JPH06263630A - Vitamin as-solubilizing eye drop - Google Patents

Vitamin as-solubilizing eye drop

Info

Publication number
JPH06263630A
JPH06263630A JP5076128A JP7612893A JPH06263630A JP H06263630 A JPH06263630 A JP H06263630A JP 5076128 A JP5076128 A JP 5076128A JP 7612893 A JP7612893 A JP 7612893A JP H06263630 A JPH06263630 A JP H06263630A
Authority
JP
Japan
Prior art keywords
vitamin
eye drop
eye
irritation
acid ester
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
Application number
JP5076128A
Other languages
Japanese (ja)
Inventor
Misao Koide
操 小出
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lion Corp
Original Assignee
Lion Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Lion Corp filed Critical Lion Corp
Priority to JP5076128A priority Critical patent/JPH06263630A/en
Publication of JPH06263630A publication Critical patent/JPH06263630A/en
Pending legal-status Critical Current

Links

Classifications

    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

PURPOSE:To obtain eye drop enhanced in preservative effect and reduced in irritation to eyes. CONSTITUTION:The vitamin As-solubilizing eye drop is obtained by blending a nonionic surfactant such as polyoxyethylene hardened castor oil or polyoxyethylenesorbitane higher fatty acid ester, vitamin As, a quaternary ammonium type cationic surfactant such as benzalkonium chloride or benzethonium chloride and chlorobutanol and/or paraoxybenzoic acid ester such as ethylparaben or methylparaben.

Description

【発明の詳細な説明】Detailed Description of the Invention

【０００１】[0001]

【産業上の利用分野】本発明は、ビタミンＡ類を可溶化
した点眼剤に関し、更に詳しくは、第４級アンモニウム
型カチオン界面活性剤及びクロロブタノール及び／また
はパラオキシ安息香酸エステルを同時配合することによ
り、防腐効果を高め、かつ、眼に対する刺激性を低減し
たビタミンＡ類可溶化点眼剤に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an eye drop in which vitamins A are solubilized, and more specifically, a quaternary ammonium type cationic surfactant and chlorobutanol and / or paraoxybenzoic acid ester are simultaneously mixed. Thus, the present invention relates to a vitamin A solubilized eye drop having an improved antiseptic effect and reduced irritation to the eye.

【０００２】[0002]

【従来の技術】ビタミンＡ油、ビタミンＡ脂肪酸エステ
ルなども含めてビタミンＡ類は、人間または動物に対す
る視覚、粘膜などの正常維持機能を有し、その欠乏によ
り夜盲症、角結膜乾燥症などを引き起こすため、眼には
欠くことのできない物質である。一方、このように有用
性の高いビタミンＡ類は、水に対する溶解性が著しく低
いため水性点眼剤として用いる場合、非イオン界面活性
剤により可溶化することが不可欠であった。しかし、こ
の非イオン界面活性剤と、汎用性が高く点眼剤に欠かす
ことのできない防腐剤である第４級アンモニウム型カチ
オン界面活性剤が共存した場合、両者が混合ミセルを形
成するなど防腐効果が著しく低下することが知られてい
た。更に、上記第４級アンモニウム型カチオン界面活性
剤は、点眼剤において通常使用する濃度（０．０２Ｗ／
Ｖ％）以上では、比較的眼に対する刺激が高いために、
防腐効力を向上する目的での高濃度配合は、極めて困難
であった。2. Description of the Related Art Vitamin A including vitamin A oil and vitamin A fatty acid ester has a normal function of maintaining visual and mucous membranes for humans or animals, and their deficiency causes night blindness, keratoconjunctival dryness, etc. Therefore, it is an indispensable substance for the eyes. On the other hand, such highly useful vitamins A have extremely low solubility in water, and therefore, when used as an aqueous eye drop, it was essential to solubilize them with a nonionic surfactant. However, when this nonionic surfactant coexists with a quaternary ammonium type cationic surfactant, which is a highly versatile and indispensable preservative for eye drops, the antiseptic effect such as the formation of mixed micelles between them is not obtained. It was known to be significantly reduced. Further, the quaternary ammonium type cationic surfactant is used at a concentration usually used in eye drops (0.02 W /
Above V%), the eye irritation is relatively high,
It was extremely difficult to add a high concentration for the purpose of improving the antiseptic effect.

【０００３】[0003]

【発明が解決しようとする課題】本発明は、ビタミンＡ
類を非イオン界面活性剤により可溶化した点眼剤の防腐
効果を高め、かつ、眼に対する刺激性を低減することを
目的とする。The present invention is directed to vitamin A
It is intended to enhance the antiseptic effect of eye drops obtained by solubilizing a salt with a nonionic surfactant and reduce the irritation to the eye.

【０００４】[0004]

【課題を解決するための手段】本発明者らは、ポリオキ
シエチレン硬化ヒマシ油等の非イオン界面活性剤を可溶
化剤としたビタミンＡ類点眼剤の防腐効果の向上及び眼
に対する刺激性の低減について鋭意研究を行った結果、
塩化ベンザルコニウム等の第４級アンモニウム型カチオ
ン界面活性剤及びクロロブタノール及び／またはパラオ
キシ安息香酸エステルを同時配合することにより、防腐
効果が高く、かつ、眼に対する刺激性が極めて低いビタ
ミンＡ類可溶化点眼剤が得られることを見い出した。即
ち、本発明のビタミンＡ類可溶化点眼剤は、非イオン界
面活性剤、ビタミンＡ類、第４級アンモニウム型カチオ
ン界面活性剤及びクロロブタノール及び／またはパラオ
キシ安息香酸エステルを配合したことを特徴とする。Means for Solving the Problems The present inventors have improved the antiseptic effect and the irritation to the eyes of vitamin A type eye drops using a nonionic surfactant such as polyoxyethylene hydrogenated castor oil as a solubilizer. As a result of earnest research on reduction,
A quaternary ammonium type cationic surfactant such as benzalkonium chloride and chlorobutanol and / or paraoxybenzoic acid ester are simultaneously mixed, so that a preservative effect is high and vitamin A having extremely low eye irritation is acceptable. It has been found that a solubilized eye drop is obtained. That is, the vitamin A solubilizing eye drop of the present invention is characterized by blending a nonionic surfactant, vitamin A, a quaternary ammonium type cationic surfactant and chlorobutanol and / or paraoxybenzoic acid ester. To do.

