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WO1999062557A1 - Composition destinee a une administration transdermique de medicaments anti-inflammatoires non steroidiens - Google Patents

Composition destinee a une administration transdermique de medicaments anti-inflammatoires non steroidiens Download PDF

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Publication number
WO1999062557A1
WO1999062557A1 PCT/KR1999/000272 KR9900272W WO9962557A1 WO 1999062557 A1 WO1999062557 A1 WO 1999062557A1 KR 9900272 W KR9900272 W KR 9900272W WO 9962557 A1 WO9962557 A1 WO 9962557A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
drug
diethylene glycol
steroidal anti
ranges
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/KR1999/000272
Other languages
English (en)
Inventor
Je Phil Ryoo
Mi Suk Choi
Jong Kun Choi
Cheol Moon
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.)
LG Corp
Original Assignee
LG Chemical Co 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 LG Chemical Co Ltd filed Critical LG Chemical Co Ltd
Priority to AU41702/99A priority Critical patent/AU4170299A/en
Priority to JP2000551811A priority patent/JP2002516879A/ja
Publication of WO1999062557A1 publication Critical patent/WO1999062557A1/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
    • A61K9/70—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
    • A61K9/7061—Polyacrylates
    • 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
    • A61K9/7084—Transdermal patches having a drug layer or reservoir, and one or more separate drug-free skin-adhesive layers, e.g. between drug reservoir and skin, or surrounding the drug reservoir; Liquid-filled reservoir patches
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the present invention relates to a composition for the transdermal administration of non-steroidal anti- inflammatory drugs, wherein a mixture of a diethylene glycol ether and a sorbitan ester is used as an absorption promoter; and to a transdermal formulation containing same.
  • transdermal drug administration alleviates the aforementioned problems and delivers a drug at a controlled rate for an extended period of prescribed time due to increased bioavailability of the drug which is degraded in the digestive tract.
  • Diethyleneglycol monoethyl ether which has been used as a solubilizer in the formulation of naproxen, nitroglycerin, phenylbutazone and prazepam, was also reported to be effective as an absorption promoter in the transdermal administration of theophylline and prostaglandin E2 (Touitou, et al . , International Journal of Pharmaceutics, 70, 159-166(1991); and Watkinson, A. et al . , ibid, 74, 229- 236(1991) ) .
  • absorption promoters disclosed in the prior art include: a mixture of linoleic acid and propyleneglycol (European Patent Publication No. 261429) ; and mixtures of N-
  • U.S. Patent No. 5,527,832 discloses a gel-type composition
  • 5,505,956 describes a multi-layered patch formulation wherein the-water containing capacities of resins included in the layes increase from the skin-faced layer to the upper layer; and U.S. Patent No. 5,656,286 teaches a simple matrix type patch using polyacrylate as an adhesive matrix.
  • the conventional transdermal formulations may be divided into three types: a reservoir type, a simple matrix type and a multi-layer lamination type.
  • the simple matrix type formulation as disclosed in U.S. Patent Nos. 4,314,577; 4,438,139; and 4,839,174, comprises a drug dispersed in a layer made of a pressure-sensitive adhesive matrix.
  • Such formulation can be produced at a low cost by a simple process.
  • it has the problem that the rate of drug release is high in the initial stage and tapers off sharply thereafter.
  • a diethylene glycol monoalkyl ether and a sorbitan ester each of which has been individually known as an absorption promoter having a limited effectiveness, provide a synergistic effect when combined, i.e., a mixture of a diethylene glycol ether and a sorbitan ester has been found to be a remarkably efficient absorption promoter for the transdermal transport of non-steroidal anti-inflammatory drugs.
  • an object of the present invention to provide an improved composition for the transdermal administration of a non-steroidal anti-inflammatory drug. It is another object of the present invention to provide a transdermal formulation comprising said composition.
  • compositions for the transdermal administration of a non-steroidal anti -inflammatory drug comprising: a therapeutically effective amount of the drug; an absorption promoter consisting essentially of a diethylene glycol ether and a sorbitan ester; and a pharmaceutically acceptable adhesive matrix.
  • Fig. 1 shows a schematic cross-sectional view of an embodiment of the inventive pharmaceutical formulation for the transdermal delivery of a non-steroidal anti- inflammatory drug
  • Fig. 2 represents the time-dependent changes in the cumulative amounts of ketoprofen transported across human cadaver skin as a function of absorption promoter used
  • Fig. 3 compares the time-dependent changes in the cumulative amounts of ketoprofen transported across human cadaver skin in the experiments employing the inventive formulation and commercially available formulations.
  • the present invention provides a composition for the transdermal administration of a non-steroidal anti- inflammatory drug, comprising: the non-steroidal anti- inflammatory drug; a mixture of diethylene glycol ether and sorbitan ester, as an absorption promoter; and a pharmaceutically acceptable adhesive matrix.
  • the total amount of the non-steroidal anti-inflammatory drug used in the inventive composition may range from 0.1 to 50 wt%, preferably, from 1 to 20 wt% based on the total weight of the composition.
  • the absorption promoter of the present invention is composed of a diethylene glycol monoalkyl ether and a sorbitan ester mixed in a weight ratio ranging from 1:4 to 4:1, preferably, from 1:2 to 2:1.
