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US 2011/0104241 A1 Ohtake Et Al US 2011 0104241A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0104241 A1 Ohtake et al. (43) Pub. Date: May 5, 2011 (54) PERCUTANEOUS ABSORPTION ENHANCER (30) Foreign Application Priority Data AND TRANSIDERMAL PREPARATION USING THE SAME Jun. 23, 2008 (JP) ................................. 2008-16273O Publication Classification (75) Inventors: Naoto Ohtake,r Fukushima (JP); (51) Int. Cl. Yuuki Koide, Saitama (JP) A 6LX 9/70 (2006.01) A63L/70 (2006.01) (73) Assignee: TOA EIYO LTD., Tokyo (JP) A6IR 9/00 (2006.01) (52) U.S. Cl. ............................ 424/443; 514/23; 424/484 (21) Appl. No.: 13/000,635 (57) ABSTRACT 1-1. Provided are a percutaneous absorption enhancer excellent in (22) PCT Filed: Jun. 22, 2009 an enhancing effect on percutaneous absorption of a wide range of drugs and excellent in compatibility with an adhesive (86). PCT No.: PCT/UP2009/002837 base, and a transdermal preparation using the percutaneous absorption enhancer. The percutaneous absorption enhancer S371 (c)(1), includes a Sulfo Succinate or a salt thereof and an alkyl glyco (2), (4) Date: Dec. 22, 2010 side or an alkylthioglycoside. US 2011/0104241 A1 May 5, 2011 PERCUTANEOUS ABSORPTION ENHANCER known to be used as percutaneous absorption enhancers (see, AND TRANSIDERMAL PREPARATION USING for example, Patent Literature 1 and Non Patent Literature 1). THE SAME 0005. On the other hand, in order to obtain a tape prepa ration, in addition to the percutaneous absorbability of drugs, FIELD OF THE INVENTION providing a good balance among requirements such as (1) drugs are released well from an adhesive layer, (2) drugs are 0001. The present invention relates to a practical percuta transferred into skin for a long time, (3) adhesiveness to the neous absorption enhancer that enhances percutaneous surface of skin is preferable, (4) neither a residual glue on the absorption of various kinds of drugs and does not adversely surface of skin nor cobwebbing occurs at the time of detach affect production of a preparation. ment, and (5) irritation to skin is slight, should be necessary. Thus, in the case of the development of the tape preparation, it has been conventionally necessary to study, for example, BACKGROUND OF THE INVENTION the chemical properties and physical properties of a target 0002 An oral administration using a tablet, a capsule, a drug, an adhesive base, a percutaneous absorption enhancer, syrup, or the like has been performed as a method of admin and other components, and interactions caused by a combi istration of a drug for various kinds of medicaments. How nation of the target drug with other Substances. As a result, ever, the oral administration has included drawbacks Such as only particularly limited drugs such as isosorbide dinitrate, insufficient sustainability of a drug effect and the fact that a nitroglycerin, Scopolamine, estradiol, and tulobuterol have concentration of a drug in blood is temporarily increased to an been put to practical use for the purpose of systemic admin excessive level after the administration, and hence an adverse istration. side effect is likely to occur. In order to eliminate such draw 0006. In order to obtain a matrix-type preparation, the backs involved in the oral administration, development of a percutaneous absorption enhancer should not only exhibit a transdermal preparation, particularly, a tape preparation in Sufficient percutaneous absorption enhancing action to a which an adhesive matrix layer containing a drug is provided drug, but also have excellent compatibilities with an adhesive on one Surface of a Support such as a plastic film has been base and other additives and not affect the agglomerating carried out. The tape preparation is expected not only to property, and adhesiveness to the Surface of skin, of an adhe compensate those drawbacks but also to exhibit advantages sive layer. However, until now, there has been no percutane Such as decreasing the number of administration, improving ous absorption enhancer obtained by studying various drugs compliance, ease of administration, and ease of stopping the and various adhesive bases from the above-mentioned view administration. Further, the tape preparation is known to be point. There has been therefore demanded a practical percu more useful for elderly patients and child patients. Moreover, taneous absorption enhancer that enhances percutaneous the tape preparation Sustains a preparation function even after absorption of a wide range of drugs, is excellent in compat cutting unlike a reservoir-type preparation, and hence adjust ibility with various adhesive bases, and does not affect the ing the dose of administration (area) depending on the age and agglomerating property, and adhesiveness to the Surface of body size of a patient is easy. skin, of an adhesive layer. 