【０００５】[0005]

【発明の実施態様】発明の第一の必須成分であるビタミ
ンＡ類とは、ビタミンＡそれ自体の他に、ビタミンＡ油
等のビタミンＡ含有混合物、ビタミンＡ脂肪酸エステル
等のビタミンＡ誘導体なども含まれる。具体的には、日
本ロシュ株式会社製パルミチン酸レチノール１７０万国
際単位（Ｉ．Ｕ．）が挙げられる。ビタミンＡ類は、通
常組成物中に０．００３〜０．１重量％配合することが
でき、好ましくは０．０１〜０．０５重量％の範囲であ
る。BEST MODE FOR CARRYING OUT THE INVENTION The first essential ingredient of the invention, vitamins A, includes, in addition to vitamin A itself, vitamin A-containing mixtures such as vitamin A oil and vitamin A derivatives such as vitamin A fatty acid ester. included. Specifically, 1.7 million international units (I.U.) of retinol palmitate manufactured by Nippon Roche Co., Ltd. may be mentioned. Vitamin A can be usually added to the composition in an amount of 0.003 to 0.1% by weight, preferably 0.01 to 0.05% by weight.

【０００６】本発明の第二の必須成分であるビタミンＡ
類を可溶化する非イオン界面活性剤としては、水溶性の
ポリオキシエチレン硬化ヒマシ油等の高級脂肪酸エステ
ル、ポリオキシエチレンソルビタン高級脂肪酸エステル
等が挙げられ、例えば、ポリオキシエチレン（ｐ＝６
０）硬化ヒマシ油、ポリオキシエチレン（ｐ＝２０）ソ
ルビタンモノオレエートがある。なお、ｐはエチレンオ
キシドの平均付加モル数を示す。具体的には日光ケミカ
ルズ株式会社製ニッコールＨＣＯ−４０，ＨＣＯ−５
０，ＨＣＯ−６０，ＴＯ−１０等がある。非イオン界面
活性剤は、通常組成物中に０．０１〜１．０重量％配合
することができ、好ましくは０．０５〜０．５重量％の
範囲である。Vitamin A which is the second essential ingredient of the present invention
Examples of the nonionic surfactant that solubilizes the compounds include higher fatty acid esters such as water-soluble polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan higher fatty acid esters, and the like. For example, polyoxyethylene (p = 6
0) hydrogenated castor oil, polyoxyethylene (p = 20) sorbitan monooleate. In addition, p shows the average addition mole number of ethylene oxide. Specifically, Nikko Chemicals Co., Ltd. Nikkor HCO-40, HCO-5
0, HCO-60, TO-10, etc. The nonionic surfactant can be usually added to the composition in an amount of 0.01 to 1.0% by weight, preferably 0.05 to 0.5% by weight.

【０００７】本発明の第三の必須成分である第４級アン
モニウム型カチオン界面活性剤としては、塩化ベンザル
コニウム、塩化ベンゼトニウム等が挙げられる。具体的
には、甘糟化学産業株式会社製塩化ベンザルコニウム液
がある。第４級アンモニウム型カチオン界面活性剤は、
通常組成物中に０．００１〜０．１重量％配合すること
ができ、好ましくは０．００３〜０．０２重量％の範囲
である。Examples of the quaternary ammonium type cationic surfactant which is the third essential component of the present invention include benzalkonium chloride and benzethonium chloride. Specifically, there is a benzalkonium chloride solution manufactured by Kanka Chemical Industry Co., Ltd. The quaternary ammonium type cationic surfactant is
The composition can be usually added in an amount of 0.001 to 0.1% by weight, preferably 0.003 to 0.02% by weight.

【０００８】本発明の第四の必須成分であるクロロブタ
ノールの具体例としては、メルク株式会社製１，１，１
−トリクロロ−２−メチル−２−プロパノールがある。
クロロブタノールは、通常組成物中に０．０１〜１．０
重量％配合することができ、好ましくは０．０３〜０．
５重量％の範囲である。Specific examples of chlorobutanol which is the fourth essential component of the present invention include 1,1,1 manufactured by Merck Ltd.
-Trichloro-2-methyl-2-propanol.
Chlorobutanol is usually 0.01 to 1.0 in the composition.
% By weight, and preferably 0.03 to 0.
It is in the range of 5% by weight.

【０００９】また、同じく本発明の第四の必須成分であ
るパラオキシ安息香酸エステルとは、パラオキシ安息香
酸エチル、パラオキシ安息香酸メチル、パラオキシ安息
香酸プロピル、パラオキシ安息香酸ブチル等を示す。具
体的には、ミドリ化学株式会社製エチルパラベン、メチ
ルパラベン、プロピルパラベン、ブチルパラベンがあ
る。パラオキシ安息香酸エステルは、通常組成物中に
０．００５〜０．２重量％配合することができ、好まし
くは０．０１〜０．１重量％の範囲である。The para-oxybenzoic acid ester which is the fourth essential component of the present invention also means ethyl para-oxybenzoate, methyl para-oxybenzoate, propyl para-oxybenzoate, butyl para-oxybenzoate and the like. Specifically, there are ethyl paraben, methyl paraben, propyl paraben, and butyl paraben manufactured by Midori Kagaku Co., Ltd. The paraoxybenzoic acid ester can be usually added to the composition in an amount of 0.005 to 0.2% by weight, preferably 0.01 to 0.1% by weight.

【００１０】また、本発明のビタミンＡ類可溶化点眼剤
には必要に応じて、他のビタミン類、イプシロンーアミ
ノカプロン酸、グリチルリチン酸二カリウム、マレイン
酸クロルフェニラミン、塩酸ナファゾリン、アスパラギ
ン酸カリウム、硫酸亜鉛、スルファメトキサゾール、ア
ラントイン、塩化リゾチームなどの薬剤；グルコン酸ク
ロルヘキシジン、ソルビン酸、安息香酸ナトリウムなど
の防腐剤；塩化カリウム、塩化ナトリウム、プロピレン
グリコール、ポリエチレングリコール、グリセリンなど
の等張化剤；クエン酸、ホウ酸、リン酸水素ナトリウ
ム、氷酢酸などの緩衝剤；マンニトールなどの糖類；ｌ
−メントールなどの香料等を配合することができる。The vitamin A solubilized eye drops of the present invention may contain other vitamins, epsilon-aminocaproic acid, dipotassium glycyrrhizinate, chlorpheniramine maleate, naphazoline hydrochloride, potassium aspartate, if necessary. Drugs such as zinc sulfate, sulfamethoxazole, allantoin and lysozyme chloride; preservatives such as chlorhexidine gluconate, sorbic acid and sodium benzoate; isotonic agents such as potassium chloride, sodium chloride, propylene glycol, polyethylene glycol and glycerin Agents; buffers such as citric acid, boric acid, sodium hydrogen phosphate, glacial acetic acid; sugars such as mannitol;
-A fragrance such as menthol or the like can be added.

