FR2774595A1 - EMULSION FOR TRANSDERMAL STEROID ADMINISTRATION - Google Patents

EMULSION FOR TRANSDERMAL STEROID ADMINISTRATION Download PDF

Info

Publication number
FR2774595A1
FR2774595A1 FR9801433A FR9801433A FR2774595A1 FR 2774595 A1 FR2774595 A1 FR 2774595A1 FR 9801433 A FR9801433 A FR 9801433A FR 9801433 A FR9801433 A FR 9801433A FR 2774595 A1 FR2774595 A1 FR 2774595A1
Authority
FR
France
Prior art keywords
sep
composition
weight
solvent
emulsion
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
FR9801433A
Other languages
French (fr)
Inventor
Jean Pascal Conduzorgues
Daniel Paul Sincholle
Valerie Muguet
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.)
RECH D INNOVATION ET DE DEV CE
Original Assignee
RECH D INNOVATION ET DE DEV CE
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 RECH D INNOVATION ET DE DEV CE filed Critical RECH D INNOVATION ET DE DEV CE
Priority to FR9801433A priority Critical patent/FR2774595A1/en
Priority to PCT/FR1999/000257 priority patent/WO1999039695A1/en
Publication of FR2774595A1 publication Critical patent/FR2774595A1/en
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles

Abstract

The invention concerns a composition for the transdermal administration of an active principle selected among steroids and antihormones, which is obtained by mixing, with an oil-in-water emulsion consisting of: a) 10 to 45 wt.% of an oil phase; b) 10 to 45 wt.% of a gelled aqueous phase; c) 2 to 10 wt.% of an emusilfier; from 0.1 to 10 wt.% relative to the emulsion weight of the steroid or antihormone solution in a solvent selected among ethers.

Description

La présente invention concerne des compositions pour l'administration transdermique de stéroïdes. The present invention relates to compositions for the transdermal administration of steroids.

Pour différents traitement thérapeutiques on cherche à administrer par voie transdermique des stéroïdes. En particulier, pour le traitement substitutif de la ménopause, on administre par voie transdermique du 1 7ss-estradiol. Toutefois, les compositions qui sont proposées sont des compositions qui contiennent comme solvant de l'alcool éthylique, compte tenu de la très faible solubilité dans l'eau du 1 7ss-estradiol. Ces compositions, qui doivent être réguliérement appliquées sur la peau, présentent des propriétés desséchantes. For different therapeutic treatments it is sought to administer transdermally steroids. In particular, for the replacement treatment of menopause, 17β-estradiol is transdermally administered. However, the compositions which are provided are compositions which contain ethyl alcohol as the solvent, in view of the very low water solubility of 17β-estradiol. These compositions, which must be regularly applied to the skin, have drying properties.

La présente invention vise à remédier à ces inconvénients en fournissant des compositions dépourvues d'alcool éthylique. The present invention aims to overcome these disadvantages by providing compositions free of ethyl alcohol.

La présente invention a ainsi pour objet une composition pour l'administration transdermique d'un principe actif choisi parmi les stéroïdes, qui est obtenue par mélange,
avec une émulsion de type huile dans l'eau formée;
a) de 10 à 45% en poids d'une phase huileuse;
b) de 10 à 45% en poids d'une phase aqueuse gélifiée;
c) de 2 à 10% en poids d'un agent émulsionnant,
de 0,1 à 10 % en poids par rapport au poids de l'émulsion d'une solution du stéroïde dans un solvant choisi parmi les éthers.The subject of the present invention is thus a composition for the transdermal administration of an active ingredient chosen from steroids, which is obtained by mixing,
with an oil-like emulsion in the formed water;
a) from 10 to 45% by weight of an oily phase;
b) from 10 to 45% by weight of a gelled aqueous phase;
c) from 2 to 10% by weight of an emulsifier,
from 0.1 to 10% by weight relative to the weight of the emulsion of a solution of the steroid in a solvent chosen from ethers.

Le stéroïde peut être notamment le 1 7ss-estradiol mais également d'autres stéroïdes administrés par voie transdermique et notamment des corticostéroides tels que la prednisone. The steroid may be in particular 1 7ss-estradiol but also other steroids administered transdermally and in particular corticosteroids such as prednisone.

Par solvant choisi parmi les éthers, on désigne à la fois des éthers linéaires et des éthers cycliques. Comme exemple d'éther linéaire, on peut citer l'éther monoéthylique du diéthylène glycol. Comme types d'éthers cycliques on peut citer
- des isosorbides, c'est-à-dire des composés de formule;

Figure img00010001

dans laquelle R1 et R2 sont choisis parmi H et un groupe alkyle en C1-C5, l'un au moins étant un groupe alkyle. Comme exemple on peut citer le diméthylisosorbide;
- des cétals cycliques tels que l'isopropylidène glycérol ou solketal, de formule
Figure img00020001

et les autres dérivés de dioxolanne décrits dans GB-B-802 022.By solvent chosen from the ethers, is meant both linear ethers and cyclic ethers. As an example of a linear ether, mention may be made of the monoethyl ether of diethylene glycol. As types of cyclic ethers, mention may be made of
isosorbides, that is to say compounds of formula;
Figure img00010001

wherein R1 and R2 are selected from H and C1-C5 alkyl, at least one being alkyl. As an example, mention may be made of dimethylisosorbide;
cyclic ketals such as isopropylidene glycerol or solketal, of formula
Figure img00020001

and the other dioxolane derivatives described in GB-B-802 022.

