CA2375083A1 - Clear oil-containing pharmaceutical compositions - Google Patents

Clear oil-containing pharmaceutical compositions Download PDF

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Publication number
CA2375083A1
CA2375083A1 CA002375083A CA2375083A CA2375083A1 CA 2375083 A1 CA2375083 A1 CA 2375083A1 CA 002375083 A CA002375083 A CA 002375083A CA 2375083 A CA2375083 A CA 2375083A CA 2375083 A1 CA2375083 A1 CA 2375083A1
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peg
pharmaceutical composition
oil
glyceryl
triglyceride
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CA002375083A
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French (fr)
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CA2375083C (en
Inventor
Feng-Jing Chen
Mahesh V. Patel
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Lipocine Inc
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Individual
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    • 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
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4808—Preparations in capsules, e.g. of gelatin, of chocolate characterised by the form of the capsule or the structure of the filling; Capsules containing small tablets; Capsules with outer layer for immediate drug release

Abstract

The present invention relates to pharmaceutical compositions and methods for improved solubilization of triglycerides and improved delivery of therapeuti c agents. Compositions of the present invention include a triglyceride and a carrier, where the carrier is formed from a combination of at least two surfactants, at least one of which is hydrophilic. Upon dilution with an aqueous solvent, the composition forms a clear, aqueous dispersion of the triglyceride and surfactants. An optional therapeutic agent can be incorporated into the composition, or can be co-administered with the composition. The invention also provides methods of enhancing triglyceride solubility and methods of treatment with therapeutic agents using these compositions.

Claims (184)

1. A pharmaceutical composition comprising:
(a) a triglyceride;
(b) a carrier comprising at least two surfactants, at least one of the surfactants being hydrophilic; and (c) a therapeutic agent which is capable of being solubilized in the triglyceride, the carrier, or both the triglyceride and the carrier, wherein the triglyceride and surfactants are present in amounts such that upon mixing with an aqueous solution the composition forms a clear aqueous dispersion.
2. The pharmaceutical composition of claim 1, wherein the triglyceride is selected from the group consisting of vegetable oils, fish oils, animal fats, hydrogenated vegetable oils, partially hydrogenated vegetable oils, synthetic triglycerides, modified triglycerides, fractionated triglycerides, and mixtures thereof.
3. The pharmaceutical composition of claim 1, wherein the triglyceride is selected from the group consisting of almond oil; babassu oil; borage oil;
blackcurrant seed oil; canola oil; castor oil; coconut oil; corn oil; cottonseed oil;
evening primrose oil;
grapeseed oil; groundnut oil; mustard seed oil; olive oil; palm oil; palm kernel oil; peanut oil; rapeseed oil; safflower oil; sesame oil; shark liver oil; soybean oil;
sunflower oil;
hydrogenated castor oil; hydrogenated coconut oil; hydrogenated palm oil;
hydrogenated soybean oil; hydrogenated vegetable oil; hydrogenated cottonseed and castor oil; partially hydrogenated soybean oil; partially soy and cottonseed oil; glyceryl tricaproate; glyceryl tricaprylate; glyceryl tricaprate; glyceryl triundecanoate; glyceryl trilaurate; glyceryl trioleate; glyceryl trilinoleate; glyceryl trilinolenate; glyceryl tricaprylate/caprate; glyceryl tricaprylate/caprate/laurate; glyceryl tricaprylate/caprate/linoleate;
glyceryl tricaprylate/caprate/stearate; saturated polyglycolized glycerides; linoleic glycerides;
caprylic/capric glycerides; modified triglycerides; fractionated triglycerides; and mixtures thereof.
4. The pharmaceutical composition of claim 1, wherein the triglyceride is selected from the group consisting of coconut oil; corn oil; olive oil; palm oil; peanut oil;
safflower oil; sesame oil; soybean oil; hydrogenated castor oil; hydrogenated coconut oil;
partially hydrogenated soybean oil; glyceryl tricaprate; glyceryl trilaurate;
glyceryl trioleate; glyceryl trilinoleate; glyceryl tricaprylate/caprate; glyceryl tricaprylate/caprate/laurate; glyceryl tricaprylate/caprate/linoleate;
glyceryl tricaprylate/caprate/stearate; saturated polyglycolized glycerides; linoleic glycerides;
caprylic/capric glycerides; modified triglycerides; fractionated triglycerides; and mixtures thereof.
5. The pharmaceutical composition of claim 1, wherein the triglyceride is a medium chain triglyceride, a long chain triglyceride, a modified triglyceride, a fractionated triglyceride, or a mixture thereof.
6. The pharmaceutical composition of claim 1, wherein the hydrophilic surfactant comprises at least one non-ionic hydrophilic surfactant having an HLB value greater than or equal to about 10.
7. The pharmaceutical composition of claim 1, wherein the hydrophilic surfactant comprises at least one ionic surfactant.
8. The pharmaceutical composition of claim 6, which further comprises at least one ionic surfactant.
9. The pharmaceutical composition of claim 6, wherein the non-ionic surfactant is selected from the group consisting of alkylglucosides;
alkylmaltosides;
alkylthioglucosides; lauryl macrogolglycerides; polyoxyethylene alkyl ethers;
polyoxyethylene alkylphenols; polyethylene glycol fatty acids esters;
polyethylene glycol glycerol fatty acid esters; polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers; polyglycerol fatty acid esters;
polyoxyethylene glycerides; polyoxyethylene sterols, derivatives, and analogues thereof;
polyoxyethylene vegetable oils; polyoxyethylene hydrogenated vegetable oils; reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; sugar esters, sugar ethers;
sucroglycerides; and mixtures thereof.
10. The pharmaceutical composition of claim 6, wherein the non-ionic hydrophilic surfactant is selected from the group consisting of polyoxyethylene alkylethers; polyethylene glycol fatty acids esters; polyethylene glycol glycerol fatty acid esters; polyoxyethylene sorbitan fatty acid esters; polyoxyethylene-polyoxypropylene block copolymers; polyglycerol fatty acid esters; polyoxyethylene glycerides;
polyoxyethylene vegetable oils; polyoxyethylene hydrogenated vegetable oils;
reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; and mixtures thereof.
11. The pharmaceutical composition of claim 10, wherein the glyceride is a monoglyceride, diglyceride, triglyceride, or a mixture thereof.
12. The pharmaceutical composition of claim 10, wherein the reaction mixture comprises the transesterification products of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
13. The pharmaceutical composition of claim 10, wherein the polyol is glycerol, ethylene glycol, polyethylene glycol, sorbitol, propylene glycol, pentaerythritol, a saccharide, or a mixture thereof.
14. The pharmaceutical composition of claim 6, wherein the hydrophilic surfactant is PEG-10 laurate, PEG-12 laurate, PEG-20 laurate, PEG-32 laurate, dilaurate, PEG-12 oleate, PEG-15 oleate, PEG-20 oleate, PEG-20 dioleate, PEG-32 oleate, PEG-200 oleate, PEG-400 oleate, PEG-15 stearate, PEG-32 distearate, PEG-40 stearate, PEG-100 stearate, PEG-20 dilaurate, PEG-25 glyceryl trioleate, PEG-32 dioleate, PEG-20 glyceryl laurate, PEG-30 glyceryl laurate, PEG-20 glyceryl stearate, PEG-20 glyceryl oleate, PEG-30 glyceryl oleate, PEG-30 glyceryl laurate, PEG-40 glyceryl laurate, PEG-40 palm kernel oil, PEG-50 hydrogenated castor oil, PEG-40 castor oil, PEG-35 castor oil, PEG-60 castor oil, PEG-40 hydrogenated castor oil, PEG-60 hydrogenated castor oil, PEG-60 corn oil, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, polyglyceryl-10 laurate, PEG-30 cholesterol, PEG-25 phyto sterol, PEG-30 soya sterol, PEG-20 trioleate, PEG-40 sorbitan oleate, PEG-80 sorbitan laurate, polysorbate 20, polysorbate 80, POE-9 lauryl ether, POE-23 lauryl ether, POE-10 oleyl ether, oleyl ether, POE-20 stearyl ether, tocopheryl PEG-100 succinate, PEG-24 cholesterol, polyglyceryl-10 oleate, Tween 40, Tween 60, sucrose monostearate, sucrose monolaurate, sucrose monopalmitate, PEG 10-100 nonyl phenol series, PEG 15-100 octyl phenol series, a poloxamer, or a mixture thereof.
