JPS60258110A - Progesterone emulsified parenteral solution injectable intravenously - Google Patents
Progesterone emulsified parenteral solution injectable intravenouslyInfo
- Publication number
- JPS60258110A JPS60258110A JP11525084A JP11525084A JPS60258110A JP S60258110 A JPS60258110 A JP S60258110A JP 11525084 A JP11525084 A JP 11525084A JP 11525084 A JP11525084 A JP 11525084A JP S60258110 A JPS60258110 A JP S60258110A
- Authority
- JP
- Japan
- Prior art keywords
- progesterone
- injection
- emulsified
- lecithin
- oil
- 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.)
- Granted
Links
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明はプロゲステロン注射液、特に静脈注射可能なプ
ロゲステロン乳化注射液に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a progesterone injection solution, particularly an intravenously injectable progesterone emulsion injection solution.
従来例の構成とその問題点
プロゲステロンは黄体ホルモンとして周知の物質であり
、婦人科領域で注射剤または錠剤の形で使用されている
。プロゲステロン注射剤は、プロゲステロンが水に殆ん
ど溶解しないため、油性注射液または水性懸濁注射液と
して提供され、これらの注射液は専ら筋肉内に投与され
る。Structure of conventional examples and their problems Progesterone is a substance well known as a progestin, and is used in the form of injections or tablets in the field of gynecology. Since progesterone hardly dissolves in water, progesterone injections are provided as oil-based injections or aqueous suspension injections, and these injections are exclusively administered intramuscularly.
プロゲステロンを治療目的に用いる場合、１回の投与量
を多くし、かつ投与を継続する必要にせまられることが
ある。かかる場合、在来の注射液で筋肉注射を続けると
、注射部位に好ましからぬ副作用、例えば硬結、疼痛等
を生じ継続長期投与に支障をきたすことがある。このた
め筋肉注射液でなく静脈投与が可能な注射液が望まれて
いる。When progesterone is used for therapeutic purposes, it may be necessary to increase the single dose and to continue administering it. In such cases, if intramuscular injections are continued with conventional injection solutions, undesirable side effects such as induration and pain may occur at the injection site, which may impede continued long-term administration. Therefore, an injection solution that can be administered intravenously rather than an intramuscular injection solution is desired.
プロゲステロンを静脈に投与できるようにするためには
、界面活性剤を用いて可溶化する方法が考えられるが、
かかる方法は合成界面活性剤の副作用（例えばショック
）の点で好ましくない。In order to make it possible to administer progesterone intravenously, one possible method is to solubilize it using a surfactant.
Such a method is unfavorable in view of the side effects (eg, shock) of synthetic surfactants.
発明の目的
本発明は静脈注射可能なプロ・ゲステロンの乳化注射液
を提供することにある。OBJECTS OF THE INVENTION The present invention provides an emulsified injection solution of progesterone that can be injected intravenously.
発明の構成
本発明はプロゲステロン、植物油およびレシチンを含有
する静脈注射可能な乳化注射液、および更に安息香酸ベ
ンジルを配合した静脈注射可能な乳化注射液にある。Structure of the Invention The present invention is an intravenously injectable emulsified injection solution containing progesterone, vegetable oil and lecithin, and an intravenously injectable emulsified injection solution further formulated with benzyl benzoate.
本発明者等は、プロゲステロンを水可溶性にするのでは
なく、静脈注射が可能な程度に微粒子状に乳化分散せし
め、かつ安定性良好で長期保存し得るような乳化注射液
を製造するため種々検討を重ねて来た。その結果プロゲ
ステロンを油溶性注射液に汎用されている植物油に溶解
し、レシチンを乳化剤として使用して水に乳化すること
により、静脈注射可能な乳化注射液を製造することに成
功し、本発明を完成した。The present inventors have conducted various studies in order to produce an emulsified injection solution that does not make progesterone water-soluble, but emulsifies and disperses it into fine particles that can be injected intravenously, and that has good stability and can be stored for a long time. I came over and over again. As a result, by dissolving progesterone in vegetable oil, which is commonly used for oil-soluble injections, and emulsifying it in water using lecithin as an emulsifier, they succeeded in producing an emulsified injection solution that can be injected intravenously. completed.