La composition contient avantageusement un promoteur d'absorption transcutanée, représentant jusqu'à 25% en poids par rapport au poids de la composition. La quantité de promoteur d'absorption transcutanée est avantageusement de 0 à 15% en poids. The composition advantageously contains a transcutaneous absorption promoter, representing up to 25% by weight relative to the weight of the composition. The amount of transcutaneous absorption promoter is preferably from 0 to 15% by weight.

Ces promoteurs d'absorption peuvent être choisis notamment parmi des esters d'acides gras tels que le myristate d'isopropyle, le myristate de l'éther monoéthylique du diéthylèneglycol, le palmitate d'isopropyle et des glycols tel que le propylèneglycol et l'hexylèneglycol.  These absorption promoters may be chosen in particular from fatty acid esters such as isopropyl myristate, diethylene glycol monoethyl ether myristate, isopropyl palmitate and glycols such as propylene glycol and hexylene glycol. .

On prefère tout particulièrement le myristate d'isopropyle, notamment en association avec le propylèneglycol. Isopropyl myristate is particularly preferred, especially in combination with propylene glycol.

La phase huileuse peut être constituée d'huiles minérales ou végétales. The oily phase may consist of mineral or vegetable oils.

Cette phase huileuse peut contenir des agents cosmétiques habituels tels que des silicones volatiles (polydiméthylsiloxanes ou cyclométhicone) et de l'alcool cétylique. This oily phase may contain usual cosmetic agents such as volatile silicones (polydimethylsiloxanes or cyclomethicone) and cetyl alcohol.

La phase aqueuse gélifiée contient comme gélifiants des gélifiants habituels et notamment des dérivés de la cellulose tels que méthylcellulose, éthylcellulose et des carbomères ou carbopols qui sont des polyméres vinyliques qui possèdent des groupes carboxy et qui doivent être neutralisés par une base pour donner une viscosité élevée. Les gélifiants sont utilisés en une quantité permettant d'avoir une viscosité apparente de 1 à 1500 Pa.s (telle que mesurée sur un rhéomètre à contrainte imposée CLS 100 (Rheo, Champlan) avec un cône/plan de 4 cm de diamètre, d'angle 3 58 et d'entrefer 110 pm.  The gelled aqueous phase contains as gelling agents usual gelling agents and in particular cellulose derivatives such as methylcellulose, ethylcellulose and carbomers or carbopols which are vinyl polymers which have carboxy groups and which must be neutralized with a base to give a high viscosity. . The gelling agents are used in an amount making it possible to have an apparent viscosity of 1 to 1500 Pa.s (as measured on a CLS 100 imposed stress rheometer (Rheo, Champlan) with a cone / plane of 4 cm in diameter, from angle 358 and air gap 110 pm.

La phase aqueuse contient avantageusement des conservateurs tels du p-hydroxybenzoate de méthyle sodé et le p-hydroxybenzoate de propyle sodé. The aqueous phase advantageously contains preservatives such as sodium p-hydroxybenzoate salt and sodium p-hydroxybenzoate soda.

Les agents émulsifiants peuvent être choisis parmi tous les émulsifiants utilisables pour réaliser des émulsions pharmaceutiques de type huile dans l'eau. Ces émulsifiants peuvent être de type anionique, cationique ou non ionique, mais on préfère en particulier des agents émulsionnants non ioniques tels que le Polysorbate 60 (mélange d'esters stéariques du sorbitol et de ses anhydrides copolymérisés avec environ 20 moles d'oxyde d'éthylène par mole de sorbitol et d'anhydride) et le monostéarate de sorbitanne (ester stéarique du sorbitol et de ses anhydrides). The emulsifying agents may be chosen from all the emulsifiers that can be used to produce oil-type pharmaceutical emulsions in water. These emulsifiers may be of anionic, cationic or nonionic type, but non-ionic emulsifiers such as Polysorbate 60 (a mixture of sorbitol stearic esters and its anhydrides copolymerized with approximately 20 moles of ethylene per mole of sorbitol and anhydride) and sorbitan monostearate (stearic ester of sorbitol and its anhydrides).

