WO1995030411A1 - Systeme d'administration de medicaments par voie transdermique, possedant des reseaux polymeres ioniques - Google Patents

Systeme d'administration de medicaments par voie transdermique, possedant des reseaux polymeres ioniques Download PDF

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Publication number
WO1995030411A1
WO1995030411A1 PCT/KR1995/000051 KR9500051W WO9530411A1 WO 1995030411 A1 WO1995030411 A1 WO 1995030411A1 KR 9500051 W KR9500051 W KR 9500051W WO 9530411 A1 WO9530411 A1 WO 9530411A1
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WO
WIPO (PCT)
Prior art keywords
polymer
drug delivery
delivery system
transdermal drug
polyelectrolyte
Prior art date
Application number
PCT/KR1995/000051
Other languages
English (en)
Inventor
Soon Hong Yuk
Hai Bang Lee
Sun Hang Cho
Original Assignee
Korea Research Institute Of Chemical Technology
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 Korea Research Institute Of Chemical Technology filed Critical Korea Research Institute Of Chemical Technology
Priority to JP7528850A priority Critical patent/JPH09506110A/ja
Priority to EP95918203A priority patent/EP0719135A1/fr
Publication of WO1995030411A1 publication Critical patent/WO1995030411A1/fr

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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
    • A61K9/7084—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

