EP1539113A2 - Modified release ketoprofen dosage form - Google Patents
Modified release ketoprofen dosage formInfo
- Publication number
- EP1539113A2 EP1539113A2 EP03795550A EP03795550A EP1539113A2 EP 1539113 A2 EP1539113 A2 EP 1539113A2 EP 03795550 A EP03795550 A EP 03795550A EP 03795550 A EP03795550 A EP 03795550A EP 1539113 A2 EP1539113 A2 EP 1539113A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- ketoprofen
- composition according
- pellets
- hours
- coated pellets
- 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- Withdrawn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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- 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
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5084—Mixtures of one or more drugs in different galenical forms, at least one of which being granules, microcapsules or (coated) microparticles according to A61K9/16 or A61K9/50, e.g. for obtaining a specific release pattern or for combining different drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Definitions
- the present invention belongs to the field of pharmaceutical technology and relates to a modified release pharmaceutical composition of ketoprofen.
- Ketoprofen [2-(3-benzoylphenyl)propionic acid] is a non-steroidal, anti-inflammatory drug which exhibits analgesic and anti-rheumatic properties.
- non-steroidal anti-inflammatory agents there is a constant need for pharmaceutical compositions that would have an immediate analgesic effect and a prolonged anti-rheumatic effect. This is difficult to achieve with conventional pharmaceutical compositions which release the entire active substance quickly, have an immediate analgesic effect and an anti-rheumatic effect is lost. Contrary, with controlled release pharmaceutical compositions due to prolonged release of the active substance from a pharmaceutical composition an anti-rheumatic effect is obtained but the concentration of the active substance released initially is too low to provide an analgesic effect.
- compositions containing pellets or granules of ketoprofen or other non- steroidal anti-inflammatory drugs, are known from prior art.
- US 4980170 describes pharmaceutical compositions of the active substances from the group of non-steroid anti-inflammatory agents, which comprise two types of the pellets.
- the first pellets comprising a two-layer coating membrane are resistant to gastric juices.
- the second pellets have a retard permeable diffusion membrane.
- US 5043167 relates to programmed release pharmaceutical compositions comprising non-steroidal anti-inflammatory drug substances, which contain two types of the granulates, the immediate release granulate and the controlled release granulate.
- the release rate of active substances is governed by the granulate composition.
- WO 99/12542 describes modified release multiple-units pharmaceutical compositions of non-steroidal anti-inflammatory drug substances which comprise two fractions of the particles with the different release profile.
- the first fraction which may be in the form of granules or coated pellets, provides a very quick onset of the therapeutic effect. At least 50% w/w of the active substance is released from the first fraction within the first 20 minutes.
- the second fraction is in a form of three-layer coated pellets adjusting release of the active substance for a relatively long period of time.
- the composition is also suitable for once-a-day administration.
- the present invention thus relates to a modified release pharmaceutical composition of ketoprofen which comprises uncoated pellets (pellet cores) which are designed to an immediate release of ketoprofen, and coated pellets which are designed to a delayed and prolonged release of ketoprofen.
- This composition is able to maintain therapeutically effective blood levels of ketoprofen over 12 hours and is suitable for twice daily administration. It solves the problem of managing pain relief and inflammation in patients in need thereof.
- the novel pharmaceutical composition is patient-friendly. In the stomach it disintegrates very quickly and the pellets are distributed inside the stomach. Local gastric irritation is thus greatly decreased in comparison with a conventional pharmaceutical composition, e.g., tablet comprising the entire dose of the active substance in a single unit and causes a strong local irritation that may also damage the mucous membrane. Coated pellets additionally protect the mucosa.
- the release rate of ketoprofen from the composition of present invention is governed by the composition of the pellet cores, the ratio of the uncoated pellets to the coated pellets and the composition and thickness of the coating.
- the uncoated pellets comprise ketoprofen and excipients which are conventionally used for the production of pellets.
