US20120259018A1 - Composition of dexibuprofen transdermal hydrogel - Google Patents

Composition of dexibuprofen transdermal hydrogel Download PDF

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Publication number
US20120259018A1
US20120259018A1 US13/525,432 US201213525432A US2012259018A1 US 20120259018 A1 US20120259018 A1 US 20120259018A1 US 201213525432 A US201213525432 A US 201213525432A US 2012259018 A1 US2012259018 A1 US 2012259018A1
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dexibuprofen
hydrogel
sodium
alcoholic
transdermal hydrogel
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Jeffrey Stuart BERGMAN
Sampathkumar DEVARAJAN
Selvakumar RAMALINGAM
Anandsenthil Vel PALANISAMY
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Shasun Pharmaceuticals Ltd
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Shasun Pharmaceuticals Ltd
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Publication of US20120259018A1 publication Critical patent/US20120259018A1/en
Assigned to SHASUN PHARMACEUTICALS LIMITED reassignment SHASUN PHARMACEUTICALS LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: RAMALINGAM, SELVAKUMAR, BERGMAN, JEFFREY STUART, DEVARAJAN, SAMPATHKUMAR, PALANISAMY, ANANDSENTHIL VEL
Assigned to SHASUN PHARMACEUTICALS LIMITED reassignment SHASUN PHARMACEUTICALS LIMITED CORRECTIVE ASSIGNMENT TO CORRECT THE THE ASSIGNMENT YEAR FOR INVENTOR SELVAKUMAR RAMALINGAM TO 6/14/2012 FROM 6/14/2013 PREVIOUSLY RECORDED ON REEL 031791 FRAME 0400. ASSIGNOR(S) HEREBY CONFIRMS THE EXECUTION DATE OF 6/14/2012 ON PAGE 2 OF THE PREVIOUSLY RECORDED ASSIGNMENT (COPY ATTACHED).. Assignors: BERGMAN, JEFFREY STUART, DEVARAJAN, SAMPATHKUMAR, PALANISAMY, ANANDSENTHIL VEL, RAMALINGAM, SELVAKUMAR
Priority to US14/824,787 priority Critical patent/US10085939B2/en
Abandoned legal-status Critical Current

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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
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • 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
    • 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
    • A61K47/02—Inorganic compounds
    • 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
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • 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
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • 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]
    • 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
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof

Definitions

  • the present invention relates to a topical pharmaceutical composition containing dexibuprofen [(S)-2-(4-isobutylphenyl) propionic acid] and the process for preparing the same.
  • Ibuprofen (2-(4-isobutylphenyl) propionic acid) has one chiral center, thus there are two enantiomers, S (+)-ibuprofen (dexibuprofen) and R ( ⁇ )-ibuprofen, also known as (S+)-ibuprofen and (R-)-ibuprofen.
  • S (+)-ibuprofen (dexibuprofen)
  • R ( ⁇ )-ibuprofen also known as (S+)-ibuprofen and (R-)-ibuprofen.
  • the racemic form consisting of equal amounts of S(+)-ibuprofen and R( ⁇ )-ibuprofen is exclusively used in the currently available commercial preparations, as well as the water soluble salts of ibuprofen such as lysinate, arginate, sodium, potassium etc are also used.
  • Racemic ibuprofen has relatively high melting point (about 78° C.), while both stereoisomer's of ibuprofen, S (+)-ibuprofen and R ( ⁇ )-ibuprofen, melt at 52° C. to 54° C. All the different forms of ibuprofen are poorly soluble in water
  • S (+) form alone appears to be responsible for the anti-inflammatory activity, not the R ( ⁇ ) form (S. Adams et al., Curr. Med. Res. Opin,. 3, 552 (1975); S. Adams et al., J. Pharm. Pharmaco., 28, 256-257 (1976)).
  • U.S. Pat. No. 5,093,133 discloses hydroalcoholic gel formulations of (S)-ibuprofen as an effective vehicle for percutaneous delivery of (S+)-ibuprofen through the skin.
  • the hydroalcoholic gel of (S+)-ibuprofen is prepared by using 40 to 60% of alcohol; 0-20% of a non-volatile solvent; 2.0 to 5.0% of gelling agents; sufficient base, to adjust the pH to between 3.5 to 6.0; and water.
  • U.S. Pat. No. 5,767,161 discloses a pharmaceutical composition in the form of cream, foam or stick containing 2.5-10% by weight (S)-2-(4-isobutylphenyl)propionic acid, 20-30% by weight ethanol and 5-50% by weight propylene glycol, the ratio of ethanol to propylene glycol is 0.6-1 to 4:1.