Les compositions selon l'invention peuvent être préparées par:
- préparation de la phase huileuse;
- préparation de la phase aqueuse contenant l'agent gélifiant;
addition progressive de la phase aqueuse gélifiée dans la phasé huileuse pour former une émulsion;
- introduction et mélange dans l'émulsion d'une solution du stéroïde jusqu'à obtenir une répartition régulière de la solution du stéroïde dans l'émulsion.The compositions according to the invention can be prepared by:
- preparation of the oily phase;
- Preparation of the aqueous phase containing the gelling agent;
gradual addition of the gelled aqueous phase in the oily phase to form an emulsion;
- introduction and mixing in the emulsion of a steroid solution until a regular distribution of the steroid solution in the emulsion.

On donnera ci-après des exemples de composition selon l'invention et de son procédé de préparation. Examples of composition according to the invention and of its preparation process will be given below.

EXEMPLE 1
Préparation d'une composition contenant 0,06 % en poids d'estradiol
On prépare une émulsion ayant la composition suivante pour 100 g
Estradiol 17Q 0,06 g Solketal 49
Paraffine liquide légère 10 9
Isohexadécane 10g
Cyclométhicone 2 g
Alcool cétylique 0,5 g
Polysorbate 60 3,5 g
Monostéarate de sorbitanne 1,5 g
Myristate d'isopropyle 13 g
Parahydroxybenzoate de méthyle
(méthyl-paraben) 0,10 9
Parahydroxybenzoate de propyle
(propyl-paraben) 0,05 g
Carbopol 974-P 0,5 g
Propylène glycol 2 g
Eau q.s.p. 100 g
Solution de soude à 10% 0,5 g.EXAMPLE 1
Preparation of a composition containing 0.06% by weight of estradiol
An emulsion having the following composition is prepared per 100 g
Estradiol 17Q 0.06 g Solketal 49
Light liquid paraffin 10 9
Isohexadecane 10g
Cyclomethicone 2 g
Cetyl alcohol 0.5 g
Polysorbate 60 3.5 g
Sorbitan monostearate 1.5 g
Isopropyl myristate 13 g
Methyl parahydroxybenzoate
(methyl paraben) 0.10 9
Propyl parahydroxybenzoate
(propyl paraben) 0.05 g
Carbopol 974-P 0.5 g
Propylene glycol 2 g
Water qs 100 g
10% sodium hydroxide solution 0.5 g.

La composition est préparée de la façon suivante:
Les conservateurs sont dissous à chaud (40 C) dans la phase aqueuse contenant 2% de propylène glycol.The composition is prepared as follows:
The preservatives are dissolved under heat (40 ° C.) in the aqueous phase containing 2% of propylene glycol.

Le Carbopol 974-P est introduit par saupoudrage sous agitation à la turbine pendant 15 minutes en chauffant légèrement (30-40 C). The Carbopol 974-P is dusted with stirring in the turbine for 15 minutes while heating slightly (30-40 C).

Un gel homogène, transparent et incolore, de viscosité relativement importante, est alors obtenu ; le carbopol a en effet été en partie neutralisé par les parabens sodés qui jouent le rôle de bases. A homogeneous gel, transparent and colorless, of relatively high viscosity, is then obtained; the carbopol has in fact been partially neutralized by the sodium parabens which play the role of bases.

Les phases aqueuse et huileuse contenant les deux tensioactifs et le myristate d'isopropyle sont chauffées au bain-marie à 70-75 C jusqu'à solubilisation totale des tensioactifs. The aqueous and oily phases containing the two surfactants and the isopropyl myristate are heated in a water bath at 70-75 ° C. until the surfactants have completely dissolved.

La phase aqueuse gélifiée est incorporée petit à petit dans la phase huileuse sous agitation à la turbine (500 tours/minute). La phase huileuse est maintenue à 70" C dans un bain-marie placé sous l'agitateur pendant toute la durée d'incorporation de la phase aqueuse gélifiée, soit pendant environ 15 minutes. The gelled aqueous phase is gradually incorporated in the oily phase with stirring at the turbine (500 rpm). The oily phase is maintained at 70 ° C in a water bath placed under the stirrer throughout the period of incorporation of the gelled aqueous phase, ie for about 15 minutes.

A l'aide d'une seringue, le volume de solution mère contenant les 60 mg d'estradiol est incorporé dans le mélange. With the aid of a syringe, the volume of stock solution containing the 60 mg of estradiol is incorporated into the mixture.

Le mélange est maintenu sous agitation pendant environ 20 minutes jusqu'à refroidissement complet de la préparation.  The mixture is stirred for about 20 minutes until complete cooling of the preparation.

Après s'être assuré de la formation de l'émulsion, 0,5 g de solution de soude à 10 % est ajouté pour terminer la neutralisation du carbopol et obtenir un pH voisin de 6. After ensuring the formation of the emulsion, 0.5 g of 10% sodium hydroxide solution is added to complete the neutralization of the carbopol and to obtain a pH close to 6.

EXEMPLE 2
On opère comme à l'exemple 1 mais en utilisant 3 g de diméthylisosorbide au lieu de 4 g de solketal. EXAMPLE 2
The procedure is as in Example 1 but using 3 g of dimethylisosorbide instead of 4 g of solketal.