- Pellet cores may comprise one or more diluents, such as lactose, saccharose, glucose, starch, microcrystalline cellulose, mannitol, sorbitol, calcium hydrogen phosphate and others, one or more binding agents, such as starch, gelatin, polyvinylpyrrolidone, sodium alginate, microcrystalline cellulose, carboxymethylcellulose, low-substituted hydroxypropyl cellulose and others, one or more disintegrants, such as starch, croscarmellose sodium, cross-linked polyvinylpyrrolidone, sodium starch glycollate and others.
- diluents such as lactose, saccharose, glucose, starch, microcrystalline cellulose, mannitol, sorbitol, calcium hydrogen phosphate and others
- binding agents such as starch, gelatin, polyvinylpyrrolidone, sodium alginate, microcrystalline cellulose, carboxymethylcellulose, low-substituted hydroxypropyl cellulose
- the pellet cores may further comprise one or more surfactants, such as ionic surfactants, e.g., sodium lauryl sulfate, nonionic surfactants, such as natural or synthesized lecithins and esters of sorbitan and fatty acids (such as Span ® ), esters of polyoxyethylenesorbitan and fatty acids (such as, Polysorbates or Tween ® ), polyoxyethylated hydrogenated castor oil (such as Cremophor ® ) or any combination of the herein above mentioned surfactants
- ionic surfactants e.g., sodium lauryl sulfate
- nonionic surfactants such as natural or synthesized lecithins and esters of sorbitan and fatty acids (such as Span ® ), esters of polyoxyethylenesorbitan and fatty acids (such as, Polysorbates or Tween ® ), polyoxyethylated hydrogenated castor oil (such as Cremophor
- Pellet cores may optionally be composed of inert seed to which ketoprofen is applied on together with a binding agent, selected from the group consisting of starch, gelatin, polyvinylpyrrolidone, sodium alginate, microcrystalline cellulose, carboxymethylcellulose, low-substituted hydroxypropyl cellulose and others.
- a binding agent selected from the group consisting of starch, gelatin, polyvinylpyrrolidone, sodium alginate, microcrystalline cellulose, carboxymethylcellulose, low-substituted hydroxypropyl cellulose and others.
- the proportion of ketoprofen in the pellet cores is from 5 to 95% w/w, preferably 60 to 90 % w/w.
- Delayed release coated pellets are the pellet cores coated with a pH independent semi-permeable polymer.
- the coating preferably comprises copolymers of acrylic and methacrylic acid esters with a low content of quaternary ammonium groups.
- a preferred coating comprises the combination of ammonio methacrylate copolymer type A and ammonio methacrylate copolymer type B (according to USP 25-NF 20) in the ratio of 7:3 to 3:7, preferably 1:1.
- the polymers are commercially available in the form of 30% aqueous dispersion as Eudragit RS 30 D and Eudragit RL 30 D from Rohm Pharma.
- the coating may further comprise one or more plasticizers, such as polyethylene glycol with different molecular weights, triethyl citrate, dibutyl sebacate, tributyl sebacate, cetyl alcohol, olive or castor oil, monoglycerides and other conventional pharmaceutically acceptable ingredients which are used for the production of coatings, such as talc, Polysorbate 80, pigments and magnesium stearate.
- plasticizers such as polyethylene glycol with different molecular weights, triethyl citrate, dibutyl sebacate, tributyl sebacate, cetyl alcohol, olive or castor oil, monoglycerides and other conventional pharmaceutically acceptable ingredients which are used for the production of coatings, such as talc, Polysorbate 80, pigments and magnesium stearate.
- the coated pellets may comprise from 3 to 50% w/w of the coating, preferably 5 to 15% w/w.
- the composition of the uncoated pellets may be the same as the composition of the pellet cores of coated pellets.
- the composition of the uncoated pellets may be different from the composition of the pellet cores of coated pellets.
- Pellet cores may be produced in the manner conventional in the pharmaceutical industry. A wet mixture of ketoprofen and excipients is extruded in a screw extruder and the resulting extrudate is spheronized into pellets in a spheronizer. The pellets thus produced are dried in a fluidized bed. The pellet cores are coated with a polymer coating by the methods conventional in the pharmaceutical technology.
