JPH03120230A - Percutaneous absorbefacient of drug active ingredient and percutaneous absorption type pharmaceutical - Google Patents
Percutaneous absorbefacient of drug active ingredient and percutaneous absorption type pharmaceuticalInfo
- Publication number
- JPH03120230A JPH03120230A JP25796789A JP25796789A JPH03120230A JP H03120230 A JPH03120230 A JP H03120230A JP 25796789 A JP25796789 A JP 25796789A JP 25796789 A JP25796789 A JP 25796789A JP H03120230 A JPH03120230 A JP H03120230A
- Authority
- JP
- Japan
- Prior art keywords
- percutaneous
- absorbefacient
- drug active
- skin
- active ingredients
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000010521 absorption reaction Methods 0.000 title claims abstract description 21
- 239000003814 drug Substances 0.000 title abstract description 11
- 229940079593 drug Drugs 0.000 title abstract description 9
- 239000004480 active ingredient Substances 0.000 title abstract 5
- 239000004615 ingredient Substances 0.000 claims abstract description 12
- 239000003623 enhancer Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 14
- 230000001737 promoting effect Effects 0.000 description 8
- 210000003491 skin Anatomy 0.000 description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 210000000434 stratum corneum Anatomy 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GHCZTIFQWKKGSB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;phosphoric acid Chemical compound OP(O)(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O GHCZTIFQWKKGSB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000037374 absorbed through the skin Effects 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000004798 organs belonging to the digestive system Anatomy 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
Abstract
Description
ｆ産業上の利用分野〕
本発明は、薬効成分を経皮投与するための吸収促進剤及
び経皮吸収型製剤に関する。
〔従来の技術〕
近年、医薬の消化器官や肝臓等による不活性化を避けた
り、長時間継続的に投与する際の過剰投与、あるいはこ
れに伴う副作用を避けるため、経皮吸収投与方法のため
の製剤の開発が進められている。
この経皮吸収を促進させる作用を有するものとして、種
々の界面活性剤が知られており、このうちでもラウリル
硫酸ナトリウムが日本薬局方に収載されていることと相
俟って、広く用いられている。
しかしながら、このラウリル硫酸ナトリウムは、いまだ
経皮吸収促進作用が充分とは云えず、満足できるもので
はなかった。
〔発明が解決しようとする課題Ｊ
本発明者は上記現状に鑑み、鋭意研究を進めた結果、驚
くべきことに、直鎖アルカンスルフォネートは、炭素数
が多くなるほど経皮吸収促進作用が高くなり、炭素数１
４〜１７のものは、ラウリル硫酸ナトリウムよりも極め
て高い経皮吸収促進作用を呈することが分かった。
本発明は、かかる知見に基づきなされたもので、本発明
の目的は経皮吸収促進作用の極めて高い経皮吸収促進剤
及び経皮吸収型製剤を提供することに有る。
〔課題を解決するための手段〕
本発明は、下記一般式（Ｉ）
ＣＨ，（ＣＨ，）ｍ−ＣＨ（Ｓｏ、Ｎａ）−（ＣＨ，）
ｎＣＨ，（Ｉ）（式中、ｍ及びｎは整数を示し、ｍ＋ｎ
は１１〜１４である）で表される直鎖アルカンスルフォ
ネートを含有することからなる薬効成分の経皮吸収促進
剤、及び薬効成分と上記一般式（Ｉ）で表される直鎖ア
ルカンスルフォネートとを含有することからなる経皮吸
収型製剤である。
上記一般式（Ｉ）で表される直鎖アルカンスルフォネー
トは、直鎖アルカンを光の存在下に、スルホキシ化或い
はクロルスルホキシ化することにより得ることができる
もので、炭素数１４以上１７以下のものを用いる。炭素
数１４未満のものは、経皮吸収促進作用が弱く、また１
８以上となると、経皮吸収促進作用が低下するためであ
る。
尚、この直鎖アルカンスルフォネートは、所定の炭素数
のものを単独で用いても良いが、炭素数の異なるものを
２種以上混合して用いても良い。
本発明の促進剤は、上記直鎖アルカンスルフォネートを
、０．００１〜６０重量％の水溶液にしてそのまま用い
ることができるが、使用のし易さや皮膚に対す感触等を
良くするために、適当な皮膚外用製剤、例えば、クリー
ム製剤、ローション製剤、軟膏製剤、エアロゾル剤、粘
着テープ剤等の基剤中に配合して用いることもできる。
また、この促進剤中には、一般的に医薬品、医薬部外品
或いは化粧料等の配合剤として用いられる成分、例えば
、アルコール、ワックス、脂肪酸、界面活性剤、キレー
ト剤、顔料、染料、防腐剤、防ばい剤、酸化防止剤、紫
外線吸収剤、香料等を加えても良い。
尚、かかる場合の当該促進剤中の直鎖アルカンスルフォ
ネートの含有量は、０．００１〜１０重量％、より好ま
しくは、０．０１〜５重量％とすると良い。
また、この直鎖アルカンスルフォネートは、薬効成分と
一緒に混合して、経皮吸収型製剤として用いることがで
きる。この場合の薬効成分としては、各種の治療薬、ビ
タミン類、ホルモン剤、診断薬、防虫剤、殺虫剤、角質
柔軟剤等、広く適用できる。また、この経皮吸収型製剤
には、上述した促進剤に用いられる基剤、配合剤を同様
に用いることができる。この経皮吸収型製剤には、直鎖
アルカンスルフォネートを０．００１〜ｌＯ重量％、薬
効成分を０．００１〜ｌＯ重量％の範囲で、適宜配合す
ることが好ましい。
本発明の経皮吸収促進剤は、これを皮膚に塗布した後そ
のまま、或いは必要によりそれを洗い流した後、さらに
は当該吸収剤とともに、薬効成分を塗布することにより
、薬効成分が速やかに皮膚から吸収される。
一方、本発明の経皮吸収型製剤は、皮膚に塗布すること
