JP2017200909A - External preparation for skin containing loxoprofen - Google Patents
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Abstract
Description
本発明は、優れた鎮痛消炎作用を有するロキソプロフェンを含有する皮膚外用液剤に関する。より詳しくは、ロキソプロフェンに特定の医薬品添加物を含有させることによって、外観でみる製造直後透明性又は保存安定性を高めたロキソプロフェン含有皮膚外用剤に関する。 The present invention relates to an external preparation for skin containing loxoprofen having an excellent analgesic / anti-inflammatory effect. More specifically, the present invention relates to a loxoprofen-containing external preparation for skin, which has improved transparency or storage stability immediately after production as seen in appearance by incorporating a specific pharmaceutical additive in loxoprofen.
プロピオン酸系非ステロイド性解熱鎮痛消炎剤（ＮＳＡＩＤ）であるロキソプロフェンは、他のＮＳＡＩＤと同様にプロスタグランジン生合成の抑制作用に基づく解熱・鎮痛・消炎作用を有する。なお、ロキソプロフェンは経口投与後に胃粘膜刺激作用の弱い未変化体のまま消化管から吸収され、体内で活性体となるプロドラッグであるため、活性体よりも胃粘膜障害は少ないという特徴を有することでも知られている（例えば、非特許文献１参照）。 Loxoprofen, which is a propionic non-steroidal antipyretic analgesic / anti-inflammatory agent (NSAID), has antipyretic / analgesic / anti-inflammatory effects based on the inhibitory action of prostaglandin biosynthesis, similar to other NSAIDs. Loxoprofen is a prodrug that is absorbed from the gastrointestinal tract and remains active in the body as an intact substance with weak gastric mucosal irritation after oral administration. However, it is also known (for example, refer nonpatent literature 1).
近年、ロキソプロフェンは外用消炎鎮痛剤としてもパップ剤、テープ剤及びゲル剤が市販され、臨床に供されている（例えば、非特許文献２参照）。なお、ロキソプロフェンは、皮膚においてもケトン還元酵素によってトランス−ＯＨ体（活性体）に変換されることが知られている（例えば、特許文献１参照）。 In recent years, loxoprofen has been put into clinical use as a topical anti-inflammatory analgesic and is used clinically (see, for example, Non-Patent Document 2). Loxoprofen is known to be converted to a trans-OH form (active form) by ketone reductase in the skin (see, for example, Patent Document 1).
イソプロパノール（イソプロピルアルコールとも言う）は、可溶化剤、基剤、保存剤、溶剤、溶解補助剤等の用途で、外用剤に用いられる医薬品添加剤である（例えば、非特許文献３参照）。 Isopropanol (also referred to as isopropyl alcohol) is a pharmaceutical additive used for external preparations in applications such as solubilizers, bases, preservatives, solvents, and solubilizing agents (see, for example, Non-Patent Document 3).
これまでに、ロキソプロフェンとエタノールを含有する外用固形剤では透明性が損なわれるが、エタノールの代わりにイソプロパノールを使用すると過酷条件下における外観でみる保存安定性が確保されたことが開示され、また、外用液剤においては何れの場合でも過酷条件下における外観でみる保存安定性に問題がなかったことも開示されている（特許文献２の表１〜２参照）。なお、これらの製剤は、いずれも総量が７０重量％もの１価低級アルコール乃至多価アルコールを含有する外用製剤である。 So far, it has been disclosed that the external solid preparation containing loxoprofen and ethanol loses transparency, but the use of isopropanol instead of ethanol has ensured the storage stability in appearance under severe conditions, It is also disclosed that there was no problem in storage stability in terms of appearance under severe conditions in any case for external use liquids (see Tables 1 and 2 of Patent Document 2). These preparations are all external preparations containing a monohydric lower alcohol or polyhydric alcohol having a total amount of 70% by weight.