0003. However, most drugs generally have low skin per meability, and hence the development of a transdermal prepa PATENT DOCUMENTS ration is difficult. The structure of skin is mainly formed of 0007 Patent Document 1 US 2007/259029 A1 epidermis, dermis, and Subcutaneous tissue. The outermost side of epidermis is covered with dead and keratinized cells NON PATENT DOCUMENTS having a thickness of 10 to 15um called a stratum corneum. The stratum corneum functions as a preventive barrier against 0008. Non Patent Document 1 Pharmazie, Germany, the inflow and outflow of chemicals including drugs and Govi-Verlag. Pharmazautischer Verlag, 2006, Vol. 61, Ver 1, water evaporation. That is, the rate-limiting step of percuta p 75-76 neous absorption lies in a process of permeating a corneum, and hence, in the case of the development of a tape prepara SUMMARY OF THE INVENTION tion, enhancing the drug permeability into the stratum cor Problems to be Solved by the Invention neum has been the most important issue. 0009. An object of the present invention is to provide a 0004 Thus, in order that the barrier function of the stratum percutaneous absorption enhancer, which is excellent for an corneum may be weakened in order for the stratum corneum to absorb a sufficient amount of drugs, studies on percutane enhancing effect of percutaneous absorption of various kinds ous absorption enhancers have been widely carried out. of drugs and excellent for compatibility with an adhesive Examples of the percutaneous absorption enhancers include: base, and a transdermal preparation using the percutaneous fatty acids, fatty alcohols, fatty acid esters, fatty acid amides, absorption enhancer. and fatty acid ethers each having 6 to 20 carbon chains; aromatic organic acids, aromatic alcohols, aromatic organic Means for Solving the Problem acid esters, and aromatic organic acid ethers; and further, 0010. The inventors of the subject invention have inten lactates, acetates, monoterpene-based compounds, sesquiter sively studied the percutaneous absorbability of drugs. As a pene-based compounds, aZone, aZone derivatives, pyrrothio result, the inventors have found that an enhancing effect for decane, glycerol fatty acid esters, propylene glycol fatty acid percutaneous absorption of drugs can be remarkably esters, Sorbitan fatty acid esters, polyethylene glycol fatty increased by combining a sulfo Succinate or a salt thereof and acid esters, polyoxyethylene hardened castor oils, polyoxy an alkyl glycoside or an alkylthioglycoside, compared with ethylene alkyl ethers, sucrose fatty acid esters, and vegetable that in the case where each of these substances is used alone. oils. Further, Surfactants such as alkyl glycosides are also Then, further studies have been made on those substances. As US 2011/0104241 A1 May 5, 2011 a result, the inventors have found that the resultant product is those, Sulfo Succinates or salts thereof, a C-C dialkyl Sul a percutaneous absorption enhancer which is excellent in fosuccinate or a salt thereof is preferred, and dioctyl sodium practical application for production of a preparation because SulfoSuccinate is more preferred. As dioctyl Sodium sulfos the resultant product has low irritation property to skin and is luccinate, dioctyl Sodium Sulfo Succinate, conforming to The excellent in compatibility with various adhesive bases that are Japanese Pharmaceutical Codex, can be used. usually used in transdermal preparations. Thus, the inventors 0019. The alkyl glycoside or the alkyl thioglycoside have completed the present invention. includes compounds which are used as nonionic Surfactants, 0011 Thus, the present invention provides a percutaneous and a C-C alkyl glycoside or a C-Cs alkylthioglycoside absorption enhancer, including a Sulfo Succinate or a salt is preferred. Examples of such surfactants include: heptyl-3- thereof and an alkyl glycoside or an alkylthioglycoside. D-glucopyranoside, n-heptyl-B-D-thioglucopyranoside, 0012. Further, the present invention provides a matrix n-octyl-C-D-glucopyranoside, n-octyl-B-D-glucopyrano type transdermal preparation, containing the above-men side, n-octyl-B-D-thioglucopyranoside, n-octyl-B-D-malto tioned percutaneous absorption enhancer and a drug. pyranoside, n-nonyl-B-D-thiomaltopyranoside, n-nonyl-3- 0013 Further, the present invention provides a use of a D-thioglucopyranoside, n-decyl-B-D-maltopyranoside, combination of a SulfoSuccinate or a salt thereof and an alkyl n-decyl-B-D-thiomaltopyranoside, n-dodecyl-B-D-glucopy glycoside oran alkylthioglycoside as a percutaneous absorp ranoside, n-dodecyl-C-D-maltopyranoside, n-dodecyl-B-D- tion enhancer. maltopyranoside, and n-dodecyl-B-D-thiomaltopyranoside. 0014 Further, the present invention is characterized in Of those, n-octyl-B-D-thioglucopyranoside, n-dodecyl-B-D- providing a method for enhancing percutaneous absorption of glucopyranoside, or the like is preferred. a drug, the method including transdermally administering the 0020. In the percutaneous absorption enhancer of the drug, a SulfoSuccinate or a salt thereof, and an alkylglycoside present invention, the blending ratio of a SulfoSuccinate or a or an alkylthioglycoside. salt thereof to an alkyl thioglycoside may be appropriately selected. The blending ratio is, in terms of a weight ratio, Effects of the Invention preferably 1:0.1 to 1:10.0, more preferably 1:0.1 to 1:5.0, or 0015.
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