またプロゲステロンを植物油に溶解する場合、安息香酸
ベンジルを併用することによって、乳化注射液中のプロ
ゲステロンの最終濃度を更に高めることができることを
見出し本発明を完成した。Furthermore, when progesterone is dissolved in vegetable oil, the inventors have discovered that the final concentration of progesterone in the emulsified injection solution can be further increased by using benzyl benzoate in combination, thereby completing the present invention.
本発明で使用しうる植物油としては、大豆油、ゴマ油、
綿実油等があり、プロゲステロンの油溶性注射液を作る
場合の溶剤として通常使用されている植物油を使用する
ことができ、特に制限はない。また本発明で使用しつる
レシチンとしては卵黄レシチン、大豆レシチン等がある
。Vegetable oils that can be used in the present invention include soybean oil, sesame oil,
Vegetable oils such as cottonseed oil, which are commonly used as solvents for producing oil-soluble injections of progesterone, can be used, and there are no particular limitations. The vine lecithin used in the present invention includes egg yolk lecithin, soybean lecithin, and the like.
大豆油１００ｆに対するプロゲステロンの溶解度（ｆ）
と温度の関係を第１図に示す。第１図から明らかな如く
、大豆油１００ｆに対するプロゲステロンの溶解度は４
℃で約１．３ｆ即ち１．３重量％、２０°Ｃで約２．２
ｆ即ち２．２重量％である。Solubility of progesterone in 100f of soybean oil (f)
The relationship between temperature and temperature is shown in Figure 1. As is clear from Figure 1, the solubility of progesterone in 100f of soybean oil is 4.
About 1.3f or 1.3% by weight at °C, about 2.2 at 20°C
f, that is, 2.2% by weight.
大豆油に卵黄レシチンを加えた混合液（卵黄レシチン１
０重量％含有）にプロゲステロンを溶解すると、混合液
１００？に対し、４℃でプロゲステロンの溶解度は約２
重量％に上昇することが判った。かかるプロゲステロン
溶解液を保存する場合、温度によってプロゲステロンが
結晶析出してはならない。従って、種々の温度で上記大
豆油および卵黄レシチン混合液にプロゲステロンを加熱
溶解し、０°Ｃで７日間保存した場合のプロゲステロン
結Ｍ析出の有無を検討した。 、ｉ：・
その結果を下表１に示す。A mixture of soybean oil and egg yolk lecithin (1 egg yolk lecithin)
When progesterone is dissolved in (containing 0% by weight), the mixed solution is 100%? On the other hand, the solubility of progesterone at 4℃ is about 2
% by weight. When storing such a progesterone solution, progesterone must not be crystallized due to temperature. Therefore, the presence or absence of progesterone M precipitation was investigated when progesterone was heated and dissolved in the soybean oil and egg yolk lecithin mixture at various temperatures and stored at 0°C for 7 days. , i:・ The results are shown in Table 1 below.
表 １
０．８？ ９１１ｆ ＋
０．６Ｆ ＋
０．５５’ ＋
０４２ ＋
０．３２ ＋
０．２ｒ −
０１２−
上記第１表の結果から大豆油および卵黄レシチン（１０
重量％含有）の混合液にプロゲステロンを溶解し、長期
保存するためには、プロゲステロンを混合液１００ｆに
対して２２、即ち２重量％とすると良いことが判る。Table 1 0.8? 911f + 0.6F + 0.55' + 042 + 0.32 + 0.2r - 012- From the results in Table 1 above, soybean oil and egg yolk lecithin (10
In order to dissolve progesterone in a mixed solution (containing 100f of progesterone by weight) and store it for a long period of time, it is found that it is best to add progesterone to 100 f of the mixed solution at a concentration of 22, ie, 2% by weight.