しかし、上記特許文献２で開示されたような、７０％ものアルコール類を含有する外用液剤では使用感に問題があり改善が望まれる。すなわち、総アルコールの含有量を低減した使用感が良好で、かつ使用時に想定される幅広い保存温度帯において外観でみる安定性に問題のないロキソプロフェンを含有する外用液剤の出現が切望されている。 However, the external use liquid containing 70% alcohol as disclosed in Patent Document 2 has a problem in use feeling and improvement is desired. That is, the appearance of a liquid preparation for external use containing loxoprofen, which has a good feeling of use with a reduced total alcohol content and has no problem in stability in appearance in a wide storage temperature range assumed at the time of use, is eagerly desired.
これまでに、ロキソプロフェンにエタノール及びプロピレングリコールを含有する経口液剤が市販されている（非特許文献４参照）が、ロキソプロフェンおよび１価の低級アルコールを含有する総アルコール濃度６０重量％以下の外用液剤は知られておらず、かかる場合において、イソプロパノールが外観でみる製造直後透明性又は保存安定性にどのように影響するかについては全く知られていない。 To date, oral liquid preparations containing ethanol and propylene glycol in loxoprofen have been commercially available (see Non-Patent Document 4). However, an external liquid preparation containing loxoprofen and a monovalent lower alcohol with a total alcohol concentration of 60% by weight or less is disclosed. It is not known, and in such a case, it is not known at all how isopropanol affects the transparency or storage stability immediately after production in appearance.
本発明の課題は、ロキソプロフェン含有皮膚外用剤の外観でみる保存安定性をさらに高める成分を見出すことである。 The subject of this invention is finding the component which further improves the storage stability seen in the external appearance of a loxoprofen containing skin external preparation.
本発明者らは、ロキソプロフェンを含有する皮膚外用液剤において、皮膚刺激性の軽減や使用感の向上を目的として、１価低級アルコール又は多価アルコールの含有量を低下させると、外観でみる保存安定性が低下することを見出した。アルコール総量の低下による外観でみる保存安定性の低下を改善させるために、１価の低級アルコールとしてイソプロパノールを選択することにより、ロキソプロフェンナトリウムを含有する皮膚外用液剤の外観でみる保存安定性が顕著に改善されることを見出し、本発明を完成させた。 When the content of monohydric lower alcohol or polyhydric alcohol is reduced for the purpose of reducing skin irritation and improving the feeling of use in a liquid preparation for external use containing loxoprofen, the inventors of the present invention have storage stability as seen in appearance. It has been found that the performance is lowered. In order to improve the decrease in storage stability as seen from the appearance due to the decrease in the total amount of alcohol, by selecting isopropanol as the monovalent lower alcohol, the storage stability as seen from the appearance of the skin external solution containing loxoprofen sodium is remarkable. As a result, the present invention has been completed.
すなわち、本発明は、
（１）ロキソプロフェン及びイソプロパノールを含有する皮膚外用剤であり、好適には
（２）イソプロパノールの配合量が、製剤全体の０．１〜６０重量％である、前記（１）に記載の皮膚外用剤、
（３）さらに、ｌ−メントールを含有する、前記（１）又は（２）に記載の皮膚外用剤、
（４）さらに、トコフェロール酢酸エステルを含有する、前記（１）〜（３）のいずれか１項に記載の皮膚外用剤
（５）鎮痛消炎用である、前記（１）〜（４）のいずれか１項に記載の皮膚外用剤、
（６）剤形が液剤である、前記（１）〜（５）のいずれか１に記載の皮膚外用剤、
又は、
（７）剤形がゲル剤である、前記（１）〜（５）のいずれか１に記載の皮膚外用剤、
である。
That is, the present invention
(1) An external preparation for skin containing loxoprofen and isopropanol, and preferably (2) an external preparation for skin according to (1), wherein the blending amount of isopropanol is 0.1 to 60% by weight of the whole preparation. ,
(3) The external preparation for skin according to (1) or (2), further containing l-menthol,
(4) Furthermore, any one of said (1)-(4) which is a skin external preparation of any one of said (1)-(3) which contains a tocopherol acetate ester, (5) For analgesic anti-inflammatory. Or a topical skin preparation according to claim 1,
(6) The external preparation for skin according to any one of (1) to (5), wherein the dosage form is a liquid agent,
Or
(7) The external preparation for skin according to any one of (1) to (5), wherein the dosage form is a gel.