On donnera ci-après les caractéristiques des émulsions ainsi obtenues.

Figure img00060001
The characteristics of the emulsions thus obtained will be given below.
Figure img00060001

<tb><Tb>

<SEP> Exemple <SEP> I <SEP> Exemple <SEP> 2
<tb> Aspect <SEP> macroscopique
<tb> - <SEP> couleur <SEP> blanche <SEP> blanche
<tb> - <SEP> consistance <SEP> assez <SEP> fluide <SEP> assez <SEP> fluide
<tb> Aspect <SEP> microscopique
<tb> - <SEP> taille <SEP> des <SEP> globules <SEP> < 4,5 <SEP> < <SEP> 4,5
<tb> huileux <SEP> (pm) <SEP>
<tb> pH <SEP> 5,3 <SEP> 5,3
<tb> Stabilité
<tb> - <SEP> au <SEP> stockage <SEP> à <SEP> 25 <SEP> C
<tb> ajour <SEP> + <SEP> +
<tb> 10 <SEP> jours <SEP> + <SEP> +
<tb> 1 <SEP> mois <SEP> + <SEP> +
<tb> 3 <SEP> mois <SEP> + <SEP> +
<tb> - <SEP> à <SEP> 40 <SEP> C <SEP>
<tb> 1 <SEP> jour <SEP> + <SEP> +
<tb> 10 <SEP> jours <SEP> + <SEP> +
<tb> 1 <SEP> mois <SEP> + <SEP> +
<tb> 3 <SEP> mois <SEP> + <SEP> +
<tb> - <SEP> à <SEP> 4 <SEP> C <SEP>
<tb> 1 <SEP> jour <SEP> + <SEP> +
<tb> 10 <SEP> jours <SEP> + <SEP> +
<tb> 1 <SEP> mois <SEP> + <SEP> +
<tb> 3 <SEP> mois <SEP> + <SEP> + <SEP>
<tb> - <SEP> centrifugation <SEP> + <SEP> +
<tb> Odeur <SEP> neutre <SEP> neutre
<tb>
On donnera ci-après les paramètres déterminés lors d'une étude rhéologique effectuée sur un rhéomètre à contrainte imposée CLS 100 (Rheo, Champlarz) avec un cône/plan de 4 cm de diamètre, d'angle 3"58 et d'entrefer 100 pm, les essais étant effectués à 20 + 0,1 C.<SEP> Example <SEP> I <SEP> Example <SEP> 2
<tb> Macroscopic <SEP> appearance
<tb> - <SEP> color <SEP> white <SEP> white
<tb> - <SEP> consistency <SEP> enough <SEP> fluid <SEP> enough <SEP> fluid
<tb> Microscopic appearance <SEP>
<tb> - <SEP> size <SEP> of <SEP> globules <SEP><4,5<SEP><<SEP> 4,5
<tb> oily <SEP> (pm) <SEP>
<tb> pH <SEP> 5.3 <SEP> 5.3
<tb> Stability
<tb> - <SEP> at <SEP> storage <SEP> at <SEP> 25 <SEP> C
<tb> ajour <SEP> + <SEP> +
<tb> 10 <SEP> days <SEP> + <SEP> +
<tb> 1 <SEP> months <SEP> + <SEP> +
<tb> 3 <SEP> months <SEP> + <SEP> +
<tb> - <SEP> to <SEP> 40 <SEP> C <SEP>
<tb> 1 <SEP> day <SEP> + <SEP> +
<tb> 10 <SEP> days <SEP> + <SEP> +
<tb> 1 <SEP> months <SEP> + <SEP> +
<tb> 3 <SEP> months <SEP> + <SEP> +
<tb> - <SEP> to <SEP> 4 <SEP> C <SEP>
<tb> 1 <SEP> day <SEP> + <SEP> +
<tb> 10 <SEP> days <SEP> + <SEP> +
<tb> 1 <SEP> months <SEP> + <SEP> +
<tb> 3 <SEP> months <SEP> + <SEP> + <SEP>
<tb> - <SEP> centrifugation <SEP> + <SEP> +
<tb> Odor <SEP> neutral <SEP> neutral
<Tb>
The parameters determined in a rheological study performed on an imposed stress rheometer CLS 100 (Rheo, Champlarz) with a cone / plane 4 cm in diameter, angle 3 "58 and gap 100 will be given below. pm, the tests being carried out at 20 + 0.1 C.

Les mesures sont effectuées en régime d'écoulement permanent avec un cycle de contrainte croissante, constante et décroissante.