15. The pharmaceutical composition of claim 6, wherein the hydrophilic surfactant is PEG-20 laurate, PEG-20 oleate, PEG-35 castor oil, PEG-40 palm kernel oil, PEG-40 hydrogenated castor oil, PEG-60 corn oil, PEG-25 glyceryl trioleate, polyglyceryl-10 laurate, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, PEG-30 cholesterol, polysorbate 20, polysorbate 80, POE-9 lauryl ether, POE-23 lauryl ether, POE-10 oleyl ether, PEG-24 cholesterol, sucrose monostearate, sucrose monolaurate, a poloxamer, or a mixture thereof.
16. The pharmaceutical composition of claim 6, wherein the hydrophilic surfactant is PEG-35 castor oil, PEG-40 hydrogenated castor oil, PEG-60 corn oil, PEG-25 glyceryl trioleate, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, polysorbate 20, polysorbate 80, tocopheryl PEG-1000 succinate, PEG-24 cholesterol, a poloxamer, or a mixture thereof.
17. The pharmaceutical composition of claim 7, wherein the ionic surfactant is selected from the group consisting of alkyl ammonium salts; bile salts, analogues, and derivatives thereof; fusidic acid and derivatives thereof; fatty acid derivatives of amino acids, oligopeptides, and polypeptides; glyceride derivatives of amino acids, oligopeptides, and polypeptides; acyl lactylates; mono-,diacetylated tartaric acid esters of mono-,diglycerides; succinylated monoglycerides; citric acid esters of mono-,diglycerides;
alginate salts; propylene glycol alginate; lecithins and hydrogenated lecithins; lysolecithin and hydrogenated lysolecithins; lysophospholipids and derivatives thereof;
carnitine fatty acid ester salts; phospholipids and derivatives thereof; salts of alkylsulfates; salts of fatty acids; sodium docusate; and mixtures thereof.
18. The pharmaceutical composition of claim 7, wherein the ionic surfactant is selected from the group consisting of bile acids and salts, analogues, and derivatives thereof; lecithins, lysolecithin, phospholipids, lysophospholipids and derivatives thereof;
carnitine fatty acid ester salts; salts of alkylsulfates; salts of fatty acids; sodium docusate;
acyl lactylates; mono-,diacetylated tartaric acid esters of mono-,diglycerides; succinylated monoglycerides; citric acid esters of mono-,diglycerides; and mixtures thereof.
19. The pharmaceutical composition of claim 7, wherein the ionic surfactant is selected from the group consisting of lecithin, lysolecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylglycerol, phosphatidic acid, phosphatidylserine, lysophosphatidylcholine, lysophosphatidylethanolamine, lysophosphatidylglycerol, lysophosphatidic acid, lysophosphatidylserine, PEG-phosphatidylethanolamine, PVP-phosphatidylethanolamine, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, cholate, taurocholate, glycocholate, deoxycholate, taurodeoxycholate, chenodeoxycholate, glycodeoxycholate, glycochenodeoxycholate, taurochenodeoxycholate, ursodeoxycholate, lithocholate, tauroursodeoxycholate, glycoursodeoxycholate, cholylsarcosine, N-methyl taurocholate, caproate, caprylate, caprate, laurate, myristate, palmitate, oleate, ricinoleate, linoleate, linolenate, stearate, lauryl sulfate, tetraacetyl sulfate, docusate, lauroyl carnitine, palmitoyl carnitine, myristoyl carnitine, and salts and mixtures thereof.
20. The pharmaceutical composition of claim 7, wherein the ionic surfactant is selected from the group consisting of lecithin, lysolecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylglycerol, lysophosphatidylcholine, PEG-phosphatidylethanolamine, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, cholate, taurocholate, glycocholate, deoxycholate, chenodeoxycholate, lithocholate, ursodeoxycholate, taurodeoxycholate, glycodeoxycholate, cholylsarcosine, caproate, caprylate, caprate, laurate, oleate, lauryl sulfate, docusate, lauroyl carnitine, palmitoyl carnitine, myristoyl carnitine, and salts and mixtures thereof.
21. The pharmaceutical composition of claim 7, wherein the ionic surfactant is selected from the group consisting of lecithin, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, chenodeoxycholate, lithocholate, ursodeoxycholate, taurocholate, caprylate, caprate, oleate, lauryl sulfate, docusate, lauroyl carnitine, palmitoyl carnitine, myristoyl carnitine, and salts and mixtures thereof.
22. The pharmaceutical composition of claim 1, wherein the carrier comprises at least two hydrophilic surfactants.
23. The pharmaceutical composition of claim 1, wherein the carrier comprises at least one hydrophilic surfactant and at least one hydrophobic surfactant.
24. The pharmaceutical composition of claim 1 wherein the hydrophobic surfactant is a compound or mixture of compounds having an HLB value less than about 10.
25. The pharmaceutical composition of claim 24, wherein the hydrophobic surfactant is selected from the group consisting of alcohols; polyoxyethylene alkylethers;

fatty acids; bile acids; glycerol fatty acid esters; acetylated glycerol fatty acid esters; lower alcohol fatty acids esters; polyethylene glycol fatty acids esters;
polyethylene glycol glycerol fatty acid esters; polypropylene glycol fatty acid esters;
polyoxyethylene glycerides; lactic acid derivatives of mono/diglycerides; propylene glycol diglycerides;
sorbitan fatty acid esters; polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers; transesterified vegetable oils; sterols;
sterol derivatives; sugar esters; sugar ethers; sucroglycerides; polyoxyethylene vegetable oils;
polyoxyethylene hydrogenated vegetable oils; reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; and mixtures thereof.
26. The pharmaceutical composition of claim 24, wherein the hydrophobic surfactant is selected from the group consisting of fatty acids; bile acids;
lower alcohol fatty acid esters; polyethylene glycol glycerol fatty acid esters;
polypropylene glycol fatty acid esters; polyoxyethylene glycerides; glycerol fatty acid esters;
acetylated glycerol fatty acid esters; lactic acid derivatives of mono/diglycerides; sorbitan fatty acid esters;
polyoxyethylene sorbitan fatty acid esters; polyoxyethylene-polyoxypropylene block copolymers; polyoxyethylene vegetable oils; polyoxyethylene hydrogenated vegetable oils; reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols;
and mixtures thereof.
27. The pharmaceutical composition of claim 24, wherein the hydrophobic surfactant is selected from the group consisting of bile acids; lower alcohol fatty acids esters; polypropylene glycol fatty acid esters; propylene glycol fatty acid esters; glycerol fatty acid esters; acetylated glycerol fatty acid esters; lactic acid derivatives of mono/diglycerides; sorbitan fatty acid esters; polyoxyethylene vegetable oils;
and mixtures thereof.
28. The pharmaceutical composition of claim 24, wherein the hydrophobic surfactant is a glycerol fatty acid ester, an acetylated glycerol fatty acid ester, or a mixture thereof.
29. The pharmaceutical composition of claim 28, wherein the glycerol fatty acid ester is a monoglyceride, diglyceride, or a mixture thereof.
30. The pharmaceutical composition of claim 29, wherein the fatty acid of the glycerol fatty acid ester is a C6 to C22 fatty acid or a mixture thereof.
31. The pharmaceutical composition of claim 24, wherein the hydrophobic surfactant is a reaction mixture of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
32. The pharmaceutical composition of claim 31, wherein the reaction mixture is a transesterification product of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
33. The pharmaceutical composition of claim 31, wherein the polyol is polyethylene glycol, sorbitol, propylene glycol, pentaerythritol, a saccharide, or a mixture thereof.