安息香酸ベンジルは植物油と相溶性であり、かつ注射液
の溶剤に使用された実績がある。安息香噛ベンジルのプ
ロゲステロンに対する溶解度は大きく、室温で約３０重
量％、０ ’Ｃで約２０重量％であった。大豆油、卵黄
レシチン混合物に更に安息香酸ベンジルを加えるとプロ
ゲステロンの溶解度は安息香酸ベンジルを加えない場合
に比し、更に増大し、例えば大豆油、レシチン、安息香
酸ベンジルの混合物（重量で１０：１：１．５）におけ
るプロゲステロンの溶解度は０°Ｃで約４重量％（混合
物１００Ｆに対しプロゲステロン約４２）であった。従
ってプロゲステロンをこの３成分混合物に溶解し、０″
Ｃでも結晶析出を生ぜしめずに保存するのに、安息香酸
ベンジルを含まぬ場合に比し、約２倍量のプロゲステロ
ンを含有させることができることが判った。Benzyl benzoate is compatible with vegetable oils and has been used as a solvent for injections. The solubility of benzyl benzyl in progesterone was high, about 30% by weight at room temperature and about 20% by weight at 0'C. When benzyl benzoate is further added to the soybean oil and egg yolk lecithin mixture, the solubility of progesterone is further increased compared to when benzyl benzoate is not added. The solubility of progesterone in :1.5) was about 4% by weight at 0°C (about 42% progesterone per 100F of the mixture). Therefore, progesterone is dissolved in this ternary mixture and 0″
It has been found that even with C, it is possible to contain approximately twice the amount of progesterone as compared to a case in which benzyl benzoate is not included, while preserving the product without causing crystal precipitation.
上述したことから本発明者等は種々検討の結果、植物油
とレシチンの２成分系では、大豆油対レシチンの割合は
重量比で１ ： ０．１〜１：１とすれば良＜１：０．
１５〜１：０．４が好ましい。Based on the above, the present inventors have conducted various studies and found that in a two-component system of vegetable oil and lecithin, the ratio of soybean oil to lecithin should be 1:0.1 to 1:1 by weight <1:0. ．．
15-1:0.4 is preferred.
この２成分系混合液に対し、プロゲステロンは２重量％
以下とするのが好ましい。Progesterone is 2% by weight in this two-component mixture.
The following is preferable.
また上述した植物油とレシチンおよび安息香酸ベンジル
の３成分系ではこれらの割合は重量比で１：０．１：０
．１〜１ ： ０．３ ： ０．３、好ましくは１：０
．１５：０．１５〜１：０．２：０．２５とする。この
場合プロゲステロンは４重量％まで含有させることがで
きる。Furthermore, in the three-component system of vegetable oil, lecithin, and benzyl benzoate mentioned above, the weight ratio of these is 1:0.1:0.
．． 1-1:0.3:0.3, preferably 1:0
．． 15:0.15 to 1:0.2:0.25. In this case, progesterone can be contained up to 4% by weight.
本発明の乳化注射液を製造するに当っては、上述したプ
ロゲステロンを植物油およびレシチンからなる溶液、ま
たは更に安息香酸ベンジルを含む溶液を、これら混合溶
液の約４〜２０倍量（容壜）の水に乳化する。乳化する
に当っては上記混合溶液を水中に添加し、通常使用され
る高圧ホモジナイザーあるいは超音波乳化機を用いて常
法どおり実施できる。なお形成されるプロゲステロン含
有液の乳化性を良好にするためオレイン酸ナトリウム、
パルミチン酸ナトリウムの如き高級脂肪学境を乳化補助
剤として、０．５重世％以下用いてもよい。また滲透圧
を血液と等張とするためぶどう糖、果糖の如き糖類。In producing the emulsified injection solution of the present invention, the above-mentioned progesterone solution consisting of vegetable oil and lecithin, or a solution further containing benzyl benzoate, is added in an amount approximately 4 to 20 times the volume (bottle) of these mixed solutions. Emulsify in water. Emulsification can be carried out in a conventional manner by adding the above mixed solution to water and using a commonly used high-pressure homogenizer or ultrasonic emulsifier. In addition, in order to improve the emulsifying properties of the progesterone-containing liquid that is formed, sodium oleate,
Higher fatty acids such as sodium palmitate may be used as emulsification aids in amounts up to 0.5%. Also, sugars such as glucose and fructose are used to make the osmotic pressure isotonic with the blood.
