WO2004014431A1 - Forme posologique parenterale d'inhibiteurs cox-2 selectifs - Google Patents

Forme posologique parenterale d'inhibiteurs cox-2 selectifs Download PDF

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Publication number
WO2004014431A1
WO2004014431A1 PCT/IB2003/003219 IB0303219W WO2004014431A1 WO 2004014431 A1 WO2004014431 A1 WO 2004014431A1 IB 0303219 W IB0303219 W IB 0303219W WO 2004014431 A1 WO2004014431 A1 WO 2004014431A1
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WO
WIPO (PCT)
Prior art keywords
dosage form
form according
selective cox
cox
solvent
Prior art date
Application number
PCT/IB2003/003219
Other languages
English (en)
Inventor
Jyoti Srivastava
Ashish Sehgal
Vinod Kumar Arora
Rajiv Malik
Original Assignee
Ranbaxy Laboratories Limited
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 Limited filed Critical Ranbaxy Laboratories Limited
Priority to AU2003249510A priority Critical patent/AU2003249510A1/en
Publication of WO2004014431A1 publication Critical patent/WO2004014431A1/fr

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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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin

Definitions

  • the present invention relates to parei ⁇ teral dosage forms of selective cyclooxygenase- 2 (COX-2) inhibitory drugs and salts thereof. More particularly, the invention relates to a pharmaceutical dosage form of selective COIX-2 inhibitors wherein the composition can be administered intramuscularly.
  • COX-2 selective cyclooxygenase- 2
  • Non-steroidal anti-inflammatory drugs are widely prescribed as effective analgesics, antipyretic and anti-inflammatory agents. Their mechanism for action is based on their ability to inliibit prostaglandin synthesis, which is controlled by the enzyme cyclooxygenase. Cyclooxygenase exists in two isomers- COX1 and COX-2. COX-1 is present in most tissue-synthesized prostaglandins and is important in regulating cell function. It is responsible for most of the gastro-protective prostaglandin synthesis which is important in regulating cell function. COX-2 is generally undetectable in most tissues but increases its expression by 10-20 fold during acute inflarr ⁇ mation. Inhibition of COX-2 by NS AIDs would give an anti-inflammatory effect, whereas inliibition of COX-1 would result in adverse effects such as gastrointestinal toxicity and nephrotoxicity.
  • Selective COX-2 inhibitory drugs represent a major advance in the art.
  • Such drugs are substituted pyrazolyl benzenesulfonamides, substituted Isoxazolyl benzenesulfonamides and substituted (methyl sulfonyl)phenylfuranones.
  • Celecoxib was first described in US Patent No. 5,466,823 assigned to Searle. Celecoxib is commercially available as lOOrxig capsules to be administered twice a day for the treatment of osteo-arthritis and rheumatoid arthritis. No other dosage forms of celecoxib have been reported. ofecoxib was described in US Patent No. 5,474,995 assigned to Merck & Co. Rofecoxib is commercially available as 12.5 mg, 25 mg and 50 mg tablets to be administered once daily and as 12.5mg/5 ml or 25 mg/5 ml oral suspensions for the treatment of osteo-arthritis and the management of acute pain. Valdecoxib has been described in US Patent No. 5,633,272 assigned to Searle. It is marketed as 10 and 20mg tablets for treating symptoms associated with osteo-arthritis and rheumatoid arthritis.
  • oral administration is the most convenient and widely used route, it is associated with a delayed onset of the desired pharmacological action. It is known that mpon oral administration, the COX-2 inhibitors take approximately 3.0 hours for peak plasma concentrations to be achieved and have an onset of action 0.5 to 0.75 hours after administration. Additionally, the intake of food further influences drug absorption. However, acute pain, as in the case of arthritis and cancer, demands immediate relief. In. such cases, a parenteral route is more efficient and prompt, as compared to the oral route.
  • Parenteral routes of administration offer numerous benefits over oral delivery, A part from providing quicker onset of action, parenteral administration results in more predictable blood serum concentrations of the drug and losses in the gastrointestinal tract due to metabolism, binding to food and other causes are eliminated. For similar reasons, parenteral administration permits dose reduction. It is also the preferred method of drug delivery in emergency situations and is useful in non-cooperative patients.
  • COX-2 inhibitors have an oral bioavailability ranging from 80-85% > , hence parenteral administration would bring about a reduction in the dose in comparison to oral dose.
  • Parecoxib when administered parenterally, is hydrolyzed to valdecoxib within the blood stream. It is commercially available as parecoxib sodium powder which may be reconstituted in a parenterally acceptable solvent liquid.
  • Pharmacia Corporation has filed a PCT Application, WO 02/080912, relating to parenterally deliverable formulations of water-soluble selective COX-2 inhibitory drugs and salts and prodrugs thereof.
