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WO2005011666A1 - Forme posologique stable de gabapentine, pour usage oral et a liberation prolongee - Google Patents

Forme posologique stable de gabapentine, pour usage oral et a liberation prolongee Download PDF

Info

Publication number
WO2005011666A1
WO2005011666A1 PCT/IB2004/051408 IB2004051408W WO2005011666A1 WO 2005011666 A1 WO2005011666 A1 WO 2005011666A1 IB 2004051408 W IB2004051408 W IB 2004051408W WO 2005011666 A1 WO2005011666 A1 WO 2005011666A1
Authority
WO
WIPO (PCT)
Prior art keywords
gabapentin
sustained release
gum
tablet
release tablet
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.)
Ceased
Application number
PCT/IB2004/051408
Other languages
English (en)
Inventor
Manish Chawla
Rajeev Singh Raghuvanshi
Ashok Rampal
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ranbaxy Laboratories Ltd
Original Assignee
Ranbaxy Laboratories Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ranbaxy Laboratories Ltd filed Critical Ranbaxy Laboratories Ltd
Publication of WO2005011666A1 publication Critical patent/WO2005011666A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants

Definitions

  • the present invention relates to stable sustained release oral dosage forms of gabapentin and methods for making these dosage forms.
  • Gabapentin (l-(aminomethyl)cyclohexaneacetic acid) is a #-amino acid analogue effective in the treatment of epilepsy. Gabapentin is indicated as an adjunctive therapy in the treatment of partial seizures with and without secondary generalization in adults with epilepsy. Gabapentin has also been approved for neuropathic pain in some countries.
  • Gabapentin has been reported to convert to a toxic lactam compound during preparation and storage. This lactam formation is also seen in formulations containing gabapentin. The lactam formation in formulation during storage is apparently a result of the catalytic effects of the excipients used. The lactam has toxicity, which exceeds that of gabapentin itself.
  • the lethal dose (LD ) of gabapentin in mice has been reported to be 8,000 mg/kg while that of the corresponding lactam is 300 mg/kg. Consequently, these impurities and the potential formation of such decomposition products during storage of pharmaceutical compositions must be reduced to a minimum for reasons of safety.
  • a stable sustained release tablet prepared from granules.
  • the granules include gabapentin; one or more hydrophilic rate- controlling polymers selected from the group consisting of hydroxypropylcellulose, polyvinylpyrrolidone and its derivatives, and polysaccharide gum; and, optionally, one or more pharmaceutical excipients.
  • Embodiments of the sustained release tablet may include one or more of the following features.
  • the lactam content of the tablet may not exceed 0.6% by weight of gabapentin when stored for three months at 40°C and 75% relative humidity.
  • the tablet may provide therapeutically effective plasma levels of gabapentin for up to about 24 hours.
  • the sustained release tablet may have a dissolution profile measured in a USP type II dissolution apparatus, at 50 rpm, at a temperature of 37 ⁇ 0.5°C in 900ml of 0.06N hydrochloric acid of at least 90% of the gabapentin being released in a time between 4 hours and 12 hours. More particularly, at least 90% of the gabapentin may be released in a time between 8 hours and 12 hours.
  • the gabapentin may make up from about 100 mg to about l,200mg by weight of the tablet.
  • the hydroxypropylcellulose may have a viscosity of between about 7 cps and about 30,000 cps.
  • the hydroxypropylcellulose may have a viscosity of between about 4,000 cps and about 15,000 cps.
  • the polyvinylpyrrolidone derivative may be selected from crospovidone, copolyvidone and physical mixtures of polyvinylpyrrolidone and polyvinylacetate.
  • the polysaccharide gum may be selected from the group consisting of guar gum, gum arabic, xanthan gum, locust bean gum, gum karaya and gum tragacanth or combinations thereof.
  • the pharmaceutical excipients may be selected from diluents, binders, lubricants and glidants.