Figure img00070001
The measurements are made in a steady flow regime with an increasing, constant and decreasing stress cycle.
Figure img00070001

<tb><Tb>

Echantillons <SEP> Gradient <SEP> de <SEP> cisaillement <SEP> Viscosité <SEP> apparente
<tb> <SEP> y <SEP> (s <SEP> - <SEP> 1) <SEP> r'(Pa.s) <SEP>
<tb> <SEP> Exemple <SEP> 1 <SEP> 0,01100 <SEP> 1318
<tb> <SEP> 0,10700 <SEP> 267,200
<tb> <SEP> 1,14700 <SEP> 41,695
<tb> <SEP> 10,56500 <SEP> 7,695
<tb> <SEP> 101,20000 <SEP> 1,789
<tb> <SEP> Exemple <SEP> 2 <SEP> 0,01270 <SEP> 1162
<tb> <SEP> 0,10670 <SEP> 243,600
<tb> <SEP> 1,01600 <SEP> 42,880
<tb> <SEP> 10,49500 <SEP> 7,184
<tb> <SEP> 101,85000 <SEP> 1,646
<tb> Samples <SEP> Gradient <SEP> of <SEP> shear <SEP> Viscosity <SEP> apparent
<tb><SEP> y <SEP> (s <SEP> - <SEP> 1) <SEP> r '(Pa.s) <SEP>
<tb><SEP> Example <SEP> 1 <SEP> 0.01100 <SEP> 1318
<tb><SEP> 0,10700 <SEP> 267,200
<tb><SEP> 1,14700 <SEP> 41,695
<tb><SEP> 10.56500 <SEP> 7.695
<tb><SEP> 101,20000 <SEP> 1,789
<tb><SEP> Example <SEP> 2 <SEP> 0.01270 <SEP> 1162
<tb><SEP> 0,10670 <SEP> 243,600
<tb><SEP> 1,01600 <SEP> 42,880
<tb><SEP> 10.49500 <SEP> 7,184
<tb><SEP> 101.85000 <SEP> 1.646
<Tb>

Claims (1)

REVENDICATIONS 1. Composition pour l'administration transdermique d'un principe actif choisi parmi les stéroïdes, qui est obtenue par mélange, avec une émulsion de type huile dans l'eau formée: a) de 10 à 45% en poids d'une phase huileuse; b) de 10 à 45% en poids d'une phase aqueuse gélifiée;1. A composition for the transdermal administration of an active ingredient selected from steroids, which is obtained by mixing with an oil-in-water emulsion formed: a) from 10 to 45% by weight of a phase oil; b) from 10 to 45% by weight of a gelled aqueous phase; c) de 2 à 10% en poids d'un agent émulsionnant, c) from 2 to 10% by weight of an emulsifier, de 0,1 à 10 % en poids par rapport au poids de l'émulsion d'une solution du stéroïde dans un solvant choisi parmi les éthers. from 0.1 to 10% by weight relative to the weight of the emulsion of a solution of the steroid in a solvent chosen from ethers. 2. Composition selon la revendication 1, dans laquelle ledit solvant est un composé de formule:2. Composition according to claim 1, wherein said solvent is a compound of formula:
Figure img00080001
Figure img00080001
 dans laquelle R1 et R2 sont choisis parmi H et un groupe alkyle en C1-C5, I'un au moins étant un groupe alkyle. wherein R 1 and R 2 are selected from H and C 1 -C 5 alkyl, at least one being alkyl. 3. Composition selon la revendication 2, dans laquelle le solvant est le diméthylisosorbide.3. The composition of claim 2, wherein the solvent is dimethylisosorbide. 4. Composition selon la revendication 1, dans laquelle ledit solvant est un cétal cyclique.The composition of claim 1, wherein said solvent is a cyclic ketal. 5. Composition selon la revendication 4, dans laquelle ledit solvant est le solketal.The composition of claim 4, wherein said solvent is solketal. 6. Composition selon l'une quelconque des revendications 1 à 5, qui contient en outre jusqu'à 25 % en poids d'un promoteur d'absorption transcutanée.The composition of any one of claims 1 to 5, which further contains up to 25% by weight of a transcutaneous absorption promoter. 7. Composition selon la revendication 6, dans laquelle le promoteur d'absorption transcutanée est le myristate d'isopropyle.The composition of claim 6, wherein the transcutaneous absorption promoter is isopropyl myristate. 8. Composition selon la revendication 7, dans laquelle le myristate d'isopropyle est en association avec du propylène glycol. The composition of claim 7, wherein the isopropyl myristate is in combination with propylene glycol.
FR9801433A 1998-02-06 1998-02-06 EMULSION FOR TRANSDERMAL STEROID ADMINISTRATION Pending FR2774595A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FR9801433A FR2774595A1 (en) 1998-02-06 1998-02-06 EMULSION FOR TRANSDERMAL STEROID ADMINISTRATION
PCT/FR1999/000257 WO1999039695A1 (en) 1998-02-06 1999-02-05 Emulsion for transdermal administration of an active principle

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9801433A FR2774595A1 (en) 1998-02-06 1998-02-06 EMULSION FOR TRANSDERMAL STEROID ADMINISTRATION

Publications (1)