34. The pharmaceutical composition of claim 24, wherein the hydrophobic surfactant is selected from the group consisting of myristic acid; oleic acid;
lauric acid;
stearic acid; palmitic acid; PEG 1-4 stearate; PEG 2-4 oleate; PEG-4 dilaurate; PEG-4 dioleate; PEG-4 distearate; PEG-6 dioleate; PEG-6 distearate; PEG-8 dioleate;

castor oil; PEG 5-10 hydrogenated castor oil; PEG 6-20 corn oil; PEG 6-20 almond oil;
PEG-6 olive oil; PEG-6 peanut oil; PEG-6 palm kernel oil; PEG-6 hydrogenated palm kernel oil; PEG-4 capric/caprylic triglyceride, mono, di, tri, tetra esters of vegetable oil and sorbitol; pentaerythrityl di, tetra stearate, isostearate, oleate, caprylate, or caprate;
polyglyceryl 2-4 oleate, stearate, or isostearate; polyglyceryl 4-10 pentaoleate;
polyglyceryl-3 dioleate; polyglyceryl-6 dioleate; polyglyceryl-10 trioleate;
polyglyceryl-3 distearate; propylene glycol mono- or diesters of a C6 to C22 fatty acid;
monoglycerides of a C6 to C22 fatty acid; acetylated monoglycerides of C6 to C22 fatty acid;
diglycerides of C6 to C22 fatty acids; lactic acid derivatives of monoglycerides; lactic acid derivatives of diglycerides; cholesterol; phytosterol; PEG 5-20 soya sterol; PEG-6 sorbitan tetra, hexastearate; PEG-6 sorbitan tetraoleate; sorbitan monolaurate; sorbitan monopalmitate;
sorbitan mono, trioleate; sorbitan mono, tristearate; sorbitan monoisostearate; sorbitan sesquioleate; sorbitan sesquistearate; PEG 2-5 oleyl ether; POE 2-4 lauryl ether; PEG-2 cetyl ether; PEG-2 stearyl ether; sucrose distearate; sucrose dipalmitate;
ethyl oleate;
isopropyl myristate; isopropyl palmitate; ethyl linoleate; isopropyl linoleate; poloxamers;
cholic acid; ursodeoxycholic acid; glycocholic acid; taurocholic acid;
lithocholic acid;
deoxycholic acid; chenodeoxycholic acid; and mixtures thereof.
35. The pharmaceutical composition of claim 24, wherein the hydrophobic surfactant is selected from the group consisting of oleic acid; lauric acid;
glyceryl monocaprate; glyceryl monocaprylate; glyceryl monolaurate; glyceryl monooleate;
glyceryl dicaprate; glyceryl dicaprylate; glyceryl dilaurate; glyceryl dioleate; acetylated monoglycerides; propylene glycol oleate; propylene glycol laurate;
polyglyceryl-3 oleate;
polyglyceryl-6 dioleate; PEG-6 corn oil; PEG-20 corn oil; PEG-20 almond oil;
sorbitan monooleate; sorbitan monolaurate; POE-4 lauryl ether; POE-3 oleyl ether; ethyl oleate;
poloxamers; cholic acid; ursodeoxycholic acid; glycocholic acid; taurocholic acid;
lithocholic acid; deoxycholic acid; chenodeoxycholic acid; and mixtures thereof.
36. The pharmaceutical composition of claim 1, wherein the therapeutic agent is a drug, a vitamin, a nutritional supplement, a cosmeceutical, or a mixture thereof.
37. The pharmaceutical composition of claim 1, wherein the therapeutic agent is a hydrophobic drug.
38. The pharmaceutical composition of claim 37, wherein the hydrophobic drug has a molecular weight of less than about 1000 g/mol.
39. The pharmaceutical composition of claim 1, wherein the therapeutic agent is a hydrophilic drug.
40. The pharmaceutical composition of claim 39, wherein the hydrophilic drug is a peptidomimetic, a peptide, a protein, an oligonucleotide, an oligodeoxynucleotide, RNA, DNA, genetic material, derivatives or analogues thereof, or a mixture thereof.
41. The pharmaceutical composition of claim 39, wherein the hydrophilic drug has a molecular weight of less than about 1000 g/mol.
42. The pharmaceutical composition of claim 1, wherein the surfactants are present in amounts such that the triglyceride can be present in an amount greater than the amount of the triglyceride that remains solubilized in an aqueous dispersion of the triglyceride and a carrier having only one surfactant, the surfactant being hydrophilic, and having the same total surfactant concentration.
43. The pharmaceutical composition of claim 22, wherein the surfactants are present in amounts such that the triglyceride can be present in an amount greater than the amount of the triglyceride that remains solubilized in an aqueous dispersion of the triglyceride and a carrier having only one surfactant, the surfactant being hydrophilic, and having the same total surfactant concentration.
44. The pharmaceutical composition of claim 23, wherein the surfactants are present in amounts such that the triglyceride can be present in an amount greater than the amount of the triglyceride that remains solubilized in an aqueous dispersion of the triglyceride and a carrier having a hydrophilic surfactant but not having a hydrophobic surfactant, and having the same total surfactant concentration.
45. The pharmaceutical composition of claim 1, wherein the triglyceride and surfactants are present in amounts such that upon mixing with an aqueous solution in an aqueous solution to composition ratio of about 10:1 by weight, the composition forms a clear aqueous dispersion.
46. The pharmaceutical composition of claim 1, wherein the triglyceride and surfactants are present in amounts such that upon mixing with an aqueous solution in an aqueous solution to composition ratio of about 100:1 by weight, the composition forms a clear aqueous dispersion.
47. The pharmaceutical composition of claim 46, wherein the clear aqueous dispersion has an absorbance of less than about 0.3 at about 400 nm.
48. The pharmaceutical composition of claim 47, wherein the absorbance is less than about 0.2.
49. The pharmaceutical composition of claim 47, wherein the absorbance is less than about 0.1.
50. The pharmaceutical composition of claim 1, which further comprises a solubilizer.
51. The pharmaceutical composition of claim 50, wherein the solubilizer is selected from the group consisting of alcohols, polyols, amides, esters, propylene glycol ethers and mixtures thereof.
52. The pharmaceutical composition of claim 51, wherein the alcohol or polyol is selected from the group consisting of ethanol, isopropanol, butanol, benzyl alcohol, ethylene glycol, propylene glycol, butanediols and isomers thereof, glycerol, pentaerythritol, sorbitol, mannitol, transcutol, maltol, maltodextrins, dimethyl isosorbide, polyethylene glycol, polypropylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose and other cellulose derivatives, cyclodextrins and cyclodextrin derivatives, and mixtures thereof.
53. The pharmaceutical composition of claim 51, wherein the amide is selected from the group consisting of 2-pyrrolidone, 2-piperidone, .epsilon.-caprolactam, N-alkylpyrrolidone, N-hydroxyalkylpyrrolidone, N-alkylpiperidone, N-alkylcaprolactam, dimethylacetamide, polyvinylpyrrolidone, and mixtures thereof.
54. The pharmaceutical composition of claim 51, wherein the ester is selected from the group consisting of ethyl propionate, tributylcitrate, acetyl triethylcitrate, acetyl tributyl citrate, triethylcitrate, ethyl oleate, ethyl caprylate, ethyl butyrate, triacetin, propylene glycol monoacetate, propylene glycol diacetate, .epsilon.-caprolactone and isomers thereof, .delta.-valerolactone and isomers thereof, .beta.-butyrolactone and isomers thereof, and mixtures thereof.
55. The pharmaceutical composition of claim 50, wherein the solubilizer is selected from the group consisting of ethanol, isopropanol, butanol, benzyl alcohol, ethylene glycol, propylene glycol, butanediol and isomers thereof, glycerol, pentaerythritol, sorbitol, mannitol, transcutol, dimethyl isosorbide, polyethylene glycol, polypropylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose and other cellulose derivatives, cyclodextrins and derivatives thereof, ethyl propionate, tributylcitrate, acetyl triethylcitrate, acetyl tributyl citrate, triethylcitrate, ethyl oleate, ethyl caprylate, ethyl butyrate, triacetin, propylene glycol diacetate, .epsilon.-caprolactone and isomers thereof, .delta.-valerolactone and isomers thereof, .beta.-butyrolactone and isomers thereof, 2-pyrrolidone, 2-piperidone, .epsilon.-caprolactam, N-methylpyrrolidone, N-ethylpyrrolidone, N-hydroxyethyl pyrrolidone, N-octylpyrrolidone, N-laurylpyrrolidone, dimethylacetamide, polyvinylpyrrolidone, glycofurol, methoxy PEG, and mixtures thereof.