【００１１】本発明のビタミンＡ類可溶化点眼剤の調製
方法は特に問わないが、例えば、ビタミンＡアセテート
などのビタミンＡ類を、ポリオキシエチレン硬化ヒマシ
油６０等の非イオン界面活性剤により水に可溶化する。
ついで、必要に応じて用いられるイプシロンーアミノカ
プロン酸等の薬剤、塩化ベンゼトニウム等の第４級アン
モニウム型カチオン界面活性剤及びパラオキシ安息香酸
メチル等のパラオキシ安息香酸エステル、更にクエン酸
などの緩衝剤を加えてｐＨを調整することにより、防腐
効果が高く、眼に対する刺激性の少ないビタミンＡ類可
溶化点眼剤を得ることができる。The method for preparing the vitamin A solubilized eye drop of the present invention is not particularly limited. For example, vitamin A such as vitamin A acetate is treated with a nonionic surfactant such as polyoxyethylene hydrogenated castor oil 60 or the like in water. Solubilized in.
Then, if necessary, a drug such as epsilon-aminocaproic acid, a quaternary ammonium type cationic surfactant such as benzethonium chloride, a paraoxybenzoic acid ester such as methyl paraoxybenzoate, and a buffering agent such as citric acid are added. By adjusting the pH by adjusting the pH, it is possible to obtain a vitamin A solubilized eye drop having a high antiseptic effect and a low eye irritation.

【００１２】本発明のビタミンＡ類可溶化点眼剤のｐＨ
は４〜９の範囲にあることが好ましく、より好ましくは
５〜８．５である。液剤のｐＨが上記範囲を外れると、
特に眼に対する刺激性が著しく強くなる。PH of the vitamin A solubilized eye drops of the present invention
Is preferably in the range of 4 to 9, and more preferably 5 to 8.5. When the pH of the liquid agent is out of the above range,
In particular, the irritation to the eyes becomes extremely strong.

【００１３】[0013]

【発明の効果】本発明によれば、ビタミンＡ類を含有す
る可溶化点眼剤において、第４級アンモニウム型カチオ
ン界面活性剤およびクロロブタノール及び／またはパラ
オキシ安息香酸エステルを配合することにより、防腐効
果を高め、かつ、眼に対する刺激性を低減することがで
きる。INDUSTRIAL APPLICABILITY According to the present invention, in a solubilized eye drop containing vitamin A, by incorporating a quaternary ammonium type cationic surfactant and chlorobutanol and / or paraoxybenzoic acid ester, an antiseptic effect is obtained. And irritation to the eye can be reduced.

【００１４】[0014]

【実施例】【Example】

実施例１〜２及び比較例１〜５ 表１に示す処方の点眼剤を調製し、容器に充填し、防腐
効果及び眼に対する刺激性を評価し、同表にその結果を
示した。尚、ｐＨはリン酸二水素ナトリウム、リン酸水
素二ナトリウムで５．５に、浸透圧は塩化ナトリウムで
２９０ｍＯｓｍにそれぞれ調整した。Examples 1 to 2 and Comparative Examples 1 to 5 Eye drops having the formulations shown in Table 1 were prepared, filled in a container, and evaluated for antiseptic effect and eye irritation, and the results are shown in the same table. The pH was adjusted to 5.5 with sodium dihydrogen phosphate and disodium hydrogen phosphate, and the osmotic pressure was adjusted to 290 mOsm with sodium chloride.

【００１５】[0015]

【表１】 実施 実施 比較 比較 比較 比較 比較 例１ 例２ 例１ 例２ 例３ 例４ 例５ 配合量(g/1000ml)： ビタミンＡパルミテート 0.2 0.2 0.2 0.2 0.2 0.2 0.2 ＴＯ−１０＊ 2.0 2.0 2.0 2.0 2.0 2.0 2.0 10％塩化ベンザルコニウム液 0.5 0.5 0.5 1.0 − − − クロロブタノール 1.0 − − − 1.0 − 1.0 メチルパラベン＊＊ − 0.1 − − − 0.1 0.1 蒸留水 適量 適量 適量 適量 適量 適量 適量 評価： 防腐効力 Ps.aeruginosa ○ ○ × ○ △ × △ E.coli. ○ ○ × ○ △ × △ A.niger ○ ○ △ ○ × × △ 眼に対する刺激性 ○ ○ ○ × ○ ○ ○ ＊ＴＯ−１０：ポリオキシエチレン(２０)ソルビタンモ
ノオレエート ＊＊メチルパラベン：パラオキシ安息香酸メチル[Table 1] Implementation Implementation Comparison Comparison Comparison Comparison Comparison Comparison Example 1 Example 2 Example 1 Example 2 Example 3 Example 4 Example 5 Blending amount (g / 1000ml): Vitamin A palmitate 0.2 0.2 0.2 0.2 0.2 0.2 0.2 TO-10 * 2.0 2.0 2.0 2.0 2.0 2.0 2.0 10% benzalkonium chloride solution 0.5 0.5 0.5 1.0 − − − Chlorobutanol 1.0 − − − 1.0 − 1.0 Methylparaben ** − 0.1 − − − 0.1 0.1 Distilled water Appropriate amount Proper amount Proper amount Proper amount Proper amount Proper amount Proper amount Evaluation: Antiseptic effect Ps.aeruginosa ○ ○ × ○ △ × △ E.coli. ○ ○ × ○ △ × △A.niger ○ ○ △ ○ × × △ Eye irritation ○ ○ ○ × ○ ○ ○ * TO-10: Polyoxyethylene (20) sorbitan
Nooleate ** Methylparaben: Methyl paraoxybenzoate

