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US20030149383A1 - Patch containing anti-inflammatory agent - Google Patents

Patch containing anti-inflammatory agent Download PDF

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Publication number
US20030149383A1
US20030149383A1 US10/258,022 US25802202A US2003149383A1 US 20030149383 A1 US20030149383 A1 US 20030149383A1 US 25802202 A US25802202 A US 25802202A US 2003149383 A1 US2003149383 A1 US 2003149383A1
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United States
Prior art keywords
mass
antiinflammatory
molecular weight
plaster
parts
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Abandoned
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US10/258,022
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English (en)
Inventor
Yasuhiro Ikeura
Miyuki Shinmura
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Hisamitsu Pharmaceutical Co Inc
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Hisamitsu Pharmaceutical Co Inc
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Publication date
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Assigned to HISAMITSU PHARMACEUTICAL CO., INC. reassignment HISAMITSU PHARMACEUTICAL CO., INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: IKEURA, YASUHIRO, SHINMURA, MIYUKI
Publication of US20030149383A1 publication Critical patent/US20030149383A1/en
Priority to US12/457,410 priority Critical patent/US8173156B2/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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • 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
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
    • 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
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • 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
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7076—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising ingredients of undetermined constitution or reaction products thereof, e.g. rosin or other plant resins
    • 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

  • This invention relates to antiinflammatory-containing plasters for percutaneous administration that are intended for anti-inflammatory, analgesic effect. More specifically, it relates to an antiinflammatory-containing plaster comprising as the medicinally effective component, an antiinflammatory having a carboxyl group or a salt thereof and which is intended for the treatment of lumbago, muscle ache and periarthritis.
  • a number of preparations for percutaneous administration are known for non-steroidal antiinflammatories that are intended for absorption through skin; plasters are also known that utilize the base comprising a thermoplastic elastomer such as natural rubber, an acrylic acid polymer, or a styrene-isoprene-styrene block copolymer.
  • a thermoplastic elastomer such as natural rubber, an acrylic acid polymer, or a styrene-isoprene-styrene block copolymer.
  • 2,816,765 proposes a plaster where an antiinflammatory belonging to the carboxylic acid type is blended with a base comprising a styrene-isoprene-styrene block copolymer and polyisobutylene (both as base polymer), a rosin ester derivative and L-menthol (both as solubilizer), and liquid paraffin (as plasticizer).
  • a base comprising a styrene-isoprene-styrene block copolymer and polyisobutylene (both as base polymer), a rosin ester derivative and L-menthol (both as solubilizer), and liquid paraffin (as plasticizer).
  • International Publication WO96/08245 proposes a plaster where an antiinflammatory having a carboxylic acid group within its molecule in addition to an esterification retardant, which is a metal salt of fatty acid, for preventing the esterification between the antiinflammatory having a carboxylic acid group and L-menthol is blended with a styrene-isoprene-styrene block copolymer and polyisobutylene (both as base polymer), L-menthol (as solubilizer), a rosin ester derivative (as tackifier), and liquid paraffin (as plasticizer).
  • an esterification retardant which is a metal salt of fatty acid
  • L-menthol acts as a solubilizer to an antiinflammatory having a carboxyl group.
  • L-menthol acts as a solubilizer to an antiinflammatory having a carboxyl group.
  • An object of the invention is to provide an antiinflammatory-containing plaster that can consistently produce, over a long period of time, a sufficient anti-inflammatory, analgesic effect by the antiinflammatory having a carboxyl group or a salt thereof without bringing harmful effects such as skin irritation and that is excellent in the stability of adhesive base as well as in its adhesion with alleviated pain upon peeling despite the fact that L-menthol is not blended therein.
  • an antiinflammatory-containing plaster can be obtained where the release rates of its medicinally effective component, the antiinflammatory, one hour and three hours later are in a predetermined range and which can produce a sufficient antiinflammatory, analgesic effect consistently over a long period of time without bringing harmful effects and which also has excellent stability of the adhesive base by including specific components in specific proportions into the plaster without combining the antiinflammatory having a carboxyl group or a salt thereof with L-menthol; the inventors have thus arrived at this invention.
  • an antiinflammatory-containing plaster of this invention comprises 5-40% by mass of a styrene-isoprene-styrene block copolymer, 1-25% by mass of a high molecular weight polyisobutylene, 0.5-24% by mass of a low molecular weight polyisobutylene, 3-50% by mass of a tackifier, 20-70% by mass of a plasticizer, 0.01-7% by mass of a dispersant, and 0.1-8% by mass of an antiinflammatory having a carboxyl group or a salt thereof as the medicament, but which contains no L-menthol.