It is.
本発明の、ロキソプロフェンナトリウム及びイソプロパノールを含有する皮膚外用剤は、低皮膚刺激性で使用感にも優れ、かつ低温および高温条件下でも外観でみる保存安定性に優れるため、臨床上極めて有用である。 The external preparation for skin containing loxoprofen sodium and isopropanol of the present invention is extremely useful clinically because of its low skin irritation, excellent usability, and excellent storage stability in terms of appearance even under low and high temperature conditions. .
本発明において、「ロキソプロフェン」とは、ロキソプロフェンまたはその塩（含水塩を含む）であり、好適には、ロキソプロフェンナトリウムまたはロキソプロフェンナトリウム・２水和物であり、さらに好適には、ロキソプロフェンナトリウム・２水和物である。 In the present invention, “loxoprofen” is loxoprofen or a salt thereof (including a hydrous salt), preferably loxoprofen sodium or loxoprofen sodium dihydrate, and more preferably loxoprofen sodium dihydrate. It is a Japanese product.
本発明のロキソプロフェンは、ロキソプロフェンナトリウム水和物として第１６改正日本薬局方に掲載されている。 The loxoprofen of the present invention is listed in the 16th revised Japanese Pharmacopoeia as loxoprofen sodium hydrate.
本発明の外用剤組成物の具体的な剤形としては、例えば、液剤、クリーム剤、軟膏剤、ゲル剤、貼付剤（テープ剤、パップ剤）、エアゾール剤等をあげることができ、各剤形に適した添加剤や基材を適宜使用し、日本薬局方などに記載される通常の方法に従い、製造することができる Specific dosage forms of the external preparation composition of the present invention include, for example, liquids, creams, ointments, gels, patches (tapes, cataplasms), aerosols, etc. Appropriately used additives and base materials suitable for the shape can be produced according to the usual method described in the Japanese Pharmacopoeia
また、本発明のイソプロパノール、ｌ−メントール、及び、トコフェロール酢酸エステルは、医薬添加物辞典２０１６に収載されている。 The isopropanol, 1-menthol and tocopherol acetate of the present invention are listed in the Pharmaceutical Additives Dictionary 2016.
本発明の外用剤において含有される、ロキソプロフェンの重量％は通常、０．１〜１０％であり、好ましくは、０．５〜５％である。これを１日１〜数回塗布する。 The weight% of loxoprofen contained in the external preparation of the present invention is usually 0.1 to 10%, preferably 0.5 to 5%. This is applied one to several times a day.
また、イソプロパノールの添加量は特に限定されないが、好ましくは、０．１〜６０％であり、より好ましくは、１〜５５％である。 Moreover, although the addition amount of isopropanol is not specifically limited, Preferably, it is 0.1 to 60%, More preferably, it is 1 to 55%.
また、ｌ−メントールの添加量は特に限定されないが、好適には０．０１〜１０％であり、より好ましくは、０．１〜７．５％である。
さらに、トコフェロール酢酸エステルの添加量は特に限定されないが、いずれも好適には０．０１〜５％であり、より好ましくは、０．０１〜１％である。
Moreover, although the addition amount of 1-menthol is not specifically limited, It is 0.01 to 10% suitably, More preferably, it is 0.1 to 7.5%.
Furthermore, although the addition amount of tocopherol acetate is not specifically limited, All are 0.01 to 5% suitably, More preferably, it is 0.01 to 1%.