【００１６】防腐効力は、石関の試験方法（防菌防黴、
１２，２９３（１９８４））により評価した。培地に添
加する菌の種類としては、Ｐｓ．ａｅｒｕｇｉｎｏｓ
ａ，Ｅ．ｃｏｌｉ．，Ａ．ｎｉｇｅｒを使用した。表１
及び後記の表２中の凡例は、以下の通りである。 ○：添加した各菌数に対する２週間放置後の菌数の割合
が０〜４％未満 △：添加した各菌数に対する２週間放置後の菌数の割合
が４〜２０％未満 ×：添加した各菌数に対する２週間放置後の菌数の割合
が２０％以上 眼に対する刺激性の評価は、厚生省科学研究報告（昭和
４５年）における点眼用保存剤眼粘膜刺激性試験短期試
験方法に準じて行った。表１及び表２中の凡例は、以下
の通りである。 ○：Ｄｒａｉｚｅ法による平均評点が０以上２点未満 △：Ｄｒａｉｚｅ法による平均評点が２以上５点未満 ×：Ｄｒａｉｚｅ法による平均評点が５点以上The antiseptic efficacy is the stone test method (antibacterial and antifungal,
12, 293 (1984)). The types of bacteria added to the medium include Ps. aeruginos
a, E. coli. , A. Niger was used. Table 1
And the legend in Table 2 below is as follows. ◯: Ratio of the number of bacteria after standing for 2 weeks to each number of added bacteria 0 to less than 4% Δ: Ratio of the number of bacteria after standing for 2 weeks to each number of added bacteria 4 to less than 20% ×: Added The ratio of the number of bacteria after standing for 2 weeks to each number of bacteria is 20% or more. The evaluation of eye irritation is based on the short-term test method of eye preservative eye mucous membrane irritation test in the Ministry of Health and Welfare Scientific Research Report (1965). went. The legends in Table 1 and Table 2 are as follows. ◯: Average score by Draize method is 0 or more and less than 2 points Δ: Average score by Draize method is 2 or more and less than 5 points ×: Average score by Draize method is 5 points or more

【００１７】実施例３ ポリオキシエチレン（６０）硬化ヒマシ油（ニッコール
ＨＣＯ−６０）３ｇ、ビタミンＥアセテート０．５ｇ、
ビタミンＡパルミテート（１７０万国際単位）０．２ｇ
を加温溶解する。これに塩酸テトラヒドロゾリン０．５
ｇ、塩化ベンゼトニウム０．０５ｇ、メチルパラベン
０．１ｇ、プロピルパラベン０．０１ｇ、ｌ−メントー
ル０．０５ｇ、プロピレングリコール５ｇ、アラントイ
ン１ｇ、パンテノール０．２ｇ、イプシロン−アミノカ
プロン酸１０ｇ、エチレンジアミン四酢酸二ナトリウム
０．０５ｇを混合し、水酸化ナトリウムでｐＨを７．０
に調整した後、精製水で全量を１０００ｍｌとし、無菌
ろ過し点眼容器に充填して点眼剤とする。後記表２に示
すように、本製剤の防腐効力は高く、しかも眼に対する
刺激性は極めて弱かった。Example 3 Polyoxyethylene (60) hydrogenated castor oil (Nikkor HCO-60) 3 g, vitamin E acetate 0.5 g,
Vitamin A palmitate (1.7 million international units) 0.2 g
Dissolve by heating. Tetrahydrozoline hydrochloride 0.5
g, benzethonium chloride 0.05 g, methylparaben 0.1 g, propylparaben 0.01 g, l-menthol 0.05 g, propylene glycol 5 g, allantoin 1 g, panthenol 0.2 g, epsilon-aminocaproic acid 10 g, ethylenediaminetetraacetic acid disodium salt Mix 0.05 g and adjust the pH to 7.0 with sodium hydroxide.
Then, the total volume is adjusted to 1000 ml with purified water, sterile filtered and filled in an eye drop container to obtain an eye drop. As shown in Table 2 below, the antiseptic effect of this preparation was high and the eye irritation was extremely weak.

【００１８】比較例６ ポリオキシエチレン（６０）硬化ヒマシ油（ニッコール
ＨＣＯ−６０）３ｇ、ビタミンＥアセテート０．５ｇ、
ビタミンＡパルミテ−ト（１７０万国際単位）０．２ｇ
を加温溶解する。これに塩酸テトラヒドロゾリン０．５
ｇ、塩化ベンゼトニウム０．１ｇ、ｌ−メントール０．
０５ｇ、プロピレングリコール５ｇ、アラントイン１
ｇ、パンテノール０．２ｇ、イプシロン−アミノカプロ
ン酸１０ｇ、エチレンジアミン四酢酸二ナトリウム０．
０５ｇを混合し、水酸化ナトリウムでｐＨを７．０に調
整した後、精製水で全量を１０００ｍｌとし、無菌ろ過
し点眼容器に充填して点眼剤とする。後記表２に示すよ
うに、本製剤の防腐効力は高かったが、眼に対する刺激
性は極めて強かった。Comparative Example 6 Polyoxyethylene (60) hydrogenated castor oil (Nikkor HCO-60) 3 g, vitamin E acetate 0.5 g,
Vitamin A palmitate (1.7 million international units) 0.2 g
Dissolve by heating. Tetrahydrozoline hydrochloride 0.5
g, benzethonium chloride 0.1 g, 1-menthol 0.
05g, propylene glycol 5g, allantoin 1
g, panthenol 0.2 g, epsilon-aminocaproic acid 10 g, ethylenediaminetetraacetic acid disodium 0.
After mixing 05 g and adjusting the pH to 7.0 with sodium hydroxide, the total amount is adjusted to 1000 ml with purified water, sterile filtered and filled in an eye drop container to obtain an eye drop. As shown in Table 2 below, the antiseptic effect of this preparation was high, but the eye irritation was extremely strong.

【００１９】比較例７ ポリオキシエチレン（６０）硬化ヒマシ油（ニッコール
ＨＣＯ−６０）３ｇ、ビタミンＥアセテート０．５ｇ、
ビタミンＡパルミテート（１７０万国際単位）０．２ｇ
を加温溶解する。これに塩酸テトラヒドロゾリン０．５
ｇ、塩化ベンゼトニウム０．０５ｇ、ｌ−メントール
０．０５ｇ、プロピレングリコール５ｇ、アラントイン
１ｇ、パンテノール０．２ｇ、イプシロン−アミノカプ
ロン酸１０ｇ、エチレンジアミン四酢酸二ナトリウム
０．０５ｇを混合し、水酸化ナトリウムでｐＨを７．０
に調整した後、精製水で全量を１０００ｍｌとし、無菌
ろ過し点眼容器に充填して点眼剤とする。後記表２に示
すように、本製剤の眼に対する刺激性は極めて弱かった
が、防腐効力は低かった。Comparative Example 7 3 g of polyoxyethylene (60) hydrogenated castor oil (Nikkor HCO-60), 0.5 g of vitamin E acetate,
Vitamin A palmitate (1.7 million international units) 0.2 g
Dissolve by heating. Tetrahydrozoline hydrochloride 0.5
g, benzethonium chloride 0.05 g, 1-menthol 0.05 g, propylene glycol 5 g, allantoin 1 g, panthenol 0.2 g, epsilon-aminocaproic acid 10 g, and ethylenediaminetetraacetic acid disodium 0.05 g are mixed, and sodium hydroxide is added. pH 7.0
Then, the total volume is adjusted to 1000 ml with purified water, sterile filtered and filled in an eye drop container to obtain an eye drop. As shown in Table 2 below, this preparation had extremely low eye irritation, but had low antiseptic effect.