56. The pharmaceutical composition of claim 50, wherein the solubilizer is selected from the group consisting of ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, 1,3-butanediol, glycerol, pentaerythritol, sorbitol, glycofurol, transcutol, dimethyl isosorbide, polyethylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose, methylcellulose, ethylcellulose, hydroxypropylcyclodextrins, sulfobutyl ether derivatives of cyclodextrins, ethyl propionate, tributylcitrate, triethylcitrate, ethyl oleate, ethyl caprylate, triacetin, .beta.-butyrolactone and isomers thereof, 2-pyrrolidone, N-methylpyrrolidone, N-ethylpyrrolidone, N-hydroxyethylpyrrolidone, N-octylpyrrolidone, N-laurylpyrrolidone, dimethylacetamide, polyvinylpyrrolidone, and mixtures thereof.
57. The pharmaceutical composition of claim 50, wherein the solubilizer is triacetin, triethylcitrate, ethyl oleate, ethyl caprylate, dimethylacetamide, N-methylpyrrolidone, N-hydroxyethylpyrrolidone, polyvinylpyrrolidone, hydroxypropyl methylcellulose, hydroxypropyl cyclodextrins, ethanol, polyethylene glycol 200-600, glycofurol, transcutol, propylene glycol, dimethyl isosorbide, or a mixture thereof.
58. The pharmaceutical composition of claim 50, wherein the solubilizer is triacetin, ethanol, polyethylene glycol 400, glycofurol, propylene glycol or a mixture thereof.
59. The pharmaceutical composition of claim 1, which further comprises an antioxidant, a bufferant, an antifoaming agent, a detackifier, a preservative, a chelating agent, a viscomodulator, a tonicifier, a flavorant, a colorant, an odorant, an opacifier, a suspending agent, a binder, a filler, a plasticizer, a lubricant, or a mixture thereof.
60. The pharmaceutical composition of claim 1, which further comprises an amount of an enzyme inhibiting agent sufficient to at least partially inhibit enzymatic degradation of the therapeutic agent.
61. The pharmaceutical composition of claim 60, wherein the enzyme inhibitor is solubilized or suspended in the preconcentrate.
62. The pharmaceutical composition of claim 1, which further comprises an aqueous medium comprising water, an aqueous palatable diluent or an aqueous beverage.
63. The pharmaceutical composition of claim 62, wherein the therapeutic agent is provided to the composition in the aqueous medium.
64. The pharmaceutical composition of claim 62, wherein the aqueous medium further comprises an amount of an enzyme inhibiting agent sufficient to at least partially inhibit enzymatic degradation of the therapeutic agent.
65. The pharmaceutical composition of claim 1 in the form of a preconcentrate in a liquid, semi-solid, or solid form, or as an aqueous or organic diluted preconcentrate.
66. A dosage form comprising the pharmaceutical composition of claim 1 processed by lyophilization, encapsulation, extruding, compression, melting, molding, spraying, coating, comminution, mixing, homogenization, sonication, granulation, or a combination thereof.
67. A dosage form comprising the pharmaceutical composition of claim 1 formulated as a pill, capsule, caplet, tablet, granule, bead or powder.
68. The dosage form of claim 67, wherein the capsule is a starch capsule, a cellulosic capsule, a hard gelatin capsule or a soft gelatin capsule.
69. The dosage form of claim 67, wherein the capsule is a starch capsule, a cellulosic capsule, or a soft gelatin capsule.
70. The dosage form of claim 67, which further comprises an enteric coating, a seal coating, or both.
71. A dosage form comprising the pharmaceutical composition of claim 1 formulated as a solution, suspension, emulsion, cream, ointment, lotion, suppository, spray, aerosol, paste, gel, drops, douche, ovule, wafer, troche, cachet, syrup or elixer.
72. A dosage form comprising a multiparticulate carrier coated onto a substrate with the pharmaceutical composition of claim 1.
73. The dosage form of claim 72, wherein the substrate is a particle, a granule or a bead, and is formed of the therapeutic agent, a pharmaceutically acceptable material, or a mixture thereof.
74. The dosage form of claim 72, wherein the multiparticulate carrier is enteric coated, seal coated, or both.
75. The pharmaceutical composition of claim 1, which further comprises an additional amount of the therapeutic agent, said additional amount not solubilized in the composition.
76. The dosage form of claim 72, wherein the dosage form is further processed by encapsulation, compression, extrusion or molding.
77. The dosage form of claim 72, wherein the capsule is a starch capsule, a cellulosic capsule, a hard gelatin capsule, or a soft gelatin capsule.
78. The dosage form of claim 72, wherein the capsule is a starch capsule, a cellulosic capsule, or a soft gelatin capsule.
79. A pharmaceutical composition comprising:
(a) a triglyceride;
(b) a carrier comprising at least one hydrophilic surfactant and at least one hydrophobic surfactant; and (c) a therapeutic agent which is capable of being solubilized in the triglyceride, the carrier, or both the triglyceride and the carrier, wherein the triglyceride and surfactants are present in amounts such that upon mixing with an aqueous solution the composition forms a clear aqueous dispersion.
80. The pharmaceutical composition of claim 79, wherein the triglyceride is selected from the group consisting of vegetable oils, fish oils, animal fats, hydrogenated vegetable oils, partially hydrogenated vegetable oils, synthetic triglycerides, modified triglycerides, fractionated triglycerides, and mixtures thereof.
81. The pharmaceutical composition of claim 79, wherein the triglyceride is selected from the group consisting of almond oil; babassu oil; borage oil;
blackcurrant seed oil; canola oil; castor oil; coconut oil; corn oil; cottonseed oil;
evening primrose oil;
grapeseed oil; groundnut oil; mustard seed oil; olive oil; palm oil; palm kernel oil; peanut oil; rapeseed oil; safflower oil; sesame oil; shark liver oil; soybean oil;
sunflower oil;
hydrogenated castor oil; hydrogenated coconut oil; hydrogenated palm oil;
hydrogenated soybean oil; hydrogenated vegetable oil; hydrogenated cottonseed and castor oil; partially hydrogenated soybean oil; partially soy and cottonseed oil; glyceryl tricaproate; glyceryl tricaprylate; glyceryl tricaprate; glyceryl triundecanoate; glyceryl trilaurate; glyceryl trioleate; glyceryl trilinoleate; glyceryl trilinolenate; glyceryl tricaprylate/caprate; glyceryl tricaprylate/caprate/laurate; glyceryl tricaprylate/caprate/linoleate;
glyceryl tricaprylate/caprate/stearate; saturated polyglycolized glycerides; linoleic glycerides;
caprylic/capric glycerides; modified triglycerides; fractionated triglycerides; and mixtures thereof.
82. The pharmaceutical composition of claim 79, wherein the triglyceride is selected from the group consisting of coconut oil; corn oil; olive oil; palm oil; peanut oil;
safflower oil; sesame oil; soybean oil; hydrogenated castor oil; hydrogenated coconut oil;
partially hydrogenated soybean oil; glyceryl tricaprate; glyceryl trilaurate;
glyceryl trioleate; glyceryl trilinoleate; glyceryl tricaprylate/caprate; glyceryl tricaprylate/caprate/laurate; glyceryl tricaprylate/caprate/linoleate;
glyceryl tricaprylate/caprate/stearate; saturated polyglycolized glycerides; linoleic glycerides;
caprylic/capric glycerides; modified triglycerides; fractionated triglycerides; and mixtures thereof.