  • the medicament release rate at one hour after the start of test is 20-64% by mass and the medicament release rate at three hours after the start of test is 40-93% by mass when the water-releasing test using a rotating cylinder described in the release test as prescribed in United State Pharmacopoeia is carried out under the following conditions:
  • Test solution distilled water
  • Solution temperature 32 ⁇ 0.5° C.
  • the tackifier is a rosin-based resin
  • the plasticizer is liquid paraffin
  • the dispersant is a metal salt of stearic acid.
  • the antiinflammatory having a carboxyl group or a salt thereof used in the antiinflammatory-containing plaster of this invention is preferably at least one member antiinflammatory selected from the group consisting of indomethacin, ketoprofen, flurbiprofen, diclofenac, loxoprofen, ketorolac, and the salts of the foregoing.
  • FIG. 1 is a graph showing the results of medicament release test.
  • the antiinflammatory-containing plaster of this invention comprises as the medicinally effective component, an antiinflammatory having a carboxyl group or a salt thereof.
  • antiinflammatories include the antiinflammatories having a carboxyl group (carboxylic acid group) such as indomethacin, ketoprofen, flurbiprofen, diclofenac, loxoprofen, and ketorolac as well as the antiinflammatories where the hydrogen atom of the carboxyl group has been substituted by a medically acceptable salt such as an inorganic salt (e.g., sodium salt, potassium salt, calcium salt, or ammonium salt) or an organic salt (e.g., tromethamine salt).
  • an inorganic salt e.g., sodium salt, potassium salt, calcium salt, or ammonium salt
  • organic salt e.g., tromethamine salt
  • the blending proportion of the antiinflammatory having a carboxyl group or a salt thereof in the plaster of this invention is 0.1-8% by mass, preferably 0.5-5% by mass.
  • the blending proportion of the antiinflammatory is less than 0.1% by mass, sufficient efficacy will not be attained.
  • the blending proportion exceeds 8% by mass, it will not be suitable from the standpoints of the occurrence of harmful effects such as skin irritation caused by excessive administration and economical efficiency.
  • the antiinflammatory-containing plaster of this invention does not contain L-menthol that acts as solubilizer to the antiinflammatory having a carboxyl group or a salt thereof. Accordingly, in the antiinflammatory-containing plaster of this invention, the esterification of the antiinflammatory is fully prevented and antiinflammatory, analgesic effect by the antiinflammatory can be consistently produced over a long period of time without bringing harmful effects such as skin irritation by including specific components in specific proportions into the plaster (as will be described hereafter), despite the fact that L-menthol, which acts as solubilizer, is not contained in the plaster.
  • the antiinflammatory-containing plaster of this invention is such that desirably the medicament release rate at one hour after the start of test is 20-70% by mass (preferably 30-65% by mass) and the medicament release rate at three hours after the start of test is 40-93% by mass (preferably 60-90% by mass) when the water-releasing test using a rotating cylinder described in the release test as prescribed in United State Pharmacopoeia is carried out under the following conditions:
  • Test solution distilled water
  • Solution temperature 32 ⁇ 0.5° C.
  • the antiinflammatory-containing plaster of this invention which is able to stably maintain such constantly high medicament release, has for the first time made it possible to provide a drug that consistently produces an excellent therapeutic effect over a long period of time without bringing harmful effects such as skin irritation upon administration.
  • the antiinflammatory-containing plaster of this invention may be obtained by including as the medicinally effective component, an antiinflammatory having a carboxyl group or a salt thereof in a specific blending proportion into a base comprising a styrene-isoprene-styrene block copolymer, a high molecular weight isobutylene, a low molecular weight isobutylene, a tackifier, a plasticizer, and a dispersant, respectively, in specific blending proportions, but which contains no L-menthol.
  • a base comprising a styrene-isoprene-styrene block copolymer, a high molecular weight isobutylene, a low molecular weight isobutylene, a tackifier, a plasticizer, and a dispersant, respectively, in specific blending proportions, but which contains no L-menthol.
  • the styrene-isoprene-styrene block copolymer according to this invention is a block copolymer of styrene and isoprene and is provided with polystyrene at both ends thereof.
  • Such styrene-isoprene-styrene block copolymers include, among others, Cariflex TR-1101, TR-1107 and Cariflex TR-1111 (trade names, available from Shell Kagaku K.
  • JSR5000 and JSR5002 (trade names, available from Japan Synthetic Rubber Co., Ltd.); Quintac 3530, 3421 and 3570C (trade names, available from Nippon Zeon Co., Ltd.); Kraton D-KX401CS and D-1107CU (trade names, available from Shell Kagaku K. K.); and Solprene 428 (trade name, available from Phillips Petroleum International, Ltd.).
  • JSR5000 and JSR5002 trade names, available from Japan Synthetic Rubber Co., Ltd.
  • Quintac 3530, 3421 and 3570C (trade names, available from Nippon Zeon Co., Ltd.)