ソルビット、マンニット、グリセリンの如キ多価アルコ
ールを加えてもよい。これらは乳化する水に予め溶解し
てもよく、あるいは乳化後乳化液に加えてもよい。Polyhydric alcohols such as sorbitol, mannitol, and glycerin may also be added. These may be dissolved in advance in the water to be emulsified, or may be added to the emulsion after emulsification.
上述した如くして製造された本発明による乳化液は、分
散している粒子径が１／ｌ以下であり、Ｏ′Ｃで長ｊｄ
間保存してもプロゲステロンの結晶が析出することはな
く安定である。また加熱減菌に対しても安定であり、粒
子径の粗大化、油滴生成、変色は見られない。本発明に
よるプロゲステロン含有乳化注射液はそのまま静脈内投
与してもよく、また各種輸液と混合して静脈内投与して
もよい。The emulsion according to the present invention produced as described above has a dispersed particle size of 1/l or less, and a length jd at O'C.
Even if stored for a long time, progesterone crystals do not precipitate and it is stable. It is also stable against heat sterilization, and no coarsening of particle size, formation of oil droplets, or discoloration is observed. The progesterone-containing emulsified injection solution according to the present invention may be administered intravenously as it is, or may be mixed with various infusion solutions and administered intravenously.
実施例の説明
以下に実施例を挙げて本発明を説明するが、本発明はこ
れら実施例に限定されるものではない。百分率は重量に
よる。DESCRIPTION OF EXAMPLES The present invention will be explained below with reference to Examples, but the present invention is not limited to these Examples. Percentages are by weight.
実施例 １
大豆油２００ ｆ１卵黄レシチン４０ｆおよびプロゲス
テロン４ｆを約８０°Ｃに加熱して均一 １１・に溶解
した。これに２．５％のグリセリンを含む水溶液（水酸
化ナトリウムでｐＨ８に調整）８ｏ。Example 1 Soybean oil 200 f1 egg yolk lecithin 40 f and progesterone 4 f were heated to about 80°C and uniformly dissolved in 11. An aqueous solution containing 2.5% glycerin (adjusted to pH 8 with sodium hydroxide) 8o.
ｍｌを、７０〜８０゛Ｃに加熱して加え、同温度に保ち
ながら、窒素気流中で’ｒｘホモミキサー（特殊機化工
業ＫＬ ’！Ｉ！ｌｊ ）を用いて６０００ ｒｐｍで
３０分間乳化した。さらにひきつづき、７５〜８５°Ｃ
を保ちながらマントンガラリンホモジナイザーで圧力４
５００ｐ８ｉ、パス回ａｉｏ回の条件で乳化した。室温
まで冷却した後、蒸留水を加えて全量１０００ ｍｌと
した。ml was heated to 70-80°C and emulsified at 6000 rpm for 30 minutes in a nitrogen stream using an 'rx homo mixer (Tokushu Kika Kogyo KL'!I!lj) while maintaining the same temperature. . Continue to 75-85°C
Pressure 4 using a Manton Galarin homogenizer while maintaining
Emulsification was carried out under the conditions of 500p8i and aio passes. After cooling to room temperature, distilled water was added to make the total volume 1000 ml.
かくして得られた乳化液は均一な乳濁液で、粒度をコー
ルタ−サブミクロンアナライザーで測定したとき平均粒
子径は０．２／ｌ、検鏡による最大粒子径は１声であっ
た。The emulsion thus obtained was a homogeneous emulsion, and when the particle size was measured using a Coulter submicron analyzer, the average particle size was 0.2/l, and the maximum particle size when measured using a microscope was 1 tone.