83. The pharmaceutical composition of claim 79, wherein the triglyceride is a medium chain triglyceride, a long chain triglyceride, a modified triglyceride, a fractionated triglyceride, or a mixture thereof.
84. The pharmaceutical composition of claim 79, wherein the hydrophilic surfactant comprises at least one non-ionic hydrophilic surfactant having an HLB value greater than or equal to about 10.
85. The pharmaceutical composition of claim 79, wherein the hydrophilic surfactant comprises at least one ionic surfactant.
86. The pharmaceutical composition of claim 84, which further comprises at least one ionic surfactant.
87. The pharmaceutical composition of claim 84, wherein the non-ionic surfactant is selected from the group consisting of alkylglucosides;
alkylmaltosides;
alkylthioglucosides; lauryl macrogolglycerides; polyoxyethylene alkyl ethers;
polyoxyethylene alkylphenols; polyethylene glycol fatty acids esters;
polyethylene glycol glycerol fatty acid esters; polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers; polyglycerol fatty acid esters;
polyoxyethylene glycerides; polyoxyethylene sterols, derivatives, and analogues thereof;
polyoxyethylene vegetable oils; polyoxyethylene hydrogenated vegetable oils; reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; sugar esters, sugar ethers;
sucroglycerides; and mixtures thereof.
88. The pharmaceutical composition of claim 84, wherein the non-ionic hydrophilic surfactant is selected from the group consisting of polyoxyethylene alkylethers; polyethylene glycol fatty acids esters; polyethylene glycol glycerol fatty acid esters; polyoxyethylene sorbitan fatty acid esters; polyoxyethylene-polyoxypropylene block copolymers; polyglycerol fatty acid esters; polyoxyethylene glycerides;
polyoxyethylene vegetable oils; polyoxyethylene hydrogenated vegetable oils;
reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; and mixtures thereof.
89. The pharmaceutical composition of claim 84, wherein the glyceride is a monoglyceride, diglyceride, triglyceride, or a mixture thereof.
90. The pharmaceutical composition of claim 88, wherein the reaction mixture comprises the transesterification products of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
91. The pharmaceutical composition of claim 88, wherein the polyol is glycerol, ethylene glycol, polyethylene glycol, sorbitol, propylene glycol, pentaerythritol, a saccharide, or a mixture thereof.
92. The pharmaceutical composition of claim 84, wherein the hydrophilic surfactant is PEG-10 laurate, PEG-12 laurate, PEG-20 laurate, PEG-32 laurate, dilaurate, PEG-12 oleate, PEG-15 oleate, PEG-20 oleate, PEG-20 dioleate, PEG-32 oleate, PEG-200 oleate, PEG-400 oleate, PEG-15 stearate, PEG-32 distearate, PEG-40 stearate, PEG-100 stearate, PEG-20 dilaurate, PEG-25 glyceryl trioleate, PEG-32 dioleate, PEG-20 glyceryl laurate, PEG-30 glyceryl laurate, PEG-20 glyceryl stearate, PEG-20 glyceryl oleate, PEG-30 glyceryl oleate, PEG-30 glyceryl laurate, PEG-40 glyceryl laurate, PEG-40 palm kernel oil, PEG-50 hydrogenated castor oil, PEG-40 castor oil, PEG-35 castor oil, PEG-60 castor oil, PEG-40 hydrogenated castor oil, PEG-60 hydrogenated castor oil, PEG-60 corn oil, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, polyglyceryl-10 laurate, PEG-30 cholesterol, PEG-25 phyto sterol, PEG-30 soya sterol, PEG-20 trioleate, PEG-40 sorbitan oleate, PEG-80 sorbitan laurate, polysorbate 20, polysorbate 80, POE-9 lauryl ether, POE-23 lauryl ether, POE-10 oleyl ether, oleyl ether, POE-20 stearyl ether, tocopheryl PEG-100 succinate, PEG-24 cholesterol, polyglyceryl-10 oleate, Tween 40, Tween 60, sucrose monostearate, sucrose monolaurate, sucrose monopalmitate, PEG 10-100 nonyl phenol series, PEG 15-100 octyl phenol series, a poloxamer, or a mixture thereof.
93. The pharmaceutical composition of claim 84, wherein the hydrophilic surfactant is PEG-20 laurate, PEG-20 oleate, PEG-35 castor oil, PEG-40 palm kernel oil, PEG-40 hydrogenated castor oil, PEG-60 corn oil, PEG-25 glyceryl trioleate, polyglyceryl-10 laurate, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, PEG-30 cholesterol, polysorbate 20, polysorbate 80, POE-9 lauryl ether, POE-23 lauryl ether, POE-10 oleyl ether, PEG-24 cholesterol, sucrose monostearate, sucrose monolaurate, a poloxamer, or a mixture thereof.
94. The pharmaceutical composition of claim 84, wherein the hydrophilic surfactant is PEG-35 castor oil, PEG-40 hydrogenated castor oil, PEG-60 corn oil, PEG-25 glyceryl trioleate, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, polysorbate 20, polysorbate 80, tocopheryl PEG-1000 succinate, PEG-24 cholesterol, a poloxamer, or a mixture thereof.
95. The pharmaceutical composition of claim 85, wherein the ionic surfactant is selected from the group consisting of alkyl ammonium salts; bile salts, analogues, and derivatives thereof; fusidic acid and derivatives thereof; fatty acid derivatives of amino acids, oligopeptides, and polypeptides; glyceride derivatives of amino acids, oligopeptides, and polypeptides; acyl lactylates; mono-,diacetylated tartaric acid esters of mono-,diglycerides; succinylated monoglycerides; citric acid esters of mono-,diglycerides;
alginate salts; propylene glycol alginate; lecithins and hydrogenated lecithins; lysolecithin and hydrogenated lysolecithins; lysophospholipids and derivatives thereof;
carnitine fatty acid ester salts; phospholipids and derivatives thereof; salts of alkylsulfates; salts of fatty acids; sodium docusate; and mixtures thereof.
96. The pharmaceutical composition of claim 85, wherein the ionic surfactant is selected from the group consisting of bile salts, analogues, and derivatives thereof;
lecithins, lysolecithin, phospholipids, lysophospholipids and derivatives thereof; carnitine fatty acid ester salts; salts of alkylsulfates; salts of fatty acids; sodium docusate; acyl lactylates; mono-,diacetylated tartaric acid esters of mono-,diglycerides;
succinylated monoglycerides; citric acid esters of mono-,diglycerides; and mixtures thereof.
97. The pharmaceutical composition of claim 85, wherein the ionic surfactant is selected from the group consisting of lecithin, lysolecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylglycerol, phosphatidic acid, phosphatidylserine, lysophosphatidylcholine, lysophosphatidylethanolamine, lysophosphatidylglycerol, lysophosphatidic acid, lysophosphatidylserine, PEG-phosphatidylethanolamine, PVP-phosphatidylethanolamine, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, cholate, chenodeoxycholate, lithocholate, ursodeoxycholate, taurocholate, glycocholate, deoxycholate, taurodeoxycholate, chenodeoxycholate, glycodeoxycholate, glycochenodeoxycholate, taurochenodeoxycholate, ursodeoxycholate, lithocholate, tauroursodeoxycholate, glycoursodeoxycholate, cholylsarcosine, N-methyl taurocholate, caproate, caprylate, caprate, laurate, myristate, palmitate, oleate, ricinoleate, linoleate, linolenate, stearate, lauryl sulfate, tetraacetyl sulfate, docusate, lauroyl carnitine, palmitoyl carnitine, myristoyl carnitine, and salts and mixtures thereof.
98. The pharmaceutical composition of claim 85, wherein the ionic surfactant is selected from the group consisting of lecithin, lysolecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylglycerol, lysophosphatidylcholine, PEG-phosphatidylethanolamine, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, cholate, taurocholate, glycocholate, deoxycholate, taurodeoxycholate, chenodeoxycholate, lithocholate, ursodeoxycholate, glycodeoxycholate, cholylsarcosine, caproate, caprylate, caprate, laurate, oleate, lauryl sulfate, docusate, lauroyl carnitine, palmitoyl carnitine, myristoyl carnitine, and salts and mixtures thereof.