  • Kraton D-KX401CS and D-1107CU (trade names, available from Shell Kagaku K. K.)
  • Solprene 428 (trade name, available from Phillips Petroleum International, Ltd.).
  • One kind or a combination of two or more kinds of the foregoing may be used.
  • the blending proportion of the styrene-isoprene-styrene block copolymer is 5-40% by mass, preferably 8-35% by mass, and more preferably 10-30% by mass based on the total weight of the plaster (adhesive preparation). If the blending proportion is less than 5% by mass, the cohesive force of the base will decrease and the shape retention of the base will degrade. On the other hand, if it exceeds 40% by mass, the cohesive force of the base will increase, thus likely resulting in a reduction in adhesive strength and lowering workability.
  • the high molecular weight polyisobutylene according to this invention is a polymer of isobutylene, preferably with an average molecular weight of 50,000-200,000.
  • high molecular weight polyisobutylene there are mentioned: Oppanol 80, 100, 120, 150, and 200 (trade names, available from BASF AG); and Vistanex MM L-80, MM L-100, MM L-120, MM L-140 (trade names, available from Exxon Chemical Japan Ltd.).
  • One kind or a combination of two or more kinds of the foregoing may be used.
  • the blending proportion of the high molecular weight polyisobutylene is 1-25% by mass, preferably 2-18% by mass, and more preferably 3.6-12% by mass based on the total weight of the plaster (adhesive preparation). If the blending proportion is less than 1% by mass, the shape retention of the base will degrade during prolonged storage, exudation will tend to appear, and the releasing-capability of the antiinflammatory will likely decrease. On the other hand, if it exceeds 25% by mass, the releasing-capability of the antiinflammatory will also likely decrease.
  • the low molecular weight polyisobutylene according to this invention is a polymer of isobutylene, preferably with an average molecular weight of 5,000-15,000.
  • low molecular weight polyisobutylene there are mentioned: Oppanol 10, 12, 12SF, 15, 15SF, 30SF, 50, 50SF (trade names, available from BASF AG); and Vistanex LM-MS, LM-MH, LM-H (trade names, available from Exxon Chemical Japan Ltd.).
  • One kind or a combination of two or more kinds of the foregoing may be used.
  • the blending proportion of the low molecular weight polyisobutylene is 0.5-24% by mass, preferably 1-20% by mass, and more preferably 2-15% by mass based on the total weight of the plaster (adhesive preparation). If the blending proportion is less than 0.5% by mass, degradation of the adhesive properties will occur to easily cause peeling during affixing and the releasing-capability of the antiinflammatory will also likely decrease. On the other hand, if it exceeds 24% by mass, the adhesive properties will excessively increase, thus likely resulting in rash or pain upon peeling.
  • the tackifier according to this invention is preferably a rosin-based resin made from rosin or a rosin derivative as a base material; and a rosin ester, a hydrogenated rosin ester, a maleic acid-modified rosin ester, or the like may preferably be used.
  • Such tackifiers include, among others, Hariester L, S and P (trade names, available from Harima Chemicals, Inc.); Super Ester A-75 and S-100, Pinecrystal KE-100 and KE-311, Ester Gum A, AA-G, H and HP (trade names, available from Arakawa Chemical Industries, Ltd.); Hercolyn D, Foral 85, 100 and 105 (trade names, available from Rika-Hercules Inc.). One kind or a combination of two or more kinds of the foregoing may be used.
  • the blending proportion of the tackifier is 3-50% by mass, preferably 4-40% by mass, and more preferably 5-30% by mass based on the total weight of the plaster (adhesive preparation). If the blending proportion is less than 3% by mass, degradation of the adhesive properties and crystallization of the antiinflammatory will occur to easily cause peeling during affixing, and the releasing-capability of the antiinflammatory will also likely decrease. On the other hand, if it exceeds 50% by mass, the adhesive properties and dissolution of the antiinflammatory will tend to increase, thus likely resulting in rash or pain upon peeling as well as in lowered medicament releasing-capability.
  • the plasticizer according to this invention is an agent compatible with the other base components and capable of providing the base with flexibility.
  • Almond oil, olive oil, camellia oil, persic oil, peanut oil, liquid paraffin, and the like may preferably be used.
  • One kind, or two or more kinds of these plasticizers may be used and among them, the liquid paraffin is particularly preferred.
  • the blending proportion of the plasticizer is 20-70% by mass, preferably 25-65% by mass, and more preferably 30-60% by mass based on the total weight of the plaster (adhesive preparation). If the blending proportion is less than 20% by mass, poor plasticity will result to likely lower adhesive properties and productivity. On the other hand, if it exceeds 70% by mass, the adhesive preparation will be too soft, likely causing the occurrence of cohesion failure of the base.