Publication Number Publication Date
FR2774595A1 true FR2774595A1 (en) 1999-08-13

Family

ID=9522693

Family Applications (1)

Application Number Title Priority Date Filing Date
FR9801433A Pending FR2774595A1 (en) 1998-02-06 1998-02-06 EMULSION FOR TRANSDERMAL STEROID ADMINISTRATION

Country Status (2)

Country Link
FR (1) FR2774595A1 (en)
WO (1) WO1999039695A1 (en)

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1227821A1 (en) * 1999-11-12 2002-08-07 HODOSH, Milton Therapeutic compositions and methods of use thereof
WO2007012977A2 (en) * 2005-04-26 2007-02-01 Foamix Ltd Steroid kit and foamable composition and uses thereof
WO2007104897A1 (en) * 2006-03-15 2007-09-20 Galderma S.A. Topical compositions in the form of an oil-in-water emulsion comprising a pro-penetrating glycol and a steroidal anti-inflammatory drug
US7645803B2 (en) 2005-05-09 2010-01-12 Foamix Ltd. Saccharide foamable compositions
US7700076B2 (en) 2002-10-25 2010-04-20 Foamix, Ltd. Penetrating pharmaceutical foam
US7704518B2 (en) 2003-08-04 2010-04-27 Foamix, Ltd. Foamable vehicle and pharmaceutical compositions thereof
US7820145B2 (en) 2003-08-04 2010-10-26 Foamix Ltd. Oleaginous pharmaceutical and cosmetic foam
US8119109B2 (en) 2002-10-25 2012-02-21 Foamix Ltd. Foamable compositions, kits and methods for hyperhidrosis
US8119106B2 (en) 2003-04-28 2012-02-21 Foamix Ltd Foamable iodine compositions
US8119150B2 (en) 2002-10-25 2012-02-21 Foamix Ltd. Non-flammable insecticide composition and uses thereof
US8343945B2 (en) 2007-12-07 2013-01-01 Foamix Ltd. Carriers, formulations, methods for formulating unstable active agents for external application and uses thereof
US8486376B2 (en) 2002-10-25 2013-07-16 Foamix Ltd. Moisturizing foam containing lanolin
US8486374B2 (en) 2003-08-04 2013-07-16 Foamix Ltd. Hydrophilic, non-aqueous pharmaceutical carriers and compositions and uses
US8512718B2 (en) 2000-07-03 2013-08-20 Foamix Ltd. Pharmaceutical composition for topical application
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

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06256218A (en) * 1993-03-04 1994-09-13 Lederle Japan Ltd Medicine for external use
JPH0710759A (en) * 1993-06-28 1995-01-13 Sekisui Chem Co Ltd Percutaneous absorption pharmaceutical preparation
WO1995022322A1 (en) * 1994-02-18 1995-08-24 Schering Aktiengesellschaft Sexual steroid-containing transdermal therapeutic systems

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06256218A (en) * 1993-03-04 1994-09-13 Lederle Japan Ltd Medicine for external use
JPH0710759A (en) * 1993-06-28 1995-01-13 Sekisui Chem Co Ltd Percutaneous absorption pharmaceutical preparation
WO1995022322A1 (en) * 1994-02-18 1995-08-24 Schering Aktiengesellschaft Sexual steroid-containing transdermal therapeutic systems

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 9441, Derwent World Patents Index; AN 94-329953, XP002081246 *
DATABASE WPI Week 9512, Derwent World Patents Index; AN 95-085338, XP002081247 *