99. The pharmaceutical composition of claim 85, wherein the ionic surfactant is selected from the group consisting of lecithin, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, chenodeoxycholate, lithocholate, ursodeoxycholate, taurocholate, caprylate, caprate, oleate, lauryl sulfate, docusate, lauroyl carnitine, palmitoyl carnitine, myristoyl carnitine, and salts and mixtures thereof.
100. The pharmaceutical composition of claim 79 wherein the hydrophobic surfactant is a compound or mixture of compounds having an HLB value less than about 10.
101. The pharmaceutical composition of claim 100, wherein the hydrophobic surfactant is selected from the group consisting of alcohols; polyoxyethylene alkylethers;
fatty acids; bile acids; glycerol fatty acid esters; acetylated glycerol fatty acid esters; lower alcohol fatty acids esters; polyethylene glycol fatty acids esters;
polyethylene glycol glycerol fatty acid esters; polypropylene glycol fatty acid esters;
polyoxyethylene glycerides; lactic acid derivatives of mono/diglycerides; propylene glycol diglycerides;
sorbitan fatty acid esters; polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers; transesterified vegetable oils; sterols;
sterol derivatives; sugar esters; sugar ethers; sucroglycerides; polyoxyethylene vegetable oils;
polyoxyethylene hydrogenated vegetable oils; reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; and mixtures thereof.
102. The pharmaceutical composition of claim 100, wherein the hydrophobic surfactant is selected from the group consisting of fatty acids; bile acids;
lower alcohol fatty acid esters; polyethylene glycol glycerol fatty acid esters;
polypropylene glycol fatty acid esters; polyoxyethylene glycerides; glycerol fatty acid esters;
acetylated glycerol fatty acid esters; lactic acid derivatives of mono/diglycerides; sorbitan fatty acid esters;
polyoxyethylene sorbitan fatty acid esters; polyoxyethylene-polyoxypropylene block copolymers; polyoxyethylene vegetable oils; polyoxyethylene hydrogenated vegetable oils; reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols;
and mixtures thereof.
103. The pharmaceutical composition of claim 100, wherein the hydrophobic surfactant is selected from the group consisting of bile acids; lower alcohol fatty acids esters; polypropylene glycol fatty acid esters; propylene glycol fatty acid esters; glycerol fatty acid esters; acetylated glycerol fatty acid esters; lactic acid derivatives of mono/diglycerides; sorbitan fatty acid esters; polyoxyethylene vegetable oils;
and mixtures thereof.
104. The pharmaceutical composition of claim 100, wherein the hydrophobic surfactant is a glycerol fatty acid ester, an acetylated glycerol fatty acid ester, or a mixture thereof.
105. The pharmaceutical composition of claim 104, wherein the glycerol fatty acid ester is a monoglyceride, diglyceride, or a mixture thereof.
106. The pharmaceutical composition of claim 105, wherein the fatty acid of the glycerol fatty acid ester is a C6 to C22 fatty acid or a mixture thereof.
107. The pharmaceutical composition of claim 100, wherein the hydrophobic surfactant is a reaction mixture of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
108. The pharmaceutical composition of claim 107, wherein the reaction mixture is a transesterification product of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
109. The pharmaceutical composition of claim 107, wherein the polyol is polyethylene glycol, sorbitol, propylene glycol, pentaerythritol, a saccharide, or a mixture thereof.
110. The pharmaceutical composition of claim 100, wherein the hydrophobic surfactant is selected from the group consisting of myristic acid; oleic acid;
lauric acid;
stearic acid; palmitic acid; PEG 1-4 stearate; PEG 2-4 oleate; PEG-4 dilaurate; PEG-4 dioleate; PEG-4 distearate; PEG-6 dioleate; PEG-6 distearate; PEG-8 dioleate;

castor oil; PEG 5-10 hydrogenated castor oil; PEG 6-20 corn oil; PEG 6-20 almond oil;
PEG-6 olive oil; PEG-6 peanut oil; PEG-6 palm kernel oil; PEG-6 hydrogenated palm kernel oil; PEG-4 capric/caprylic triglyceride, mono, di, tri, tetra esters of vegetable oil and sorbitol; pentaerythrityl di, tetra stearate, isostearate, oleate, caprylate, or caprate;
polyglyceryl 2-4 oleate, stearate, or isostearate; polyglyceryl 4-10 pentaoleate;
polyglyceryl-3 dioleate; polyglyceryl-6 dioleate; polyglyceryl-10 trioleate;
polyglyceryl-3 distearate; propylene glycol mono- or diesters of a C6 to C22 fatty acid;
monoglycerides of a C6 to C22 fatty acid; acetylated monoglycerides of C6 to C22 fatty acid;
diglycerides of C6 to C22 fatty acids; lactic acid derivatives of monoglycerides; lactic acid derivatives of diglycerides; cholesterol; phytosterol; PEG 5-20 soya sterol; PEG-6 sorbitan tetra, hexastearate; PEG-6 sorbitan tetraoleate; sorbitan monolaurate; sorbitan monopalmitate;
sorbitan mono, trioleate; sorbitan mono, tristearate; sorbitan monoisostearate; sorbitan sesquioleate; sorbitan sesquistearate; PEG 2-5 oleyl ether; POE 2-4 lauryl ether; PEG-2 cetyl ether; PEG-2 stearyl ether; sucrose distearate; sucrose dipalmitate;
ethyl oleate;
isopropyl myristate; isopropyl palmitate; ethyl linoleate; isopropyl linoleate; poloxamers;
cholic acid; ursodeoxycholic acid; glycocholic acid; taurocholic acid;
lithocholic acid;
deoxycholic acid; chenodeoxycholic acid; and mixtures thereof.
111. The pharmaceutical composition of claim 100, wherein the hydrophobic surfactant is selected from the group consisting of oleic acid; lauric acid;
glyceryl monocaprate; glyceryl monocaprylate; glyceryl monolaurate; glyceryl monooleate;
glyceryl dicaprate; glyceryl dicaprylate; glyceryl dilaurate; glyceryl dioleate; acetylated monoglycerides; propylene glycol oleate; propylene glycol laurate;
polyglyceryl-3 oleate;
polyglyceryl-6 dioleate; PEG-6 corn oil; PEG-20 corn oil; PEG-20 almond oil;
sorbitan monooleate; sorbitan monolaurate; POE-4 lauryl ether; POE-3 oleyl ether; ethyl oleate;
poloxamers; cholic acid; ursodeoxycholic acid; glycocholic acid; taurocholic acid;
lithocholic acid; deoxycholic acid; chenodeoxycholic acid; and mixtures thereof.
112. The pharmaceutical composition of claim 79, wherein the therapeutic agent is a drug, a vitamin, a nutritional supplement, a cosmeceutical, or a mixture thereof.
113. The pharmaceutical composition of claim 79, wherein the therapeutic agent is a hydrophobic drug.
114. The pharmaceutical composition of claim 113, wherein the hydrophobic drug has a molecular weight of less than about 1000 g/mol.
115. The pharmaceutical composition of claim 79, wherein the therapeutic agent is a hydrophilic drug.
116. The pharmaceutical composition of claim 115, wherein the hydrophilic drug is a peptidomimetic, a peptide, a protein, an oligonucleotide, an oligodeoxynucleotide, RNA, DNA, genetic material, derivatives or analogues thereof, or a mixture thereof.
117. The pharmaceutical composition of claim 115, wherein the hydrophilic drug has a molecular weight of less than about 1000 g/mol.
118. The pharmaceutical composition of claim 79, wherein the surfactants are present in amounts such that the triglyceride can be present in an amount greater than the amount of the triglyceride that remains solubilized in an aqueous dispersion of the triglyceride and a carrier having a hydrophilic surfactant but not having a hydrophobic surfactant, and having the same total surfactant concentration.
119. The pharmaceutical composition of claim 79, wherein the triglyceride and surfactants are present in amounts such that upon mixing with an aqueous solution in an aqueous solution to composition ratio of about 10:1 by weight, the composition forms a clear aqueous dispersion.