  • a dispersing agent is further included in a specific blending proportion in the base containing the styrene-isoprene-styrene block copolymer, the high molecular weight polyisobutylene, the low molecular weight polyisobutylene, the tackifier, and the plasticizer as described above.
  • the dispersing agent according to the invention is an agent capable of enhancing dispersibility of different components in the preparation, particularly those of the styrene-isoprene-styrene block copolymer and the high molecular weight- and low molecular weight-polyisobutylenes.
  • Synthetic aluminum silicate, hydrated aluminum silicate, aluminum hydroxide, magnesium silicate, zinc oxide, titanium oxide, metal salts of fatty acid such as metal salts of stearic acid may be used.
  • metal salts of stearic acid e.g., zinc stearate, calcium stearate, aluminum stearate, and magnesium stearate
  • zinc stearate is especially preferred.
  • the blending proportion of the dispersing agent is 0.01-7% by mass, preferably 0.05-6% by mass, and more preferably 0.1-5% by mass, based on the total weight of the plaster (adhesive preparation). If the blending proportion is less than 0.01% by mass, the dispersibility of the high molecular weight polyisobutylene and the diffusibility of the antiinflammatory in the base will be poor, resulting in the lowered releasing-capability of the antiinflammatory. On the other hand, if it exceeds 7% by mass, the dispersant itself will leak to lower adhesive properties and to likely cause peeling during affixing.
  • an antiinflammatory having a carboxyl group or a salt thereof as the medicinally effective component is contained in the above-mentioned base in a 0.1-8% by mass proportion as described above.
  • the plaster of this invention having the above-stated composition
  • various components are uniformly dispersed in the preparation without cohesion and the uniform dispersibility of the antiinflammatory is adequately maintained. This will stably sustain the constantly high medicament release in the plaster of this invention despite the fact that it contains no L-menthol which would serve to dissolve the antiinflammatory.
  • the sufficient anti-inflammatory, analgesic effect by the antiinflammatory will be consistently produced over a long period of time without bringing harmful effects such as skin irritation.
  • the excellent stability of the adhesive base and adhesion of preparations as well as alleviated pain upon peeling can be realized.
  • the plaster of this invention may further contain, as necessary, other additive components such as an antioxidant, a filler, a crosslinking agent, a preservative, an ultraviolet light absorber, and an absorption enhancer in addition to the styrene-isoprene-styrene block copolymer, the high molecular weight polyisobutylene, the low molecular weight polyisobutylene, the tackifier, the plasticizer, the dispersant, and the antiinflammatory as described above.
  • the blending proportion of the other additive components is not particularly limited, but is preferably 0.01-7% by mass, and more preferably 0.1-5% by mass based on the total weight of the plaster (adhesive preparation).
  • Preferred as such a antioxidant are tocopherol, tocopherol derivatives, ascorbic acid, esters of ascorbic acid and stearic acid, nordihydroguaiaretic acid, dibutylhydroxytoluene, butylhydroxyanisole and the like.
  • the filler are calcium carbonate, magnesium carbonate, silicates (e.g., aluminum silicate and magnesium silicate), silicic acid, barium sulfate, calcium sulfate, calcium zincate, zinc oxide, titanium oxide, and the like.
  • crosslinking agent examples include thermosetting resins (e.g., amino resin, phenol resin, epoxy resin, alkyd resin, and unsaturated polyester), isocyanates, and blocked isocyanates and inorganic crosslinkers such as metals or metal compounds.
  • thermosetting resins e.g., amino resin, phenol resin, epoxy resin, alkyd resin, and unsaturated polyester
  • isocyanates e.g., amino resin, phenol resin, epoxy resin, alkyd resin, and unsaturated polyester
  • blocked isocyanates e.g., blocked isocyanates and inorganic crosslinkers such as metals or metal compounds.
  • preservative ethyl paraben, propyl paraben, butyl paraben, and the like.
  • ultraviolet light absorber p-aminobenzoic acid derivatives, anthranilic acid derivatives, salicylic acid derivatives, coumarin derivatives, amino acid derivatives, imidazoline derivatives, pyridine derivatives, and dioxane derivatives.
  • the absorption enhancers include, among others, terpene oils such as d-limonene, esters of fatty acid (e.g., glycerol monolaurate, glycerol monooleate, and diethyl sebacate), azone, azacycloalkanes such as 1-[2-(decylthio)ethyl]azacyclopentan-2-one, and higher fatty acids such as oleic acid, lauric acid, and myristic acid.
  • terpene oils such as d-limonene
  • esters of fatty acid e.g., glycerol monolaurate, glycerol monooleate, and diethyl sebacate
  • azacycloalkanes such as 1-[2-(decylthio)ethyl]azacyclopentan-2-one
  • higher fatty acids such as oleic acid, lauric acid, and myristic acid.