  • the sustained release tablet may be formulated such that the granules do not contain hydroxymethyl propylcellulose.
  • the sustained release tablet may further include one or more pharmaceutical excipients mixed with the granules.
  • Embodiments of the process may include one or more of the following features.
  • the lactam content of the tablet may not exceed 0.6% by weight of gabapentin when stored for three months at 40°C and 75% relative humidity.
  • the tablet may provide therapeutically effective plasma levels of gabapentin for up to about 24 hours.
  • the sustained release tablet may have a dissolution profile measured in a USP type II dissolution apparatus, at 50 rpm, at a temperature of 37 ⁇ 0.5°C in 900ml of 0.06N hydrochloric acid of at least 90% of the gabapentin being released in a time between 4 hours and 12 hours. More particularly, at least 90% of the gabapentin may be released in a time between 8 hours and 12 hours.
  • the gabapentin may make up between about 100 mg and about 1 ,200 mg by weight of the tablet.
  • the hydroxypropylcellulose may have a viscosity of between about 7 cps and about 30,000 cps.
  • the hydroxypropylcellulose may have a viscosity of between about 4,000 cps and about 15,000 cps.
  • the polyvinylpyrrolidone derivative is selected from crospovidone, copolyvidone and physical mixtures of polyvinylpyrrolidone and polyvinylacetate.
  • the polysaccharide gum is selected from the group consisting of guar gum, gum arabic, xanthan gum, locust bean gum, gum karaya and gum tragacanth or combinations thereof.
  • the other pharmaceutical excipients are selected from diluents, binders, lubricants and glidant.
  • the process may further include granulating one or more pharmaceutical excipients with the mixture of gabapentin and one or more hydrophilic rate-controlling polymers.
  • a method of treating a medical condition includes providing an oral pharmaceutical sustained release tablet prepared from granules comprising gabapentin, one or more hydrophilic rate controlling polymers selected from the group consisting of hydroxypropylcellulose, polyvinylpyrrolidone and its derivatives, and polysaccharide gum and optionally one or more pharmaceutical excipients.
  • Embodiments of the method of treating may include one or more of the following features or those described above.
  • the medical condition may be one or both of epilepsy and neuropathic pain.
  • sustained release gabapentin tablets can be prepared using hydrophilic polymers selected from the group consisting of hydroxypropylcellulose, polyvinylpyrrolidone and its derivatives, and polysaccharide gums and one or more pharmaceutically acceptable excipients.
  • hydrophilic polymers selected from the group consisting of hydroxypropylcellulose, polyvinylpyrrolidone and its derivatives, and polysaccharide gums and one or more pharmaceutically acceptable excipients.
  • these sustained release tablets of gabapentin are believed to be capable of maintaining plasma levels of gabapentin in a therapeutic range over an extended time period for up to about 24 hours. This can be accomplished, for example, by varying the concentration of polymers within the granules and possibly outside the granules.
  • the stability conditions as defined herein include tolerance of ⁇ 2 ° C in temperature and a tolerance of ⁇ 5% in relative humidity.
  • Gabapentin may be present as a free base, hydrated form such as monohydrate or any other pharmaceutically acceptable salts thereof. Gabapentin may comprise from about 100 mg to about 1200 mg by weight of the tablet.
  • Hydroxypropylcellulose as used herein, can be of different viscosity grades such as sold by Aqualon under the brand name of Klucel® and also by Nippon Soda Co. Ltd, Japan. Suitable grades are those having viscosity of from about 7 to about 30,000 cps. Especially suitable among these hydroxypropylcelluloses are those having viscosity of 4000 to about 30,000 cps. Typically the amount of hydroxypropylcellulose can be from about 3% to about 40%, particularly from about 5% to about 30% and more particularly from about 5% to about 25% by weight of granules.