この乳化液をミリポアフィルタ−で濾過し、１ＯＮアン
プルに分注し、空間を窒素で置換して溶閉し、１００°
Ｃで６０分間滅菌した。滅菌後、油滴生成、油層分離の
ような外観変化は認められず、粒度は平均粒子径０．３
ｐ 、最大粒子径１声と変化はなかった。プロゲステ
ロン含量を滅菌前後で測定したが、残存率は９７％であ
った（定量法二日局、プロゲスゾロン注射液、定置法を
準用）。またアンプルを氷水中に１ガ月間放置したが結
晶の析出は認められなかった。This emulsion was filtered with a Millipore filter, dispensed into 1ON ampoules, and the space was replaced with nitrogen to melt and seal, and the temperature was increased to 100°.
Sterilized at C for 60 minutes. After sterilization, no changes in appearance such as oil droplet formation or oil layer separation were observed, and the average particle size was 0.3.
p, the maximum particle size remained unchanged at 1 tone. The progesterone content was measured before and after sterilization, and the residual rate was 97% (quantitative method, progestolone injection, and stationary method applied mutatis mutandis). Further, the ampoule was left in ice water for one month, but no crystal precipitation was observed.
実施例 ２
プロゲステロン１０ｔに安息香酸ベンジル３０１を加え
、水浴中で約８０゛Ｃに加熱して溶解した。これに大豆
油２００ｆ、卵黄レシチン４０１を約８０°Ｃに加熱し
て加え、均一に混合した。Example 2 301 parts of benzyl benzoate was added to 10 tons of progesterone and dissolved by heating to about 80°C in a water bath. To this, 200f of soybean oil and 401 egg yolk lecithin were heated to about 80°C and mixed uniformly.
５％ソルビット水溶液（水酸化ナトリウムでｐＨ８に調
整）７５０ｍｌを７０〜８０”Ｃに加熱して加え、同温
度に保ちなから窒素気流中でＴＫホモミキサーで６００
０ ｒｐｍで３０分間乳化した。Add 750 ml of 5% sorbitol aqueous solution (adjusted to pH 8 with sodium hydroxide) heated to 70-80"C, keep at the same temperature, and mix in a nitrogen stream with a TK homomixer for 600 ml.
Emulsification was carried out for 30 minutes at 0 rpm.
さらにひきつづき７５〜８５°Ｃに保ちながらマントン
ガラリンホモジナイザーで、圧力５０００ｐｓｉ、パス
回数１０回で乳化した。室温まで冷却した後、蒸留水を
加えて全１１１０００ｍとした。The mixture was then emulsified using a Manton Galarin homogenizer at a pressure of 5000 psi and 10 passes while maintaining the temperature at 75-85°C. After cooling to room temperature, distilled water was added to make a total of 111,000 m.
かくして得られた乳化液は均一な乳濁液で、粒度をコー
ルタ−サブミクロンアナライザーで測定したとき平均粒
子径は０．２声、検鏡による最大粒子径は１／Ｉであっ
た。The emulsion thus obtained was a homogeneous emulsion, and when the particle size was measured using a Coulter submicron analyzer, the average particle size was 0.2 tones, and the maximum particle size measured using a microscope was 1/I.
この乳化液を実施例１と同じようにアンプルに分注し、
滅菌した。滅菌後、油滴生成、油層分離のような外観変
化は認められなかった。粒度は平均粒子径０．３ 、Ｉ
Ｉ％最大粒子径２μと変化はなかった。プロゲステロン
含量を滅菌前後で測定したが残存率は９８％であった。Dispense this emulsion into ampoules in the same manner as in Example 1,
Sterilized. After sterilization, no changes in appearance such as oil droplet formation or oil layer separation were observed. The particle size is an average particle size of 0.3, I
There was no change in I% maximum particle size of 2μ. Progesterone content was measured before and after sterilization, and the residual rate was 98%.
また、アンプルを氷水中に１力月間放置したが結晶の析
出を認めなかった。Further, the ampoule was left in ice water for one month, but no crystal precipitation was observed.
実施例 ３
プロゲステロン１０２に安息香酸ベンジル３５２を加え
、水浴中で約８０°Ｃに加熱して溶解した。これに大豆
油１５０り、大豆レシチン３０１を約８０″Ｃに加熱し
て加え、均一に混合した。Example 3 Benzyl benzoate 352 was added to progesterone 102 and dissolved by heating to about 80°C in a water bath. 150 parts of soybean oil and 30 parts of soybean lecithin were heated to about 80''C and mixed uniformly.