【００２０】実施例４ ポリオキシエチレン（６０）硬化ヒマシ油（ニッコール
ＨＣＯ−６０）３ｇ、ビタミンＥアセテート０．５ｇ、
ビタミンＡパルミテート（１７０万国際単位）０．２ｇ
を加温溶解する。これに塩酸テトラヒドロゾリン０．５
ｇ、塩化ベンゼトニウム０．０５ｇ、クロロブタノール
１ｇ、ｌ−メントール０．０５ｇ、プロピレングリコー
ル５ｇ、アラントイン１ｇ、パンテノール０．２ｇ、イ
プシロン−アミノカプロン酸１０ｇ、エチレンジアミン
四酢酸二ナトリウム０．０５ｇを混合し、希塩酸でｐＨ
を５．５に調整した後、精製水で全量を１０００ｍｌと
し、無菌ろ過し点眼容器に充填して点眼剤とする。後記
表２に示すように、本製剤の防腐効力は高く、しかも眼
に対する刺激性は極めて弱かった。Example 4 3 g of polyoxyethylene (60) hydrogenated castor oil (Nikkor HCO-60), 0.5 g of vitamin E acetate,
Vitamin A palmitate (1.7 million international units) 0.2 g
Dissolve by heating. Tetrahydrozoline hydrochloride 0.5
g, benzethonium chloride 0.05 g, chlorobutanol 1 g, 1-menthol 0.05 g, propylene glycol 5 g, allantoin 1 g, panthenol 0.2 g, epsilon-aminocaproic acid 10 g, and ethylenediaminetetraacetic acid disodium 0.05 g are mixed, PH with dilute hydrochloric acid
After adjusting to 5.5, the total volume is adjusted to 1000 ml with purified water, sterile filtered and filled in an eye drop container to give an eye drop. As shown in Table 2 below, the antiseptic effect of this preparation was high and the eye irritation was extremely weak.

【００２１】比較例８ ポリオキシエチレン（６０）硬化ヒマシ油（ニッコール
ＨＣＯ−６０）３ｇ、ビタミンＥアセテート０．５ｇ、
ビタミンＡパルミテート（１７０万国際単位）０．２ｇ
を加温溶解する。これに塩酸テトラヒドロゾリン０．５
ｇ、塩化ベンゼトニウム０．０５ｇ、ｌ−メントール
０．０５ｇ、プロピレングリコール５ｇ、アラントイン
１ｇ、パンテノール０．２ｇ、イプシロン−アミノカプ
ロン酸１０ｇ、エチレンジアミン四酢酸二ナトリウム
０．０５ｇを混合し、希塩酸でｐＨを５．５に調整した
後、精製水で全量を１０００ｍｌとし、無菌ろ過し点眼
容器に充填して点眼剤とする。後記表２に示すように、
本製剤の防腐効力は低く、また眼に対する刺激性は極め
て強かった。Comparative Example 8 3 g of polyoxyethylene (60) hydrogenated castor oil (Nikkor HCO-60), 0.5 g of vitamin E acetate,
Vitamin A palmitate (1.7 million international units) 0.2 g
Dissolve by heating. Tetrahydrozoline hydrochloride 0.5
g, benzethonium chloride 0.05 g, 1-menthol 0.05 g, propylene glycol 5 g, allantoin 1 g, panthenol 0.2 g, epsilon-aminocaproic acid 10 g, and ethylenediaminetetraacetic acid disodium 0.05 g are mixed, and the pH is adjusted with diluted hydrochloric acid. After adjusting to 5.5, the total volume is made 1000 ml with purified water, sterile filtered and filled in an eye drop container to give an eye drop. As shown in Table 2 below,
The preservative efficacy of this preparation was low, and the irritation to the eye was extremely strong.

【００２２】実施例５ ポリオキシエチレン（６０）硬化ヒマシ油（ニッコール
ＨＣＯ−６０）３ｇ、ビタミンＥアセテート０．５ｇ、
ビタミンＡパルミテート（１７０万国際単位）０．２ｇ
を加温溶解する。これに塩酸テトラヒドロゾリン０．５
ｇ、塩化ベンゼトニウム０．０２５ｇ、クロロブタノー
ル１．０ｇ、メチルパラベン０．０５ｇ、プロピルパラ
ベン０．００５ｇ、ｌ−メントール０．０５ｇ、プロピ
レングリコール５ｇ、アラントイン１ｇ、パンテノール
０．２ｇ、イプシロン−アミノカプロン酸１０ｇ、エチ
レンジアミン四酢酸二ナトリウム０．０５ｇを混合し、
水酸化ナトリウムでｐＨを７．０に調整した後、精製水
で全量を１０００ｍｌとし、無菌ろ過し点眼容器に充填
して点眼剤とする。後記表２に示すように、本製剤の防
腐効力は高く、しかも眼に対する刺激性は極めて弱かっ
た。尚、実施例３〜５及び比較例６〜８の防腐効力及び
眼に対する刺激性の評価結果一覧を表２に示した。Example 5 3 g of polyoxyethylene (60) hydrogenated castor oil (Nikkor HCO-60), 0.5 g of vitamin E acetate,
Vitamin A palmitate (1.7 million international units) 0.2 g
Dissolve by heating. Tetrahydrozoline hydrochloride 0.5
g, benzethonium chloride 0.025 g, chlorobutanol 1.0 g, methylparaben 0.05 g, propylparaben 0.005 g, l-menthol 0.05 g, propylene glycol 5 g, allantoin 1 g, panthenol 0.2 g, epsilon-aminocaproic acid 10 g , 0.05 g of disodium ethylenediamine tetraacetate,
After adjusting the pH to 7.0 with sodium hydroxide, the total amount is adjusted to 1000 ml with purified water, sterile filtered and filled in an eye drop container to obtain an eye drop. As shown in Table 2 below, the antiseptic effect of this preparation was high and the eye irritation was extremely weak. In addition, Table 2 shows a list of evaluation results of antiseptic efficacy and eye irritation of Examples 3 to 5 and Comparative Examples 6 to 8.