  • the thickness (not including thickness of a backing and a released liner as described hereafter) of the plaster (i.e., the plaster layer) of this invention prepared using the various components is preferably 50-300 ⁇ m and more preferably 80-200 ⁇ m.
  • the thickness is less than 50 ⁇ m, the duration of adhesiveness and adhesion will tend to decrease.
  • it exceeds 300 ⁇ m the cohesive force will tend to decrease and the shape retention will tend to degrade.
  • the plaster of this invention freely expands and contracts longitudinally and laterally, thus achieving the affixing feeling at high level.
  • the antiinflammatory-containing plaster of this invention it becomes possible to employ a backing with flexibility, and adhesion will be realized such that the plaster can be affixed even to a flexion site like elbow or knee with adequate compatibility and without being peeled off over a long period of time.
  • the backing of plaster of this invention is desirably one that does not affect release of the medicament from the plaster of the invention; and flexible or non-flexible materials may be used.
  • Usable backings for the invention include, among others, a film, a sheet, a sheet porous body, a sheet foam, and a woven or non-woven fabric of a synthetic resin such as polyethylene, polypropylene, polybutadien, an ethylene-vinyl acetate copolymer, polyvinyl chloride, a polyester, nylon, or a polyurethane; paper; fabric; non-woven fabric; and a laminated product of the foregoing.
  • Its load at 30%-elongation (modulus) is preferably 100-800 g longitudinally (lengthwise) and 500-2500 g laterally (widthwise), more preferably 100-500 g longitudinally and 500-2000 g laterally, under such measurement conditions that the sample width is 50 mm, the sample length 200 mm, and the elongation speed is 200 mm/min.
  • its recovery factor at 50%-elongation is preferably 75-95% longitudinally and 65-85% laterally, more preferably 80-95% longitudinally and 70-85% laterally, under such measurement conditions that the sample width is 50 mm, the sample length is 200 mm, and the elongation speed is 200 mm/min. If the load at 30%-elongation for these backings is below the lower limit, the backing will lose its sturdiness when affixed and handling tends to be difficult. On the other hand, if it exceeds the upper limit, adhesion to the flexion site over a long period of time tends to be difficult.
  • the plaster of this invention through the use of a highly flexible backing, can firmly be affixed to flexion sites with vigorous movement such as elbow and knee. Furthermore, the basic weight (weight per unit area) of the backing according to the invention is preferably 100 ⁇ 30 g/m 2 .
  • the styrene-isoprene-styrene block copolymer, the high molecular weight polyisobutylene, the low molecular weight polyisobutylene, the tackifier, the plasticizer, the dispersing agent, and any components are blended at the respectively predetermined proportions to yield a mixture, and the mixture is heated and stirred under an inert atmosphere of nitrogen or the like to yield a dissolved material.
  • the temperature upon stirring is preferably 110-200° C. and the stirring time is preferably 30-120 minutes.
  • the antiinflammatory (the medicinally effective component), together with any antioxidant or absorption enhancer if it is to be included, is added to the aforementioned dissolved material and the mixture is then stirred preferably at 110-200° C. and preferably for 5-30 minutes, thereby yielding a uniformly dissolved material.
  • the various components described above may be added to an organic solvent such as hexane or toluene or ethyl acetate so as to give their predetermined proportions, and may be stirred to yield a uniformly dissolved material.
  • this dissolved material is spread directly over the backing by an ordinary method, and then it is cut into desired shapes after being covered with a released liner (peeled cover).
  • a released liner peeled cover
  • this dissolved material is allowed to cover the backing and after the dissolved material is pressed and transferred onto the backing, it may be cut into desired shapes.
  • a uniformly dissolved material has been obtained using an organic solvent, it is dried with a dryer, after having been spread over the backing, and the organic solvent is removed by evaporation, after which the dissolved material may be covered with a released liner; or alternatively, after which the dissolved material may preferably be pressed and transferred onto the backing.
  • Such released liners include, among others, a released paper processed by release treatment (treatment for facilitating release); cellophane; and a synthetic resin film of polyethylene, polypropylene, polyester, or the like.
  • plasters containing an antiinflammatory of this invention will be described in more detail by way of examples and comparative examples; however, they are not to be limited to those described in the following examples.
  • “part(s)” mean “part(s) by mass” unless otherwise stated specifically.
  • a plaster was prepared in the formulation described above according to the aforementioned preparation method. Specifically, the components other than the antiinflammatory in the formulation described above were blended to yield a mixture and the mixture was heated and stirred under the nitrogen atmosphere to yield a dissolved material. Subsequently, the antiinflammatory, which was the medicinally effective component, was added to the dissolved material and the mixture was heated and stirred to yield a uniformly dissolved material. Then, this dissolved material was spread over a backing (non-woven fabric of polypropylene) so that the thickness of the plaster layer obtained was 150 ⁇ m.