５％ブドウ糖および０．５％オレイン酸ナトリウムを含
む水溶液７５０ｍ１を７０〜８０°Ｃに加熱して加え、
同温度に保ちながら窒素気流中でＴＫホモミキサーで６
Ｑ ＯＯｒｐｍで３０分間乳化した。さらにひきつづ
き７５〜８５°Ｃに保ちながらマントンガラリンホモジ
ナイザーで圧力５０００ｐｓｉ、パス回数１０回で乳化
した。室温まで冷却した後蒸留水を加えて全量１０００
ｍ７とした。Add 750 ml of an aqueous solution containing 5% glucose and 0.5% sodium oleate heated to 70-80 °C,
6 in a TK homomixer in a nitrogen stream while keeping the same temperature.
Emulsification was carried out for 30 minutes at QOOrpm. The mixture was then emulsified using a Manton Galarin homogenizer at a pressure of 5000 psi and 10 passes while maintaining the temperature at 75-85°C. After cooling to room temperature, add distilled water to make a total volume of 1,000 ml.
It was set as m7.
かくして得られた乳化液は均一な乳濁液で、平均粒子径
は０．２、最大粒子径は１μであった。The emulsion thus obtained was a uniform emulsion, with an average particle size of 0.2 and a maximum particle size of 1 μm.
この乳化液を実施例１と同じようにアンプルに分注９後
、油滴生成、油層分離のような外観変化は認められず、
粒度は平均粒子径０．３戸、最大粒子径２戸であった。After dispensing this emulsion into ampoules in the same manner as in Example 1, no changes in appearance such as oil droplet formation or oil layer separation were observed.
The average particle size was 0.3 and the maximum particle size was 2.
プロゲステロンの滅菌後残存率は９８．５％と安定であ
った。また、アンプルを氷水中に１力月間放置したが、
結晶の析出を認めなかった。The residual rate of progesterone after sterilization was stable at 98.5%. In addition, the ampoule was left in ice water for one month,
No crystal precipitation was observed.
第１図はプロゲステロンの大豆油に対する溶解度と温度
の関係を示す図である。
特許出願人 大五栄養化学株式会社
￥ｔ２FIG. 1 is a diagram showing the relationship between the solubility of progesterone in soybean oil and temperature. Patent applicant: Daigo Nutritional Chemical Co., Ltd. ￥t2
Claims (1)
る静脈注射可能な乳化注射液。 ２、 プロゲステロン、植物油およびレシチンを含有し
た静脈注射可能な乳化注射液において、安息香酸ベンジ
ルを配合したことを特徴とする乳化注射液。[Claims] 1. An intravenously injectable emulsified injection solution containing progesterone, vegetable oil, and lecithin. 2. An emulsified injection solution that can be injected intravenously and contains progesterone, vegetable oil, and lecithin, and is characterized in that it contains benzyl benzoate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11525084A JPS60258110A (en) | 1984-06-05 | 1984-06-05 | Progesterone emulsified parenteral solution injectable intravenously |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11525084A JPS60258110A (en) | 1984-06-05 | 1984-06-05 | Progesterone emulsified parenteral solution injectable intravenously |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60258110A true JPS60258110A (en) | 1985-12-20 |
| JPH047724B2 JPH047724B2 (en) | 1992-02-12 |
Family
ID=14658044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11525084A Granted JPS60258110A (en) | 1984-06-05 | 1984-06-05 | Progesterone emulsified parenteral solution injectable intravenously |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60258110A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62192322A (en) * | 1986-02-13 | 1987-08-22 | カビ・フアーマシア・アクチエボラーグ | Novel pharmaceutical composition |
| US4927816A (en) * | 1987-08-20 | 1990-05-22 | Ester George C | Formulae and methods for sublingual ingestion of natural progesterone |
| DE4440337A1 (en) * | 1994-11-11 | 1996-05-15 | Dds Drug Delivery Services Ges | Pharmaceutical nanosuspensions for drug application as systems with increased saturation solubility and dissolution rate |