【００２３】[0023]

【表２】 実施 比較 比較 実施 比較 実施 例３ 例６ 例７ 例４ 例８ 例５ 評価結果： 防腐効力 Ps.aeruginosa ○ ○ × ○ △ ○ E.coli. ○ ○ × ○ △ ○ A.niger ○ ○ △ ○ × ○ 眼に対する刺激性 ○ × ○ ○ × ○ [Table 2] Comparative comparison Comparative comparative Example 3 Example 6 Example 7 Example 4 Example 8 Example 5 Evaluation results: Antiseptic effect Ps.aeruginosa ○ ○ × ○ △ ○ E.coli. ○ ○ × ○ △ ○ A.niger ○ ○ △ ○ × ○ Eye irritation ○ × ○ ○ × ○

Claims (1)

【特許請求の範囲】[Claims] 【請求項１】 非イオン界面活性剤、ビタミンＡ類、第
４級アンモニウム型カチオン界面活性剤およびクロロブ
タノール及び／またはパラオキシ安息香酸エステルを配
合したことを特徴とするビタミンＡ類可溶化点眼剤。1. A vitamin A solubilized eye drop comprising a nonionic surfactant, vitamin A, a quaternary ammonium type cationic surfactant and chlorobutanol and / or paraoxybenzoic acid ester.
JP5076128A 1993-03-10 1993-03-10 Vitamin as-solubilizing eye drop Pending JPH06263630A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP5076128A JPH06263630A (en) 1993-03-10 1993-03-10 Vitamin as-solubilizing eye drop

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP5076128A JPH06263630A (en) 1993-03-10 1993-03-10 Vitamin as-solubilizing eye drop

Publications (1)

Publication Number Publication Date
JPH06263630A true JPH06263630A (en) 1994-09-20

Family

ID=13596303

Family Applications (1)

Application Number Title Priority Date Filing Date
JP5076128A Pending JPH06263630A (en) 1993-03-10 1993-03-10 Vitamin as-solubilizing eye drop

Country Status (1)

Country Link
JP (1) JPH06263630A (en)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009263374A (en) * 2001-03-01 2009-11-12 Lonza Inc Preservative blend containing quaternary ammonium compound
US8343945B2 (en) 2007-12-07 2013-01-01 Foamix Ltd. Carriers, formulations, methods for formulating unstable active agents for external application and uses thereof
US8362091B2 (en) 2003-08-04 2013-01-29 Foamix Ltd. Foamable vehicle and pharmaceutical compositions thereof
US8435498B2 (en) 2002-10-25 2013-05-07 Foamix Ltd. Penetrating pharmaceutical foam
US8486375B2 (en) 2003-04-28 2013-07-16 Foamix Ltd. Foamable compositions
US8486376B2 (en) 2002-10-25 2013-07-16 Foamix Ltd. Moisturizing foam containing lanolin
US8512718B2 (en) 2000-07-03 2013-08-20 Foamix Ltd. Pharmaceutical composition for topical application
US8518378B2 (en) 2003-08-04 2013-08-27 Foamix Ltd. Oleaginous pharmaceutical and cosmetic foam
US8518376B2 (en) 2007-12-07 2013-08-27 Foamix Ltd. Oil-based foamable carriers and formulations
US8618081B2 (en) 2009-10-02 2013-12-31 Foamix Ltd. Compositions, gels and foams with rheology modulators and uses thereof
US8636982B2 (en) 2007-08-07 2014-01-28 Foamix Ltd. Wax foamable vehicle and pharmaceutical compositions thereof
US8709385B2 (en) 2008-01-14 2014-04-29 Foamix Ltd. Poloxamer foamable pharmaceutical compositions with active agents and/or therapeutic cells and uses
US8722021B2 (en) 2002-10-25 2014-05-13 Foamix Ltd. Foamable carriers
US8795635B2 (en) 2006-11-14 2014-08-05 Foamix Ltd. Substantially non-aqueous foamable petrolatum based pharmaceutical and cosmetic compositions and their uses
US8795693B2 (en) 2003-08-04 2014-08-05 Foamix Ltd. Compositions with modulating agents
US8900554B2 (en) 2002-10-25 2014-12-02 Foamix Pharmaceuticals Ltd. Foamable composition and uses thereof
US9072667B2 (en) 2009-07-29 2015-07-07 Foamix Pharmaceuticals Ltd. Non surface active agent non polymeric agent hydro-alcoholic foamable compositions, breakable foams and their uses
US9167813B2 (en) 2009-07-29 2015-10-27 Foamix Pharmaceuticals Ltd. Non surfactant hydro-alcoholic foamable compositions, breakable foams and their uses
US9211259B2 (en) 2002-11-29 2015-12-15 Foamix Pharmaceuticals Ltd. Antibiotic kit and composition and uses thereof
US9265725B2 (en) 2002-10-25 2016-02-23 Foamix Pharmaceuticals Ltd. Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof
US9320705B2 (en) 2002-10-25 2016-04-26 Foamix Pharmaceuticals Ltd. Sensation modifying topical composition foam
US9439857B2 (en) 2007-11-30 2016-09-13 Foamix Pharmaceuticals Ltd. Foam containing benzoyl peroxide
US9539208B2 (en) 2002-10-25 2017-01-10 Foamix Pharmaceuticals Ltd. Foam prepared from nanoemulsions and uses
US9622947B2 (en) 2002-10-25 2017-04-18 Foamix Pharmaceuticals Ltd. Foamable composition combining a polar solvent and a hydrophobic carrier
US9668972B2 (en) 2002-10-25 2017-06-06 Foamix Pharmaceuticals Ltd. Nonsteroidal immunomodulating kit and composition and uses thereof
US9849142B2 (en) 2009-10-02 2017-12-26 Foamix Pharmaceuticals Ltd. Methods for accelerated return of skin integrity and for the treatment of impetigo
US9884017B2 (en) 2009-04-28 2018-02-06 Foamix Pharmaceuticals Ltd. Foamable vehicles and pharmaceutical compositions comprising aprotic polar solvents and uses thereof
US10398641B2 (en) 2016-09-08 2019-09-03 Foamix Pharmaceuticals Ltd. Compositions and methods for treating rosacea and acne