Cited By (92)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1227821A4 (en) * 1999-11-12 2004-09-22 Milton Hodosh Therapeutic compositions and methods of use thereof
EP1227821A1 (en) * 1999-11-12 2002-08-07 HODOSH, Milton Therapeutic compositions and methods of use thereof
US8512718B2 (en) 2000-07-03 2013-08-20 Foamix Ltd. Pharmaceutical composition for topical application
US9622947B2 (en) 2002-10-25 2017-04-18 Foamix Pharmaceuticals Ltd. Foamable composition combining a polar solvent and a hydrophobic carrier
US9492412B2 (en) 2002-10-25 2016-11-15 Foamix Pharmaceuticals Ltd. Penetrating pharmaceutical foam
US10821077B2 (en) 2002-10-25 2020-11-03 Foamix Pharmaceuticals Ltd. Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof
US10117812B2 (en) 2002-10-25 2018-11-06 Foamix Pharmaceuticals Ltd. Foamable composition combining a polar solvent and a hydrophobic carrier
US7700076B2 (en) 2002-10-25 2010-04-20 Foamix, Ltd. Penetrating pharmaceutical foam
US9265725B2 (en) 2002-10-25 2016-02-23 Foamix Pharmaceuticals Ltd. Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof
US8900554B2 (en) 2002-10-25 2014-12-02 Foamix Pharmaceuticals Ltd. Foamable composition and uses thereof
US9320705B2 (en) 2002-10-25 2016-04-26 Foamix Pharmaceuticals Ltd. Sensation modifying topical composition foam
US8119109B2 (en) 2002-10-25 2012-02-21 Foamix Ltd. Foamable compositions, kits and methods for hyperhidrosis
US9713643B2 (en) 2002-10-25 2017-07-25 Foamix Pharmaceuticals Ltd. Foamable carriers
US8119150B2 (en) 2002-10-25 2012-02-21 Foamix Ltd. Non-flammable insecticide composition and uses thereof
US10322085B2 (en) 2002-10-25 2019-06-18 Foamix Pharmaceuticals Ltd. Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof
US9539208B2 (en) 2002-10-25 2017-01-10 Foamix Pharmaceuticals Ltd. Foam prepared from nanoemulsions and uses
US8435498B2 (en) 2002-10-25 2013-05-07 Foamix Ltd. Penetrating pharmaceutical foam
US8486376B2 (en) 2002-10-25 2013-07-16 Foamix Ltd. Moisturizing foam containing lanolin
US8840869B2 (en) 2002-10-25 2014-09-23 Foamix Ltd. Body cavity foams
US8741265B2 (en) 2002-10-25 2014-06-03 Foamix Ltd. Penetrating pharmaceutical foam
US8722021B2 (en) 2002-10-25 2014-05-13 Foamix Ltd. Foamable carriers
US9668972B2 (en) 2002-10-25 2017-06-06 Foamix Pharmaceuticals Ltd. Nonsteroidal immunomodulating kit and composition and uses thereof
US11033491B2 (en) 2002-10-25 2021-06-15 Vyne Therapeutics Inc. 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
US8119106B2 (en) 2003-04-28 2012-02-21 Foamix Ltd Foamable iodine compositions
US7820145B2 (en) 2003-08-04 2010-10-26 Foamix Ltd. Oleaginous pharmaceutical and cosmetic foam
US8362091B2 (en) 2003-08-04 2013-01-29 Foamix Ltd. Foamable vehicle and pharmaceutical compositions thereof
US9050253B2 (en) 2003-08-04 2015-06-09 Foamix Pharmaceuticals Ltd. Oleaginous pharmaceutical and cosmetic foam
US8703105B2 (en) 2003-08-04 2014-04-22 Foamix Ltd. Oleaginous pharmaceutical and cosmetic foam
US9101662B2 (en) 2003-08-04 2015-08-11 Foamix Pharmaceuticals Ltd. Compositions with modulating agents
US8795693B2 (en) 2003-08-04 2014-08-05 Foamix Ltd. Compositions with modulating agents
US8486374B2 (en) 2003-08-04 2013-07-16 Foamix Ltd. Hydrophilic, non-aqueous pharmaceutical carriers and compositions and uses
US9636405B2 (en) 2003-08-04 2017-05-02 Foamix Pharmaceuticals Ltd. Foamable vehicle and pharmaceutical compositions thereof
US8518378B2 (en) 2003-08-04 2013-08-27 Foamix Ltd. Oleaginous pharmaceutical and cosmetic foam
US8114385B2 (en) 2003-08-04 2012-02-14 Foamix Ltd. Oleaginous pharmaceutical and cosmetic foam
US7704518B2 (en) 2003-08-04 2010-04-27 Foamix, Ltd. Foamable vehicle and pharmaceutical compositions thereof
WO2007012977A2 (en) * 2005-04-26 2007-02-01 Foamix Ltd Steroid kit and foamable composition and uses thereof
WO2007012977A3 (en) * 2005-04-26 2007-07-12 Foamix Ltd Steroid kit and foamable composition and uses thereof
US7645803B2 (en) 2005-05-09 2010-01-12 Foamix Ltd. Saccharide foamable compositions
US8551504B2 (en) 2006-03-15 2013-10-08 Galderma S.A. Topical anti-inflammatory compositions comprising O/W emulsions containing pro-penetrating glycols
WO2007104897A1 (en) * 2006-03-15 2007-09-20 Galderma S.A. Topical compositions in the form of an oil-in-water emulsion comprising a pro-penetrating glycol and a steroidal anti-inflammatory drug
FR2898499A1 (en) * 2006-03-15 2007-09-21 Galderma Sa NOVEL TOPIC COMPOSITIONS IN THE FORM OF O / W EMULSION COMPRISING PRO-PENETRANT GLYCOL
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
US10369102B2 (en) 2007-08-07 2019-08-06 Foamix Pharmaceuticals Ltd. Wax foamable vehicle and pharmaceutical compositions thereof
US8636982B2 (en) 2007-08-07 2014-01-28 Foamix 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
US8900553B2 (en) 2007-12-07 2014-12-02 Foamix Pharmaceuticals Ltd. Oil and liquid silicone foamable carriers and formulations
US9549898B2 (en) 2007-12-07 2017-01-24 Foamix Pharmaceuticals Ltd. Oil and liquid silicone foamable carriers and formulations
US8518376B2 (en) 2007-12-07 2013-08-27 Foamix Ltd. Oil-based foamable carriers and formulations
US11433025B2 (en) 2007-12-07 2022-09-06 Vyne Therapeutics Inc. Oil 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
US8343945B2 (en) 2007-12-07 2013-01-01 Foamix Ltd. Carriers, formulations, methods for formulating unstable active agents for external application and uses thereof
US9795564B2 (en) 2007-12-07 2017-10-24 Foamix Pharmaceuticals 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
US10588858B2 (en) 2009-04-28 2020-03-17 Foamix Pharmaceuticals Ltd. Foamable vehicles and pharmaceutical compositions comprising aprotic polar solvents and uses thereof
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
US9884017B2 (en) 2009-04-28 2018-02-06 Foamix Pharmaceuticals Ltd. Foamable vehicles and pharmaceutical compositions comprising aprotic polar solvents and uses thereof
US10092588B2 (en) 2009-07-29 2018-10-09 Foamix Pharmaceuticals Ltd. Foamable compositions, breakable foams and their uses
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
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
US11219631B2 (en) 2009-07-29 2022-01-11 Vyne Pharmaceuticals Inc. 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
US10463742B2 (en) 2009-10-02 2019-11-05 Foamix Pharmaceuticals Ltd. Topical tetracycline compositions
US8865139B1 (en) 2009-10-02 2014-10-21 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
US8618081B2 (en) 2009-10-02 2013-12-31 Foamix 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
US9849142B2 (en) 2009-10-02 2017-12-26 Foamix Pharmaceuticals Ltd. Methods for accelerated return of skin integrity and for the treatment of impetigo
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
US10029013B2 (en) 2009-10-02 2018-07-24 Foamix Pharmaceuticals Ltd. Surfactant-free, water-free formable composition and breakable foams and their uses
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
US8871184B2 (en) 2009-10-02 2014-10-28 Foamix Ltd. Topical tetracycline compositions
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
US10137200B2 (en) 2009-10-02 2018-11-27 Foamix Pharmaceuticals Ltd. Surfactant-free water-free foamable compositions, breakable foams and gels 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
US8945516B2 (en) 2009-10-02 2015-02-03 Foamix Pharmaceuticals Ltd. Surfactant-free water-free foamable compositions, breakable foams and gels and their uses
US8992896B2 (en) 2009-10-02 2015-03-31 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