  • Polyvinylpyrrolidone or PVP refers to a polymer containing N-vinylpyrrolidone as the monomeric unit and is known to the pharmaceutical industry under a variety of designations including povidone, polyvidone, polyvidonum, polyvidonum soluble, and poly(l-vinyl-2-pyrrolidone).
  • Cross-linked polyvinylpyrrolidone known as crospovidone available as Kollidon CL and Kollidon CL-M is also included.
  • the polyvinylpyrrolidone derivatives include among others the copolymer of N- vinyl-2-pyrrolidone and vinyl acetate which is known as copolyvidon, copolyvidone, and copolyvidonum.
  • Polyvinylpyrrolidone and polyvinyl acetate are also included. These mixtures can be in a ratio such as, but not limited to, 20:80 (PVP: polyvinylacetate) like Kollidon SR. It is apparent that other derivatives of polyvinylpyrrolidone known to those skilled in the art can also be used. Polyvinylpyrrolidone is available in a wide range of molecular weights. Particularly suitable are grades having molecular weights between about 8,000 to about 1,300,000 such as Plasdone K-90, Plasdone K-90D. Typically the amount of polyvinylpyrrolidone and its derivatives can be from about 3% to about 40%, particularly from about 3% to about 30% by weight of granules.
  • Polysaccharide gums may be selected from the group consisting of guar gum, gum arabic, xanthan gum, locust bean gum, gum karaya and gum tragacanth. Particularly suitable is guar gum. Typically the amount of polysaccharide gum can be from about 3% to about 80%), particularly from about 3% to about 70% and more particularly from about 3% to about 60% by weight of the granules.
  • the other pharmaceutical excipients are selected from the group consisting of diluents, binders, lubricants and glidants.
  • Suitable diluents include powdered sugar, calcium phosphate, calcium sulfate, microcrystalline cellulose, lactose, mannitol, kaolin, dry starch, sorbitol, etc.
  • Suitable binders include polyvinylpyirolidone and its derivatives; xanthan gum, guar gum; cellulose ethers such as carboxymethylcellulose, methylcellulose, hydroxypropyl methylcellulose (extragranularly only, not intra- granularly), hydroxypropyl cellulose, ethyl cellulose; gelatin, starch and its derivatives.
  • the granulating liquid can be, but is not limited to, water, ethanol, isopropyl alcohol, acetone, dichloromethane and the like.
  • the binder can be dissolved in the granulating liquid and used as a solution.
  • Lubricants can be talc, stearic acid, vegetable oil, calcium stearate, zinc stearate and magnesium stearate and glidants include talc, silicon dioxide and cornstarch.
  • stable gabapentin sustained release tablets may be prepared by
  • [36] Blending gabapentin with hydrophilic rate-controlling polymer(s) like hydroxypropylcellulose, polyvinylpyrrolidone and its derivatives or polysaccharide gum and other pharmaceutical excipients (but not HPMC) in a mixer. 2. Granulating the blend of step (1) with a granulating liquid or a binder solution. 3. Drying and sizing the granules. 4. Mixing the sized granules with other pharmaceutical excipients and compressing into tablet.
  • hydrophilic rate-controlling polymer(s) like hydroxypropylcellulose, polyvinylpyrrolidone and its derivatives or polysaccharide gum and other pharmaceutical excipients (but not HPMC) in a mixer. 2. Granulating the blend of step (1) with a granulating liquid or a binder solution. 3. Drying and sizing the granules. 4. Mixing the sized granules with other pharmaceutical excipients and compressing into tablet.
  • stable gabapentin sustained release tablets may be prepared by following the steps of
  • Tablets can additionally be coated with non-rate-controlling polymer(s) compositions like Opadry® sold by Colorcon to impart aesthetic appeal.
  • a coating may comprise about 2% by weight of the tablet.
  • Stable gabapentin sustained release tablets and process for the preparation thereof described herein is further illustrated by the following examples but these should not be construed as limiting the scope of the invention.