上記外用剤において、例えば、経時的な含量安定性や使用感の更なる向上を目的として必要に応じ、各種抗酸化剤や清涼化剤等を添加することができる。また、上記外用剤に含有される成分は、湿潤剤として、プロピレングリコール、１，３−ブチレングリコール、濃グリセリン、ｄｌ−ピロリドンカルボン酸ナトリウム液、及び、マクロゴール２００等を、ｐＨ調整剤として、塩酸、水酸化ナトリウム、水酸化カリウム、トリエタノールアミン等を用いることができる。 In the above-mentioned external preparation, for example, various antioxidants and cooling agents can be added as needed for the purpose of further improving the content stability over time and the feeling of use. Moreover, the component contained in the said external preparation contains propylene glycol, 1, 3- butylene glycol, concentrated glycerin, dl-pyrrolidone sodium carboxylate liquid, Macrogol 200, etc. as a wetting agent, Hydrochloric acid, sodium hydroxide, potassium hydroxide, triethanolamine and the like can be used.
本発明の皮膚外用剤のｐＨは、上記に挙げられたｐＨ調節剤を用いて調節することができ、ｐＨ５．０〜６．９に調整するのが好ましい。 The pH of the external preparation for skin of the present invention can be adjusted using the pH adjusting agents listed above, and is preferably adjusted to pH 5.0 to 6.9.
以下に、実施例をあげて本発明を更に具体的に説明する。 Hereinafter, the present invention will be described more specifically with reference to examples.
（製剤例１）液剤 (Formulation Example 1) Solution
上記成分及び分量を取り、日本薬局方製剤総則「液剤」の項に準じて液剤を製造した。 The above components and amounts were taken, and a liquid preparation was produced according to the section of the Japanese Pharmacopoeia General Formulation “Liquid Preparation”.
（製剤例２）ゲル剤 (Formulation example 2) Gel agent
上記成分及び分量を取り、日本薬局方製剤総則「ゲル剤」の項に準じてゲル剤を製造した。 The above ingredients and amounts were taken, and a gel was produced according to the section of the Japanese Pharmacopoeia General Formulation “Gel”.
（試験例）ロキソプロフェン含有皮膚外用剤の外観でみる保存安定性試験
（１）試験材料
ロキソプロフェンナトリウム・２水和物は第一三共ケミカルファーマ（株）製のものを、イソプロパノールは小堺製薬（株）製のものを、ｌ−メントールは鈴木薄荷（株）製のものを、トコフェロール酢酸エステルはエーザイフードケミカル（株）製のものを、無水エタノールは今津薬品工業（株）製のものを、プロピレングリコールは丸石製薬（株）製のものを、１，３−ブチレングリコールは（株）ダイセル製のものを、濃グリセリンは小堺製薬（株）製のものを、ｄｌ−ピロリドンカルボン酸ナトリウム液は味の素（株）製のものを、及び、マクロゴール２００は三洋化成工業（株）製のものを、それぞれ使用した。
(Test example) Storage stability test as seen from the external appearance of loxoprofen-containing external skin preparation (1) Test materials Loxoprofen sodium dihydrate is from Daiichi Sankyo Chemical Pharma Co., Ltd. ), L-menthol is manufactured by Suzuki Hikaru Co., tocopherol acetate is manufactured by Eisai Food Chemical Co., and anhydrous ethanol is manufactured by Imazu Pharmaceutical Co., Ltd. Glycol is manufactured by Maruishi Pharmaceutical Co., Ltd., 1,3-butylene glycol is manufactured by Daicel Co., Ltd., concentrated glycerin is manufactured by Kominato Pharmaceutical Co., Ltd., and dl-pyrrolidonecarboxylate sodium solution is Ajinomoto. The thing made by Corporation | Co., Ltd. and the macrogol 200 used the thing by Sanyo Chemical Industries Ltd., respectively.
（２）検体の調製
以下の表１〜３に記載した成分を混合して溶解後、ｐＨ６．５になるよう塩酸で調整し、実施例１〜１０及び比較例１〜１０の液剤を得た。
(2) Preparation of specimens The components described in Tables 1 to 3 below were mixed and dissolved, and then adjusted with hydrochloric acid so as to have a pH of 6.5 to obtain solutions of Examples 1 to 10 and Comparative Examples 1 to 10. .
