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(12) United States Patent (10) Patent No.: US 7,220,424 B2 Gans Et Al

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(12) United States Patent (10) Patent No.: US 7,220,424 B2 Gans Et Al USOO7220424B2 (12) United States Patent (10) Patent No.: US 7,220,424 B2 Gans et al. (45) Date of Patent: May 22, 2007 (54) COMPOSITIONS AND METHODS FOR (58) Field of Classification Search ................ 514/169, ENHANCING CORTICOSTEROID 514/170, 171, 172, 177-180, 424/400 401 DELIVERY See application file for complete search history. (56) References Cited (75) Inventors: Eugene H. Gans, Westport, CT (US); U.S. PATENT DOCUMENTS Mitchell S. Wortzman, Scottsdale, AZ 3,934,013 A 1/1976 Poulsen ...................... 514,170 (US) 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, pp. 2299-2300, for (*) Notice: Subject to any 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.: 10/407,380 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/O176408 A1 Sep. 18, 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 15 Claims, No Drawings US 7,220,424 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 1 GlaxoWellcome Cream O.05% propionate amcinolone acetonide, and triamcinolone. Temovate (R) Clobetasone 1 GlaxoWellcome Hydrocortisone was the first corticosteroid found to be ointment 0.05% propionate topically effective. Other more potent glueoeorticoids, Diprolene (R) Betamethasone 1 Schering Corp. cream O.O.5% ipropionate 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% ipropionate nounced anti-inflammatory activity, have since been devel Psorcon (R) Diflorasone 1 Dermik Laboratories, oped. Currently, topical steroids are among the most fre ointment iacetate 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 ipropionate 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% ipropionate phospholipase A2, the enzyme responsible for liberating Elocon (R) MometaSone 2 Schering Corp. arachidonic acid from cell membranes, thus inhibiting the 50 ointment 0.1% O8c arachidonic acid pathway. Currently, it is believed that Florone (R) Diflorasone 2 Dermilk ointment 0.05% iacetate glucocorticoids inhibit phospholipase A2, in cells by directly 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 Pharmaceuticals nated and nonfluorinated. Fluorinated steroids have been 55 O.05% Corp. Lidex (R) cream Fluocinonide 2 Medicis Pharmaceuticals chemically modified to increase potency. These modifica O.05% Corp. tions, such as halogenation and methylation, can result in Lidex (R) Fluocinonide 2 Medicis Pharmaceuticals improved activity within the target cell and in decreased ointment 0.05% Corp. breakdown to inactive metabolites. These modifications can Maxiflor (R) Diflorasone 2 Allergan Herbert ointment 0.05% diacetate also lead to more systemic side effects. However, modifi 60 Topicort (R) DeSoximetasome 2 Medicis Pharmaceuticals cation of the chemical structure of the steroid is not the only cream 0.25% Corp. way to increase potency. Topicort (R) gel DeSoximetasome 2 Medicis Pharmaceuticals The potency of topical steroid preparations is strongly O.05% Corp. Topicort (R) DeSoximetasome 2 Medicis Pharmaceuticals correlated to their absorption through the skin. Treatment of ointment 0.25% Corp. the skin prior to application of the topical steroid may also 65 Aristocort A (R) Triamcinolone 3 Fujisawa affect the absorption of the compounds into the skin. Treat ointment 0.1% acetonide ments with keratolytics or with fat solvents (such as acetone) US 7,220,424 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 3 GlaxoWellcome ointment propionate 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 3 Dermilk the potency of a given formulation because the vehicle O.05% diacetate 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 Pharmaceutical compositions, the vehicle is as much as 99% of the total cream O.O.5% Corp. composition.
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