  • This patent also reports an increase in cutaneous permeation of the active ingredient with respect to those obtained by known topical pharmaceutical compositions containing an equivalent or higher amount of Ibuprofen.
  • U.S. Pat. No. 6,368,618 discloses a novel two phase liquid topical formulation for delivery of S(+)-ibuprofen, which is characterized by enhanced transdermal absorption and efficacy.
  • two phase system consist of an aqueous and oil phases, the oil phase contains a relatively high concentration of the S (+)-ibuprofen making it directly available for partitioning into the stratum corneum without the rate-limiting diffusion process from the inert oil phase as in a conventional cream.
  • U.S. Pat. No. 5,696,165 discloses pharmaceutical compositions for oral, rectal or topical administration containing (S)-Ibuprofen sodium salt as an active ingredient.
  • This patent reports that the S( ⁇ )sodium 2-(4-isobutylphenyl) propionate has advantage over S(+) 2-(4-isobutylphenyl)propionate for preparing pharmaceutical compositions containing water and additional formulation advantage is that S( ⁇ )sodium 2-(4-isobutylphenyl)propionate will resist esterification with excipients which contain a hydroxyl group for example mono-, di-, tri- or polyhydric alcohols.
  • dexibuprofen is formulated into topical formulations either using high amount of alcohol or using a two phase system to enhance the transdermal absorption and efficacy.
  • One of the objective(s) of the present invention is to prepare a non-alcoholic transdermal hydrogel of dexibuprofen.
  • Another objective of the present invention is to prepare a clear transparent non-alcoholic transdermal hydrogel of dexibuprofen.
  • the present invention relates to a pharmaceutical composition for topical use containing dexibuprofen, more particularly to a non-alcoholic dexibuprofen transdermal hydrogel and process of preparing the same.
  • Stable non-alcoholic transdermal hydrogel of dexibuprofen was prepared by using a simple manufacturing process, and the experimental trials showed that the pH modifying agent, antioxidant and water miscible solvent are the essential excipients to obtain stable non-alcoholic transdermal hydrogel of dexibuprofen.
  • the dexibuprofen hydrogel prepared using carbopol as a gelling polymer produced an opaque gel
  • hydrogel prepared using hyroxypropyl methylcellulose (HPMC) as a gelling polymer produced a transparent gel.
  • the present invention relates to a pharmaceutical composition for topical use containing dexibuprofen, more particularly to a non-alcoholic transdermal hydrogel of dexibuprofen and process of preparing the same.
  • Topical NSAIDs preparations are commonly use to treat pain and inflammation associated with joints and muscles. Topical NSAIDs have three major advantages over oral treatment of pain and inflammation associated with joints and muscles:
  • Ibuprofen topical preparations are available for the treatment of pain and inflammation associated with joints and muscles.
  • Ibuprofen (2-(4-isobutylphenyl) propionic acid) has one chiral center, thus there are two enantiomers, S (+)-ibuprofen (dexibuprofen) and R ( ⁇ )-ibuprofen, also known as (S)-ibuprofen and (R)-ibuprofen.
  • S (+)-ibuprofen distalibuprofen
  • R ( ⁇ )-ibuprofen also known as (S)-ibuprofen and (R)-ibuprofen.
  • the S(+) form alone appears to be responsible for the anti-inflammatory activity, not the R( ⁇ ) form (S. Adams et al., Curr. Med. Res. Opin. 3, 552 (1975); S. Adams et al., J. Pharm. Pharmaco., 28, 256-257 (1976)).
  • the popular topical NSAIDs preparations include cream, ointment and gel, now a day's topical hydrogels are gaining popularity because of their cooling effect, and non-greasy nature.
  • dexibuprofen is formulated into topical gel formulations either using high amount of alcohol or using a two phase system to enhance the transdermal absorption and efficacy.
  • the present invention relates to a pharmaceutical composition for topical use containing dexibuprofen more particularly to non-alcoholic transdermal hydrogel of dexibuprofen and process of preparing the same.
  • process of preparing a non-alcoholic transdermal hydrogel of dexibuprofen comprising the steps of:
  • step (i) disperse the gelling polymer(s) in purified water and allow it to soak overnight
  • step (ii) dissolve the preservative(s) in purified water and then disperse dexibuprofen in it,
  • step (iii) dissolve the menthol in triethanolamine
  • step (iv) mix step (iii) with step (ii) with continuous stirring
  • step (v) mix propylene glycol and PEG 400; add this mixture to transcutol-P followed by the addition of lavender oil and mix well,
  • step (vi) add step (v) to step (iv) and mix well
  • step (vii) finally add step (vi) to step (i) with constant stirring to obtain homogenous gel.