- Pellet cores may optionaly be prepared by coating the inert core seeds with ketoprofen and binding agent.
- Uncoated pellets and coated pellets in the desired ratio may be encapsulated into gelatin capsules. They may be also compressed into tablets together with the excipients such as, for example, lactose, saccharose, glucose, starch microcrystalline cellulose, mannitol, sorbitol, calcium hydrogen phosphate, neutral pellet cores and others.
- excipients such as, for example, lactose, saccharose, glucose, starch microcrystalline cellulose, mannitol, sorbitol, calcium hydrogen phosphate, neutral pellet cores and others.
- the ratio of uncoated pellets to the coated pellets in the formulation of the present invention may be from 80:20 to 20:80, preferably about 60:40 to the dose of ketoprofen in the pharmaceutical composition. It means that 60% w/w of the ketoprofen dose is in a form of the pellet cores and 40% w/w of the ketoprofen dose in a form of the coated pellets.
- the pharmaceutical composition of the present invention may contain from 50 to 250 mg of ketoprofen, preferably 150 mg.
- the object of the present invention is a modified release composition of ketoprofen wherefrom 15 to 35% w/w of ketoprofen is released within the first two hours, 50 to 80%) w/w of ketoprofen after 6 hours and at least 80% w/w after 8 hours, measured 2 hours in 1000 ml of simulated gastric juice having a pH of 1.2, 4 hours in 1000 ml of phosphate buffer having a pH of 4.5 and 2 hours in 1000 ml of phosphate buffer having a pH of 6.8, in he rotating basket (USP 25) at 50 rpm.
- the object of the present invention is a hard gelatine capsule containing 150 mg of ketoprofen. 60% w/w of the ketoprofen dose is in the form of uncoated pellets and 40% w/w of the ketoprofen dose is in the form of coated pellets.
- Ketoprofen, microcrystalline cellulose, lactose and polyvinylpyrrolidone were mixed and 140 g of demineralized water was added.
- the wet mixture was extruded in a screw extruder and the resulting extrudate was spheronized into pellets in a spheronizer.
- the wet pellets thus obtained were dried in a fluidized bed. 60% w/w of the dry pellets (pellet cores) was set aside to be capsulated, and the remainder 40% w/w was coated.
- Te pellet cores were placed in a fluidized bed apparatus and sprayed with an aqueous dispersion Eudragit RS 30 D and Eudragit RL 30 D by further added triethyl citrate, Polysorbate and talc.
- the pellet cores and the coated pellets were dosed into capsules using a capsule filling machine. Each capsule contained 60% w/w pellet cores and 40% w/w coated pellets.
- Ketoprofen, microcrystalline cellulose, lactose and polyvinylpyrrolidone were mixed and 140 g of demineralized water was added.
- the wet mixture was extruded on a screw extruder and resulting extrudate was spheronized into pellets in a spheronizer.
- the wet pellets thus obtained were dried in a fluidized bed. 60% w/w of the dry pellets (pellet cores) was set aside to be capsulated, and the remainder 40% w/w was coated.
- Te pellet cores were placed in a fluidized bed apparatus and sprayed with an aqueous dispersion Eudragit RS 30 D and Eudragit RL 30 D by further added triethyl citrate, Poysorbate and talc.
- the pellet cores and the coated pellets were dosed into capsules using a capsule filling machine. Each capsule contained 60% w/w pellet cores and 40% w/w coated pellets.