  • the backing used here was one of which the load at 30%-elongation was 250 g longitudinally and 1200 g laterally and the recovery factor at 50%-elongation was 90% longitudinally and 75% laterally.
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above.
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above.
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above.
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above.
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above.
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above.
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above.
  • styrene-isoprene-styrene block copolymer 30.00 parts (JSR 5000) high molecular weight polyisobutylene 5.00 parts (Vistanex MM L-80) low molecular weight polyisobutylene 1.00 parts (Vistanex LM-MH) rosin-based resin 30.00 parts (Foral 85) liquid paraffin 33.40 parts aluminum silicate 0.10 parts indomethacin 0.50 parts
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above.
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above.
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above and L-menthol and the antiinflammatory were together added to the dissolved material.
  • styrene-isoprene-styrene block copolymer 25.00 parts (Cariflex TR-1111) rosin-based resin 5.00 parts (Pinecrystal KE-311) liquid paraffin 68.00 parts ketoprofen 0.50 parts L-menthol 1.50 parts
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above and L-menthol and the antiinflammatory were together added to the dissolved material.
  • styrene-isoprene-styrene block copolymer 15.00 parts (Cariflex TR-1111) high molecular weight polyisobutylene 5.00 parts (Vistanex MM L-120) rosin-based resin 40.00 parts (Pinecrystal KE-311) liquid paraffin 23.00 parts ketoprofen 5.00 parts L-menthol 10.00 parts butylhydroxytoluene 2.00 parts
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above and L-menthol, butylhydroxytoluene, and the antiinflammatory were together added to the dissolved material.
  • styrene-isoprene-styrene block copolymer 24.00 parts (Cariflex TR-1111) rosin-based resin 5.00 parts (Pinecrystal KE-311) liquid paraffin 68.00 parts zinc stearate 1.00 parts ketoprofen 0.50 parts L-menthol 1.50 parts
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above and L-menthol and the antiinflammatory were together added to the dissolved material.
  • styrene-isoprene-styrene block copolymer 15.00 parts (Cariflex TR-1111) high molecular weight polyisobutylene 5.00 parts (Vistanex MM L-120) rosin-based resin 37.00 parts (Pinecrystal KE-311) liquid paraffin 23.00 parts zinc stearate 5.00 parts ketoprofen 5.00 parts L-menthol 10.00 parts
  • a plaster was prepared similarly to Example 1, except that it was formulated as described above and L-menthol and the antiinflammatory were together added to the dissolved material.
  • a test for the medicament releasing-capabilities of the plasters produced in Examples 1 to 4 was carried out according to the rotating cylinder method described in the release test as prescribed in United state pharmacopoeia (USP) under the following conditions:
  • Test solution distilled water
  • Solution temperature 32 ⁇ 0.5° C.
  • the plasters produced in Examples 1, 2, 3, and 4 were cut into small pieces (2 cm ⁇ 2 cm) and they were affixed onto the skin of forearms of 10 healthy adults. Twelve hours after affixing, the peripheries of the plaster were fixed by a clip connected to a digital force gage. The digital force gage was raised at a constant rate and the plaster was retained without being peeled for a predetermined period while it was kept at 90° to the human skin. Force was then measured when peeled. The averages of the evaluation results for ten people are shown in Table 3. Numerical criteria for judgment are as follows: 100-200 g shows desirable adhesive strength; with less than that the adhesive strength is not sufficient and causes peeling upon affixing; and with above that the adhesive strength is too strong and causes pain upon peeling.
  • an antiinflammatory-containing plaster that can consistently produce, over a long period of time, sufficient anti-inflammatory, analgesic effect by the antiinflammatory having a carboxyl group or a salt thereof without bringing harmful effects such as skin irritation and that is additionally excellent in its adhesion as well as in the stability of adhesive base with alleviated pain upon peeling, despite the fact that L-menthol is not blended therein. Accordingly, this invention is capable of providing an antiinflammatory-containing plaster useful as a drug (plaster for external application) that is intended for anti-inflammation and analgesia.