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention se rapporte à une forme posologique stable de gabapentine, pour usage oral et à libération prolongée, ainsi qu'à des procédés de préparation de telles formes posologiques. Le comprimé stable à libération prolongée est préparé à partir de granulés. Ces granulés contiennent du gabapentine; un ou plusieurs polymères hydrophiles à régulation de vitesse de libération, choisis dans le groupe composé d'hydroxypropylcellulose, de polyvinylpyrrolidone et de ses dérivés, et d'une gomme glucidique; et, éventuellement, un ou plusieurs excipients pharmaceutiques.
PCT/IB2004/051408 2003-08-05 2004-08-05 Forme posologique stable de gabapentine, pour usage oral et a liberation prolongee Ceased WO2005011666A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN968/DEL/2003 2003-08-05
IN968DE2003 2003-08-05

Publications (1)

Publication Number Publication Date
WO2005011666A1 true WO2005011666A1 (fr) 2005-02-10

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ID=34113378

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2004/051408 Ceased WO2005011666A1 (fr) 2003-08-05 2004-08-05 Forme posologique stable de gabapentine, pour usage oral et a liberation prolongee

Country Status (2)

Country Link
CN (1) CN1832736A (fr)
WO (1) WO2005011666A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006077492A1 (fr) * 2005-01-24 2006-07-27 Ranbaxy Laboratories Limited Formes dosifiées orales à libération prolongée de gabapentine
WO2006113568A3 (fr) * 2005-04-19 2007-04-05 Alza Corp Combinaison de tramadol et de matieres renfermant la gabapentine
KR100715354B1 (ko) 2005-08-30 2007-05-08 주식회사 대웅제약 유연물질의 발생이 억제된 안정한 가바펜틴 제제 및 그의제조 방법
WO2007086694A1 (fr) * 2006-01-27 2007-08-02 Cj Cheiljedang Corporation Comprimé à libération prolongée contenant du zaltoprofène et procédé de préparation dudit comprimé
FR2897267A1 (fr) * 2006-02-16 2007-08-17 Flamel Technologies Sa Formes pharmaceutiques multimicroparticulaires pour administration per os
WO2011042793A1 (fr) * 2009-10-06 2011-04-14 Micro Labs Limited Composition pharmaceutique stabilisée contenant de la gabapentine et présentant des niveaux minimaux d'excipients inertes pharmaceutiquement acceptables
US20150147405A1 (en) * 2012-04-10 2015-05-28 Alpina Laudanum Institute Of Phytopharmaceutical Science Ag Wet granulation process and granulate material comprising arabic gum
US20170216212A1 (en) * 2007-11-23 2017-08-03 Gruenenthal Gmbh Tapentadol compositions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102688216A (zh) * 2012-04-16 2012-09-26 杭州天诚药业有限公司 一种加巴喷丁片剂及其制备方法
CN110583654A (zh) * 2019-09-18 2019-12-20 北京农学院 一种植物源杀线虫剂

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6294198B1 (en) * 1999-08-24 2001-09-25 Purepac Pharmaceutical Co. Pharmaceutical tablet formulation containing gabapentin with improved physical and chemical characteristics and method of making the same
US20020091159A1 (en) * 2000-09-26 2002-07-11 Spiridon Spireas Stable solid dosage forms of amino acids and processes for producing same
WO2003103634A1 (fr) * 2002-06-07 2003-12-18 Ranbaxy Laboratories Limited Formes posologiques orales a liberation prolongee de gabapentine

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6294198B1 (en) * 1999-08-24 2001-09-25 Purepac Pharmaceutical Co. Pharmaceutical tablet formulation containing gabapentin with improved physical and chemical characteristics and method of making the same
US20030008004A1 (en) * 1999-08-24 2003-01-09 Zalman Vilkov Pharmaceutical tablet formulation containing gabapentin with improved physical and chemical characteristics and method of making the same
US20020091159A1 (en) * 2000-09-26 2002-07-11 Spiridon Spireas Stable solid dosage forms of amino acids and processes for producing same
WO2003103634A1 (fr) * 2002-06-07 2003-12-18 Ranbaxy Laboratories Limited Formes posologiques orales a liberation prolongee de gabapentine

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006077492A1 (fr) * 2005-01-24 2006-07-27 Ranbaxy Laboratories Limited Formes dosifiées orales à libération prolongée de gabapentine
WO2006113568A3 (fr) * 2005-04-19 2007-04-05 Alza Corp Combinaison de tramadol et de matieres renfermant la gabapentine
KR100715354B1 (ko) 2005-08-30 2007-05-08 주식회사 대웅제약 유연물질의 발생이 억제된 안정한 가바펜틴 제제 및 그의제조 방법
WO2007086694A1 (fr) * 2006-01-27 2007-08-02 Cj Cheiljedang Corporation Comprimé à libération prolongée contenant du zaltoprofène et procédé de préparation dudit comprimé
FR2897267A1 (fr) * 2006-02-16 2007-08-17 Flamel Technologies Sa Formes pharmaceutiques multimicroparticulaires pour administration per os
WO2007093642A3 (fr) * 2006-02-16 2007-10-04 Flamel Tech Sa Formes pharmaceutiques multimicroparticulaires qui resistent a la decharge immediate du principe actif en presence d'alcool
JP2009526825A (ja) * 2006-02-16 2009-07-23 フラメル・テクノロジーズ 経口投与用の多微粒子状医薬製剤
US20170216212A1 (en) * 2007-11-23 2017-08-03 Gruenenthal Gmbh Tapentadol compositions
WO2011042793A1 (fr) * 2009-10-06 2011-04-14 Micro Labs Limited Composition pharmaceutique stabilisée contenant de la gabapentine et présentant des niveaux minimaux d'excipients inertes pharmaceutiquement acceptables
US20150147405A1 (en) * 2012-04-10 2015-05-28 Alpina Laudanum Institute Of Phytopharmaceutical Science Ag Wet granulation process and granulate material comprising arabic gum
US10092518B2 (en) * 2012-04-10 2018-10-09 Alpina Laudanum Institute Of Phytopharmaceutical Sciences Ag Wet granulation process and granulate material comprising Arabic gum

Also Published As

Publication number Publication date
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