  • Diethyleneglycol monoalkyl ethers which may be suitably used in the present invention include diethylene glycol monoethyl ether and diethylene glycol monomethyl ether, and suitable sorbitan esters include sorbitan monolaurate and sorbitan monooleate .
  • the total amount of the mixture of diethylene glycol ether and sorbitan ester used in the inventive composition may range from 5 to 30 wt%, preferably, from 5 to 25 wt% based on the total weight of the composition, wherein the weight ratio of said two components is kept within the aforementioned range.
  • the pharmaceutically acceptable adhesive matrix used in the present ⁇ invention may be any of those known in the art, e.g., polyacrylate adhesives such as ethyl-, butyl- and 2- ethylhexyl acrylate, polyisobutylene and silicon rubber.
  • composition of the present invention may further comprise flavoring agents, preservatives, anti-oxidants, stabilizers and pigments.
  • the transdermal formulation of a non-steroidal anti- inflammatory drug in accordance with another aspect of the present invention may be constructed using: a protective backing layer which is impermeable to the non-steroidal anti -inflammatory drug; a drug reservoir layer containing the aforementioned composition of the present invention, one side of which is laminated on the protective backing layer; and a peel layer attached to the other side of the drug reservoir layer, said peel layer being capable of protecting the composition from the environment until it is removed to bring the drug reservoir layer into contact with the skin.
  • the formulation of the present invention may further comprise a supplementary adhesive layer which is selected from those known in the art, e.g., a ring-shaped adhesive layer sealably attached to the periphery of the drug reservoir layer and the protective backing layer.
  • Fig. 1 shows a schematic cross-sectional view of an embodiment of the transdermal formulation of the present invention, which comprises peel layer (1), drug reservoir layer(2), protective backing layer(3) and supplementary adhesive layer(4).
  • the transdermal formulation of the present invention may be in the form of patches, plasters, pastes, cataplasms, gels, ointments and the like, which can be applied to the skin for a desired time period to achieve a desired blood level of non-steroidal anti-inflammatory drugs.
  • the inventive composition for the transdermal delivery of a non-steroidal anti-inflammatory drug has advantages in that : it is a simple matrix-type which can be prepared at a low cost; the use of the improved absorption promoter disclosed above makes it possible to maintain a high flux of the drug for an extended period, the apparent drug permeation rate following zero-order kinetics; and the formation of drug crystals is inhibited even at a high drug loading level owing to the use of said improved absorption promoter.
  • the dosage administered to a patient by using the composition of the present invention can be controlled by adjusting the contents of the drug and the absorption promoter.
  • the flux, or the skin permeation rate, of a drug through a skin sample was determined by the following procedure .
  • a skin sample either human cadaver skin or a skin piece excised from 6 week-old female hairless mouse, was installed in Valia-Chien diffusion cell (Crown Glass, U.S.A.) such that the stratum corneum of the skin faced outward from the cell, and then a transdermal formulation containing one or more drugs was fixed on the skin.
  • 3.4 m£ of physiological saline solution containing 40% of polyethyleneglycol 400 (Sigma Scientific Co.) was added to the cell and stirred for the whole period of experiment. Thereafter, lOO ⁇ l samples of the physiological saline solution were taken periodically and subjected to high performance liquid chromatography to determine the cumulative amount of the drug transported across the skin.
  • the skin permeation rate ( ⁇ g/cm 2 /hr) of the drug through the skin was calculated by regression analysis of the time- dependent cumulative amounts of the drug.
  • ketoprofen (KF) and an absorption promoter listed in Table 1 were added to a polyacrylate adhesive (Durotac 87-2074, National Starch Chem. Co.), and then the mixture was stirred sufficiently to dissolve the drugs in the adhesive.
  • the mixture thus obtained was poured onto an impermeable protective backing layer (Scotchpak 1109, 3M Co.) to coat a matrix layer having a thickness of lOOO ⁇ m.
  • the resulting material consisting of the protective backing layer coated with the matrix layer was dried in an oven by raising the temperature stepwise from 60°C to 120°C.
  • the resulting material was cured in open air for 1 hour and a peel layer (Scotchpak 1012, 3M Co.) was laminated thereon.
  • the resulting transdermal formulation was stored at room temperature .
  • Fig. 2 represents the time-dependent changes in the cumulative amounts of ketoprofen transported across human cadaver skin as a function of absorption promoter used.
  • a transdermal delivery composition was prepared and tested by the procedure of Reference Example 1, except that 3.0 wt% of KF was employed together with the absorption promoters listed in Table 2.
  • Ketotop Pacific Pharmaceutical Co., LTD, Korea
  • Kepentec Jeil Pharmaceutical Co., LTD., Korea
  • Fig. 3 compares the time-dependent changes in the cumulative amount of ketoprofen transported across human cadaver skin in the experiments employing the inventive formulation and commercially available formulations.
  • the inventive composition containing a mixture of diethylene glycol monoethyl ether (TC) and sorbitan monolaurate (SML) (Example 1) as the absorption promoter exhibits higher permeation rate than those of Comparative Examples 1 and 2 by a factor of 2 to 4.
  • transdermal delivery compositions were prepared and tested by the procedure of Reference Example 1, except that 3.0 wt% of ibuprofen was employed together with the absorption promoters listed in Table 3.
  • transdermal delivery compositions were prepared and tested by the procedure of Reference Example 1, except that 3.0 wt% of diclofenac was employed together with the absorption promoters listed in Table 5.

