EP1165141A2 - Neue formulierungen mit lipid regulierenden wirkstoffen - Google Patents
Neue formulierungen mit lipid regulierenden wirkstoffenInfo
- Publication number
- EP1165141A2 EP1165141A2 EP00919496A EP00919496A EP1165141A2 EP 1165141 A2 EP1165141 A2 EP 1165141A2 EP 00919496 A EP00919496 A EP 00919496A EP 00919496 A EP00919496 A EP 00919496A EP 1165141 A2 EP1165141 A2 EP 1165141A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- polyoxyethylene
- caprylic
- oil
- lipid
- 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.)
- Withdrawn
Links
Classifications
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Definitions
- the present invention relates to novel formulations comprising lipid-regulating agents.
- 2- [4- (4-chlorobenzoyl) phenoxy] -2 -methyl -propanoic acid, 1-methylethylester, also known as fenofibrate, is representative of a broad class of compounds having pharmaceutical utility as lipid regulating agents. More specifically, this compound is part of a lipid-regulating agent class of compounds commonly known as fibrates, and is disclosed in U.S. Patent No. 4,058,552.
- Fenofibrate has been prepared in several different formulations, c.f., U.S. Patent No. 4,800,079 and U.S. Patent No. 4,895,726.
- U.S. Patent No. 4,895,726 discloses a co-micronized formulation of fenofibrate and a solid surfactant .
- U.S. Patent No. 4,961,890 discloses a process for preparing a controlled release formulation containing fenofibrate in an intermediate layer in the form of crystalline microparticles included within pores of an inert matrix.
- the formulation is prepared by a process involving the sequential steps of dampening said inert core with a solution based on said binder, then projecting said fenofibrate microparticles in a single layer onto said dampened core, and thereafter drying, before said solution based on said binder dissolves said fenofibrate microparticles, and repeating said three steps in sequence until said intermediate layer is formed.
- EP0793958A2 discloses a process for producing a fenofibrate solid dosage form utilizing fenofibrate, a surface active agent and polyvinyl pyrrolidone in which the fenofibrate particles are mixed with a polyvinyl pyrrolidone solution. The thus obtained mixture is granulated with an aqueous solution of one or more surface active agents, and the granulate thus produced is dried.
- PCT Publication No. WO 82/01649 discloses a fenofibrate formulation having granules that are comprised of a neutral core that is a mixture of saccharose and starch.
- the neutral core is covered with a first layer of fenofibrate, admixed with an excipient and with a second microporous outer layer of an edible polymer.
- U.S. Patent No. 5,645,856 describes the use of a carrier for hydrophobic drugs, including fenofibrate, and pharmaceutical compositions based thereon.
- the carrier comprises a digestible oil and a pharmaceutically-acceptable surfactant component for dispersing the oil in vivo upon administration of the carrier, which comprises a hydrophilic surfactant, said surfactant component being such as not to substantially inhibit the in vivo lipolysis of the digestible oil.
- Gemfibrozil is another member of the fibrate class of lipid-regulating agents.
- U.S. Patent No. 4,927,639 discloses a disintegratable formulation of gemfibrozil providing both immediate and sustained release, comprising a tablet compressed from a mixture of a first and second granulation, and a disintegration excipient operable to effect partial or complete disintegration in the stomach.
- the first granulation comprises finely divided particles of pure gemfibrozil granulated with at least one cellulose derivative
- the second granulation comprises finely divided particles of pure gemfibrozil granulated with a pharmaceuitcally-acceptable water soluble or insoluble polymer which are then uniformly coated with a pharmaceuitcally-acceptable (meth) acylate copolymer prior to admixture with the first granulation.
- the first and second granulations are present in the final composition in a ratio of from about 10:1 to about 1:10.
- U.S. Patent 4,925,676 discloses a disintegratable gemfibrozil tablet providing both immediate and enteric release, which is compressed from a mixture of a first granulation of gemfibrozil with at least one acid- disintegratable binder, and a second granulation formed from the first granulation, but regranulated or coated with an alkali-disintegratable formulation of at least one substantially alkali-soluble and substantially acid- insoluble polymer.
- statins Another class of lipid-regulating agents are commonly known as statins, of which pravastatin and atorvastatin are members.