により、薬効成分が速やかに皮膚から吸収される。Field of Industrial Application] The present invention relates to an absorption enhancer and a transdermal preparation for transdermally administering a medicinal ingredient. [Prior art] In recent years, in order to avoid inactivation of pharmaceuticals by the digestive organs, liver, etc., excessive administration during long-term continuous administration, and associated side effects, transdermal absorption administration methods have been developed. The development of a formulation is underway. Various surfactants are known to have the effect of promoting transdermal absorption, and among these, sodium lauryl sulfate is listed in the Japanese Pharmacopoeia, making it one of the most widely used surfactants. There is. However, this sodium lauryl sulfate still cannot be said to have a sufficient transdermal absorption promoting effect, and has not been satisfactory. [Problem to be Solved by the Invention J] In view of the above-mentioned current situation, the present inventor conducted intensive research and found that, surprisingly, the higher the carbon number of linear alkanesulfonates, the higher the transdermal absorption promoting effect. , carbon number 1
It was found that compounds Nos. 4 to 17 exhibited an extremely higher transdermal absorption promoting effect than sodium lauryl sulfate. The present invention was made based on this knowledge, and an object of the present invention is to provide a transdermal absorption enhancer and a transdermal absorption type preparation that have an extremely high transdermal absorption promoting effect. [Means for Solving the Problems] The present invention has the following general formula (I) CH, (CH,)m-CH(So, Na)-(CH,)
nCH, (I) (where m and n represent integers, m+n
is a linear alkanesulfonate represented by 11 to 14), and a medicinal ingredient and a linear alkanesulfonate represented by the above general formula (I). This is a transdermal absorption preparation containing phonate. The linear alkanesulfonate represented by the above general formula (I) can be obtained by sulfoxylating or chlorosulfoxylating a linear alkane in the presence of light, and has 14 to 17 carbon atoms. Use the following: Those with less than 14 carbon atoms have a weak transdermal absorption promoting effect, and 1
This is because when it is 8 or more, the transdermal absorption promoting effect decreases. Note that this linear alkanesulfonate having a predetermined number of carbon atoms may be used alone, or two or more types of linear alkanesulfonates having different numbers of carbon atoms may be used as a mixture. The accelerator of the present invention can be used as it is by making the linear alkanesulfonate into an aqueous solution of 0.001 to 60% by weight, but in order to improve ease of use and feel on the skin, It can also be used by incorporating it into the base of suitable external skin preparations, such as cream preparations, lotion preparations, ointment preparations, aerosol preparations, and adhesive tape preparations. In addition, this accelerator contains ingredients that are generally used as compounding agents for pharmaceuticals, quasi-drugs, or cosmetics, such as alcohol, wax, fatty acids, surfactants, chelating agents, pigments, dyes, and preservatives. Agents, fungicides, antioxidants, ultraviolet absorbers, fragrances, etc. may be added. In this case, the content of the linear alkanesulfonate in the promoter is preferably 0.001 to 10% by weight, more preferably 0.01 to 5% by weight. Moreover, this linear alkanesulfonate can be mixed with a medicinal ingredient and used as a transdermal absorption type preparation. In this case, the medicinal ingredients can be widely applied, such as various therapeutic drugs, vitamins, hormones, diagnostic drugs, insect repellents, insecticides, and keratin softeners. In addition, the same bases and compounding agents used for the above-mentioned accelerator can be used in this transdermal preparation. It is preferable that the transdermal preparation contains a linear alkanesulfonate in an amount of 0.001 to 10% by weight, and a medicinal ingredient in an amount of 0.001 to 10% by weight, as appropriate. The transdermal absorption enhancer of the present invention can be applied directly to the skin, or after washing it off if necessary, and then applied together with the absorbent to quickly remove the medicinal ingredient from the skin. Absorbed. On the other hand, when the transdermal absorption type preparation of the present invention is applied to the skin, the medicinal ingredient is rapidly absorbed through the skin.