（３）試験方法
得られた各液剤を透明ガラスバイアルに分注し、密栓した。製造直後の外観を目視にて確認した後、それぞれを５℃、２５℃相対湿度６０％、５０℃にて保存し、２週間後に外観を目視にて確認した。
(3) Test method Each solution obtained was dispensed into transparent glass vials and sealed. After visually confirming the appearance immediately after production, each was stored at 5 ° C., 25 ° C., 60% relative humidity, and 50 ° C., and the appearance was visually confirmed after 2 weeks.
（４）試験結果
外観確認結果を表１〜３に記載した。比較例１〜３の結果より、１価の低級アルコールとしてエタノールを使用した液剤処方では、外観でみる製造直後透明性又は保存安定性が著しく低いことが判明した。
(4) Test result The external appearance confirmation result was described in Tables 1-3. From the results of Comparative Examples 1 to 3, it was found that the liquid formulation using ethanol as the monovalent lower alcohol had extremely low transparency or storage stability immediately after production as seen from the appearance.
一方、実施例１〜３に示した１価の低級アルコールとして、エタノールの代わりにイソプロパノールを使用した液剤処方では、外観でみる製造直後透明性又は保存安定性が顕著に向上した。 On the other hand, the liquid formulation using isopropanol instead of ethanol as the monovalent lower alcohol shown in Examples 1 to 3 significantly improved the transparency or storage stability immediately after production as seen from the appearance.
さらに、使用感の向上を目的として、比較例１および実施例１それぞれに、湿潤剤として、各種多価アルコールまたはｄｌ−ピロリドンカルボン酸ナトリウム液を添加した処方（比較例４〜８および実施例４〜８）においても同様に、１価の低級アルコールとして、エタノールの代わりにイソプロパノールを使用することにより外観でみる製造直後透明性又は保存安定性が向上した。 Furthermore, for the purpose of improving the feeling of use, each of Comparative Example 1 and Example 1 was formulated with various polyhydric alcohols or sodium dl-pyrrolidonecarboxylate as a wetting agent (Comparative Examples 4 to 8 and Example 4). Similarly in -8), transparency or storage stability immediately after production was improved by using isopropanol instead of ethanol as a monovalent lower alcohol.
また、ロキソプロフェンナトリウム及び１価の低級アルコールを含有する処方にトコフェロール酢酸エステルを添加した処方（比較例９、１０および実施例９、１０）においても同様に、１価の低級アルコールとして、エタノールの代わりにイソプロパノールを使用することにより外観でみる製造直後透明性又は保存安定性が向上した。 Similarly, in the formulations (Comparative Examples 9, 10 and Examples 9 and 10) in which tocopherol acetate was added to a formulation containing loxoprofen sodium and a monovalent lower alcohol, instead of ethanol as a monovalent lower alcohol By using isopropanol, transparency or storage stability immediately after production was improved.