120. The pharmaceutical composition of claim 79, wherein the triglyceride and surfactants are present in amounts such that upon mixing with an aqueous solution in an aqueous solution to composition ratio of about 100:1 by weight, the composition forms a clear aqueous dispersion.
121. The pharmaceutical composition of claim 79, wherein the clear aqueous dispersion has an absorbance of less than about 0.3 at about 400 nm when the composition is diluted with an aqueous solution in an aqueous solution to composition ratio of 100:1 by weight.
122. The pharmaceutical composition of claim 121, wherein the absorbance is less than about 0.2.
123. The pharmaceutical composition of claim 121, wherein the absorbance is less than about 0.1.
124. The pharmaceutical composition of claim 79, which further comprises a solubilizer.
125. The pharmaceutical composition of claim 124, wherein the solubilizer is selected from the group consisting of alcohols, polyols, amides, esters, propylene glycol ethers and mixtures thereof.
126. The pharmaceutical composition of claim 125, wherein the alcohol or polyol is selected from the group consisting of ethanol, isopropanol, butanol, benzyl alcohol, ethylene glycol, propylene glycol, butanediols and isomers thereof, glycerol, pentaerythritol, sorbitol, mannitol, transcutol, maltol, maltodextrins, dimethyl isosorbide, polyethylene glycol, polypropylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose and other cellulose derivatives, cyclodextrins and cyclodextrin derivatives, and mixtures thereof.
127. The pharmaceutical composition of claim 125, wherein the amide is selected from the group consisting of 2-pyrrolidone, 2-piperidone, E-caprolactam, N-alkylpyrrolidone, N-hydroxyalkylpyrrolidone, N-alkylpiperidone, N-alkylcaprolactam, dimethylacetamide, polyvinylpyrrolidone, and mixtures thereof.
128. The pharmaceutical composition of claim 125, wherein the ester is selected from the group consisting of ethyl propionate, tributylcitrate, acetyl triethylcitrate, acetyl tributyl citrate, triethylcitrate, ethyl oleate, ethyl caprylate, ethyl butyrate, triacetin, propylene glycol monoacetate, propylene glycol diacetate, .epsilon.-caprolactone and isomers thereof, .delta.-valerolactone and isomers thereof, .beta.-butyrolactone and isomers thereof, and mixtures thereof.
129. The pharmaceutical composition of claim 124, wherein the solubilizer is selected from the group consisting of ethanol, isopropanol, butanol, benzyl alcohol, ethylene glycol, propylene glycol, butanediol and isomers thereof, glycerol, pentaerythritol, sorbitol, mannitol, transcutol, dimethyl isosorbide, polyethylene glycol, polypropylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose and other cellulose derivatives, cyclodextrins and derivatives thereof, ethyl propionate, tributylcitrate, acetyl triethylcitrate, acetyl tributyl citrate, triethylcitrate, ethyl oleate, ethyl caprylate, ethyl butyrate, triacetin, propylene glycol diacetate, .epsilon.-caprolactone and isomers thereof, .delta.-valerolactone and isomers thereof, .beta.-butyrolactone and isomers thereof, 2-pyrrolidone, 2-piperidone, .epsilon.-caprolactam, N-methylpyrrolidone, N-ethylpyrrolidone, N-hydroxyethyl pyrrolidone, N-octylpyrrolidone, N-laurylpyrrolidone, dimethylacetamide, polyvinylpyrrolidone, glycofurol, methoxy PEG, and mixtures thereof.
130. The pharmaceutical composition of claim 124, wherein the solubilizer is selected from the group consisting of ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, 1,3-butanediol, glycerol, pentaerythritol, sorbitol, glycofurol, transcutol, dimethyl isosorbide, polyethylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose, methylcellulose, ethylcellulose, hydroxypropylcyclodextrins, sulfobutyl ether derivatives of cyclodextrins, ethyl propionate, tributylcitrate, triethylcitrate, ethyl oleate, ethyl caprylate, triacetin, .beta.-butyrolactone and isomers thereof, 2-pyrrolidone, N-methylpyrrolidone, N-ethylpyrrolidone, N-hydroxyethylpyrrolidone, N-octylpyrrolidone, N-laurylpyrrolidone, dimethylacetamide, polyvinylpyrrolidone, and mixtures thereof.
131. The pharmaceutical composition of claim 124, wherein the solubilizer is triacetin, triethylcitrate, ethyl oleate, ethyl caprylate, dimethylacetamide, N-methylpyrrolidone, N-hydroxyethylpyrrolidone, polyvinylpyrrolidone, hydroxypropyl methylcellulose, hydroxypropyl cyclodextrins, ethanol, polyethylene glycol 200-600, glycofurol, transcutol, propylene glycol, dimethyl isosorbide, or a mixture thereof.
132. The pharmaceutical composition of claim 124, wherein the solubilizer is triacetin, ethanol, polyethylene glycol 400, glycofurol, propylene glycol or a mixture thereof.
133. The pharmaceutical composition of claim 79, which further comprises an antioxidant, a bufferant, an antifoaming agent, a detackifier, a preservative, a chelating agent, a viscomodulator, a tonicifier, a flavorant, a colorant, an odorant, an opacifier, a suspending agent, a binder, a filler, a plasticizer, a lubricant, or a mixture thereof.
134. The pharmaceutical composition of claim 79, which further comprises an amount of an enzyme inhibiting agent sufficient to at least partially inhibit enzymatic degradation of the therapeutic agent.
135. The pharmaceutical composition of claim 134, wherein the enzyme inhibitor is solubilized or suspended in the preconcentrate.
136. The pharmaceutical composition of claim 79, which further comprises an aqueous medium comprising water, an aqueous palatable diluent or an aqueous beverage.
137. The pharmaceutical composition of claim 136, wherein the therapeutic agent is provided to the composition in the aqueous medium.
138. The pharmaceutical composition of claim 136, wherein the aqueous medium further comprises an amount of an enzyme inhibiting agent sufficient to at least partially inhibit enzymatic degradation of the therapeutic agent.
139. The pharmaceutical composition of claim 79 in the form of a preconcentrate in a liquid, semi-solid, or solid form, or as an aqueous or organic diluted preconcentrate.
140. A dosage form comprising the pharmaceutical composition of claim 79 processed by lyophilization, encapsulation, extruding, compression, melting, molding, spraying, coating, comminution, mixing, homogenization, sonication, granulation, or a combination thereof.
141. A dosage form comprising the pharmaceutical composition of claim 79 formulated as a pill, capsule, caplet, tablet, granule, bead or powder.
142. The dosage form of claim 141, wherein the capsule is a starch capsule, a cellulosic capsule, a hard gelatin capsule or a soft gelatin capsule.
143. The dosage form of claim 141, wherein the capsule is a starch capsule, a cellulosic capsule, or a soft gelatin capsule.
144. The dosage form of claim 141, which further comprises an enteric coating, a seal coating, or both.
145. A dosage form comprising the pharmaceutical composition of claim 79 formulated as a solution, suspension, emulsion, cream, ointment, lotion, suppository, spray, aerosol, paste, gel, drops, douche, ovule, wafer, troche, cachet, syrup or elixer.
146. A dosage form comprising a multiparticulate carrier coated onto a substrate with the pharmaceutical composition of claim 79.
147. The dosage form of claim 146, wherein the substrate is a particle, a granule or a bead, and is formed of the therapeutic agent, a pharmaceutically acceptable material, or a mixture thereof.
148. The dosage form of claim 146, wherein the multiparticulate carrier is enteric coated, seal coated, or both.
149. The pharmaceutical composition of claim 79, which further comprises an additional amount of the therapeutic agent, said additional amount not solubilized in the composition.
150. The dosage form of claim 146, wherein the dosage form is further processed by encapsulation, compression, extrusion or molding.
151. The dosage form of claim 146, wherein the capsule is a starch capsule, a cellulosic capsule, a hard gelatin capsule, or a soft gelatin capsule.
152. The dosage form of claim 146, wherein the capsule is a starch capsule, a cellulosic capsule, or a soft gelatin capsule.