Cited By (77)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8512718B2 (en) 2000-07-03 2013-08-20 Foamix Ltd. Pharmaceutical composition for topical application
JP2009263374A (en) * 2001-03-01 2009-11-12 Lonza Inc Preservative blend containing quaternary ammonium compound
US9492412B2 (en) 2002-10-25 2016-11-15 Foamix Pharmaceuticals Ltd. Penetrating pharmaceutical foam
US9622947B2 (en) 2002-10-25 2017-04-18 Foamix Pharmaceuticals Ltd. Foamable composition combining a polar solvent and a hydrophobic carrier
US8900554B2 (en) 2002-10-25 2014-12-02 Foamix Pharmaceuticals Ltd. Foamable composition and uses thereof
US9539208B2 (en) 2002-10-25 2017-01-10 Foamix Pharmaceuticals Ltd. Foam prepared from nanoemulsions and uses
US10117812B2 (en) 2002-10-25 2018-11-06 Foamix Pharmaceuticals Ltd. Foamable composition combining a polar solvent and a hydrophobic carrier
US9320705B2 (en) 2002-10-25 2016-04-26 Foamix Pharmaceuticals Ltd. Sensation modifying topical composition foam
US9265725B2 (en) 2002-10-25 2016-02-23 Foamix Pharmaceuticals Ltd. Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof
US9713643B2 (en) 2002-10-25 2017-07-25 Foamix Pharmaceuticals Ltd. Foamable carriers
US8435498B2 (en) 2002-10-25 2013-05-07 Foamix Ltd. Penetrating pharmaceutical foam
US10322085B2 (en) 2002-10-25 2019-06-18 Foamix Pharmaceuticals Ltd. Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof
US11033491B2 (en) 2002-10-25 2021-06-15 Vyne Therapeutics Inc. Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof
US8722021B2 (en) 2002-10-25 2014-05-13 Foamix Ltd. Foamable carriers
US8741265B2 (en) 2002-10-25 2014-06-03 Foamix Ltd. Penetrating pharmaceutical foam
US8486376B2 (en) 2002-10-25 2013-07-16 Foamix Ltd. Moisturizing foam containing lanolin
US9668972B2 (en) 2002-10-25 2017-06-06 Foamix Pharmaceuticals Ltd. Nonsteroidal immunomodulating kit and composition and uses thereof
US8840869B2 (en) 2002-10-25 2014-09-23 Foamix Ltd. Body cavity foams
US10821077B2 (en) 2002-10-25 2020-11-03 Foamix Pharmaceuticals Ltd. Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof
US9211259B2 (en) 2002-11-29 2015-12-15 Foamix Pharmaceuticals Ltd. Antibiotic kit and composition and uses thereof
US8486375B2 (en) 2003-04-28 2013-07-16 Foamix Ltd. Foamable compositions
US9101662B2 (en) 2003-08-04 2015-08-11 Foamix Pharmaceuticals Ltd. Compositions with modulating agents
US8518378B2 (en) 2003-08-04 2013-08-27 Foamix Ltd. Oleaginous pharmaceutical and cosmetic foam
US8795693B2 (en) 2003-08-04 2014-08-05 Foamix Ltd. Compositions with modulating agents
US9050253B2 (en) 2003-08-04 2015-06-09 Foamix Pharmaceuticals Ltd. Oleaginous pharmaceutical and cosmetic foam
US8362091B2 (en) 2003-08-04 2013-01-29 Foamix Ltd. Foamable vehicle and pharmaceutical compositions thereof
US8703105B2 (en) 2003-08-04 2014-04-22 Foamix Ltd. Oleaginous pharmaceutical and cosmetic foam
US9636405B2 (en) 2003-08-04 2017-05-02 Foamix Pharmaceuticals Ltd. Foamable vehicle and pharmaceutical compositions thereof
US9682021B2 (en) 2006-11-14 2017-06-20 Foamix Pharmaceuticals Ltd. Substantially non-aqueous foamable petrolatum based pharmaceutical and cosmetic compositions and their uses
US8795635B2 (en) 2006-11-14 2014-08-05 Foamix Ltd. Substantially non-aqueous foamable petrolatum based pharmaceutical and cosmetic compositions and their uses
US8636982B2 (en) 2007-08-07 2014-01-28 Foamix Ltd. Wax foamable vehicle and pharmaceutical compositions thereof
US10369102B2 (en) 2007-08-07 2019-08-06 Foamix Pharmaceuticals Ltd. Wax foamable vehicle and pharmaceutical compositions thereof
US11103454B2 (en) 2007-08-07 2021-08-31 Vyne Therapeutics Inc. Wax foamable vehicle and pharmaceutical compositions thereof
US9662298B2 (en) 2007-08-07 2017-05-30 Foamix Pharmaceuticals Ltd. Wax foamable vehicle and pharmaceutical compositions thereof
US9439857B2 (en) 2007-11-30 2016-09-13 Foamix Pharmaceuticals Ltd. Foam containing benzoyl peroxide
US8343945B2 (en) 2007-12-07 2013-01-01 Foamix Ltd. Carriers, formulations, methods for formulating unstable active agents for external application and uses thereof
US9549898B2 (en) 2007-12-07 2017-01-24 Foamix Pharmaceuticals Ltd. Oil and liquid silicone foamable carriers and formulations
US9161916B2 (en) 2007-12-07 2015-10-20 Foamix Pharmaceuticals Ltd. Carriers, formulations, methods for formulating unstable active agents for external application and uses thereof
US8900553B2 (en) 2007-12-07 2014-12-02 Foamix Pharmaceuticals Ltd. Oil and liquid silicone foamable carriers and formulations
US11433025B2 (en) 2007-12-07 2022-09-06 Vyne Therapeutics Inc. Oil foamable carriers and formulations
US9795564B2 (en) 2007-12-07 2017-10-24 Foamix Pharmaceuticals Ltd. Oil-based foamable carriers and formulations
US8518376B2 (en) 2007-12-07 2013-08-27 Foamix Ltd. Oil-based foamable carriers and formulations
US8709385B2 (en) 2008-01-14 2014-04-29 Foamix Ltd. Poloxamer foamable pharmaceutical compositions with active agents and/or therapeutic cells and uses
US10363216B2 (en) 2009-04-28 2019-07-30 Foamix Pharmaceuticals Ltd. Foamable vehicles and pharmaceutical compositions comprising aprotic polar solvents and uses thereof
US10213384B2 (en) 2009-04-28 2019-02-26 Foamix Pharmaceuticals Ltd. Foamable vehicles and pharmaceutical compositions comprising aprotic polar solvents and uses thereof
US10588858B2 (en) 2009-04-28 2020-03-17 Foamix Pharmaceuticals Ltd. Foamable vehicles and pharmaceutical compositions comprising aprotic polar solvents and uses thereof
US9884017B2 (en) 2009-04-28 2018-02-06 Foamix Pharmaceuticals Ltd. Foamable vehicles and pharmaceutical compositions comprising aprotic polar solvents and uses thereof
US10350166B2 (en) 2009-07-29 2019-07-16 Foamix Pharmaceuticals Ltd. Non surface active agent non polymeric agent hydro-alcoholic foamable compositions, breakable foams and their uses
US9572775B2 (en) 2009-07-29 2017-02-21 Foamix Pharmaceuticals Ltd. Non surfactant hydro-alcoholic foamable compositions, breakable foams and their uses
US10092588B2 (en) 2009-07-29 2018-10-09 Foamix Pharmaceuticals Ltd. Foamable compositions, breakable foams and their uses
US11219631B2 (en) 2009-07-29 2022-01-11 Vyne Pharmaceuticals Inc. Foamable compositions, breakable foams and their uses
US9072667B2 (en) 2009-07-29 2015-07-07 Foamix Pharmaceuticals Ltd. Non surface active agent non polymeric agent hydro-alcoholic foamable compositions, breakable foams and their uses
US9167813B2 (en) 2009-07-29 2015-10-27 Foamix Pharmaceuticals Ltd. Non surfactant hydro-alcoholic foamable compositions, breakable foams and their uses
US10463742B2 (en) 2009-10-02 2019-11-05 Foamix Pharmaceuticals Ltd. Topical tetracycline compositions
US8992896B2 (en) 2009-10-02 2015-03-31 Foamix Pharmaceuticals Ltd. Topical tetracycline compositions
US10265404B2 (en) 2009-10-02 2019-04-23 Foamix Pharmaceuticals Ltd. Compositions, gels and foams with rheology modulators and uses thereof
US10322186B2 (en) 2009-10-02 2019-06-18 Foamix Pharmaceuticals Ltd. Topical tetracycline compositions
US9675700B2 (en) 2009-10-02 2017-06-13 Foamix Pharmaceuticals Ltd. Topical tetracycline compositions
US10213512B2 (en) 2009-10-02 2019-02-26 Foamix Pharmaceuticals Ltd. Topical tetracycline compositions
US9849142B2 (en) 2009-10-02 2017-12-26 Foamix Pharmaceuticals Ltd. Methods for accelerated return of skin integrity and for the treatment of impetigo
US10137200B2 (en) 2009-10-02 2018-11-27 Foamix Pharmaceuticals Ltd. Surfactant-free water-free foamable compositions, breakable foams and gels and their uses
US8618081B2 (en) 2009-10-02 2013-12-31 Foamix Ltd. Compositions, gels and foams with rheology modulators and uses thereof
US10086080B2 (en) 2009-10-02 2018-10-02 Foamix Pharmaceuticals Ltd. Topical tetracycline compositions
US10517882B2 (en) 2009-10-02 2019-12-31 Foamix Pharmaceuticals Ltd. Method for healing of an infected acne lesion without scarring
US10238746B2 (en) 2009-10-02 2019-03-26 Foamix Pharmaceuticals Ltd Surfactant-free water-free foamable compositions, breakable foams and gels and their uses
US10610599B2 (en) 2009-10-02 2020-04-07 Foamix Pharmaceuticals Ltd. Topical tetracycline compositions
US8945516B2 (en) 2009-10-02 2015-02-03 Foamix Pharmaceuticals Ltd. Surfactant-free water-free foamable compositions, breakable foams and gels and their uses
US10821187B2 (en) 2009-10-02 2020-11-03 Foamix Pharmaceuticals Ltd. Compositions, gels and foams with rheology modulators and uses thereof
US10835613B2 (en) 2009-10-02 2020-11-17 Foamix Pharmaceuticals Ltd. Compositions, gels and foams with rheology modulators and uses thereof
US10029013B2 (en) 2009-10-02 2018-07-24 Foamix Pharmaceuticals Ltd. Surfactant-free, water-free formable composition and breakable foams and their uses
US10946101B2 (en) 2009-10-02 2021-03-16 Vyne Therapeutics Inc. Surfactant-free water-free foamable compositions, breakable foams and gels and their uses
US10967063B2 (en) 2009-10-02 2021-04-06 Vyne Therapeutics Inc. Surfactant-free, water-free formable composition and breakable foams and their uses
US8871184B2 (en) 2009-10-02 2014-10-28 Foamix Ltd. Topical tetracycline compositions
US8865139B1 (en) 2009-10-02 2014-10-21 Foamix Pharmaceuticals Ltd. Topical tetracycline compositions
US10849847B2 (en) 2016-09-08 2020-12-01 Foamix Pharamaceuticals Ltd. Compositions and methods for treating rosacea and acne
US11324691B2 (en) 2016-09-08 2022-05-10 Journey Medical Corporation Compositions and methods for treating rosacea and acne
US10398641B2 (en) 2016-09-08 2019-09-03 Foamix Pharmaceuticals Ltd. Compositions and methods for treating rosacea and acne

