United States Patent to 11, 4,006,218 Sipos (45) Feb

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United States Patent to 11, 4,006,218 Sipos (45) Feb United States Patent to 11, 4,006,218 Sipos (45) Feb. 1, 1977 54) POTENTIATED MEDICAMENTS organic halogen derivatives and iodophores derived from nonionic surface active agents and from polyvi 75) Inventor: Tibor Sipos, Jackson, N.J. nylpyrrolidone by combining the antimicrobial agent 73 Assignee: Johnson & Johnson, New Brunswick, with an effective amount of a potentiator. The potenti N.J. ator is an alcohol or phenol derivative selected from the group consisting of (a) aliphatic straight or 22 Filed: July 14, 1975 branched chain primary, secondary and tertiary mono 21 Appl. No.: 595,986 hydric alcohols wherein the straight chain alcohols have from about 5 to about 10 carbon atoms; and the branched chain alcohols have up to about 17 carbon Related U.S. Application Data atoms, their longest straight chain of carbon to carbon 63 Continuation of Ser. No. 486,287, July 8, 1974, bonds having from about 5 to about 10 carbon atoms; abandoned, which is a continuation-in-part of Ser. No. (b) a primary, secondary or tertiary cyclohexylalkanol 285,682, Sept. 1, 1972, abandoned. or alkylcyclohexylalkanol where the alkanol is as more 52 U.S. Cl. ................................. 424/54; 424/249; fully defined hereinafter; (c) a primary, secondary or 424/258; 424/263; 424/329; 424/343 tertiary phenylalkanol, halophenylalkanol or C to Ca (51 Int. Cl.’................. A61K 7/22; A61K 3 1/O45; alkylphenylalkanol where the alkanol has from about 3 A61 K. 3 1/14; AOlN 9/24 to about 9 carbon atoms; and (d) a cyclohexyl phenol 58 Field of Search ............ 424/54, 329, 343, 249, which may have a substituent on the phenyl ring se 424/258, 263 lected from the group consisting of C to Ca alkyl and alkoxy, hydroxy, halo, amino and alkyl and dialkyl (56) References Cited amino-substituents. UNITED STATES PATENTS Also provided are topically active compositions wherein topical activity of a medicament is enhanced 2,830,929 4/1958 Fries et al. ......................... 424.1343 3,075,881 f1963 Nordmann ... ... 424/343 by combining the medicament with an effective 3, 183,151 5/1965 Nordmann ......................... 424/343 amount of a potentiator as defined in (a), (b) or (c) above. FOREIGN PATENTS OR APPLICATIONS The compositions comprising an antimicrobial agent 1,467,836 2/1968 Germany ............................. 424/54 and a potentiating agent in a suitable carrier are useful for killing susceptible organisms on various surfaces. OTHER PUBLICATIONS The novel compositions find special applications as The Merck Index, 1968, 8th Ed., Merck Co., Inc., surgical scrub solutions, and for use in dressing topical Rahway, N.J. p. 397. wounds where the presence of blood and wound exu Primary Examiner-Donald B. Moyer date would otherwise inhibit the action of the antimi crobial agent if it were to be used alone. 57 ABSTRACT The topical compositions of the invention find special Antimicrobial compositions are provided wherein application as topical anesthetics, cell regulatory there is obtained an enhancement of the activity of an agents, antimicrobials, anti-inflammatory composi antimicrobial agent exemplified by quaternary ammo tions, and the like. nium compounds, bisdiguanides, anti-fungal agents, phenols, hydroxydiphenyls, carbanilides, salicylani lides, organo-metalic antiseptics, antibiotics, halogens, 12 Claims, No Drawings 4,006,218 1 2 Because of the impermeable nature of the stratum corneum, it has been a long desired goal to temporarily POTENTIATED MEDICAMENTs modify the barrier property of this layer in order to CROSS-REFERENCE TO RELATED APPLICATION enhance the penetration of topically applied drugs. 5 Especially in dermatological conditions, topical appli This is a continuation division of Application Ser. cation of medicaments is preferred over systemic ad No. 486,287 filed July 8, 1974, which application is in ministration, because the topically applied drug di turn a continuation-in-part of application, Ser. No. rectly attacks the affected target cells. Furthermore, 285,682, filed Sept. 1, 1972, both now abandoned. topical treatment eliminates systemic side effects that BACKGROUND OF THE INVENTION 10 are frequently associated with long term oral therapy. In one aspect, this invention relates to antimicrobial Previous studies have shown that dimethylsulfoxide compositions. More particularly, it relates to the dis (DMSO) can enhance the absorption of topically ap covery that a broad group of known antimicrobial plied drugs through the stratum corneum. Similarly, agents have increased activity, either in terms of spec dimethyl formamide (DMFA) and N,N-dimethyl 5 acetamide (DMA) and their derivatives are claimed to trum, killing power, or both, when used in combination do the same. Some of these combinations are described with the potentiating agents of this invention. in U.S. Pat. Nos. 3,551,554 and 3,472,931. Ordinarily, the activity or killing power of known Other recent studies on the physico-chemical proper antimicrobial agents are inhibited in the presence of ties of the stratum corneum and the absorption of topi blood, wound exudates and other proteinaceous matter 20 cally applied drugs therethrough include: Scheuplein, including serum proteins, together with saliva, sebac R.J., J. Invest. Dermatol. 