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US20030109819A1 (en) * 1999-12-15 2003-06-12 Kiyomi Tsuruda Adhesive preparations
US20050004508A1 (en) * 2003-06-30 2005-01-06 Ying Sun Methods of reducing the appearance of pigmentation with galvanic generated electricity
US20050147813A1 (en) * 2003-12-05 2005-07-07 Tesa Aktiengesellschaft High-tack adhesive, method of its preparation and the use thereof
US20060165764A1 (en) * 2005-01-26 2006-07-27 Akinori Hanatani Tape preparation
US20060172002A1 (en) * 2003-03-18 2006-08-03 Hisamitsu Pharmaceutical Co., Inc. Patch containing nonsteroidal antinflammatory and analgesic agent
US20060198880A1 (en) * 2003-05-07 2006-09-07 Hisamitsu Pharmaceutical Co., Inc. Ultraviolet-shielding type patch
US20060263420A1 (en) * 2005-03-10 2006-11-23 Hisamitsu Pharmaceutical Co., Inc. Adhesive and plaster
US20070009588A1 (en) * 2002-09-13 2007-01-11 Hisamitsu Pharmaceutical Co., Inc. Adhesive patch
US20080113010A1 (en) * 2004-11-05 2008-05-15 Lead Chemical Co., Ltd. Nonaqueous Preparation for Percutaneous Absorption Containing Nonsteroidal Anti-Inflammatory Analgesic
US20090028806A1 (en) * 2005-02-25 2009-01-29 Shigeo Suzuki Medicine for External Application Containing Anti-Inflammatory Agent and Soy Lecithin
US20090238860A1 (en) * 2005-08-10 2009-09-24 Hisamitsu Pharmaceutical Co., Inc. Adhesive Patch Less Irritative to Skin
US20090238846A1 (en) * 2004-08-31 2009-09-24 Aspion Co., Ltd. S/O type external preparation
US20110003893A1 (en) * 2007-12-12 2011-01-06 Teikoku Seiyaku Co., Ltd. Aqueous loxoprofen-containing patches
US9833417B2 (en) 2010-11-02 2017-12-05 Teikoku Seiyaku Co., Ltd. Felbinac-containing external patch
US20190240167A1 (en) * 2016-10-18 2019-08-08 Lts Lohmann Therapie-Systeme Ag Two-layer topical therapeutic system
US11872320B2 (en) 2021-02-25 2024-01-16 Hisamitsu Pharmaceutical Co., Inc. Method for treating osteoarthritis
US12178922B2 (en) 2016-12-28 2024-12-31 Hisamitsu Pharmaceutical Co., Inc. Patch with DMSO in adhesive layer

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JP4593471B2 (ja) 2003-10-20 2010-12-08 久光製薬株式会社 皮膚外用貼付剤
TWI341736B (en) * 2003-12-26 2011-05-11 Hisamitsu Pharmaceutical Co Anti-infammatory adhesive preparations
JP4869583B2 (ja) * 2004-11-30 2012-02-08 久光製薬株式会社 角質剥離が少ない貼付剤
WO2006095820A1 (ja) * 2005-03-10 2006-09-14 Hisamitsu Pharmaceutical Co., Inc. 粘着剤及び貼付剤
PT1864655T (pt) * 2005-03-10 2017-02-10 Hisamitsu Pharmaceutical Co Adesivo e penso adesivo
JP5684441B2 (ja) * 2005-12-28 2015-03-11 久光製薬株式会社 インドメタシン含有貼付剤
CN101502499B (zh) * 2009-03-13 2011-07-27 北京化工大学 一种布洛芬经皮释放贴剂及其制备方法
WO2011129269A1 (ja) * 2010-04-13 2011-10-20 東亞合成株式会社 医療用粘着剤組成物、医療用貼付剤及び該組成物の製造方法
JP6014813B2 (ja) * 2010-09-03 2016-10-26 株式会社 ケイ・エム トランスダーム 経皮吸収製剤および皮膚貼付用粘着シート
CN103849100A (zh) * 2012-12-03 2014-06-11 中国石油化工股份有限公司 一种用于膏药或贴剂的载体苯乙烯-异戊二烯嵌段共聚组合物及胶粘剂的制备
JP5767417B1 (ja) 2015-02-05 2015-08-19 久光製薬株式会社 貼付剤
CN106692110B (zh) * 2015-08-19 2019-12-17 天津市山佳医药科技有限公司 一种芳基丙酸类非甾体抗炎药贴剂及其制备方法
CN106692111A (zh) * 2015-11-13 2017-05-24 北京泰德制药股份有限公司 一种含有酮洛芬的皮肤外用贴剂及其制备方法
CN106822049B (zh) * 2015-12-07 2020-10-20 北京乳凝创智生物技术研发中心（有限合伙） 新型化药贴剂酮洛芬贴片及其制备方法
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US20230120384A1 (en) * 2021-10-19 2023-04-20 Heather Sloan Menthol- and magnesium-infused kinesiology tape
DE102021128912A1 (de) * 2021-11-05 2023-05-11 Lts Lohmann Therapie-Systeme Ag. Okklusives pflaster mit flexibler backing
CN117159508B (zh) * 2023-09-18 2024-11-15 湖南九典制药股份有限公司 热熔型贴剂及其制备方法
CN120346189B (zh) * 2025-06-23 2025-09-16 杭州百诚医药科技股份有限公司 一种热熔型洛索洛芬钠贴剂及其制备方法

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Cited By (27)

* Cited by examiner, † Cited by third party
