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(12) United States Patent (10) Patent No.: US 6,765,001 B2 Gans Et Al

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(12) United States Patent (10) Patent No.: US 6,765,001 B2 Gans Et Al USOO6765001B2 (12) United States Patent (10) Patent No.: US 6,765,001 B2 Gans et al. (45) Date of Patent: Jul. 20, 2004 (54) COMPOSITIONS AND METHODS FOR 4.017,615. A 4/1977 Shastri ENHANCING CORTICOSTEROID 6,075,056. A 6/2000 Quigley DELIVERY 6,300,326 B1 10/2001 Dobbs (75) Inventors: Eugene H. Gans, Westport, CT (US); OTHER PUBLICATIONS Mitchell S. Wortzman, Scottsdale, AZ (US) PDR 2000, Synalar/Lidex entries, pp. 1726–1727.* (73) Assignee: Medicis Pharmaceutical Corporation, Mori, et al. “Topical Corticosteroidsand Unwanted Local Scottsdale, AZ (US) Effects,” Drug Safey, 10 (5) 1994, p. 406-412. Schafer-Korting, et al. “Topical Glucocorticoids with (*) Notice: Subject to any disclaimer, the term of this Improved Risk-BenefitRatio,” Drug Safety Jun. 1996; 14 patent is extended or adjusted under 35 (6), p. 375–385. U.S.C. 154(b) by 0 days. Dermatology in General Medicine, 5th ed. CD-ROM, 1999, Chapter 243, p. 1-10, Tables 243-1 and 243-3. (21) Appl. No.: 10/037,360 (22) Filed: Dec. 21, 2001 * cited by examiner (65) Prior Publication Data Primary Examiner. Shengjun Wang US 2003/0130247 A1 Jul. 10, 2003 (74) Attorney, Agent, or Firm William J. McNichol, Jr.; (51) Int. Cl." ........................ A61K 31/58; A61K 31/56; Maryellen Feehery; Reed Smith LLP A61K 47/00; A61 K9/00 (57) ABSTRACT (52) U.S. Cl. ....................... 514/172; 514/169; 514/170; 514/180; 514/177; 514/178; 514/179; 514/769; The present invention comprises a composition, method of 514/785; 424/400 enhancing potency and method of delivering corticosteroids (58) Field of Search ................................. 514/169, 170, in a vehicle comprising at least two penetration enhancers, 514/172, 177-180, 769, 785; 424/400 and Solvents and emulsifiers. The propylene glycol and penetration enhancers are present in ratio to the total of the (56) References Cited propylene glycol, penetration enhancers, and Solvents and emulsifiers of at least about 0.70. U.S. PATENT DOCUMENTS 3,934,013 A * 1/1976 Poulsen 17 Claims, No Drawings US 6,765,001 B2 1 2 COMPOSITIONS AND METHODS FOR Once absorbed through the skin, topical corticosteroids ENHANCING CORTICOSTEROID are handled through pharmacokinetic pathways Similar to DELIVERY Systemically administered corticosteroids. The potencies of corticosteroids vary greatly and it is a challenge to increase the potency of any particular Steroid. FIELD OF THE INVENTION Topical corticosteroids are useful for their anti BACKGROUND OF THE INVENTION inflammatory, anti-pruritic and vasoconstrictive actions. Corticosteroids (or corticoids) are any Steroids (lipids that The clinical effectiveness of corticoids is related to four contain a hydrogenated cyclopentoperhydrophenanthrene basic properties: vasoconstriction, antiproliferative effects, ring System) elaborated by the adrenal cortex (except Sex immunosuppression, and anti-inflammatory effects. Topical hormones of adrenal origin) in response to the release of Steroids cause the capillaries in the Superficial dermis to adrenocorticotrophin or adrenocorticotropic hormone by the constrict, thus reducing erythema. The ability of a given pituitary gland, or to any Synthetic equivalent, or to angio glucocorticoid agent to cause vasoconstriction usually cor tensin II. Corticosteroids include but are not limited to 15 relates with its anti-inflammatory potency. Vasoconstrictor alclometaSone dipropionate, amcinonide, amcinafel, assays are used in the art and by the U.S. Food and Drug amcinafide, beclamethasone, betamethasone, betametha Administration for determining the potency of topical cor Sone dipropionate, betamethasone Valerate, clobetaSone ticosteroid preparations. Topical glucocorticoid preparations propionate, chloroprednisone, clocortelone, cortisol, have been divided in the field into seven classes based on cortisone, cortodoxone, difluoroSone diacetate, descinolone, potency based on double-blind clinical Studies and vasocon de Sonide, de flu pred nate, dihydroxy cortis one, Strictor assayS. Class 1 includes the most potent, while class deSoximetasone, dexamethasone, deflazacort, diflorasone 7 contains the least potent. diacetate, dichlorisone, esters of betamethasone, flucetonide, The following glucocorticoid preparations were desig flucloronide, fluorocortisone, flumethasone, flunisolide, nated in Fitzpatrick, Dermatology in General Medicine, 5" fluocinonide, fluocinolone acetonide, flucortolone, 25 edition, CD-ROM, 1999, Table 243-1, with the following fluperolone, fluprednisolone, fluroandrenolone acetonide, classes. fluocinolone acetonide, flurandrenolide, fluorametholone, fluticasone propionate, hydrocortisone, hydrocortisone TABLE 1. butyrate, hydrocortisone