複数のウィスター（Ｗｉｓｔａｒ）系雄性ラット（体重
：２５０〜３００ｇ）から腹部除毛皮膚を摘出し、複数
個のフランツ型セル（Ｆｒａｎｔｚ−ｔｙｐｅ ｃｅｌ
ｌ、有効透過断面積＝１，１３ｍ）に装着した。この各
々のセルの真皮側受容室にＰＨ７，４の等張リン酸緩衝
液１１．４ｍｌを満たし、角質側表面を炭素数１０ （
ＳＡＳ−ＣＩＯ）、ｌ ｌ （ＳＡＳ−Ｃ１ｌ）、１２
（ＳＡＳ−Ｃ１２）、１３ （ＳＡＳ−Ｃ１３）、ｌ
４ （ＳＡＳ−Ｃ１４）の単独、及び１５〜１７の混
合物（ＳＡＳ−ＣＩ５〜１７）からなる２０ミリモル濃
度の直鎖アルカンスルホン酸ナトリウムのＰＨ７，０の
等張リン酸緩衝液２ｍｌを薬物供給室に入れて２時間処
理し、次いで、この角質表面を生理食塩水で充分洗浄し
た後、薬物供給室に５モル濃度のサルチル酸を溶解した
ＰＨ３，０のクエン酸−リン酸緩衝液を２ＩＩｌ投与し
た。１２時間後の受容室中のサリチル酸濃度を高速液体
クロマトグラフィで定量して受容室へ透過したサリチル
酸の量を算出し、第１表に、対照液（角質側表面を直鎖
アルカンスルホン酸ナトリウムを含まないＰＨ７，０の
等張リン酸緩衝液で処理したもの）に対する比で示した
。尚、比較のため、直鎖アルカンスルホン酸ナトリウム
に代えてラウリル硫酸ナトリウム（ＳＬＳ）を用いて同
様の操作を行った。この結果も合わせて第１表に記載し
た。
第１表
ものは経皮吸収促進効果が著しく高いことが分かる。
〔発明の効果〕
本発明は、炭素数が１４〜１７の直鎖アルカンスルフォ
ネートを経皮吸収促進剤及び経皮吸収型製剤に用いるた
め、薬効成分を皮膚から極めてよく吸収させることがで
きると云う格別の効果を奏する。The abdominal hair-free skin was removed from multiple Wistar male rats (body weight: 250-300 g) and placed into multiple Frantz-type cells.
1, effective transmission cross-sectional area = 1.13 m). The dermis-side receiving chamber of each cell was filled with 11.4 ml of isotonic phosphate buffer with a pH of 7.4, and the stratum corneum surface was filled with a carbon number of 10 (
SAS-CIO), l l (SAS-C1l), 12
(SAS-C12), 13 (SAS-C13), l
4 (SAS-C14) alone and a mixture of 15 to 17 (SAS-CI5 to 17) in an isotonic phosphate buffer solution of 20 mmolar sodium alkanesulfonate at pH 7.0 in the drug supply chamber. After washing the stratum corneum surface thoroughly with physiological saline, 2 liters of citric acid-phosphate buffer with pH 3.0 containing 5 molar salicylic acid dissolved in the drug supply chamber was administered. did. The concentration of salicylic acid in the receiving chamber after 12 hours was determined by high-performance liquid chromatography, and the amount of salicylic acid that permeated into the receiving chamber was calculated. (treated with isotonic phosphate buffer at pH 7.0). For comparison, the same operation was performed using sodium lauryl sulfate (SLS) in place of the linear sodium alkanesulfonate. These results are also listed in Table 1. It can be seen that the products in Table 1 have a significantly high transdermal absorption promoting effect. [Effects of the Invention] Since the present invention uses a linear alkanesulfonate having 14 to 17 carbon atoms in a transdermal absorption enhancer and a transdermal absorption type preparation, medicinal ingredients can be absorbed extremely well through the skin. It has a special effect.