45,334 (1966); Blank, I.H., J. cous secretions, nasal and other mucous secretions. Invest. Dermatol. 43, 415 (1964); Hadgraft, J.W. and Although it has been realized for some time that Somers, G.F., J. Pharm. Pharmacol. 8, 625 (1956); and antibacterial agents lose their efficacy in the presence Grasso, P. and Lansdown, A.B.G., J. Soc. Cosmet. of blood, bodily secretions such as milk serum and 25 Chem. 23 481-521 (1972). wound exudates, the cause of this loss of efficacy or Thus, in accordance with another feature of the pre inactivation is not as yet fully understood. It has been sent invention, there are provided topical compositions postulated, however, that the lipophilic character of comprising a known medicament, exemplified by the the antimicrobial agent is responsible for both protein anesthetics, and a potentiator, whereby the penetration binding and antimicrobial activity. In the presence of 30 of topically applied anesthetic or other agents through such extraneous proteinaceous matter as blood, the the stratum corneum are substantially enhanced. As an antimicrobial agent preferentially binds to the serum example, enhanced penetration of the anesthetic agent proteins or other proteinaceous matter rather than to by the action of the potentiator or accelerator results in the bacterial cells. Under conditions where this unde a quicker onset and deeper anesthesia at the treated sired preferential binding can occur, the antimicrobial 35 site, than that which is obtained without the accelera agent is either ineffective or its efficacy is so reduced tor. Furthermore, anesthesia at the site of application that greatly increased dosage levels are required. The lasts up to several hours. Conventional preparations extent of this loss in activity can approach 90 percent elicit only surface anesthesia and onset times some or more. For example, the antimicrobial activity of times extend to hours. Most conventional preparations, quaternary ammonium compounds can be so sup 40 moreover, have been reported to be ineffective on pressed in the presence of proteinaceous body fluids intact skin Andriani, J. and Dalili, H. Anesthesia and that activity losses in excess of 96 percent have been Analgesia, Current Researches, Vol. 50, No. 5 (Sept recorded. -Oct. 1971)). While the lack of precise knowledge and understand SUMMARY OF THE INVENTION ing of the inactivation mechanism has hampered the 45 development of topical antimicrobial preparations It has now been discovered that the foregoing and which are effective in the presence of the inactivating other advantages which will become apparent upon materials above referred to, it has long been a desired further reading are achieved, in one embodiment of the and sought for goal to develop antimicrobial composi invention, by providing an antimicrobial composition tions that could overcome this inactivation. 50 which includes, together with an antimicrobial agent, a Therefore, an important feature of the present inven potentiator therefor as defined herein. The antimicro tion is to provide compositions which include known bial agent can be selected from the group consisting of antibacterial, antiviral or antifungal agents together quaternary ammonium compounds, bisdiguanides, an with a potentiator or such agents so as to overcome the ti-fungal agents, phenols, hydroxydiphenyls, carbani deactivating effect of proteinaceous substances and to 55 lides, salicylanilides, organometallic antiseptics, antibi significantly increase the killing efficacy or to extend otics, iodine and organic iodine derivatives and iodo the antimicrobial spectrum of the antimicrobial agent, phores derived from nonionic wetting agents and from or to have both enhancing effects. polyvinylpyrrolidone, and is used in accordance with Enhancement of drug absorption through the intact the present invention in combination with a potentiator skin has been pursued by many investigators in recent 60 of the type hereinafter described. times. Most of these studies showed that the stratum It has also been discovered, in accordance with an corneum of the skin, the uppermost or horny layer, acts other embodiment of the present invention, that en as a protective barrier against the exterior environ hanced penetration through the skin of known medica
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