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(12) United States Patent (10) Patent No.: US 7,217,422 B2 Gans Et Al

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(12) United States Patent (10) Patent No.: US 7,217,422 B2 Gans Et Al US007217422B2 (12) United States Patent (10) Patent No.: US 7,217,422 B2 Gans et al. (45) Date of Patent: May 15, 2007 (54) COMPOSITIONS AND METHODS FOR (58) Field of Classification Search ................ 514/169, ENHANCING CORTICOSTEROID 514/170, 172, 177-180, 171,69–180; 424/400, See application file for complete search history. (75) (56) References Cited Inventors: Eugene H. Gans, Westport, CT (US); Mitchell S. Wortzman, Scottsdale, AZ U.S. PATENT DOCUMENTS (US) 3,934,013 A 1/1976 Poulsen ...................... 514,170 FOREIGN PATENT DOCUMENTS EP O 020 794. A 1, 1981 (73) Assignee: Medicis Pharmaceutical Corporation, WO WO 91.08733. A 6, 1991 Scottsdale, AZ (US) OTHER PUBLICATIONS Physicians’ Desk Reference, 51 Edition, 1997, pp. 2299-2300, for *) Notice: Subject to anyy disclaimer, the term of this example.* patent is extended or adjusted under 35 Bennett et al., “Optimization of bioavailability of topical steroids: U.S.C. 154(b) by 382 days. non-occluded penetration enhancers under thermodynamic con trol”, Journal of Pharmacy and Pharmacology, vol. 37, No. 5, 1985, (21) Appl. No.: 10/407.354 pp. 298-304. * cited by examiner (22) Filed: Apr. 4, 2003 Primary Examiner San-Ming Hui (65) Prior Publication Data (74) Attorney, Agent, or Firm William J. McNichol, Jr.; Maryellen Feehery Hank; Reed Smith LLP US 2003/O186951 A1 Oct. 2, 2003 (57) ABSTRACT Related U.S. Application Data The present invention comprises a composition, method of (62) Division of application No. 10/037.360, filed on Dec. enhancing potency and method of delivering corticosteroids 21, 2001, now Pat. No. 6,765,001. in a vehicle comprising at least two penetration enhancers, and solvents and emulsifiers. The propylene glycol and (51) Int. Cl. penetration enhancers are present in ratio to the total of the A6 IK3I/56 (2006.01) propylene glycol, penetration enhancers, and solvents and A6 IK 47/44 (2006.01) emulsifiers of at least about 0.70. (52) U.S. Cl. ...................... 424/400: 514/171; 514/180; 514/169 16 Claims, No Drawings US 7,217,422 B2 1. 2 COMPOSITIONS AND METHODS FOR disrupt the epidermal barrier and increase penetration. ENHANCING CORTICOSTEROID Hydrating the skin has also been shown to increase the DELIVERY penetration of the corticosteroids. Once absorbed through the skin, topical corticosteroids RELATED APPLICATIONS are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. The potencies of This application is a divisional of U.S. Ser. No. 10/037, corticosteroids vary greatly and it is a challenge to increase 360, filed Dec. 21, 2001 now U.S. Pat. No. 6,765,001. the potency of any particular steroid. FIELD OF THE INVENTION 10 BACKGROUND OF THE INVENTION Topical corticosteroids are useful for their anti-inflamma The clinical effectiveness of corticoids is related to four tory, anti-pruritic and vasoconstrictive actions. Corticoster basic properties: vasoconstriction, antiproliferative effects, oids (or corticoids) are any steroids (lipids that contain a immunosuppression, and anti-inflammatory effects. Topical hydrogenated cyclopentoperhydrophenanthrene ring sys 15 steroids cause the capillaries in the Superficial dermis to tem) elaborated by the adrenal cortex (except sex hormones constrict, thus reducing erythema. The ability of a given of adrenal origin) in response to the release of adrenocorti glucocorticoid agent to cause vasoconstriction usually cor cotrophin or adrenocorticotropic hormone by the pituitary relates with its anti-inflammatory potency. Vasoconstrictor gland, or to any synthetic equivalent, or to angiotensin II. assays are used in the art and by the U.S. Food and Drug Corticosteroids include but are not limited to alclometasone Administration for determining the potency of topical cor dipropionate, amcinonide, amcinafel, amcinafide, bec ticosteroid preparations. Topical glucocorticoid preparations lamethasone, betamethasone, betamethasone dipropionate, have been divided in the field into seven classes based on betamethasone Valerate, clobetaSone propionate, chloro potency based on double-blind clinical Studies and vasocon prednisone, clocortelone, cortisol, cortisone, cortodoxone, strictor assays. Class 1 includes the most potent, while class difluorosone diacetate, descinolone, desonide, deflupred 25 nate, dihydroxycortisone, desoximetaSone, dexamethasone, 7 contains the least potent. deflazacort, diflorasone diacetate, dichlorisone, esters of The following glucocorticoid preparations were desig betamethasone, flucetonide, flucloronide, fluorocortisone, nated in Fitzpatrick, Dermatology in General Medicine, 5" flumethasone, flunisolide, fluocinonide, fluocinolone edition, CD-ROM, 1999, Table 