Claims (2)
Ｈ＿２）ｎＣＨ＿２（ I ）（式中、ｍ及びｎは整数を
示し、ｍ＋ｎは１１〜１４である）で表される直鎖アル
カンスルフォネートを含有することからなる薬効成分の
経皮吸収促進剤。(1) The following general formula (I) CH_2(CH_2)m-CH(SO_2Na)-(C
H_2) Transdermal absorption enhancer for medicinal ingredients containing a linear alkanesulfonate represented by nCH_2(I) (where m and n are integers, and m+n is 11 to 14) .
Ｈ＿２）ｎＣＨ＿２（ I ）（式中、ｍ及びｎは整数を
示し、ｍ＋ｎは１１〜１４である）で表される直鎖アル
カンスルフォネートとを含有することからなる経皮吸収
型製剤(2) Medicinal ingredients and the following general formula (I) CH_2(CH_2)m-CH(SO_2Na)-(C
H_2) a linear alkanesulfonate represented by nCH_2(I) (where m and n are integers, and m+n is 11 to 14).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25796789A JPH03120230A (en) | 1989-10-04 | 1989-10-04 | Percutaneous absorbefacient of drug active ingredient and percutaneous absorption type pharmaceutical |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25796789A JPH03120230A (en) | 1989-10-04 | 1989-10-04 | Percutaneous absorbefacient of drug active ingredient and percutaneous absorption type pharmaceutical |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03120230A true JPH03120230A (en) | 1991-05-22 |
Family
ID=17313704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25796789A Pending JPH03120230A (en) | 1989-10-04 | 1989-10-04 | Percutaneous absorbefacient of drug active ingredient and percutaneous absorption type pharmaceutical |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03120230A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001501609A (en) * | 1996-09-27 | 2001-02-06 | ヘキスト・アクチエンゲゼルシヤフト | Antifungal gel with high active compound release |
| JP2008543788A (en) * | 2005-06-17 | 2008-12-04 | バイタル ヘルス サイエンシズ プロプライアタリー リミティド | Carrier |
| US9314527B2 (en) | 2010-03-30 | 2016-04-19 | Phosphagenics Limited | Transdermal delivery patch |
| US10071030B2 (en) | 2010-02-05 | 2018-09-11 | Phosphagenics Limited | Carrier comprising non-neutralised tocopheryl phosphate |
| US10188670B2 (en) | 2011-03-15 | 2019-01-29 | Phosphagenics Limited | Composition |
| US10973761B2 (en) | 2015-12-09 | 2021-04-13 | Phosphagenics Limited | Pharmaceutical formulation |
| US11753435B2 (en) | 2016-12-21 | 2023-09-12 | Avecho Biotechnology Limited | Process |
-
1989
- 1989-10-04 JP JP25796789A patent/JPH03120230A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001501609A (en) * | 1996-09-27 | 2001-02-06 | ヘキスト・アクチエンゲゼルシヤフト | Antifungal gel with high active compound release |
| JP2008543788A (en) * | 2005-06-17 | 2008-12-04 | バイタル ヘルス サイエンシズ プロプライアタリー リミティド | Carrier |
| US10071030B2 (en) | 2010-02-05 | 2018-09-11 | Phosphagenics Limited | Carrier comprising non-neutralised tocopheryl phosphate |
| US9314527B2 (en) | 2010-03-30 | 2016-04-19 | Phosphagenics Limited | Transdermal delivery patch |
| US10188670B2 (en) | 2011-03-15 | 2019-01-29 | Phosphagenics Limited | Composition |
| US10973761B2 (en) | 2015-12-09 | 2021-04-13 | Phosphagenics Limited | Pharmaceutical formulation |
| US11753435B2 (en) | 2016-12-21 | 2023-09-12 | Avecho Biotechnology Limited | Process |
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