  • the invention describes dosage forms that are prepared as lyophilized powders for reconstitution.
  • U.S. Patent No. 6,589,557, assigned to Acusphere describes porous matrices of celecoxib with an enhanced rate of dissolution. The porous matrix may be reconstituted with an aqueous medium and administered parenterally.
  • COX-2 inhibitors have extremely low solubility in water, which is the main reason for preparing a reconstitutable powder composition. Due to limited chemical stability, it is preferable to reconstitute the composition within a short period of time before administration.
  • parenteral dosage forms for selective COX-2 inhibitors are challenging for the pharmaceutical formulator because of low chemical and physical stability.
  • An injectable solution composition prepared by reconstituting a powder composition in a parenterally acceptable solvent, preferably an aqueous solvent has limited chemical stability, in which case it is preferred to reconstitute the composition within a short period of time before administration.
  • lyophilized powders require increased handling and processing time. Furthermore, it requires costly and complex equipment.
  • intravenous intravenous
  • intramuscular infra- arterial, subcutaneous, intraperitoneal, etc.
  • intramuscular is the most convenient and easily administrable routes. This route is considered less hazardous than the intravenous route.
  • a parenteral pharmaceutical dosage form comprising at least one selective COX-2 inhibitor dissolved in at least one non-aqueous protic solvent, other than isosorbide type solvent.
  • This dosage form can be administered intramuscularly.
  • the dosage form my include various selective COX-2 inhibitors including celecoxib, deracoxib, valdecoxib, rofecoxib, etoricoxib and parecoxib.
  • the non-aqueous protic solvent of the dosage form comprises one or more of polyethylene glycol, polyvinylpyrrolidone, propylene glycol and glycerol.
  • the dosage form may also comprise co-solvents, for example ethyl alcohol and water.
  • the dosage form may also comprise other pharmaceutically acceptable excipients, for example surfactants or solubilizers, preservatives and antioxidants.
  • Suitable surfactants or solubilizers include polyoxyethylene sorbitan fatty acid esters and ethoxylated alcohols.
  • Suitable preservatives include one or more of methylparaben, propylparaben and benzyl alcohol.
  • Suitable antioxidants comprise one or more of ascorbic acid, alpha-tocopherol, ascorbyl palmitate, butylated hydroxy anisole and butylated hydroxy toluene.
  • the dosage form comprises the selective COX-2 inhibitor celecoxib at a concentration of about 1 mg to about 400 mg/ml.
  • the dosage form comprises the selective COX-2 inhibitor comprises valdecoxib, at a concentration of about 1 mg to about 25 mg/ml.
  • the dosage form comprises the selective COX-2 inhibitor comprises rofecoxib at a concentration of about 1 mg to about 25 mg/ml.
  • a process for preparing a parenteral pharmaceutical dosage form of selective COX-2 inhibitors comprising dissolving the COX-2 inhibitor in a non-aqueous protic solvent, sterilizing the solution, and filling the solution into ampoules or vials.
  • the dosage form- may further comprise co-solvents and pharmaceutically acceptable excipients.
  • Suitable sterilization techniques include aseptic filtration, autoclaving, steaming or irradiation, hi the preferred embodiment, aseptic filtration is utilized.
  • a method of treating or preventing COX-2 mediated disorders in a human subject comprising administering a parenteral pharmaceutical dosage form comprising at least one selective COX-2 inhibitor dissolved in at least one non- aqueous protic solvent.
  • the parenteral administration comprises intramuscular injection.
  • the pharmaceutical dosage form of the present invention comprises at least one therapeutic agent selected from selective COX-2 inhibitory drugs and at least one non- aqueous protic solvents other than isosorbide type solvents.
  • Selective COX-2 inhibitory drugs include those drugs, prodrugs or salts of drugs which exhibit selective inhibition of COX-2, such as celecoxib, rofecoxib, etoricoxib, valdecoxib, parecoxib and deracoxib.
  • non-aqueous protic solvent means a non-aqueous solvent which contains hydrogen attached to oxygen or nitrogen so that it is able to form hydrogen bonds or donate a proton.
  • the solvents used in the parenteral dosage forms should be non-irritating, non-toxic, non-sensitizing, should not have pharmacological activity of its own and should not affect the activity of the drug.
  • non-aqueous protic solvents are polyvinylpyrrolidone (PNP), polyethylene glycols (PEGs), propylene glycol (PG) and glycerol.
  • chemical stability means that an acceptable percentage of degradation products produced by chemical pathways, such as oxidation or hydrolysis, is formed.
  • a formulation is considered chemically stable if it passes a standard test for chemical purity of the therapeutic agent, as may be required for approval by a regulatory authority.
