmable using variable threshold transistors, e.g. FAMOS comprising cells containing floating gate transistors comprising cells containing a single floating gate transistor and one or more separate select transistors
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11C—STATIC STORES
    • G11C2216/00—Indexing scheme relating to G11C16/00 and subgroups, for features not directly covered by these groups
    • G11C2216/02—Structural aspects of erasable programmable read-only memories
    • G11C2216/10—Floating gate memory cells with a single polysilicon layer

Abstract

The present invention comprises a composition, method of enhancing potency and method of delivering corticosteroids in a vehicle comprising at least two penetration enhancers, and solvents and emulsifiers. The propylene glycol and penetration enhancers are present in ratio to the total of the propylene glycol, penetration enhancers, and solvents and emulsifiers of at least about 0.70.

Claims (60)

1. A composition comprising One or more corticosteroids;
Two or more penetration enhancers; and One or more of the group consisting of solvents and emulsifiers, wherein the penetration enhancers are present in a ratio to a total of the penetration enhancers, and solvents and emulsifiers of at least about 0.70.
2. The composition of claim 1 wherein the corticosteroid comprises a fluorinated corticosteroid.
3. The composition of claim 1 wherein the corticosteroid comprises fluocinonide.
4. The composition of claim 1 wherein the corticosteroid comprises fluocinolone acetonide.
5. The composition of claim 1, 2, 3 or 4 wherein the corticosteroid is present at about 0.10%.
6. The composition of claim 1, 2, 3 or 4 wherein the corticosteroid is present at at least about 0.50%.
7. The composition of claim 1, 2, 3 or 4 wherein the corticosteroid is present at at least about 0.25%.
8. The composition of claim 1 ,2, 3 or 4 wherein the penetration enhancers comprise two or more of the group consisting of propylene glycol, diisopropyl adipate, dimethyl isosorbide, 1,2,6 hexanetriol, and benzyl alcohol.
9. The composition of claim 1, 2, 3 or 4 wherein the penetration enhancers comprise two or more of the group consisting of propylene glycol, diisopropyl adipate and dimethyl isosorbide.
10. The composition of claim 1, 2, 3, or 4 wherein one penetration enhancer comprises propylene glycol.
11. The composition of claim 1 wherein the ratio is at least about 0.80.
12. The composition of claim 1 wherein the ratio is at least about 0.90.
13. The composition of claim 1 wherein the ratio is at least about 0.95.
14. The composition of claim 1 wherein the solvents and emulsifiers comprise one or more of the group consisting of dehydrated alcohol, alcohol (95% v/v)USP, 3-Cyclohexene-1-Methanol, oc4-Dimethyl-a-(4-Methyl-3-Pentenyl)-, Steareth-2, Steareth-21, citric acid, CPE-215, diisopropanolamine (1:9), DIPA/PG (1:9), ethoxydiglycol, Potassium hydroxide (10%), PEG-40 Stearate, PEG-7000, Polysorbate 60, potassium hydroxide (1%), propylene carbonate USP, propylethylene glycol 4, oleyl alcohol, sodium lauryl sulfate, sorbitan monostearate, sorbitan stearate, and 1,2,3-Propanetriyl Ester.
15. The composition of claim 1 further comprising one or more non-solvent/emulsifier ingredients.
16. The composition of claim 14 wherein the non-solvent/emulsifier ingredients comprise one or more of the group consisting of Glyceryl Stearate (and) PEG-Stearate, carbopol 980, cyclomethicone NF, glyceryl monostearate, hydroxyethyl cellulose, hydroxypropyl cellulose, isopropyl myristate, methyl paraben NF, mineral oil, oleic acid NF, PEG-100 Stearate, petrolatum, propyl paraben NF, purified water, stearyl alcohol, white petrolatum, and white wax.
17. The composition of claim 1 wherein the solvents and emulsifiers are present at about 4-5%.
18. The composition of claim 15 wherein the non-solvent/emulsifier ingredients are present at about 11% to about 53%.
19. The composition of claim 15 wherein the non-solvent/emulsifier ingredients are present at about 11 % to about 27%.
20. A composition comprising about 0.10% fluocinonide, about 74.9% propylene glycol, about 3.0% diisopropyl adipate, about 5.0% isopropyl myristate, about 2.5%