- U.S. Patents 5,030,447 and 5,180,589 describe stable pharmaceutical compositions, which when dispersed in water have a pH of at least 9, and include a medicament which is sensitive to a low pH environment, such as prevastatin, one or more fillers such as lactose and/or microcrystalline cellulose, one or more binders, such as microcrystalline cellulose (dry binder) or polyvinylpyrrolidone (wet binder) , one or more disintegrating agents such as croscarmellose sodium, one or more lubricants such as magnesium stearate and one or more basifying agents such as magnesium oxide.
- prevastatin one or more fillers such as lactose and/or microcrystalline cellulose
- binders such as microcrystalline cellulose (dry binder) or polyvinylpyrrolidone (wet binder)
- the present invention is directed to a formulation comprising a lipid-regulating agent dissolved in a mixture of an oil and one or more surfactants to form a concentrate.
- This concentrate forms fine and stable emulsions upon gentle mixing with water or any aqueous solutions.
- the emulsions result in an increase in drug solubility and oral bioavailability .
- the formulation may be administered directly, diluted into an appropriate vehicle for administration, encapsulated into soft or hard gelatin capsules for administration, or administered by other means obvious to those skilled in the art.
- Figure 1 is a graph showing the plasma concentration in fasted dogs of the formulation of Example 1 and a reference compound .
- the bulk lipid-regulating agent may be prepared by any available method, as for example the compound fenofibrate may be prepared by the procedure disclosed in U.S. Patent No. 4,058,552, or the procedure disclosed in U.S. Patent No. 4,739,101, both herein incorporated by reference.
- the solution comprising the lipid-regulating agent is prepared by premixing the oil and one and more surfactants, then adding the lipid-regulating agent to the premix and mixing the resulting mixture well until dissolved.
- the delivery system of the present invention results in increased solubility, half-life and bioavailability of the lipid-regulating agent. It can be further diluted with additional liquids or it may be thickened and/or stabilized with various pharmaceutical excipients to vary its existing properties .
- Suitable oils include, but are not limited to, any pharmaceutically acceptable oil, such as, for example, Myvacet 9-08 (distillated acetylated monoglycerides: manufacturer) , Myvacet 9-40 (distillated acetylated monoglycerides: manufacturer), Capmul PG-8 (propylene glycol and mono/di-caprylate; Abitec) , Arlamol E (polyoxypropylene (15) stearyl alcohol; ICI) , Captex 300 (glyceryl tricaprylate/caprate; Abitec), Labrafac Lipophile W 1349 (triglyceride of caprylic/capric acid; Gattefosse) , olive oil, Miglyol 812 ((caprylic/capric triglycerides ; HULS America), sesame oil, Novol (oleyl alcohol; Croda) .
- Preferred oils include Myvacet 9-08, Myvacet 9-40, and Capmul PG-8 (
- Suitable surfactants include any surfactant in which fenofibrate is highly soluble. Such surfactants will typically be those with HLB values ranging from about 1 to about 20. Representative surfactants include Labrafac
- Lipophile WL 1349 (triglyceride of caprylic/capric acid; Gattefosse ), Lauroglycol FCC (propylene glycol laurate; Gattefosse) , Labrafil M 1944 CS (glyceryl and polyethylene glycol esters; Gattefosse), Span 80 (sorbitan monooleate; Sigma) , Capmul MCM (mono/diglycerides of caprylic/capric acid in glycerol; Abitec), Arlacel 83 (sorbitan sesquioleate; ICI) , Brij 93 (polyoxyethylene (2) oleyl ether; READ ICI) , Acconon E (polyoxypropylene 15 stearyl ether; Abitec) , Labrafil M 2125 CS (unsaturated polyglycolyzed glycerides; Gattefose) , Maisine 35-1
- Gattefosse Labrafac CM 12 (polyglycolysed glycerides; Gattefosse) , Labrasol (saturated C8-C10 polyglycolysed glycerides; Gattefosse), Tween 80 (polyoxyethylene (20) sorbitan monooleate; Sigma), Tween 85 (polyoxyethylene (20) sorbitan trioleate; Sigma), Pluronic L43 (copolymers of propylene oxide and ethylene oxide; BASF) , Pluronic 17R4 (copolymers of propylene oxide and ethylene oxide; BASF) , Cremophor EL (polyoxyl 35 castor oil; BASF), Accomid PK (palm kernelamide DEA; Abitec) , Brij 30 (polyoxyethylene 4 lauryl ether; READ ICI) , Arlasolve 200 liquid
- Preferred surfactants include Labrafac Lipophile WL 1349 (triglyceride of caprylic/capric acid; Gattefosse) , Labrofac CM 10 and CM 12 (polyglycolysed glycerides; Gattefosse) , Lauroglycol FCC (propylene glycol laurate; Gattefosse) , Peceol (glyceryl monooleate; Gattefosse) , Caprol 3G0 (triglyceryl monoleate; Abitec) , Capmul MCM (mono/diglycerides of caprylic/capric acid in glycerol; Abitec) , Labrasol (saturated C8-C10 polyglycolysed glycerides; Gattefosse) , Tween 80 (polyoxyethylene (20) sorbitan monooleate; Sigma), Pluronic L43 (copolymers of propylene oxide; BASF), Pluronic 17R4 (copolymers
- antioxidants such as, for example, tocopherol, ascorbyl palmitate, ascorbic acid, butylated hydroxytoluene, butylated hydroxyanisole, propyl gallate, etc.
