WO2007016073A1 - Pharmaceutical emulsion compositions comprising cyclosporin - Google Patents
Pharmaceutical emulsion compositions comprising cyclosporin Download PDFInfo
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- WO2007016073A1 WO2007016073A1 PCT/US2006/028788 US2006028788W WO2007016073A1 WO 2007016073 A1 WO2007016073 A1 WO 2007016073A1 US 2006028788 W US2006028788 W US 2006028788W WO 2007016073 A1 WO2007016073 A1 WO 2007016073A1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A61K38/13—Cyclosporins
-
- 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
- A61K9/0048—Eye, e.g. artificial tears
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Ophthalmology & Optometry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
Abstract
A composition is described herein comprising cyclosporin A, polysorbate 80, a polyoxyethyleηe stearate, and an oil; wherein the composition is an emulsion which is ophthalmically acceptable. Methods of treating diseases or conditions using said compositions, and medicaments related thereto, are also disclosed herein.
Description
INVENTION TITLE
PHARMACEUTICAL EMULSION COMPOSITIONS COMPRISING
CYCLOSPORIN
DESCRIPTION
[Para 1] A composition is described herein comprising cyclosporin A, polysorbate 80, a polyoxyethylene stearate, and an oil; wherein the composition is an emulsion which is ophthalmically acceptable. [Para 2] A therapeutically effective concentration of cyclosporin is a concentration useful to observe a therapeutic effect as compared to a placebo composition having the same composition sans cyclosporin, and can be determined by a person of ordinary skill in the art without undue experimentation. In one embodiment the cyclosporin concentration is 0.001 % or greater. In other embodiments, the concentration of cyclosporin is greater than 0.01 %. In other embodiments, the concentration of cyclosporin is greater than 0.02%. In other embodiments, the concentration of cyclosporin is at least 0.05%. For the treatment of dry eye disease, a cyclosporin concentration of less than or equal to 1 % is often adequate. In other words, in certain compositions, the concentration of the cyclosporin is at or below 1 %. In other embodiments, the concentration of cyclosporin is at or below 0.2%. In other embodiments, the concentration of cyclosporin is at or below 0.1 5%. In other embodiments, the concentration of cyclosporin is at or below 2%. In other embodiments, the concentration of cyclosporin is
about 0.05%. In other embodiments, the concentration of cyclosporin is about 0.1%.
[Para 3] A polyoxyethylene stearate is an ester of polyoxyethylene HO(-CH2CH2θ)n-OH and stearic acid. Such esters include, but are not limited to the following, where the average number for n is indicated as polyoxyethylene n stearate: polyoxyethylene 6 stearate, polyoxyethylene 8 stearate, polyoxyethylene 12 stearate, polyoxyethylene 20 stearate, polyoxyethylene 40 stearate, polyoxyethylene 50 stearate, and polyoxyethylene 100 stearate. Distearates may also be used. [Para 4] The concentration of the polyoxyethylene stearate may vary. In one embodiment, the concentration of polyoxyethylene stearate is from 0.01 % to 20%. In another embodiment, the concentration of polyoxyethylene stearate is from 0.01 % to 10%. In another embodiment, the concentration of polyoxyethylene stearate is from 0.01 to 5.0%. [Para 5] In one embodiment, the polyoxyethylene stearate is polyoxyethylene 40 stearate. In one embodiment, the concentration of polyoxyethylene 40 stearate is from 0.01 % to 20%. In another embodiment, the concentration of polyoxyethylene 40 stearate is from 0.01 % to 1 0%. In another embodiment, the concentration of polyoxyethylene 40 stearate is from 0.01 to 5.0%. [Para 6] The concentration of polysorbate 80 may vary. In one embodiment, the concentration of polysorbate 80 is from 0.01 % to 12%.
In another embodiment, the concentration of polysorbate 80 is from 0.01 % to 5.0%. In another embodiment, the concentration of polysorbate 80 is from 0.01 % to 3.0%.
[Para 7] An oil is a hydrophobic and lipophilic liquid. In other words, it dissolves lipophilic materials, but is substantially insoluble in water. The term oil as applied herein means a single oil or a blend thereof unless otherwise indicated. There are a number of different oils which are suitable for preparing the emulsions disclosed herein. These are known to those of ordinary skill in the art.
[Para 8] While not a necessary consideration, the specific gravity may be important to the stability of the emulsion. Certain embodiments use an oil having a specific gravity of from about 0.9 to about 1 .1 . Other embodiments use an oil having a specific gravity of from about 0.95 to about 1 .1 . Other embodiments us an oil having a specific gravity of about 1 . A combination of oils may be used to tune the specific gravity as desired.