  • the process for the preparation of the injection dosage forms of the present invention involves the dissolution of the active ingredient in a suitable non aqueous protic solvent.
  • the pharmaceutical dosage forms may optionally comprise co-solvents such as ethyl alcohol and water.
  • the pharmaceutical dosage forms may optionally comprise pharmaceutically acceptable excipients such as surfactants or solubilizers, preservatives and antioxidants.
  • Suitable surfactants or solubilizers may comprise one or more of polyoxyethylene sorbitan fatty acid esters and ethoxylated alcohols.
  • Suitable preservatives may comprise one or more of methylparaben, propylparaben and benzyl alcohol.
  • Suitable antioxidants may comprise one or more of ascorbic acid, alpha- tocopherol, ascorbyl palmitate, butylated hydroxy anisole and butylated hydroxy toluene.
  • the final dosage form must be sterile and stable.
  • Techniques such as aseptic filtration, autoclaving, steaming and irradiation may be used for sterilization.
  • compositions of the invention are useful in the treatment and prevention of a wide range of disorders in humans mediated by COX-2, including but not restricted to disorders characterized by inflammation, pain and or fever.
  • Such compositions are especially useful as anti-inflammatory agents, such as in treatment of arthritis, with the additional benefit of having significantly less harmful side effects than compositions of conventional NSAIDs that lack selectivity for COX-2.
  • the dosage forms of the present invention have a reduced potential for gastrointestinal toxicity and irritation, including upper gastrointestinal ulceration and bleeding, by comparison with compositions of conventional NSAIDs.
  • the dosage forms of the invention are particularly useful as an alternative to conventional NSAIDs where NSAIDs are contraindicated.
  • Such dosage forms are useful in the treatment of pain, including but not limited to postoperative pain, dental pain, muscular pain, and pain resulting from cancer.
  • the dosage forms are used for the treatment of rheumatoid arthritis and osteoarthritis, for pain management, for treatment of Alzheimer's disease, and for colon cancer chemoprevention.
  • compositions of the invention are useful for veterinary treatment of animals, particularly mammals.
  • the present invention is further directed to a therapeutic method of treating a condition or disorder where treatment with a COX-2 inhibitory drug is indicated, the method comprising parenteral administration of the dosage form of the invention to a subject in need thereof.
  • the dosage regimen to prevent, give relief from, or ameliorate the condition or disorder preferably corresponds to once-a-day or twice-a-day treatment, but can be modified in accordance with a variety of factors. These include the type, age, weight, sex, diet and medical condition of the subject and the nature and severity of the disorder. Thus, the dosage regimen actually employed can vary widely and can therefore deviate from the preferred dosage regimens set forth above.
  • the intramuscular injectable formulation made in accordance with example 1 was subjected to sub chronic intramuscular toxicity study in Swiss albino mice. Celecoxib injections were administered to mice via intramuscular route at dose levels ranging from 0 g/kg to 200mg /kg body weight and the results of the study showed that:
  • NOEL no observed effect level
  • a slurry (10%w/v) of rofecoxib was made in water for injection and it was nanonised to a particle size of less than 1.0 micron for rofecoxib.
  • Polyethylene glycol 400 was added under stirring to a nanonised slurry of rofecoxib till it dissolved completely.
  • polyoxyethylene sorbitan ester was added and was stirred continuously to get a clear solution.
  • Benzyl alcohol was added to this solution and stirred till it mixes completely.
  • the volume was made up with polyethylene glycol 400.
  • the solution was filtered through 0.2-micron filter and filled into 3.0 ml clear glass sterile USP Type-I ampoules.
  • step 5 The volume was made up with propylene glycol. 6.
  • the solution of step 5 was filtered through 2.0 / 0.2 ⁇ nylon membrane filter and filled in 2 ml clear glass vials (USP Type I) and sealed with rubber stopper and aluminum seal.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention se rapporte à des formes posologiques parentérales de médicaments inhibiteurs sélectifs de la cyclooxygénase-2 (COX-2) et leurs sels. L'invention se rapporte plus particulièrement à une forme posologique pharmaceutique d'inhibiteurs COX-2 sélectifs, la forme posologique étant administrée par voie intramusculaire.
PCT/IB2003/003219 2002-08-12 2003-08-08 Forme posologique parenterale d'inhibiteurs cox-2 selectifs WO2004014431A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003249510A AU2003249510A1 (en) 2002-08-12 2003-08-08 A parenteral dosage form of selective cox-2 inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN830DE2002 2002-08-12
IN830/DEL/2002 2002-08-12