  • non-alcoholic transdermal hydrogel of dexibuprofen may be transparent or translucent or opaque in nature.
  • the present invention comprises one or more pharmaceutically acceptable excipient(s) selected from the group comprising of gelling agent, pH modifying agent, spreadability modifying agent, water miscible solvent, soothing agent, preservative, antioxidant, surfactant, chelating agent, permeation enhancer, antifoaming agent and flavoring agent etc.
  • one or more gelling agent(s) can be selected from the group comprising of carbomer, hydroxypropyl methylcellulose (HPMC), hydroxyethyl cellulose (HEC), poloxamer, hydroxypropyl cellulose (HPC), methylcellulose (MC), collagen, gelatin, agar, alginic acid and its sodium salts such as sodium alginate, carrageenans and its sodium or potassium salts, tragacanth, pectin, guar gum, xanthan gum, gellan gum, polyacrylamide, polyvinyl alcohol, polyethylene and its co-polymers and the like.
  • HPMC hydroxypropyl methylcellulose
  • HEC hydroxyethyl cellulose
  • HPC hydroxypropyl cellulose
  • MC methylcellulose
  • collagen gelatin
  • agar alginic acid and its sodium salts such as sodium alginate, carrageenans and its sodium or potassium salts
  • tragacanth pectin
  • guar gum x
  • one or more pH modifying agent(s) can be selected from the group comprising of sodium hydroxide, citric acid, sodium citrate, triethanolamine, diethanolamine and the like.
  • one or more soothing agent(s) can be selected from the group comprising of menthol, thymol, camphor and the like.
  • one or more preservative(s) can be selected from the group comprising of sodium salts of methyl paraben, propyl paraben, other preservatives like salicylic acid and its salts, chlorhexidine hydrochloride, phenoxyethanol, sodium benzoate, methyl para-hydroxybenzoate, ethyl para-hydroxybenzoate, propyl para-hydroxybenzoate, butyl para-hydroxybenzoate and the like.
  • At least one oil-soluble and/or water soluble antioxidant(s) can be selected from the group comprising of butylated hydroxytoluene (BHT), ascorbyl palmitate, butylated hydroxanisole (BHA), phenyl- ⁇ -naphthylamine, hydroquinone, propyl gallate, nordihydroguiaretic acid, ascorbic acid, sodium benzoate, sodium metabisulfite, sodium bisulfite, sodium thiosulfite, sodium formaldehyde sulfoxylate, isoascorbic acid, thioglyerol, thiosorbitol, thiourea, thioglycolic acid, cysteine hydrochloride, 1,4-diazobicyclo-(2,2,2)-octane and the like,
  • BHT butylated hydroxytoluene
  • BHA butylated hydroxanisole
  • one or more surfactant(s) can be selected from the group comprising of sodium alkyl sulfates such as sodium lauryl sulfate and sodium myristyl sulfate, sodium N-acyl sarcosinates such as sodium N-lauroyl sarcosinate and sodium N-myristoyl sarcosinate, sodium dodecylbenzenesulfonate, sodium hydrogenated coconut fatty acid monoglyceride sulfate, sodium lauryl sulfoacetate, N-acyl glutamates such as N-palmitoyl glutamate, N-methylacyltaurin sodium salt, N-methylacylalanine sodium salt, sodium a-olefin sulfonate, sodium dioctylsulfosuccinate; N-alkylaminoglycerols such as N-lauryldiaminoethylglycerol and N-myristyl
  • one or more spreadability modifying agent(s) can be selected from the group comprising of polyethylene glycol, propylene glycol, glycerin, light liquid paraffin and the like.
  • one or more water miscible solvent can be selected from the group comprising of polyethylene glycol, propylene glycol, glycerin and the like.
  • the water miscible solvent i.e. a cosolvent
  • one or more permeation enhancer(s) can be selected from the group comprising of caprylic acid and its derivatives, polyoxylglycerides and its derivatives, triglycerides and its derivatives, lauric acid and its derivatives, oleic acid and its derivatives, diethylene glycol monoethyl ether (Transcutol-P), and the like.
  • one or more chelating agent(s) can be selected from the group comprising of ethylenediaminetetraacetic acid (EDTA), sodium EDTA, disodium EDTA, citric acid, tartaric acid and the like.
  • EDTA ethylenediaminetetraacetic acid
  • sodium EDTA sodium EDTA
  • disodium EDTA citric acid
  • tartaric acid tartaric acid
  • one or more antifoaming agents can be selected from the group comprising of simethicone, dimethicone and the like.