[Para 9] Oils having a specific gravity of from 0.95 to 1.1 include anise oil, castor oil, clove oil, cassia oil, cinnamon oil, and the like. Oils having a specific gravity of from 0.90 to 0.95 include almond oil, corn oil, arachis oil, cottonseed oil, safflower oil, maize oil, linseed oil, rapeseed oil, soybean oil, olive oil, caraway oil, rosemary oil, peanut oil, peppermint oil, sunflower oil, eucalpytus oil, sesame oil, and the like.
[Para 10] One embodiment comprises an oil having a specific gravity from 0.95 to 1 .1 .
[Para 1 1 ] Another embodiment comprises Anise oil.
[Para 12] Another embodiment comprises Castor oil.
[Para 13] Another embodiment comprises Clove oil.
[Para 14] Another embodiment comprises Cassia oil.
[Para 15] Another embodiment comprises Cinnamon oil.
[Para 16] Another embodiment comprises an oil having a specific gravity between 0.90 and 0.95.
[Para 17] Another embodiment comprises Almond oil.
[Para 18] Another embodiment comprises Corn oil.
[Para 19] Another embodiment comprises Arachis oil.
[Para 20] Another embodiment comprises Cottonseed oil.
[Para 21 ] Another embodiment comprises Safflower oil.
[Para 22] Another embodiment comprises Maize oil.
[Para 23] Another embodiment comprises Linseed oil.
[Para 24] Another embodiment comprises Rapeseed oil.
[Para 25] Another embodiment comprises Soybean oil.
[Para 26] Another embodiment comprises Olive oil.
[Para 27] Another embodiment comprises Caraway oil.
[Para 28] Another embodiment comprises Rosemary oil.
[Para 29] Another embodiment comprises Peanut oil.
[Para 30] Another embodiment comprises Peppermint oil.
[Para 31 ] Another embodiment comprises Sunflower oil.
[Para 32] Another embodiment comprises Eucalpytus oil.
[Para 33] Another embodiment comprises Sesame oil.
[Para 34] Another embodiment comprises an oil having a specific gravity below 0.9.
[Para 35] Another embodiment comprises Mineral oil.
[Para 36] Another embodiment comprises Coriander oil.
[Para 37] Another embodiment comprises Lavender oil.
[Para 38] Another embodiment comprises Citronella oil.
[Para 39] Another embodiment comprises Juniper oil.
[Para 40] Another embodiment comprises Lemon oil.
[Para 41 ] Another embodiment comprises Orange oil.
[Para 42] Another embodiment comprises Clary sage oil.
[Para 43] Another embodiment comprises Nutmeg oil.
[Para 44] Another embodiment comprises Tea tree oil.
[Para 45] The amount of oil may vary depending upon the circumstances. In one embodiment, the amount of oil is from 0.01 % to
10%. In another embodiment, the amount of oil is from 0.01 % to 5.0%.
In another embodiment, the amount of oil is from 0.01 % to 3.0%.
[Para 46] One embodiment comprises from 0.01 % to 10% castor oil. Another embodiment comprises from 0.01 % to 5.0% castor oil. Another embodiment comprises from 0.01 % to 3.0% castor oil. [Para 47] A liquid which is intended for ophthalmic use or ophthalmically acceptable is formulated such that it can be administered topically to the eye. The comfort should be maximized as much as possible, although sometimes formulation considerations may necessitate less than optimal comfort. In the case that comfort cannot be maximized, the liquid should be formulated such that the liquid is tolerable to the patient for topical ophthalmic use. Additionally, an ophthalmically acceptable liquid may be packaged for single use, or contain a preservative to prevent contamination over multiple uses. [Para 48] As is known in the art, buffers are commonly used to adjust the pH to a desirable range for ophthalmic use. Generally, a pH of around 5-8 is desired, however, this may need to be adjusted due to considerations such as the stability or solubility of the therapeutically active agent or other excipients. Many buffers including salts of inorganic acids such as phosphate, borate, and sulfate are known. [Para 49] Another commonly used excipient in ophthalmic compositions is a viscosity-enhancing, or a thickening agent. Thickening agents may be used for a variety of reasons, ranging from improving the form of the formulation for convenient administration to improving the
contact with the eye to improve bioavailability. The thickening agent may comprise a polymer containing hydrophilic groups such as monosaccharides, polysaccharides, ethylene oxide groups, hydroxyl groups, carboxylic acids or other charged functional groups. While not intending to limit the scope of the invention, some examples of useful thickening agents are sodium carboxymethylcellulose, hydroxypropylmethylcellulose, povidone, polyvinyl alcohol, and polyethylene glycol.