- pH stabilizers such as, for example, citric acid, tartaric acid, fumaric acid, acetic acid, glycine, arginine, lysine, potassium hydrogen phosphate, etc.
- thickeners/suspending agents such as, for example, hydrogenated vegetable oils, beeswax, colloidal silicon dioxide, gums, celluloses, silicates, bentonite, etc.
- flavoring agents such as, for example, cherry, lemon, aniseed flavors, etc.
- sweeteners such as, for example, aspartame, saccharin, cyclamates, etc.
- co-solvents such as, for example, ethanol
- the resulting liquid comprising the lipid-regulating agent may be dosed directly for oral administration, diluted into an appropriate vehicle for oral administration, filled into soft or hard shells or capsules for oral administration, or delivered by some other means obvious to those skilled in the art.
- the said liquid can be used to improve the oral bioavailability and solubility of the said lipid-regulating agent.
- Myvacet 9-08 (40.2 gm) was mixed with propylene glycol laurate (13.4 gm) . Fenofibrate (6.7 gm) was then added to the above mixture and mixed until completely dissolved. One drop of the solution was diluted with 10 ml of water and the droplet size was measured by laser light scattering as 2.95 (m. 670 mg of the mixture (containing 67 mg of fenofibrate) was added to each soft gelatin capsule.
- Myvacet 9-08 (40.2 g) is mixed with propylene glycol laurate (13.4 g) .
- Pravastatin 5.0 g is then added to the above mixture and mixed until well dissolved. Appropriate amount of solution may be filled into capsules to provide the desired dose.
- the plasma concentrations of fenofibric acid were determined by HPLC . Concentrations were normalized to a 6.7 mg/kg dose in each dog.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28335699A | 1999-03-31 | 1999-03-31 | |
US283356 | 1999-03-31 | ||
PCT/US2000/007459 WO2000057918A2 (en) | 1999-03-31 | 2000-03-21 | Novel formulations comprising lipid-regulating agents |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1165141A2 true EP1165141A2 (de) | 2002-01-02 |
Family
ID=23085656
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00919496A Withdrawn EP1165141A2 (de) | 1999-03-31 | 2000-03-21 | Neue formulierungen mit lipid regulierenden wirkstoffen |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1165141A2 (de) |
JP (1) | JP2002540174A (de) |
AU (1) | AU4017500A (de) |
CA (1) | CA2367995A1 (de) |
HK (1) | HK1044704A1 (de) |
MX (1) | MXPA01009839A (de) |
WO (1) | WO2000057918A2 (de) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6982281B1 (en) | 2000-11-17 | 2006-01-03 | Lipocine Inc | Pharmaceutical compositions and dosage forms for administration of hydrophobic drugs |
US7276249B2 (en) | 2002-05-24 | 2007-10-02 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
FR2819720B1 (fr) | 2001-01-22 | 2004-03-12 | Fournier Lab Sa | Nouveaux comprimes de fenofibrate |
DE60219307T2 (de) * | 2001-06-12 | 2008-01-10 | Galephar M/F | Oral anzuwendende arzneizusammensetzung enthaltend ein statinderivat |
US20030219465A1 (en) * | 2002-05-23 | 2003-11-27 | Suresh Kumar Gidwani | Composition for delivery of dithranol |
US9173847B2 (en) | 2003-10-10 | 2015-11-03 | Veloxis Pharmaceuticals A/S | Tablet comprising a fibrate |