Similar Documents

Publication Publication Date Title
JPH06263630A (en) Vitamin as-solubilizing eye drop
JP3689123B2 (en) Vitamin A solubilized aqueous eye drops
JP2003183157A (en) Ophthalmologic composition
JP2002356420A (en) Table aqueous liquid medicine
JP2003252800A (en) External composition for mucosa
CA2615108A1 (en) Preservative composition for ophthalmic use
JPH06340525A (en) Stable eye lotion containing solubilized vitamin a and having low stimulation to eye
JP4753448B2 (en) Retinol palmitate, method for stabilizing retinol and aqueous vitamins
JP2939082B2 (en) Stable vitamin A palmitate and vitamin E solubilized eye drops
JPH05271053A (en) Stable eye lotion
EP2919755B1 (en) Aqueous liquid composition containing 2-amino-3-(4-bromobenzoyl)phenylacetic acid
JP3551977B2 (en) Stable vitamin A and vitamin E solubilized eye drops
JP2003002837A (en) Composition for aqueous skin care preparation and method for preventing clouding of liquid composition
JPH08198746A (en) Solubilized eye drop
JP2002114711A (en) External preparation composition
JP4801300B2 (en) Liquid composition for external use
JP5013735B2 (en) Ocular mucosa application
JPH05139955A (en) Stable instillation
JP5246182B2 (en) Eye drops, preservatives and preservatives
KR100791871B1 (en) Aseptics
JP3802328B2 (en) Vitamin A solubilized aqueous solution and eye drops
JP4157988B2 (en) Water-soluble preparations with no contraindications
JP4132461B2 (en) Ophthalmic liquid composition
JP4524538B2 (en) Ophthalmic composition
JP6704702B2 (en) Aqueous external composition containing iodine-based bactericidal component