[Para 50] In ophthalmic solutions, tonicity agents may be used to adjust the composition of the formulation to the desired isotonic range. Tonicity agents are well known in the art and some examples include glycerin, mannitol, sorbitol, sodium chloride, and other electrolytes. [Para 51 ] Preservatives may be used to prevent bacterial contamination in multiple-use ophthalmic preparations. Preservatives are well known in the art, and, while not intending to be limiting, examples include polyhexamethylenebiguanidine (PHMB), benzalkonium chloride (BAK), stabilized oxychloro complexes (otherwise known as Purite®), phenylmercuric acetate, chlorobutanol, benzyl alcohol, parabens, and thimerosal are examples of useful preservatives. [Para 52] In ophthalmic compositions, a chelating agent may be used to enhance preservative effectiveness. Suitable chelating agents are those known in the art, and, while not intending to be limiting, edetate
(EDTA) salts like edetate disodium, edetate calcium disodium, edetate sodium, edetate trisodium, and edetate dipotassium are examples of useful chelating agents.
[Para 53] The compositions disclosed herein are useful in the treatment of dry eye disease, and in the preparation of medicaments for the treatment of dry eye disease. However, certain compositions disclosed herein are also useful for the treatment or prevention of other conditions or diseases which are related to immune response, inflammatory response, or parasitic or other infection.
[Para 54] The compositions disclosed herein are also useful for parenteral administration of a cyclosporin. A composition which is formulated for parenteral use is a composition which is formulated with the intention of administering the composition parenterally. Parenteral administration is generally characterized by injection, either subcutaneously, intramuscularly or intravenously.
[Para 55] The best mode of making and using the present invention are described in the following examples. These examples are given only to provide direction and guidance in how to make and use the invention, and are not intended to limit the scope of the invention in any way.
[Para 56] Example 1
[Para 57] An emulsion having the composition in the table below was prepared as described below.
[Para 58] Part I
[Para 59] CsA (0.5 gm) was added to 50 ml of 10% POE-40 S stock solution. The mixture was stirred for about 20 minutes at room temperature until most of CsA was dissolved in the POE-40-S solution. Castor oil (1 gm) was added and stirred another 1 5 minutes at room temperature. CMC stock solution (5%, 50 ml_) was added and stirred about 20 minutes at room temperature. [Para 60] Part Il
[Para 61 ] Polysorbate 80 (1 .0 gm) was added to water (-380 mL) and stirred at room temperature until dissolved. Glycerine (5.0 g) was added and the mixture was stirred at room temperature until the glycerine was dissolved. Boric acid (3.0 g) was then added to the solution, and stirred at room temperature until dissolved. [Para 62] Part I and Part Il were mixed for about 30 minutes, and the pH was adjusted to pH 7.3 using NaOH (1 .0 N, ~ 3 ml). The mixture was heated to 60 0C with mixing in a closed system to prevent water loss, homogenized at 12,000 rpm at 60 °C for 1 5 minutes, and cooled to room temperature. Purite (2.26 g, 2.21 %) was added to the emulsion and mixed well, water was added to the mixture to make 500 ml, and the emulsion was thoroughly mixed. Finally, the emulsion was sterile filtered using a 0.22 um filter.
Ingredients
[Para 63] Example 2
[Para 64] An emulsion having the composition in the table below was prepared as described below.
[Para 65] Part I
[Para 66] CsA (0.5 gm) was added to 2.5 gm of Castor oil. The mixture was stirred for about 20 minutes at room temperature until most of CsA was dissolved in the Castor oil. 50 ml of 1 0% POE-40 S stock solution was added to above mixture and stirred another 1 5 minutes at room temperature. 2.5 gm of Polysorbate-80 was added and stirred about 20 minutes at room temperature.
[Para 67] Part Il
[Para 68] Glycerine (7.0 g) was added to water (-380 mL) and stirred at room temperature until the glycerine was dissolved. Boric acid (3.0 g) was then added to the solution, and stirred at room temperature until dissolved. CMC stock solution (5%, 50 mL) was added and the mixture was stirred at room temperature for another 20 minutes. [Para 69] Part I and Part Il were mixed for about 30 minutes, and the pH was adjusted to pH 7.3 using NaOH (1.0 N, ~ 3 ml). The mixture was heated to 60 °C with mixing in a closed system to prevent water loss, homogenized at 12,000 rpm at 60 °C for 20 minutes, and cooled to room temperature. Purite (2.26 g, 2.21%) was added to the emulsion and mixed well, water was added to the mixture to make 500 ml, and the emulsion was thoroughly mixed. Finally, the emulsion was sterile filtered using a 0.22 um filter.