本発明の、ロキソプロフェンナトリウム及びイソプロパノールを含有する皮膚外用剤は、皮膚刺激性が低く、使用感にも優れ、かつ使用時に想定される幅広い保存温度帯において外観でみる保存安定性に優れるため、極めて有用である。 The topical skin preparation containing loxoprofen sodium and isopropanol of the present invention has low skin irritation, excellent usability, and excellent storage stability in terms of appearance in a wide range of storage temperatures assumed during use. Useful.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019119684A (en) * | 2017-12-28 | 2019-07-22 | 小林製薬株式会社 | External composition |
| JP2019119683A (en) * | 2017-12-28 | 2019-07-22 | 小林製薬株式会社 | External composition |
| JP2020045315A (en) * | 2018-09-20 | 2020-03-26 | 興和株式会社 | Pharmaceutical preparations containing loxoprofen |
| JP2020059666A (en) * | 2018-10-09 | 2020-04-16 | 小林製薬株式会社 | External pharmaceutical composition |
| JP2020158502A (en) * | 2019-03-25 | 2020-10-01 | 第一三共ヘルスケア株式会社 | Skin external preparation containing loxoprofen |
| JP2021172638A (en) * | 2020-04-30 | 2021-11-01 | 小林製薬株式会社 | External pharmaceutical preparation |
| JP2024014507A (en) * | 2022-07-22 | 2024-02-01 | 同仁医薬化工株式会社 | External liquid preparation containing loxoprofen |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013191293A1 (en) * | 2012-06-22 | 2013-12-27 | 興和株式会社 | Pharmaceutical composition containing loxoprofen |
| JP2015027971A (en) * | 2013-07-31 | 2015-02-12 | 興和株式会社 | Loxoprofen-containing external application agent |
| JP2015083563A (en) * | 2013-09-18 | 2015-04-30 | 第一三共ヘルスケア株式会社 | Loxoprofen-containing external liquid preparation for skin |
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| JP4880813B2 (en) | 2000-10-26 | 2012-02-22 | 第一三共株式会社 | Anti-inflammatory analgesic composition for external use |
| JP6449554B2 (en) | 2014-03-30 | 2019-01-09 | 小林製薬株式会社 | Pharmaceutical composition for external use |
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- 2023-06-05 JP JP2023092411A patent/JP7557010B2/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2013191293A1 (en) * | 2012-06-22 | 2013-12-27 | 興和株式会社 | Pharmaceutical composition containing loxoprofen |
| JP2015027971A (en) * | 2013-07-31 | 2015-02-12 | 興和株式会社 | Loxoprofen-containing external application agent |
| JP2015083563A (en) * | 2013-09-18 | 2015-04-30 | 第一三共ヘルスケア株式会社 | Loxoprofen-containing external liquid preparation for skin |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7086597B2 (en) | 2017-12-28 | 2022-06-20 | 小林製薬株式会社 | External composition |
| JP2019119683A (en) * | 2017-12-28 | 2019-07-22 | 小林製薬株式会社 | External composition |
| JP2019119684A (en) * | 2017-12-28 | 2019-07-22 | 小林製薬株式会社 | External composition |
| JP7086596B2 (en) | 2017-12-28 | 2022-06-20 | 小林製薬株式会社 | External composition |
| JP2023090875A (en) * | 2018-09-20 | 2023-06-29 | 興和株式会社 | Pharmaceutical formulation containing loxoprofen |
| JP2020045315A (en) * | 2018-09-20 | 2020-03-26 | 興和株式会社 | Pharmaceutical preparations containing loxoprofen |
| JP2025092756A (en) * | 2018-09-20 | 2025-06-19 | 興和株式会社 | Pharmaceutical preparations containing loxoprofen |
| JP2020059666A (en) * | 2018-10-09 | 2020-04-16 | 小林製薬株式会社 | External pharmaceutical composition |
| JP7226957B2 (en) | 2018-10-09 | 2023-02-21 | 小林製薬株式会社 | External pharmaceutical composition |
| JP2020158502A (en) * | 2019-03-25 | 2020-10-01 | 第一三共ヘルスケア株式会社 | Skin external preparation containing loxoprofen |
| JP7515277B2 (en) | 2019-03-25 | 2024-07-12 | 第一三共ヘルスケア株式会社 | Skin care product containing loxoprofen |
| JP2021172638A (en) * | 2020-04-30 | 2021-11-01 | 小林製薬株式会社 | External pharmaceutical preparation |
| JP7646298B2 (en) | 2020-04-30 | 2025-03-17 | 小林製薬株式会社 | External medicinal preparations |
| JP2024014507A (en) * | 2022-07-22 | 2024-02-01 | 同仁医薬化工株式会社 | External liquid preparation containing loxoprofen |
Also Published As
| Publication number | Publication date |
|---|---|
| JP7325168B2 (en) | 2023-08-14 |
| JP2023106625A (en) | 2023-08-01 |
| JP7557010B2 (en) | 2024-09-26 |
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