Landscapes

  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cette composition, destinée à une administration transdermique d'un médicament anti-inflammatoire non stéroïdien, contient une dose de médicament, efficace sur le plan thérapeutique, un promoteur d'absorption se composant essentiellement d'éther de diéthylèneglycol et d'un ester de sorbitane, ainsi qu'un support adhésif, acceptable sur le plan pharmacologique.
PCT/KR1999/000272 1998-06-02 1999-06-02 Composition destinee a une administration transdermique de medicaments anti-inflammatoires non steroidiens Ceased WO1999062557A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU41702/99A AU4170299A (en) 1998-06-02 1999-06-02 Composition for the transdermal administration of non-steroidal anti-inflammatory drugs
JP2000551811A JP2002516879A (ja) 1998-06-02 1999-06-02 非ステロイド性消炎鎮痛剤の経皮投与用組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1019980020378A KR100294084B1 (ko) 1998-06-02 1998-06-02 비-스테로이드성소염진통제의경피흡수투여용조성물및이를포함하는경피흡수투여용제형
KR1998/20378 1998-06-02

Publications (1)

Publication Number Publication Date
WO1999062557A1 true WO1999062557A1 (fr) 1999-12-09

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Application Number Title Priority Date Filing Date
PCT/KR1999/000272 Ceased WO1999062557A1 (fr) 1998-06-02 1999-06-02 Composition destinee a une administration transdermique de medicaments anti-inflammatoires non steroidiens

Country Status (5)

Country Link
JP (1) JP2002516879A (fr)
KR (1) KR100294084B1 (fr)
CN (1) CN1304321A (fr)
AU (1) AU4170299A (fr)
WO (1) WO1999062557A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10032537A1 (de) * 2000-07-05 2002-01-31 Labtec Gmbh Dermales System, enthaltend 2-(3-Benzophenyl)Propionsäure
DE10049225A1 (de) * 2000-09-28 2002-04-11 Labtec Gmbh Dermales System, enthaltend Diclofenac
TR201009220A1 (tr) * 2010-11-08 2012-05-21 Sanovel �La� San. Ve T�C. A.�. Flurbiprofen ve metil salisilat topikal farmasötik bileşimleri.
CN102970986A (zh) * 2010-05-27 2013-03-13 艾毕赛斯公司 含有吡罗昔康的骨架型贴剂以及局部治疗急性和慢性疼痛及其相关炎症的方法
US9492420B2 (en) 2010-12-15 2016-11-15 Olatec Therapeutics Llc 3-methanesulfonylpropionitrile for treating inflammation and pain
CN114191416A (zh) * 2021-12-27 2022-03-18 河南省超亚医药器械有限公司 一种非甾体抗炎药透皮给药系统及其制备工艺