[Para 70] Example 3
[Para 71 ] Dry eye is treated using a composition of Example 1 or 2.
Relief of symptoms is experienced.
Claims
What is claimed is:
[Claim 1 ] A composition comprising cyclosporin A, polysorbate 80, a polyoxyethylene stearate, and an oil; wherein the composition is an emulsion which is ophthalmically acceptable.
[Claim 2] The composition of claim 1 wherein the cyclosporin A has a concentration of from 0.01 % to 2.0%.
[Claim 3] The composition of claim 2 wherein cyclosporin A is from has a concentration of from 0.01 % to 0.1 5%.
[Claim 4] The composition of claim 3 wherein the polyoxyethylene stearate is polyoxyethylene 40 stearate.
[Claim 5] The composition of claim 4 wherein polyoxyethylene 40 stearate has a concentration of from 0.1%, to 2.0%.
[Claim 6] The composition of claim 5 wherein the polysorbate 80 has a concentration of from 0.1% to 2.0%.
[Claim 7] The composition of claim 6 wherein the polyoxyethylene 40 stearate has a concentration of about 1 .0% and the polysorbate 80 has a concentration of about 0.5%.
[Claim 8] The composition of claim 7 consisting of 0.1 % cyclosporin A, 0.5% castor oil, 1 .0% polyoxyethylene 40 stearate, 0.5% polysorbate 80, 1 .4% glycerin, 0.6% boric acid, 0.5% carboxymethyl cellulose, 100 ppm purite, with the pH adjusted to from 7.3 to 7.5 with sodium hydroxide, and the remainder water.
[Claim 9] The composition of claim 6 where the polyoxyethylene 40 stearate has a concentration of about 0.75% and the polysorbate 80 has a concentration of about 0.2%.
[Claim 1 0] The composition of claim 9 consisting of 0.1 % cyclosporin
A, 0.2% castor oil, 0.75% polyoxyethylene 40 stearate, 0.2% polysorbate
80, 1 % glycerin, 0.6% boric acid, 0.5% carboxy methyl cellulose, 100 ppm purite, with the pH adjusted to from 7.3 to 7.5 with sodium hydroxide, and the remainder water.
[Claim 1 1 ] The composition of claim 1 having from 0.01 % to 20% polyoxyethylene 40 stearate.
[Claim 1 2] The composition of claim 1 having from 0.01 % to 2.0% cyclosporin A.
[Claim 1 3] The composition of claim 1 having from 0.01 % to 5% oil.
[Claim 1 4] The composition of claim 1 3 having from 0.01% to 3% castor oil.
[Claim 1 5] The composition of claim 1 3 having from 0.01% to 0.
1 5% cyclosporin A.
[Claim 1 6] A method consisting of administering a composition comprising an emulsion comprising cyclosporin A, polysorbate 80, a polyoxyethylene stearate, and an oil, to a eye of a person for the treatment of dry eye disease.
[Claim 1 7] The method of claim 16 wherein the composition has a cyclosporin A concentration of from 0.001 % to 2%.
[Claim 1 8] The method of claim 1 7 wherein the composition has from 0.01% to 10% oil.
[Claim 1 9] The method of claim 18 wherein the oil is castor oil.
[Claim 20] The method of claim 18 wherein the composition has a cyclosporin A concentration of from 0.02% to 0.1 5%.
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US11/161,218 | 2005-07-27 | ||
US11/161,218 US7501393B2 (en) | 2005-07-27 | 2005-07-27 | Pharmaceutical compositions comprising cyclosporins |
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Cited By (9)
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WO2009046967A1 (en) * | 2007-10-08 | 2009-04-16 | Fovea Pharmaceuticals Sa | Aqueous ophthalmic formulations |
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WO2007008894A3 (en) * | 2005-07-13 | 2007-06-28 | Allergan Inc | Cyclosporin compositions |
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WO2013120025A1 (en) | 2012-02-10 | 2013-08-15 | Virun, Inc. | Beverage compositions containing non-polar compounds |
US10874122B2 (en) | 2012-02-10 | 2020-12-29 | Virun, Inc. | Beverage compositions containing non-polar compounds |
US9861611B2 (en) | 2014-09-18 | 2018-01-09 | Virun, Inc. | Formulations of water-soluble derivatives of vitamin E and soft gel compositions, concentrates and powders containing same |
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US8906861B2 (en) | 2014-12-09 |
US20090131307A1 (en) | 2009-05-21 |
US20070027072A1 (en) | 2007-02-01 |
US7501393B2 (en) | 2009-03-10 |
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