243-1, with the following classes. acetonide, flucortolone, fluperolone, fluprednisolone, 30 fluroandrenolone acetonide, fluocinolone acetonide, fluran drenolide, fluorametholone, fluticasone propionate, hydro TABLE 1. cortisone, hydrocortisone butyrate, hydrocortisone Valerate, Corticosteroid hydrocortamate, medrysone, meprednisone, methylpred Preparation Corticosteroid Class Source nisone, methylprednisolone, mometaSone furoate, 35 paramethasone, prednisone, prednisolone, prednidone, tri Temovate (R) ClobetaSone propionate 1 GlaxoWellcome Cream O.05% amcinolone acetonide, and triamcinolone. Temovate (R) ClobetaSone propionate 1 GlaxoWellcome Hydrocortisone was the first corticosteroid found to be ointment 0.05% topically effective. Other more potent glucocorticoids, Diprolene (R) Betamethasone 1 Schering Corp. cream O.O.5% dipropionate which are a subset of corticosteroids that affect carbohydrate 40 Diprolene (R) Betamethasone 1 Schering Corp. metabolism, inhibit corticotropin secretion, and possess pro ointment 0.05% dipropionate nounced anti-inflammatory activity, have since been devel Psorcon (R) Diflorasone diacetate 1 Dermilk oped. Currently, topical steroids are among the most fre ointment Laboratories, Inc. quently prescribed of all dermatological drug products. Cyclocort (R) Amcinonide 2 Fujisawa ointment 0.1% It is believed that glucocorticoids exert their potent anti 45 Diprolene (R) Betamethasone 2 Schering Corp. inflammatory effects by inhibiting the formation of prostag cream AF dipropionate landins and other derivatives of the arachidonic acid path O.05% Diprosone (R) Betamethasone 2 Schering Corp. way. It is known that glucocorticoids inhibit the release of ointment 0.05% dipropionate phospholipase A2, the enzyme responsible for liberating Elocon (R) Mometasome furoate 2 Schering Corp. arachidonic acid from cell membranes, thus inhibiting the 50 ointment 0.1% arachidonic acid pathway. Currently, it is believed that Florone (R) Diflorasone diacetate 2 Dermilk glucocorticoids inhibit phospholipase A2, in cells by directly ointment 0.05% Halog (R) cream Halcinonide 2 Westwood-Squibb inducing phosphorylation of the enzyme. O.1% Steroids are commonly divided into two classes, fluori Lidex (R) gel Fluocinonide 2 Medicis Pharma nated and nonfluorinated. Fluorinated steroids have been 55 O.05% ceuticals Corp. Lidex (R) cream Fluocinonide 2 Medicis Pharma chemically modified to increase potency. These modifica O.05% ceuticals Corp. tions, such as halogenation and methylation, can result in Lidex (R) Fluocinonide 2 Medicis Pharma improved activity within the target cell and in decreased ointment 0.05% ceuticals Corp. breakdown to inactive metabolites. These modifications can Maxiflor (R) Diflorasone diacetate 2 Allergan Herbert ointment 0.05% also lead to more systemic side effects. However, modifi 60 Topicort (R) DeSoximetaSone 2 Medicis Pharma cation of the chemical structure of the steroid is not the only cream 0.25% ceuticals Corp. way to increase potency. Topicort (R) gel DeSoximetaSone 2 Medicis Pharma The potency of topical steroid preparations is strongly O.05% ceuticals Corp. Topicort (R) DeSoximetaSone 2 Medicis Pharma correlated to their absorption through the skin. Treatment of ointment 0.25% ceuticals Corp. the skin prior to application of the topical steroid may also 65 Aristocort A (R) Triamcinolone acetonide 3 Fujisawa affect the absorption of the compounds into the skin. Treat ointment 0.1% ments with keratolytics or with fat solvents (such as acetone) US 7,217,422 B2 3 4 loneR cream or ointment of Schering and Class 1 Psorcon R TABLE 1-continued ointment of Dermik Laboratories, Inc. Corticosteroid Several factors such as the vehicle, the integrity of the Preparation Corticosteroid Class Source epidermal barrier, and the use of occlusive dressings affect the percutaneous absorption and resulting potency of corti Cultivate (R) FluticaSone propionate 3 GlaxoWellcome ointment costeroids regardless of the intrinsic potency of the gluco O.005% corticosteroid (or glucocorticoid) molecule. Further, inflam Cyclocort (R) Amcinonide 3 Fujisawa mation and/or other disease processes in the skin increase cream 0.1% Cyclocort (R) Amcinonide 3 Fujisawa 10 percutaneous absorption. Lotion 0.1% The vehicle in which the corticoid is incorporated may be Diprosone (R) Betamethasone 3 Schering Corp. cream O.O.5% dipropionate as important as the corticoid molecule itself in determining Florone (R) cream Diflorasone diacetate 3 Dermilk the potency of a given formulation because the vehicle O.05% affects the amount of corticoid that is released in any given Halog (R) Halcinonide 3 Westwood-Squibb 15 ointment 0.1% period of time, and its absorption. In many corticosteroid Lidex (R) E Fluocinonide 3 Medicis Pharma compositions, the vehicle is as much as 99% of the total cream O.O.5% ceutical
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