Valerate, hydrocort amate, me dry Sone, me prednisone, methylprednisone, Corticosteroid methylprednisolone, mometasone furoate, paramethasone, Preparation Corticosteroid Class Source prednisone, prednisolone, prednidone, triamcinolone Temovate (R) Cream Clobetasome 1 Glaxo acetonide, and triamcinolone. O.05% propionate Wellcome Temovate (E) ointment Clobetasome 1 Glaxo Hydrocortisone was the first corticosteroid found to be 35 O.05% propionate Wellcome topically effective. Other more potent glucocorticoids, Diprolene (R) cream Betamethasone 1 Schering Corp. which are a subset of corticosteroids that affect carbohydrate O.05% dipropionate Diprolene (R) ointment Betamethasone 1 Schering Corp. metabolism, inhibit corticotropin Secretion, and possess pro O.05% dipropionate nounced anti-inflammatory activity, have since been devel Psorcon (E) ointment Diflorasone diacetate 1 Dermik oped. Currently, topical Steroids are among the most fre 40 Laboratories, quently prescribed of all dermatological drug products. Inc. Cyclocort (R) ointment Amcinonide 2 Fujisawa It is believed that glucocorticoids exert their potent anti O.1% inflammatory effects by inhibiting the formation of prostag Diprolene (R) cream AF Betamethasone 2 Schering Corp. landins and other derivatives of the arachidonic acid path O.05% dipropionate Diprosone (R) ointment Betamethasone 2 Schering Corp. way. It is known that glucocorticoids inhibit the release of 45 O.05% dipropionate phospholipase A2, the enzyme responsible for liberating Elocom (E) ointment 0.1%. Mometasome furoate 2 Schering Corp. arachidonic acid from cell membranes, thus inhibiting the Florone (E) ointment Diflorasone diacetate 2 Dermik arachidonic acid pathway. Currently, it is believed that O.05% Halog (R) cream 0.1% Halcinomide 2 Westwood glucocorticoids inhibit phospholipase A2, in cells by directly Squibb inducing phosphorylation of the enzyme. 50 Lidex (R) gel 0.05% Fluocinonide 2 Medicis Steroids are commonly divided into two classes, fluori Pharma nated and nonfluorinated. Fluorinated Steroids have been ceuticals Corp. chemically modified to increase potency. These Lidex (E) cream 0.05% Fluocinonide 2 Medicis modifications, Such as halogenation and methylation, can Pharma result in improved activity within the target cell and in 55 ceuticals decreased breakdown to inactive metabolites. These modi Corp. Lidex (R) ointment 0.05% Fluocinomide 2 Medicis fications can also lead to more Systemic Side effects. Pharma However, modification of the chemical structure of the ceuticals Steroid is not the only way to increase potency. Corp. Maxiflor (R) ointment Diflorasone diacetate 2 Allergan The potency of topical Steroid preparations is Strongly 60 O.05% Herber correlated to their absorption through the skin. Treatment of Topicort (R) cream 0.25% Desoximetasone 2 Medicis the skin prior to application of the topical Steroid may also Pharma ceuticals affect the absorption of the compounds into the skin. Treat Corp. ments with keratolytics or with fat Solvents (Such as acetone) Topicort (R) gel 0.05% Desoximetasone 2 Medicis disrupt the epidermal barrier and increase penetration. 65 Pharma Hydrating the skin has also been shown to increase the ceuticals penetration of the corticosteroids. US 6,765,001 B2 3 4 TABLE 1-continued TABLE 1-continued Corticosteroid Corticosteroid Preparation Corticosteroid Class Source Preparation Corticosteroid Class Source Corp. flumethasone, Topicort (R) ointment Desoximetasone Medicis prednisolone, and O.25% Pharma methylprednisolone ceuticals Corp. All percentages given are weight percentages unless otherwise noted. Aristocort A (R) ointment Triamcinolone Fujisawa Although there is no significant difference between potencies within Class O.1% acetonide 2, within Class 1 Temovate (R) cream or ointment is significantly more Cultivate (R) ointment Fluticasone propionate Glaxo potent than Class 1 Diprolone (R) cream or ointment of Schering and Class O.OO5% Wellcome 1 Psorcon (E) ointment of Dermik Laboratories, Inc. Cyclocort (R) cream 0.1% Amcinonide Fujisawa Cyclocort (R) Lotion Amcinonide Fujisawa Several factorS Such as the vehicle, the integrity of the O.1% 15 Diprosone (R) cream Betamethasone Schering Corp. epidermal barrier, and the use of occlusive dressings affect O.05% dipropionate the percutaneous absorption and resulting potency of corti Florone (E) cream 0.05% Diflorasone diacetate Dermik costeroids regardless of the intrinsic potency of the gluco Halog (R) ointment 0.1% Halcinomide Westwood corticosteroid (or glucocorticoid) molecule. Further, inflam Squibb Lidex (E) E cream 0.05% Fluocinonide Medicis mation and/or other disease processes in the skin increase Pharma percutaneous absorption. ceutical The vehicle in which the corticoid is incorporated may be Corp. Maxiflor (E) cream 0.05% Diflorasone diacetate Allergan as important as the corticoid molecule
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