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US20030109819A1 (en) * 1999-12-15 2003-06-12 Kiyomi Tsuruda Adhesive preparations
US7250546B2 (en) 1999-12-15 2007-07-31 Hisamitsu Pharmaceuticals Co., Inc. Adhesive preparations
US20070083139A1 (en) * 1999-12-15 2007-04-12 Hisamitsu Pharmaceutical Co., Inc. Adhesive preparations
US20070009588A1 (en) * 2002-09-13 2007-01-11 Hisamitsu Pharmaceutical Co., Inc. Adhesive patch
US7785622B2 (en) 2002-09-13 2010-08-31 Hisamitsu Pharmaceutical Co., Inc. Adhesive patch for fentanyl administration
US20060172002A1 (en) * 2003-03-18 2006-08-03 Hisamitsu Pharmaceutical Co., Inc. Patch containing nonsteroidal antinflammatory and analgesic agent
US8034374B2 (en) 2003-03-18 2011-10-11 Hisamitsu Pharmaceutical Co., Inc. Patch containing nonsteroidal anti-inflammatory and analgesic agent
US20060198880A1 (en) * 2003-05-07 2006-09-07 Hisamitsu Pharmaceutical Co., Inc. Ultraviolet-shielding type patch
US20050004508A1 (en) * 2003-06-30 2005-01-06 Ying Sun Methods of reducing the appearance of pigmentation with galvanic generated electricity
US20050147813A1 (en) * 2003-12-05 2005-07-07 Tesa Aktiengesellschaft High-tack adhesive, method of its preparation and the use thereof
US7494707B2 (en) 2003-12-05 2009-02-24 Tesa Aktiengesellschaft High-tack adhesive, method of its preparation and the use thereof
US20090238846A1 (en) * 2004-08-31 2009-09-24 Aspion Co., Ltd. S/O type external preparation
US20080113010A1 (en) * 2004-11-05 2008-05-15 Lead Chemical Co., Ltd. Nonaqueous Preparation for Percutaneous Absorption Containing Nonsteroidal Anti-Inflammatory Analgesic
US8551979B2 (en) * 2004-11-05 2013-10-08 Lead Chemical Co., Ltd. Nonaqueous preparation for percutaneous absorption containing nonsteroidal anti-inflammatory analgesic
US20060165764A1 (en) * 2005-01-26 2006-07-27 Akinori Hanatani Tape preparation
US20090028806A1 (en) * 2005-02-25 2009-01-29 Shigeo Suzuki Medicine for External Application Containing Anti-Inflammatory Agent and Soy Lecithin
US20060263420A1 (en) * 2005-03-10 2006-11-23 Hisamitsu Pharmaceutical Co., Inc. Adhesive and plaster
US20100249236A1 (en) * 2005-03-10 2010-09-30 Hisamitsu Pharmaceutical Co., Inc. Adhesive and plaster
US20080292670A1 (en) * 2005-03-10 2008-11-27 Hisamitsu Pharmaceutical Co., Inc. Adhesive and plaster
US20090238860A1 (en) * 2005-08-10 2009-09-24 Hisamitsu Pharmaceutical Co., Inc. Adhesive Patch Less Irritative to Skin
EP1925299A4 (en) * 2005-08-10 2012-02-01 Hisamitsu Pharmaceutical Co ADHESIVE PATTERN WITH LOW SKIN IRRITATION
US20110003893A1 (en) * 2007-12-12 2011-01-06 Teikoku Seiyaku Co., Ltd. Aqueous loxoprofen-containing patches
US10098858B2 (en) * 2007-12-12 2018-10-16 Teikoku Seiyaku Co., Ltd. Aqueous loxoprofen-containing patches
US9833417B2 (en) 2010-11-02 2017-12-05 Teikoku Seiyaku Co., Ltd. Felbinac-containing external patch
US20190240167A1 (en) * 2016-10-18 2019-08-08 Lts Lohmann Therapie-Systeme Ag Two-layer topical therapeutic system
US12178922B2 (en) 2016-12-28 2024-12-31 Hisamitsu Pharmaceutical Co., Inc. Patch with DMSO in adhesive layer
US11872320B2 (en) 2021-02-25 2024-01-16 Hisamitsu Pharmaceutical Co., Inc. Method for treating osteoarthritis

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ATE517614T1 (de) 2011-08-15
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CN1200696C (zh) 2005-05-11
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EP1277466B1 (en) 2011-07-27
US20090258952A1 (en) 2009-10-15
ES2367541T3 (es) 2011-11-04
CA2406261C (en) 2010-12-07
WO2001078690A1 (en) 2001-10-25
US8173156B2 (en) 2012-05-08
KR100600456B1 (ko) 2006-07-13
PT1277466E (pt) 2011-09-01
TWI283587B (en) 2007-07-11
CA2406261A1 (en) 2002-10-17

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