United States Patent (19) [11] 3,886,268 Halpern (45) May 27, 1975

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United States Patent (19) [11] 3,886,268 Halpern (45) May 27, 1975 United States Patent (19) [11] 3,886,268 Halpern (45) May 27, 1975 (54) IODOPHOR-STEROID COMPOUND "Antibacterial Agents Not Presently Employed As PHARMACEUTICAL COMPOSITIONS Preservatives in Ophthalmic Preparations Found Ef fective Against Pseudomonas Auruginosa'. (PVP-Io 75) Inventor: Alfred Halpern, Great Neck, N.Y. dine). 73 Assignee: Synergistic, New York, N.Y. Higuchi et al.; J. Am. Pharm. Assoc. Scl. Ed.43:3- 22 Filed: Mar. 29, 1974 98-401, July 1954, “Study of Possible Complex For mation Between Macromolecules and Certain Phar (21 Appl. No.: 456,333 maceuticals I'. (PVP-Cortisone). Related U.S. Application Data GAF (1967), PVP-An Annotated Bibliography E63) Continuation-in-part of Ser. No. 257,505, May 30, 1951-1966, Vol. I, 53, pp. esp. pp. 17-19, “Chemical 1972, abandoned. Complexes' Mfg. Brochure. 52 U.S. Cl................... 424/80; 260/88.3; 424/243 GAF (1967), PVP-An Annotated Bibliography 51 Int. Cl....................... A61k 17700; A61k 27112 1951-1966, Vol. II, 51 pp. esp. pp. 15-20 “PVP-Io 58 Field of Search .............. 424/80, 243; 260/88.3 dine' Mfg. Brochure. (56) References Cited Primary Examiner-Shep K. Rose UNITED STATES PATENTS Attorney, Agent, or Firm-Wolder & Gross 2,861,920 l l (1958 Dale et al............................. 424/80 2,897,120 7/1959 Cronin et al............ ... 424/80 X 3,062,712 11/1962 Dale et al............................. 424/8O 57 ABSTRACT 3, 190,855 6/1965 Miki...................................... 260/63 3,671545 6/1972 Halpern..................... 260/326.5 FL Iodophor-steroid complex compounds and composi 3,751,565 8/1973 Santorelli.............................. 424/80 tion employing the same, exhibiting synergistic anti 3,764,669 10/1973 Santorelli.............................. 424/80 inflammatory action, greater than the sum of the anti FOREIGN PATENTS OR APPLICATIONS inflammatory potency of the respective moieties. 1,319,413 6/1973 United Kingdom Methods for the preparation and use of the aforesaid 2,166,215 5/1973 United Kingdom iodophorsteroid complex compounds in the treatment of inflammatory, dermatologic disease are described, OTHER PUBLICATIONS Kohn et al.; J. Pharm. Scl. 52(12):I 126, Dec. 1963, 31 Claims, No Drawings 3,886,268 2 EODOPHOR-STEROD COMPOUND widely used for its germicidal properties because it re PHARMACEUTICAL COMPOSITIONS tains the broad microbiologic spectrum of elemental This application is a continuation-in-part application iodine but avoids its harmful tissue properties. The de of applicant's co-pending application, Ser. No. sirable germicidal properties of polyvinylpyrrolidone 257,505, filed May 30, 1972, now abandoned. iodine are due to its available iodine content, which This invention relates to synergistic, anti chemically is elemental iodine. Thus, it would be ex inflammatory iodophor-steroid complex compounds, pected that the well known chemical incompatibility pharmaceutical compositions employing the same and between a steroid anti-inflammatory compound and el methods for their use in the treatment of inflammatory emental iodine would remain when polyvinylpyrroli skin disease of humans and animals. In particular, it re 10 done-iodine is used in combination with a steroid com lates to a new molecular complex compound formed pound, although the harmful toxic effects of iodine between polyvinylpyrrolidone-iodine and an anti would be avoided. However, it was unexpectedly found inflammatory steroid compound, as for example, corti that when an iodophor compound, as for example, sone, cortisone acetate, hydrocortisone, hydrocorti polyvinylpyrrolidone-iodine, is combined with a steroid sone acetate, prednisone, prednisone acetate, prednis 15 anti-inflammatory compound, as for example, corti olone and prednisolone acetate, said new compound sone, cortisone acetate, hydrocortisone, hydrocorti complexes possessing an increased topical anti Sone acetate, prednisone, prednisone acetate, prednis inflammatory potency which is greater than the sum of olone and prednisolone acetate, that a new molecular topical anti-inflammatory activity determined for the complex compound is formed which possesses both an respective component moities when these are used ti-inflammatory and germicidal properties. The molec alone. ular complex formed between said steroid compound It is an object of this invention to describe a method and said iodophor compound does not exhibit the oxi for preparation of the synergistic iodophor-steroid dative degradation of the steroid moiety, such as is complexes and compositions employing the same, as known to occur for steroids in the presence of iodine well as to describe a method for treating inflammatory 25 and for the first time, stable pharmaceutical