| FR2832065A1 (en) * | 2001-11-13 | 2003-05-16 | Besins Int Belgique | PHARMACEUTICAL COMPOSITION BASED ON MICRONIZED PROGESTERONE, PREPARATION METHOD THEREOF AND USES THEREOF |
| JP2006527736A (en) * | 2003-06-18 | 2006-12-07 | ベー・ブラウン・メルズンゲン・アクチエンゲゼルシャフト | Oil emulsion for postnatal hormone replacement |
| JP2009534425A (en) * | 2006-04-20 | 2009-09-24 | アムゲン インコーポレイティッド | Stable emulsion formulation |
| WO2011134937A2 (en) | 2010-04-26 | 2011-11-03 | Besins Healthcare Luxembourg Sarl | Pharmaceutical emulsion compositions comprising progestogen |
| WO2013127728A1 (en) | 2012-02-29 | 2013-09-06 | B. Braun Melsungen Ag | Hormone containing emulsion |
| EP3178479A1 (en) * | 2015-12-08 | 2017-06-14 | Verano Ilac Sanayi Ve Ticaret A.S. | An injectable composition of ricobendazole |
| CN111346054A (en) * | 2020-03-10 | 2020-06-30 | 上海图珐医药科技有限公司 | Progesterone emulsion type injection and its preparing method |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102233126B1 (en) * | 2020-08-11 | 2021-03-26 | 주식회사 신세계아이앤씨 | System and method for verifying barcode scanning |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2715886A1 (en) * | 1976-04-14 | 1977-11-03 | Exxon Research Engineering Co | INJECTABLE MEDICINAL MIXTURE |
| JPS56135416A (en) * | 1980-03-27 | 1981-10-22 | Mitsubishi Chem Ind Ltd | Pharmaceutical preparation for skin |
| JPS56167616A (en) * | 1980-05-15 | 1981-12-23 | Green Cross Corp:The | Steroid preparation |
-
1984
- 1984-06-05 JP JP11525084A patent/JPS60258110A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2715886A1 (en) * | 1976-04-14 | 1977-11-03 | Exxon Research Engineering Co | INJECTABLE MEDICINAL MIXTURE |
| JPS56135416A (en) * | 1980-03-27 | 1981-10-22 | Mitsubishi Chem Ind Ltd | Pharmaceutical preparation for skin |
| JPS56167616A (en) * | 1980-05-15 | 1981-12-23 | Green Cross Corp:The | Steroid preparation |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62192322A (en) * | 1986-02-13 | 1987-08-22 | カビ・フアーマシア・アクチエボラーグ | Novel pharmaceutical composition |
| US4927816A (en) * | 1987-08-20 | 1990-05-22 | Ester George C | Formulae and methods for sublingual ingestion of natural progesterone |
| DE4440337A1 (en) * | 1994-11-11 | 1996-05-15 | Dds Drug Delivery Services Ges | Pharmaceutical nanosuspensions for drug application as systems with increased saturation solubility and dissolution rate |
| US5858410A (en) * | 1994-11-11 | 1999-01-12 | Medac Gesellschaft Fur Klinische Spezialpraparate | Pharmaceutical nanosuspensions for medicament administration as systems with increased saturation solubility and rate of solution |
| FR2832065A1 (en) * | 2001-11-13 | 2003-05-16 | Besins Int Belgique | PHARMACEUTICAL COMPOSITION BASED ON MICRONIZED PROGESTERONE, PREPARATION METHOD THEREOF AND USES THEREOF |
| WO2003041720A1 (en) * | 2001-11-13 | 2003-05-22 | Besins International Belgique | Pharmaceutical composition based on micronized progesterone, preparation method and uses thereof |
| JP2006527736A (en) * | 2003-06-18 | 2006-12-07 | ベー・ブラウン・メルズンゲン・アクチエンゲゼルシャフト | Oil emulsion for postnatal hormone replacement |
| JP2009534425A (en) * | 2006-04-20 | 2009-09-24 | アムゲン インコーポレイティッド | Stable emulsion formulation |
| WO2011134937A2 (en) | 2010-04-26 | 2011-11-03 | Besins Healthcare Luxembourg Sarl | Pharmaceutical emulsion compositions comprising progestogen |
| WO2011134944A2 (en) | 2010-04-26 | 2011-11-03 | Besins Healthcare Luxembourg Sarl | Low-oil pharmaceutical emulsion compositions comprising progestogen |