  • one or more flavoring agent(s) can be selected from the group comprising of lavender oil, rose oil, menthol, anethole, carvone, eugenol, limonene, ocimene, n-decylalcohol, citronellol, ⁇ -terpineol, methyl salicylate, methyl acetate, citronellyl acetate, cineole, linalool, ethyl linalool, vanillin, thymol, spearmint oil, peppermint oil, lemon oil, orange oil, sage oil, rosemary oil, cinnamon oil, pimento oil, cinnamon leaf oil, wintergreen oil, clove oil, eucalyptus oil and the like.
  • Dexibuprofen non-alcoholic transdermal hydrogel prepared by using carbopol as gelling polymer: Sr. No Ingredients % by weight 1. Dexibuprofen 10.00 2. Carbopol 971P 2.50 3. Transcutol-P 3.30 4. Triethanolamine 7.20 5. Propylene glycol 1.00 6. Polyethylene glycol 400 1.00 7. Menthol 0.05 8. Sodium metabisulphite 0.20 9. Sodium benzoate 0.20 10. Lavender oil 0.05 11. Purified water q.s to make 100 Total 100.00
  • step 3 Add step 3 to step 2 with constant stirring to get clear solution.
  • step 5 Add step 5 to step 4 and mix well.
  • step 6 Finally add step 6 to step 1 with constant stirring to obtain homogenous gel.
  • Dexibuprofen non-alcoholic transdermal hydrogel prepared by using HPMC as gelling polymer: Sr. No Ingredients % by weight 1. Dexibuprofen 10.0 2. HPMC K4M 2.5 3. HPMC E5 0.3 4. Lutrol F68 5.0 5. Transcutol-P 3.3 6. Propylene glycol 1.0 7. Polyethylene glycol 400 3.0 8. Menthol 0.1 9. Sodium metabisulphite 0.2 10. Sodium benzoate 0.2 11. Triethanolamine 7.2 12. Simethicone 0.00016 13. Lavender oil 0.1 14. Purified water q.s to make 100 Total 100.0
  • step 4 Add step 4 to step 3 with constant stirring to get clear solution.
  • step 6 Add step 6 to step 5.
  • Step 7 Add Step 7 to step 2 with constant stirring to obtain a homogenous gel.
  • Dexibuprofen non-alcoholic transdermal hydrogel prepared by using carbopol as gelling polymer: Sr. No Ingredients % by weight 1. Dexibuprofen 5.00 2. Carbopol 971P 2.50 3. Transcutol-P 3.30 4. Triethanolamine 7.20 5. Propylene glycol 1.00 6. Polyethylene glycol 400 1.00 7. Menthol 0.05 8. Sodium metabisulphite 0.20 9. Sodium benzoate 0.20 10. Lavender oil 0.05 11. Purified water q.s to make 100 Total 100.00
  • step 3 Add step 3 to step 2 with constant stirring to get clear solution.
  • step 5 Add step 5 to step 4 and mix well.
  • step 6 Finally add step 6 to step 1 with constant stirring to obtain homogenous gel.
  • Dexibuprofen non-alcoholic transdermal hydrogel prepared by using HPMC as gelling polymer: Sr. No Ingredients % by weight 1. Dexibuprofen 5.0 2. HPMC K4M 2.5 3. HPMC E5 0.3 4. Lutrol F68 5.0 5. Transcutol-P 3.3 6. Propylene glycol 1.0 7. Polyethylene glycol 400 3.0 8. Menthol 0.1 9. Sodium metabisulphite 0.2 10. Sodium benzoate 0.2 11. Triethanolamine 7.2 12. Simethicone 0.00016 13. Lavender oil 0.1 14. Purified water q.s to make 100 Total 100.0
  • step 4 Add step 4 to step 3 with constant stirring to get clear solution.
  • step 6 Add step 6 to step 5.
  • Step 7 Add Step 7 to step 2 with constant stirring to obtain a homogenous gel.
  • the experimental trials showed that the pH modifying agent, antioxidant and water miscible solvent are essential excipients for obtaining stable non-alcoholic transdermal hydrogel of dexibuprofen.
  • the hydrogels prepared according to example 1 and 3 using carbopol as gelling polymer produced opaque gel, whereas hydrogels prepared according to example 2 and 4 using HPMC as gelling polymer produced transparent gel. Further the hydrogels prepared according to example 1, 2, 3 and 4 were subjected for stability study at 40° C./75% RH for 3 months in laminated tubes and there was no significant change with respect to physical description, pH, assay value and related substances.

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