1,2,6 trihydroxyhexane, about 1.0% carbopol 980, about 1.0% diisopropanolamine 85%: propylene glycol (1:9), about 0.01% citric acid, about 2.49% purified water, about 2.5% glyceryl monostearate, and about 7.5% glyceryl monostearate & PEG
stearate.
21. A composition comprising about 0.10% fluocinonide, about 70.0% propylene glycol, about 15.0% dimethyl isosorbide, about 1.2% carbopol 980, about 1.2%
diisopropanolamine 85%: propylene glycol (1:9), about 0.01% citric acid, about 2.49% purified water, about 2.5% glyceryl monostearate, and about 7.5%
glyceryl monostearate & PEG stearate.
22. A composition comprising about 0.10% fluocinonide, about 66.8% propylene glycol, about 5.0% dimethyl isosorbide, about 5.0% isopropyl myristate, about 0.5%
carbopol 980, about 0.5% diisopropanolamine 85%: propylene glycol (1:9), about 5.0% white petrolatum USP, about 6.0% glyceryl monostearate, about 6.0% PEG
100 stearate, about 5.0% stearyl alcohol, and about 0.10% sodium lauryl sulfate.
23. A composition comprising about 0.10% fluocinonide, about 69.9% propylene glycol, about 2.0% diisopropyl adipate, about 5.0% isopropyl myristate, about 0.5%
carbopol 980, about 0.5% diisopropanolamine 85%: propylene glycol (1:9), about 5.0% white petrolatum USP, about 6.0% glyceryl monostearate, about 6.0% PEG
100 stearate, and about 5.0% stearyl alcohol.
24. A method for enhancing potency of corticosteroids comprising Combining one or more corticosteroids with two or more penetration enhancers, and one or more of the group consisting of solvents and emulsifiers, wherein the penetration enhancers are present in a ratio to a total of penetration enhancers, and solvents and emulsifiers of at least about 0.70.
25. The method of claim 24 wherein the corticosteroid comprises a fluorinated corticosteroid.
26. The method of claim 24 wherein the corticosteroid comprises fluocinonide.
27. The method of claim 24 wherein the corticosteroid comprises fluocinolone acetonide.
28. The method of claim 24, 25, 26 or 27 wherein the corticosteroid is present at about 0.10%.
29. The method of claim 24, 25, 26 or 27 wherein the corticosteroid is present at at least about 0.50%.
30. The method of claim 24, 25, 26 or 27 wherein the corticosteroid is present at at least about 0.25%.
31. The method of claim 24, 25, 26 or 27 wherein the penetration enhancers comprise two or more of the group consisting of propylene glycol, diisopropyl adipate, dimethyl isosorbide, 1,2,6 hexanetriol, and benzyl alcohol.
32. The method of claim 24, 25, 26 or 27 wherein the penetration enhancers comprise two or more of the group consisting of propylene glycol, diisopropyl adipate and dimethyl isosorbide.
33. The method of claim 24, 25, 26 or 27 wherein one penetration enhancer comprises propylene glycol.
34. The method of claim 24 wherein the ratio is at least about 0.80.
35. The method of claim 24 wherein the ratio is at least about 0.90.
36. The method of claim 24 wherein the ratio is at least about 0.95.
37. The method of claim 24 wherein the solvents and emulsifiers comprise one or more of the group consisting of dehydrated alcohol, alcohol (95% v/v) USP, 3-Cyclohexene-1-Methanol, oc4-Dimethyl-a-(4-Methyl-3-Pentenyl)-, Steareth-2, Steareth-21, citric acid, CPE-215, diisopropanolamine (1:9), DIPA/PG (1:9), ethoxydiglycol, Potassium hydroxide (10%), PEG-40 Stearate, PEG-7000, Polysorbate 60, potassium hydroxide (1%), propylene carbonate USP, propylethylene glycol 4, oleyl alcohol, sodium lauryl sulfate, sorbitan monostearate, sorbitan stearate, and 1,2,3-Propanetriyl Ester.
38. The method of claim 24 wherein the composition further comprises one or more non-solvent/emulsifier ingredients.
39. The method of claim 38 wherein the non-solvent/emulsifier ingredients comprise one or more of the group consisting of Glyceryl Stearate (and) PEG-100 Stearate, carbopol 980, cyclomethicone NF, glyceryl monostearate, hydroxyethyl cellulose, hydroxypropyl cellulose, isopropyl myristate, methyl paraben NF, mineral oil, oleic acid NF, PEG-100 Stearate, petrolatum, propyl paraben NF, purified water, stearyl alcohol, white petrolatum, and white wax.