Also Published As

Publication number Publication date
WO1999039695A1 (en) 1999-08-12

Similar Documents

Publication Publication Date Title
FR2774595A1 (en) EMULSION FOR TRANSDERMAL STEROID ADMINISTRATION
FI108277B (en) Topical preparation containing a suspension of solid lipid particles
EP1265617B1 (en) Novel topical oestroprogestational compositions with systemic effect
EP0412865B1 (en) Aqueous gel containing spheroids from solid, non-hydrophilic lipid substance in suspension form
LU88114A1 (en) NEW PHARMACEUTICAL COMPOSITIONS FOR LOCAL APPLICATION
FR2632519A1 (en) AQUEOUS PHASE-CONTAINING PERFUME COMPOSITION HAVING A HIGH PERFUME CONCENTRATION
JPS6322515A (en) Skin tanning agent
FR2763844A1 (en) Increasing viscosity of oil-based cosmetic and pharmaceutical compositions
EP0175609B1 (en) Transdermal anaesthetic composition for topical use and process for its application
OA12750A (en) Pharmaceutical compositions based on azetidine derivatives.
EP0835652A1 (en) Use of at least one glycol in the solubilisation of melatonin in water and compositions containing them
CA2173815C (en) Use of a hydrofluorocarbon in an emulsion; composition and emulsion containing such a compound
HUE027718T2 (en) Oil-in-water emulsion of mometasone and propylene glycol
FR2903602A1 (en) INJECTABLE FORMULATION WITH PROLONGED RELEASE OF ACTIVE INGREDIENTS, PROCESS FOR ITS PREPARATION
CN111867574B (en) Emulsified gel composition containing diclofenac
FR2703601A1 (en) Emulsion of the oil type in water containing milk.
EP0957938A1 (en) Composition with base of coconut oil and its use
EP0753341B1 (en) Use of hydrofluorocarbon thiolesters in emulsions, cosmetic or dermatalogical applications
RU2076699C1 (en) Antimastopathy ointment
FR2786408A1 (en) Water in oil emulsion, for perfuming the skin and hair, comprises water, glycol, silicone surfactant, volatile silicone and fragrance
LT4329B (en) External antiinflammatory agent
FR2835748A1 (en) Stable, surfactant free lachrymal fluid substitute, used for treating ophthalmological disorders such as dry eye syndrome, comprises aqueous and lipid phases each containing thickener
FI84696B (en) Method for the production of a cream composition containing indomethacin
JP2023140460A (en) Emulsified composition containing anti-inflammatory ingredient
FR2721212A1 (en) New dermo-pharmaceutical compsn.