JP5069001B2 (ja) | 2003-10-10 | 2012-11-07 | ベロクシス ファーマシューティカルズ エー/エス | フィブラートを含む固体投与形態 |
ES2255426B1 (es) | 2004-10-19 | 2007-08-16 | Gp Pharm, S.A. | Formulacion farmaceutica que comprende microcapsulas de estatinas suspendidas en ester alquilicos de acidos grasos poliinsaturados (pufa). |
BRPI0518426A2 (pt) * | 2004-12-06 | 2008-11-25 | Reliant Pharmaceuticals Inc | composiÇÕes farmacÊuticas compreendendo fenofibratos e sistemas solventes |
JP5186159B2 (ja) * | 2006-08-31 | 2013-04-17 | あすか製薬株式会社 | フェノフィブラート含有組成物 |
JP2013047282A (ja) * | 2006-08-31 | 2013-03-07 | Aska Pharmaceutical Co Ltd | フェノフィブラート含有組成物 |
US11304960B2 (en) | 2009-01-08 | 2022-04-19 | Chandrashekar Giliyar | Steroidal compositions |
WO2010098906A1 (en) * | 2009-02-24 | 2010-09-02 | Madeira Therapeutics | Liquid statin formulations |
US9034858B2 (en) | 2010-11-30 | 2015-05-19 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
US9358241B2 (en) | 2010-11-30 | 2016-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
US20120148675A1 (en) | 2010-12-10 | 2012-06-14 | Basawaraj Chickmath | Testosterone undecanoate compositions |
CN102247598A (zh) * | 2011-06-13 | 2011-11-23 | 浙江爱生药业有限公司 | 油溶性药物组合物 |
WO2015185240A1 (en) | 2014-06-04 | 2015-12-10 | Sigma-Tau Industrire Farmaceutiche Riunite S.P.A. | Compositions containing simvastatin in omega-3 polyunsaturated fatty acids |
WO2016033549A2 (en) | 2014-08-28 | 2016-03-03 | Lipocine Inc. | (17-ß)-3-OXOANDROST-4-EN-17-YL TRIDECANOATE COMPOSITIONS AND METHODS OF THEIR PREPARATION AND USE |
WO2016033556A1 (en) | 2014-08-28 | 2016-03-03 | Lipocine Inc. | BIOAVAILABLE SOLID STATE (17-β)-HYDROXY-4-ANDROSTEN-3-ONE ESTERS |
JP2020503269A (ja) | 2016-11-28 | 2020-01-30 | リポカイン インコーポレーテッド | 経口ウンデカン酸テストステロン療法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5030447A (en) * | 1988-03-31 | 1991-07-09 | E. R. Squibb & Sons, Inc. | Pharmaceutical compositions having good stability |
GB9405304D0 (en) * | 1994-03-16 | 1994-04-27 | Scherer Ltd R P | Delivery systems for hydrophobic drugs |
BE1011363A3 (fr) * | 1997-09-11 | 1999-08-03 | Smb Technology | Capsules semi-solides autoemulsionnables matricielles a action prolongee. |
WO1999029300A1 (en) * | 1997-12-10 | 1999-06-17 | Rtp Pharma Inc. | Self-emulsifying fenofibrate formulations |
-
2000
- 2000-03-21 CA CA002367995A patent/CA2367995A1/en not_active Abandoned
- 2000-03-21 EP EP00919496A patent/EP1165141A2/de not_active Withdrawn
- 2000-03-21 MX MXPA01009839A patent/MXPA01009839A/es unknown
- 2000-03-21 JP JP2000607667A patent/JP2002540174A/ja not_active Withdrawn
- 2000-03-21 WO PCT/US2000/007459 patent/WO2000057918A2/en not_active Application Discontinuation
- 2000-03-21 AU AU40175/00A patent/AU4017500A/en not_active Abandoned
-
2002
- 2002-06-25 HK HK02104718.1A patent/HK1044704A1/zh unknown
Non-Patent Citations (1)
Title |
---|
See references of WO0057918A2 * |
Also Published As
Publication number | Publication date |
---|---|
HK1044704A1 (zh) | 2002-11-01 |
CA2367995A1 (en) | 2000-10-05 |
WO2000057918A2 (en) | 2000-10-05 |
AU4017500A (en) | 2000-10-16 |
MXPA01009839A (es) | 2002-06-21 |
JP2002540174A (ja) | 2002-11-26 |
WO2000057918A3 (en) | 2001-01-18 |
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