153. A pharmaceutical composition comprising:
(a) a triglyceride;
(b) a carrier comprising at least two surfactants, at least one of the surfactants being hydrophilic, wherein the triglyceride and surfactants are present in amounts such that upon mixing with an aqueous solution the composition forms a clear aqueous dispersion;
(c) a first amount of a therapeutic agent, said first amount being solubilized in the triglyceride, the carrier, or both the triglyceride and the carrier;
and (d) a second amount of a therapeutic agent, said second amount not solubilized in the triglyceride or the carrier.
154. A pharmaceutical composition comprising:
(a) a triglyceride; and (b) a carrier comprising at least two surfactants, at least one of the surfactants being hydrophilic, wherein the triglyceride and surfactants are present in amounts such that upon mixing with an aqueous solution the composition forms a clear aqueous dispersion, and wherein the triglyceride is present in an amount greater than the amount of the triglyceride that remains solubilized in an aqueous dispersion of the triglyceride and a carrier having only one surfactant, the surfactant being hydrophilic, and having the same total surfactant concentration.
155. The composition of claim 154, wherein the triglyceride comprises a digestible oil.
156. The pharmaceutical composition of claim 154, wherein the triglyceride is selected from the group consisting of vegetable oils, fish oils, animal fats, hydrogenated vegetable oils, partially hydrogenated vegetable oils, synthetic triglycerides, and mixtures thereof.
157. The pharmaceutical composition of claim 154, wherein the triglyceride is selected from the group consisting of almond oil; babassu oil; borage oil;
blackcurrant seed oil; canola oil; castor oil; coconut oil; corn oil; cottonseed oil;
evening primrose oil;
grapeseed oil; groundnut oil; mustard seed oil; olive oil; palm oil; palm kernel oil; peanut oil; rapeseed oil; safflower oil; sesame oil; shark liver oil; soybean oil;
sunflower oil;
hydrogenated castor oil; hydrogenated coconut oil; hydrogenated palm oil;
hydrogenated soybean oil; hydrogenated vegetable oil; hydrogenated cottonseed and castor oil; partially hydrogenated soybean oil; partially soy and cottonseed oil; glyceryl tricaproate; glyceryl tricaprylate; glyceryl tricaprate; glyceryl triundecanoate; glyceryl trilaurate; glyceryl trioleate; glyceryl trilinoleate; glyceryl trilinolenate; glyceryl tricaprylate/caprate; glyceryl tricaprylate/caprate/laurate; glyceryl tricaprylate/caprate/linoleate;
glyceryl tricaprylate/caprate/stearate; saturated polyglycolized glycerides; linoleic glycerides;
caprylic/capric glycerides; and mixtures thereof.
158. The pharmaceutical composition of claim 154, wherein the triglyceride is selected from the group consisting of coconut oil; corn oil; olive oil; palm oil; peanut oil;
safflower oil; sesame oil; soybean oil; hydrogenated castor oil; hydrogenated coconut oil;
partially hydrogenated soybean oil; glyceryl tricaprate; glyceryl trilaurate;
glyceryl trioleate; glyceryl trilinoleate; glyceryl tricaprylate/caprate; glyceryl tricaprylate/caprate/laurate; glyceryl tricaprylate/caprate/linoleate;
glyceryl tricaprylate/caprate/stearate; saturated polyglycolized glycerides; linoleic glycerides;
caprylic/capric glycerides; and mixtures thereof.
159. The pharmaceutical composition of claim 154, wherein the triglyceride is a medium chain triglyceride, a long chain triglyceride, or a mixture thereof.
160. The pharmaceutical composition of claim 154, which further comprises a therapeutic agent.
161. A method of treating an animal with a therapeutic agent, the method comprising:
(a) providing a dosage form of a pharmaceutical composition comprising:
(i) a triglyceride; and (ii) a carrier comprising at least two surfactants, at least one of the surfactants being hydrophilic, wherein the triglyceride and surfactants are present in amounts such that upon mixing with an aqueous solution the composition forms a clear aqueous dispersion;
(b) providing a therapeutic agent; and (c) administering said dosage form to said animal.
162. The method of claim 161, wherein the dosage form comprises the pharmaceutical composition processed by lyophilization, encapsulation, extruding, compression, melting, molding, spraying, coating, comminution, mixing, homogenization, sonication, granulation, or a combination thereof.
163. The method of claim 161, wherein the dosage form comprises the pharmaceutical composition formulated as a pill, capsule, caplet, tablet, granule, bead or powder.
164. The method of claim 163, wherein the capsule is a starch capsule, a cellulosic capsule, a hard gelatin capsule or a soft gelatin capsule.
165. The method of claim 163, wherein the capsule is a starch capsule, a cellulosic capsule, or a soft gelatin capsule.
166. The method of claim 163, wherein the capsule further comprises an enteric coating, a seal coating, or both.
167. The method of claim 161, wherein the dosage form comprises the pharmaceutical composition formulated as a solution, suspension, emulsion, cream, ointment, lotion, suppository, spray, aerosol, paste, gel, drops, douche, ovule, wafer, troche, cachet, syrup or elixer.
168. The method of claim 161, wherein the dosage form comprises a multiparticulate carrier coated onto a substrate with the pharmaceutical composition.
169. The method of claim 168, wherein the substrate is a particle, a granule or a bead, and is formed of the therapeutic agent, a pharmaceutically acceptable material or a mixture thereof.
170. The method of claim 168, wherein the multiparticulate carrier is enteric coated, seal coated, or both.
171. The method of claim 168, wherein the dosage form is further processed by encapsulation, compression, extrusion or molding.
172. The method of claim 168, wherein the capsule is a starch capsule, a cellulosic capsule, a hard gelatin capsule, or a soft gelatin capsule.
173. The method of claim 168, wherein the capsule is a starch capsule, a cellulosic capsule, or a soft gelatin capsule.
174. The method of claim 161, wherein the therapeutic agent is provided by solubilizing the therapeutic agent in the triglyceride, in the carrier, or in both the triglyceride and the carrier.
175. The method of claim 161, wherein the therapeutic agent is provided separately from the dosage form of the pharmaceutical composition.
176. The method of claim 161, wherein the dosage form is administered by an oral, parenteral, buccal, topical, transdermal, ocular, pulmonary, vaginal, rectal or transmucosal route.
177. The method of claim 161, wherein the animal is a mammal.
178. The method of claim 177, wherein the mammal is a human.
179. A method of increasing the amount of a triglyceride that can be solubilized in a clear aqueous dispersion, the method comprising:
(a) providing a composition comprising a triglyceride and a carrier, the carrier comprising at least two surfactants, at least one of the surfactants being hydrophilic; and (b) dispersing the composition in an aqueous solution, wherein the triglyceride and surfactants are present in amounts such that upon mixing with an aqueous solution the composition forms a clear aqueous dispersion, and wherein the triglyceride is present in an amount greater than the amount of the triglyceride that remains solubilized in an aqueous dispersion of the triglyceride and a carrier having only one surfactant and having the same total surfactant concentration.
180. The method of claim 179, wherein the step of dispersing the composition comprises mixing the composition with an aqueous solution in vitro.
181. The method of claim 179, wherein the step of dispersing the composition comprises allowing the composition to contact an aqueous biological solution in vivo upon administering the composition to an animal.
182. A method of treating an animal with a therapeutic agent, the method comprising:
(a) providing a dosage form of a pharmaceutical composition comprising:
(i) an effective amount of a triglyceride; and (ii) a carrier comprising at least two surfactants, at least one of the surfactants being hydrophilic, wherein the triglyceride and surfactants are present in amounts such that upon mixing with an aqueous solution the composition forms a clear aqueous dispersion; and (b) administering said dosage form to said animal.
183. The method of claim 182, wherein the effective amount of the triglyceride is a nutritionally effective amount of a digestible oil.
184. The method of claim 182, wherein the effective amount of the triglyceride is an amount sufficient to improve the bioabsorption of a therapeutic agent co-administered with the dosage form of the pharmaceutical composition.
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