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SI200200220A SI21301A (sl) | 2002-09-11 | 2002-09-11 | Farmacevtska oblika z nadzorovanim sproščanjem |
SI200200220 | 2002-09-11 | ||
PCT/SI2003/000033 WO2004024128A2 (en) | 2002-09-11 | 2003-09-10 | Modified release ketoprofen dosage form |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1539113A2 true EP1539113A2 (en) | 2005-06-15 |
Family
ID=31989658
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP03795550A Withdrawn EP1539113A2 (en) | 2002-09-11 | 2003-09-10 | Modified release ketoprofen dosage form |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1539113A2 (sl) |
AU (1) | AU2003261067A1 (sl) |
SI (1) | SI21301A (sl) |
WO (1) | WO2004024128A2 (sl) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2529984C (en) | 2003-06-26 | 2012-09-25 | Isa Odidi | Oral multi-functional pharmaceutical capsule preparations of proton pump inhibitors |
US10624858B2 (en) | 2004-08-23 | 2020-04-21 | Intellipharmaceutics Corp | Controlled release composition using transition coating, and method of preparing same |
WO2006132440A1 (ja) * | 2005-06-09 | 2006-12-14 | Takeda Pharmaceutical Company Limited | 固形製剤 |
US10064828B1 (en) | 2005-12-23 | 2018-09-04 | Intellipharmaceutics Corp. | Pulsed extended-pulsed and extended-pulsed pulsed drug delivery systems |
KR100762847B1 (ko) * | 2006-01-27 | 2007-10-04 | 씨제이 주식회사 | 멀티플 유닛 타입 서방성 경구 제제 및 그 제조방법 |
EP2007360B1 (en) | 2006-04-03 | 2014-11-26 | Isa Odidi | Controlled release delivery device comprising an organosol coat |
US20190083399A9 (en) * | 2006-04-03 | 2019-03-21 | Isa Odidi | Drug delivery composition |
US10960077B2 (en) | 2006-05-12 | 2021-03-30 | Intellipharmaceutics Corp. | Abuse and alcohol resistant drug composition |
KR101872189B1 (ko) | 2010-06-16 | 2018-06-29 | 다케다 파마슈티칼스 유에스에이, 인코포레이티드 | 크산틴 옥시도리덕타제 억제제 또는 크산틴 옥시다제 억제제의 신규한 조절 방출 제형 |
ES2394888B1 (es) * | 2011-06-15 | 2013-09-23 | Farmalider, S.A. | Forma farmacéutica de liberación modificada de dexketoprofeno e inhibidor de la bomba de protones y uso de la misma. |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6144811A (ja) * | 1984-08-10 | 1986-03-04 | Ss Pharmaceut Co Ltd | 徐放性ジクロフエナクナトリウム製剤 |
DE3822095A1 (de) * | 1988-06-30 | 1990-01-04 | Klinge Co Chem Pharm Fab | Neue arzneimittelformulierung sowie verfahren zu deren herstellung |
IE66933B1 (en) * | 1990-01-15 | 1996-02-07 | Elan Corp Plc | Controlled absorption naproxen formulation for once-daily administration |
EA002806B1 (ru) * | 1997-09-11 | 2002-10-31 | Нюкомед Данмарк А/С | Многоединичные композиции с модифицированным высвобождением нестероидных противовоспалительных лекарственных веществ (nsaid) |
FR2792527B1 (fr) * | 1999-04-22 | 2004-08-13 | Ethypharm Lab Prod Ethiques | Microgranules de ketoprofene, procede de preparation et compositions pharmaceutiques |
-
2002
- 2002-09-11 SI SI200200220A patent/SI21301A/sl not_active IP Right Cessation
-
2003
- 2003-09-10 EP EP03795550A patent/EP1539113A2/en not_active Withdrawn
- 2003-09-10 AU AU2003261067A patent/AU2003261067A1/en not_active Abandoned
- 2003-09-10 WO PCT/SI2003/000033 patent/WO2004024128A2/en not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO2004024128A2 * |
Also Published As
Publication number | Publication date |
---|---|
SI21301A (sl) | 2004-04-30 |
AU2003261067A8 (en) | 2004-04-30 |
WO2004024128A3 (en) | 2004-07-08 |
AU2003261067A1 (en) | 2004-04-30 |
WO2004024128A2 (en) | 2004-03-25 |
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