40. The method of claim 24 wherein the solvents and emulsifiers are present at about 4-5%.
41. The method of claim 39 wherein the non-solvent/emulsifier ingredients are present at about 11% to about 53%.
42. The method of claim 39 wherein the non-solvent/emulsifier ingredients are present at about 11 % to about 27%.
43. A method of delivering corticosteroids to skin comprising Topically applying a composition comprising one or more corticosteroids with two or more penetration enhancers, and one or more of the group consisting of solvents and emulsifiers, wherein the penetration enhancers are present in ratio to a total of the penetration enhancers, and solvents and emulsifiers of at least about 0.70.
44. The method of claim 43 wherein the corticosteroid comprises a fluorinated corticosteroid.
45. The method of claim 43 wherein the corticosteroid comprises fluocinonide.
46. The method of claim 43 wherein the corticosteroid comprises fluocinolone acetonide.
47. The method of claim 43, 44, 45 or 46 wherein the corticosteroid is present at about 0.10%.
48. The method of claim 43, 44, 45 about 0.50%.
49. The method of claim 43, 44, 45 or 46 wherein the corticosteroid is present at at least about 0.25%.
50. The method of claim 43, 44, 45 or 46 wherein the penetration enhancers comprise two or more of the group consisting of propylene glycol, diisopropyl adipate dimethyl isosorbide, 1,2,6 hexanetriol, and benzyl alcohol.
51. The method of claim 43, 44, 45 or 46 wherein the penetration enhancers comprise two or more of the group consisting of propylene glycol, diisopropyl adipate and dimethyl isosorbide.
52. The method of claim 43, 44, 45 or 46 wherein one penetration enhancer comprises propylene glycol.
53. The method of claim 43 wherein the ratio is at least about 0.85.
54. The method of claim 43 wherein the ratio is at least about 0.90.
55. The method of claim 43 wherein the solvents and emulsifiers comprise one or more of the group consisting of dehydrated alcohol, alcohol (95% v/v)USP, 3-Cyclohexene-1-Methanol, oc4-Dimethyl-a-(4-Methyl-3-Pentenyl)-, Steareth-2, Steareth-21, citric acid, CPE-215, diisopropanolamine (1:9), DIPA/PG (1:9), ethoxydiglycol, Potassium hydroxide (10%), PEG-40 Stearate, PEG-7000, Polysorbate 60, potassium hydroxide (1%), propylene carbonate USP, propylethylene glycol 4, oleyl alcohol, sodium lauryl sulfate, sorbitan monostearate, sorbitan stearate, and 1,2,3-Propanetriyl Ester.
56. The method of claim 43 wherein the composition further comprises one or more non-solvent/emulsifier ingredients.
57. The method of claim 56 wherein the non-solvent/emulsifier ingredients comprise one or more of the group consisting of Glyceryl Stearate (and) PEG-100 Stearate, carbopol 980, cyclomethicone NF, glyceryl monostearate, hydroxyethyl cellulose, hydroxypropyl cellulose, isopropyl myristate, methyl paraben NF, mineral oil, oleic acid NF, PEG-100 Stearate, petrolatum, propyl paraben NF, purified water, stearyl alcohol, white petrolatum, and white wax.
58. The method of claim 43 wherein the solvents and emulsifiers are present at about 4-5%.
59. The method of claim 57 wherein the non-solvent/emulsifier ingredients are present at about 11% to about 53%.
60. The method of claim 57 wherein the non-solvent/emulsifier ingredients are present at about 11% to about 27%.
CA2471041A 2001-12-21 2002-12-12 Compositions and methods for enhancing corticosteriod delivery Expired - Lifetime CA2471041C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/037,360 US6765001B2 (en) 2001-12-21 2001-12-21 Compositions and methods for enhancing corticosteroid delivery
US10/037,360 2001-12-21
PCT/US2002/039882 WO2003055445A2 (en) 2001-12-21 2002-12-12 Compositions and methods for enhancing corticosteriod delivery

Publications (2)

Publication Number Publication Date
CA2471041A1 true CA2471041A1 (en) 2003-07-10
CA2471041C CA2471041C (en) 2012-07-03

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US (8) US6765001B2 (en)
EP (2) EP1465636A4 (en)
JP (2) JP2005524614A (en)
CN (1) CN1617730A (en)
BR (1) BR0215254A (en)
CA (1) CA2471041C (en)
IL (1) IL162581A0 (en)
MX (1) MXPA04006014A (en)
WO (1) WO2003055445A2 (en)

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