Publications (1)

Publication Number Publication Date
WO2004014431A1 true WO2004014431A1 (fr) 2004-02-19

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006126214A2 (fr) * 2005-05-27 2006-11-30 Panacea Biotec Ltd. Nouvelles compositions injectables et procede de preparation desdites compositions
JP2013545819A (ja) * 2010-12-16 2013-12-26 ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム 非経口投与のためのアゾール医薬製剤ならびにその調製方法およびアゾール化合物に対して感受性の疾患の処置としてのその使用方法
US10548890B2 (en) 2011-04-28 2020-02-04 Platform Brightworks Two, Ltd. Parenteral formulations of lipophilic pharmaceutical agents and methods for preparing and using the same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999021585A1 (fr) * 1997-10-27 1999-05-06 Laboratoires Upsa Combinaison pharmaceutique d'un inhibiteur de la cyclooxygenase-2 et de l'acetaminophene ou un opiace
WO2000032189A1 (fr) * 1998-11-30 2000-06-08 G. D. Searle & Co. Compositions a base de celecoxib
WO2002005799A2 (fr) * 2000-07-13 2002-01-24 Pharmacia Corporation Composes vasomodulateurs et inhibiteurs selectifs de la cyclo-oxygenase-2 pour le traitement des douleurs generalisees et des cephalees
WO2002058620A2 (fr) * 2001-01-26 2002-08-01 Osmotica Corp. Compositions pharmaceutiques contenant un inhibiteur de cox-ii et un relaxant musculaire

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999021585A1 (fr) * 1997-10-27 1999-05-06 Laboratoires Upsa Combinaison pharmaceutique d'un inhibiteur de la cyclooxygenase-2 et de l'acetaminophene ou un opiace
WO2000032189A1 (fr) * 1998-11-30 2000-06-08 G. D. Searle & Co. Compositions a base de celecoxib
WO2002005799A2 (fr) * 2000-07-13 2002-01-24 Pharmacia Corporation Composes vasomodulateurs et inhibiteurs selectifs de la cyclo-oxygenase-2 pour le traitement des douleurs generalisees et des cephalees
WO2002058620A2 (fr) * 2001-01-26 2002-08-01 Osmotica Corp. Compositions pharmaceutiques contenant un inhibiteur de cox-ii et un relaxant musculaire
EP1362585A2 (fr) * 2001-01-26 2003-11-19 Osmotica Corp. Compositions pharmaceutiques contenant un inhibiteur de cox-ii et un relaxant musculaire

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006126214A2 (fr) * 2005-05-27 2006-11-30 Panacea Biotec Ltd. Nouvelles compositions injectables et procede de preparation desdites compositions
WO2006126214A3 (fr) * 2005-05-27 2007-06-07 Panacea Biotec Ltd Nouvelles compositions injectables et procede de preparation desdites compositions
JP2013545819A (ja) * 2010-12-16 2013-12-26 ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム 非経口投与のためのアゾール医薬製剤ならびにその調製方法およびアゾール化合物に対して感受性の疾患の処置としてのその使用方法
JP2017114869A (ja) * 2010-12-16 2017-06-29 プラットフォーム ブライトワークス トゥー， リミテッド 非経口投与のためのアゾール医薬製剤ならびにその調製方法およびアゾール化合物に対して感受性の疾患の処置としてのその使用方法
US10307418B2 (en) 2010-12-16 2019-06-04 Platform Brightworks Two, Ltd. Azole pharmaceutical formulations for parenteral administration and methods for preparing and using the same as treatment of diseases sensitive to azole compounds
US10548890B2 (en) 2011-04-28 2020-02-04 Platform Brightworks Two, Ltd. Parenteral formulations of lipophilic pharmaceutical agents and methods for preparing and using the same
US11045466B2 (en) 2011-04-28 2021-06-29 Platform Brightworks Two, Ltd. Parenteral formulations of lipophilic pharmaceutical agents and methods for preparing and using the same

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