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020037616A (ko) * 2000-11-15 2002-05-22 서경배 케토롤락의 경피흡수제제
JP4969050B2 (ja) * 2005-01-07 2012-07-04 ロート製薬株式会社 皮膚外用剤
CN103948571A (zh) * 2006-07-18 2014-07-30 天津昕晨泰飞尔医药科技有限公司 具有快速皮肤穿透率的带正电荷的水溶性布洛芬前药
EP2854784B1 (fr) * 2012-06-05 2019-12-04 Olatec Therapeutics LLC Méthode de traitement de maladies inflammatoires de la peau
KR101882679B1 (ko) * 2017-08-11 2018-07-27 이태완 저자극성 진통소염용 경피제제 및 이의 제조방법
WO2024125322A1 (fr) * 2022-12-16 2024-06-20 智泽童康(广州)生物科技有限公司 Dipyridamole pour prévenir et traiter des maladies allergiques et/ou inflammatoires et sa préparation

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990011064A1 (fr) * 1989-03-22 1990-10-04 Cygnus Research Corporation Compositions ameliorant la penetration a travers la peau
WO1993018752A1 (fr) * 1992-03-26 1993-09-30 Pharmos Corp. Systeme d'apport topique et transdermique utilisant des spheres d'huile aux dimensions de l'ordre du sous-micron
WO1993023083A1 (fr) * 1992-05-11 1993-11-25 Agouron Pharmaceuticals, Inc. Formulations anhydres permettant d'administrer des agents lipophiles
WO1994023713A1 (fr) * 1993-04-22 1994-10-27 Minnesota Mining And Manufacturing Company Composition transdermique anti-inflammatoire
WO1998032465A1 (fr) * 1997-01-27 1998-07-30 Lg Chemical Limited Composition pour l'administration transdermique de medicaments steroides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990011064A1 (fr) * 1989-03-22 1990-10-04 Cygnus Research Corporation Compositions ameliorant la penetration a travers la peau
WO1993018752A1 (fr) * 1992-03-26 1993-09-30 Pharmos Corp. Systeme d'apport topique et transdermique utilisant des spheres d'huile aux dimensions de l'ordre du sous-micron
WO1993023083A1 (fr) * 1992-05-11 1993-11-25 Agouron Pharmaceuticals, Inc. Formulations anhydres permettant d'administrer des agents lipophiles
WO1994023713A1 (fr) * 1993-04-22 1994-10-27 Minnesota Mining And Manufacturing Company Composition transdermique anti-inflammatoire
WO1998032465A1 (fr) * 1997-01-27 1998-07-30 Lg Chemical Limited Composition pour l'administration transdermique de medicaments steroides

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10032537A1 (de) * 2000-07-05 2002-01-31 Labtec Gmbh Dermales System, enthaltend 2-(3-Benzophenyl)Propionsäure
DE10049225A1 (de) * 2000-09-28 2002-04-11 Labtec Gmbh Dermales System, enthaltend Diclofenac
CN102970986A (zh) * 2010-05-27 2013-03-13 艾毕赛斯公司 含有吡罗昔康的骨架型贴剂以及局部治疗急性和慢性疼痛及其相关炎症的方法
CN102970986B (zh) * 2010-05-27 2015-06-03 南京前沿生物技术有限公司 含有吡罗昔康的骨架型贴剂以及局部治疗急性和慢性疼痛及其相关炎症的方法
TR201009220A1 (tr) * 2010-11-08 2012-05-21 Sanovel �La� San. Ve T�C. A.�. Flurbiprofen ve metil salisilat topikal farmasötik bileşimleri.
EP2455074A1 (fr) * 2010-11-08 2012-05-23 Sanovel Ilac Sanayi ve Ticaret A.S. Compositions pharmaceutiques locales de flurbiprofène et salicylate de méthyle
US9492420B2 (en) 2010-12-15 2016-11-15 Olatec Therapeutics Llc 3-methanesulfonylpropionitrile for treating inflammation and pain
US9770428B2 (en) 2010-12-15 2017-09-26 Olatec Therapeutics Llc 3-methanesulfonylpropionitrile for treating inflammation and pain
US10080735B2 (en) 2010-12-15 2018-09-25 Olatec Therapeutics Llc 3-methanesulfonylpropionitrile for treating inflammation and/or pain
US10500184B2 (en) 2010-12-15 2019-12-10 Olatec Therapeutics Llc 3-methanesulfonylpropionitrile for treating inflammation and/or pain
CN114191416A (zh) * 2021-12-27 2022-03-18 河南省超亚医药器械有限公司 一种非甾体抗炎药透皮给药系统及其制备工艺
CN114191416B (zh) * 2021-12-27 2023-09-15 河南省超亚医药器械有限公司 一种非甾体抗炎药透皮给药系统及其制备工艺

Also Published As

Publication number Publication date
KR20000000640A (ko) 2000-01-15
JP2002516879A (ja) 2002-06-11
AU4170299A (en) 1999-12-20
CN1304321A (zh) 2001-07-18
KR100294084B1 (ko) 2001-09-22

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