dosage skin diseases utilizing the aforesaid compositions. forms which are useful in the treatment of inflamma When a steroid anti-inflammatory compound is ap tory skin disease may be prepared to provide concur plied to the skin during therapy of inflammatory skin rent anti-inflammatory and germicidal activity. diseases, certain inherent defects limit the therapeutic When the new iodophor-steroid compound is sub utility of these compounds. It is known for example, jected to stability control testing, either in its pure form that increased anti-inflammatory activity renders the or when combined with a pharmaceutically acceptable skin more sensitive to infection and presents a serious non-toxic carrier, we find significant differences in the threat to the patient unless adequate antimicrobial pro stability of the new iodophor-steroid compound and cedures are employed. Thus, when a steroid anti compositions containing the same, when these are inflammatory compound is intended to be used in treat 35 compared to the behavior of a mixture of the separate ing dermatologic disease of humans and animals, which components. is complicated by infection, good germicidal activity In an experiment to determine the comparative sta must be present together with the anti-inflammatory bility of the new compound, polyvinylpyrrollidone action in order to avoid a septic state. iodine-hydrocortisone acetate molecular complex Of the antiseptic agents utilized to counteract surface 40 compound, its separate components, as for example, infections, iodine is considered to be one of the best polyvinylpyrrolidone-iodine and hydrocortisone ace germicidal agents because of its broad spectrum, rapid tate and a mixture of elemental iodine and hydrocorti microbicidal action against virtually every species of sone acetate were subjected to ambient room tempera micro-organism. However, elemental iodine is a strong ture storage for a period of two years, the samples were corrosive, oxidative halogen compound that interacts 45 stored as the dry powder in glass vials. The respective with many organic substances as well as to possess nox samples were analyzed for available iodine content and ious toxicologic and pharmacologic properties when hydrocortisone acetate content as specified intervals applied to the skin. When elemental iodine comes in and the respective analyses compared to the initial val contact with an anti-inflammatory steroid compound, ues. The results of this test is described in Table I, and oxidative degradation of the steroid compound results establishes that the new molecular complex, polyvinyl so that the anti-inflammatory potency of the composi pyrrolidone-iodine-hydrocortisone acetate compound tion is greatly reduced and, in many cases, even elimi is stable when stored for two years at room temperature nated. Elemental iodine stains the skin, causes burning whereas a mixture of iodine and hydrocortisone acetate and local tissue irritation and preparations containing showed marked decomposition within one month. elemental iodine cannot be bandaged. These and other 55 In a second experiment, a pharmaceutical solution well known chemical and toxicologic incompatibilities containing 10% of polyvinylpyrrolidone-iodine have prevented the formulation of a steroid compound hydrocortisone acetate molecular complex was com with elemental iodine into pharmaceutical preparations pared to a mixture of a solution of iodine and hydrocor for use in the treatment of infected inflammatory skin 60 tisone acetate. The concentration of the respective disease. moieties was adjusted to be equivalent to the molecular Recent years witnessed great advances in eliminating proportions of iodine and hydrocortisone acetate pres certain of the limitations of elemental iodine as a ger ent in the newly formed complex compound, polyvinyl micide. The introduction of polyvinylpyrrollidone pyrrollidone-iodine-hydrocortisone acetate. The re iodine marked a great step forward in avoiding the nox spective solutions were aged in a temperature ious toxicologic properties associated with iodine. 65 controlled oven set at 37°C. 2C. and assayed at de Polyvinylpyrrolidone-iodine is a well known compound termined intervals of 1 day, 3 days, 6 days, and 10 days. (see National Formulary XIII, page 581, (1970), and is The results of this test are reported in Table II and es 3,886,268 3 4 tablished that polyvinylpyrrolidone-iodine powders and ointments. The same inert pharmaceuti cally acceptable vehicles were used for preparing the hydrocortisone acetate is stable whereas a total degra respective test preparations. The respective samples dation of the hydrocortisone acetate and in iodine con were assayed at 1 month, 3 months, 6 months and 12 tent occurred with the mixture which made the mixture month intervals. The results reported in Table
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