| WO2011134937A3 (en) * | 2010-04-26 | 2012-02-02 | Besins Healthcare Luxembourg Sarl | Pharmaceutical emulsion compositions comprising progestogen |
| WO2011134944A3 (en) * | 2010-04-26 | 2012-02-09 | Besins Healthcare Luxembourg Sarl | Low-oil pharmaceutical emulsion compositions comprising progestogen |
| EP2801353A1 (en) | 2010-04-26 | 2014-11-12 | Besins Healthcare Luxembourg | Pharmaceutical Emulsion Compositions Comprising Progestogen |
| EP2857042A1 (en) | 2010-04-26 | 2015-04-08 | Besins Healthcare Luxembourg | Low-oil pharmaceutical emulsion compositions comprising progestogen |
| WO2013127728A1 (en) | 2012-02-29 | 2013-09-06 | B. Braun Melsungen Ag | Hormone containing emulsion |
| WO2013127727A1 (en) | 2012-02-29 | 2013-09-06 | B. Braun Melsungen Ag | Hormone containing emulsion comprising krill phospholipids |
| EP3178479A1 (en) * | 2015-12-08 | 2017-06-14 | Verano Ilac Sanayi Ve Ticaret A.S. | An injectable composition of ricobendazole |
| WO2017097855A1 (en) * | 2015-12-08 | 2017-06-15 | Verano Ilac Sanayi Ticaret Anonim Sirketi | An injectable composition of ricobendazole |
| CN111346054A (en) * | 2020-03-10 | 2020-06-30 | 上海图珐医药科技有限公司 | Progesterone emulsion type injection and its preparing method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH047724B2 (en) | 1992-02-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Collins-Gold et al. | Parenteral emulsions for drug delivery | |
| JP5165249B2 (en) | Preparation of microemulsion of high concentration propofol for anesthesia | |
| US5753259A (en) | Method of preparing controlled-release preparations for biologically active materials and resulting compositions | |
| JPH0822815B2 (en) | Stable emulsions of highly fluorinated organic compounds | |
| JPS6139924B2 (en) | ||
| JPS60258110A (en) | Progesterone emulsified parenteral solution injectable intravenously | |
| JPS63150221A (en) | Emulsified composition containing crystalline drug | |
| JPS5924132B2 (en) | Manufacturing method for nutritional supplement emulsion | |
| DE1467907C3 (en) | Process for the production of soft gelatine capsules | |
| CN102038635A (en) | Taxane medicine solution containing pH value regulator and preparation method thereof | |
| JPS6372624A (en) | Medicine supply system | |
| US1791878A (en) | Water-oil emulsion and suspension for medical purposes and process for manufacturing the same | |
| WO2000056325A2 (en) | Ibuprofen solution | |
| JPH06511482A (en) | Method for producing sterile-filterable active substance solutions | |
| US2687981A (en) | Steroidal composition and method of preparing same | |
| JPH059112A (en) | Transfusion pharmaceutical | |
| JP3615284B2 (en) | Production method of fat emulsion | |
| WO2011047639A1 (en) | Pharmaceutical solution of taxanes comprising chelating agent and preparation method thereof | |
| JPH0737381B2 (en) | Vitamin E aqueous preparation | |
| JPH0314002B2 (en) | ||
| JPH0647559B2 (en) | Anticancer drug emulsion for targeted chemotherapy having improved stability and sustained release effect and method for producing the same | |
| US3318770A (en) | Intravenously injectable anesthetic composition | |
| KR20010055736A (en) | Composition of microemulsified propofol | |
| JPH0565220A (en) | Transfusion pharmaceutical | |
| JPH01226807A (en) | Fat emulsion and production thereof |