Definitions

  • the present invention relates to transdermal drug delivery system, and more particulary, to the transdermal drug delivery system using ionic polymer (polyelectrolyte) networks.
  • transdermal delivery system a number of transdermal delivery system have been described. They may be classified broadly into three general categories.
  • Transdermal drug delivery system is composed of a drug reservoir in the form of a suspension of drug in a liquid medium. This is encapsulated a compartment surrounded in an impermeable laminate. This compartment is enclosed by a permeation-controlling polymeric membrane.
  • Transdermal drug delivery system of this type which have been described, include Transderm Scop., Transderm Nitro and Estraderm, which are available commercially from Ciba Geigy Corporation (Drug Dev. Ind. Pharm.. 9,627,1983; Am. Heart J.. 108, 217, 1984; U.S. Pat. No. 4,397,454; U.S. Pat. No. 4,618,584).
  • Transdermal drug delivery system is matrix diffusion controlled transdermal drug delivery system.
  • the matrix is manufactured by homogeneously dispersing the drug in a polymer matrix which is then molded into a disc with defined surface area and thickness.
  • Transdermal drug delivery system of this type which have been described include Nitrodur and Nitrodur II systems, which are available commercially from KEY/SCHERING-PLOUGH corporation.
  • the matrix diffusion controlled transdermal drug delivery system is disclosed in EP patent application No. 91 306 457.2 of Chatfield Pharmaceutical Company.
  • this system has the disadvantage that the amount of ionizable drug loading into sodium alginate matrix is limited because sodium alginate used in the present invention has low concentration of ionic group.
  • the microsealed category is represented by the Nitro-Disc device which is available from SEAR E Corporation.
  • the reservoir is formed by dispersing nitroglycerin absorbed to lactose in a hydrophilic solvent, which is subsequently distribute in a silicone elastomer by mechanical force to form thousands of microscopic drug compartment.
  • the drug loading amount can be easily controlled by changing the composition of polyelectrolyte gel.
  • the present invention provides a transdermal drug delivery system comprising a polyelectrolyte gel matrix composed of two chemically independent polymers resulting in interpenetrating networks (IPNs) .
  • IPPNs interpenetrating networks
  • the present invention also provides a process for preparing transdermal drug delivery system comprising the steps of dissolving an ionic polymer (polyelectrolyte) in the water to prepare a first solution, dissolving a polymer in the water to prepare a second solution mixing said first solution and said second solution to form a polymer solution mixture, the coagulation of polymer solution mixture to form a solidified polyelectrolyte gel matrix having interpenetrating networks, and immersing said polyelectrolyte gel matrix into drug solution.
  • an ionic polymer polyelectrolyte
  • the present inventors developed polymer matrix with the maximum ionic concentration using the concept of IPNs, and applied to transdermal drug delivery system to solve the problems of conventional matrix diffusion controlled transdermal drug delivery system.
  • transdermal drug delivery system of the present invention drug is ionized at specific pH condition and it is loaded into polyelectrolyte gel matrix in the form of ionic bond.
  • drug delivery system of the present invention uses the concept of matrix diffusion controlled transdermal drug delivery system, it is an advanced form of transdermal drug delivery system where drug is dispersed in polymer matrix with the form of ionic bond.
  • FIG. 1 is a schematic representation of gelation mechanism of sodium alginate
  • FIG. 2 is a schematic representation of IPNs structure of polysaccharide and polyacrylic acid
  • FIG. 3 is a schematic cross-sectional view of one embodiment of the transdermal drug delivery systems according to the present invention.
  • FIG. 4 is a schematic view of the apparatus for measuring * the drug release from transdermal drug delivery system
  • FIG.5 shows the drug release from the transdermal drug delivery system containing sodium alginate/polyacrylic acid
  • FIG. 6 shows the drug release from the transdermal drug delivery system containing acylamide/polyacrylic acid.
  • FIG. 7 shows the drug release from the transdermal drug delivery system containing agar/polyaerylie acid.
  • a transdermal drug delivery system comprises a polyelectrolyte gel matrix having interpenetrating networks and an ionizable drug ionically bonded to the ionic functional group of polyelectrolyte
  • the polyelectrolyte gel matrix comprises a polymer having a cosolvent where polymer or monomer is capable of dissolving together with polyelectrolyte to increase the concentration of ionic group.
  • the polymer of the present invention is one or the mixture selected from the group consisting of polysaccharide, acrylic polymer and methacrylic polymer.
  • the polysaccharide is preferably one or the mixture selected from the group consisting of sodium alginate, pectin, Xanthomonas campestris, agar and carboxymethyl cellulose.
  • the acrylic polymer may be' one or the mixture selected from the group consisting of acrylamide, isopropyl acrylamide and their derivatives.
  • the methacrylic polymer is one or the mixture selected from the group consisting of methyl methacrylate, ethoxy methacrylate, methoxyethoxyethyl methacrylate, aminoethyl methacrylate and diethylaminoethyl methacrylate.
  • polyelectrolyte is one or the mixture selected from the group consisting of polyacrylic acid, polyamino acid, polysulfonic acid and polyethylamine.
  • the mixing ratio of the polymer having a cosolvent where polymer or monomer are capable of dissolving together with polyelectrolyte to polyelectrolyte is 100
  • the polyelectrolyte gel matrix may further comprises initiator and/or cross-linking agent.
  • transdermal drug delivery system of the present invention The process for preparing transdermal drug delivery system of the present invention is described below.
  • Aqueous polymer solution is prepared from sodium alginate which is a representative example of polysaccharides
  • aqueous polyelectrolyte solution is prepared from polyacrylic acid which is a representative example of polyelectrolyte.
  • the polymer solution mixtures are prepared by mixing two above solutions, followed by coagulation of the polymer solution mixture with the addition of CaCl 2 solution.
  • sodium alginate forms a gel matrix as illustrated in Fig. 1, and polyacrylic acid entangles through the coagulated sodium alginate to form IPNs (Interpenetrating Networks) as shown in Fig. 2.
  • Polyelectrolyte gel matrix can be prepared in the form of paper type, bead type, or linear type in accordance with the coagulation condition.
  • Various polyelectrolyte gels can be prepared based on the IPNs concepts. Firstly, a monomer solution is prepared using acrylamide, and a polyelectrolyte solution is prepared from polyacrylic acid as a polyelectrolyte. The prepared two solutions are mixed at a prescribed ratio and an appropriate amount of initiator and cross-linking agents are added and then ultraviolet ray is irradiated for the polymerization. Then, acrylamide forms a crosslinked gel network and polyacrylic acid entangles through crosslinked gel networks resulting in IPNs. The role of acrylamide is to provide a crosslinked gel networks and that of polyacrylic acid is to increase the ion concentration in gel networks.
  • Agar instead of sodium alginate, can be used to prepare polyelectrolyte gel matrix by mixing agar and water, followed by adding polyacrylic acid as an polyelectrolyte at a prescribed mixing ratio.
  • the polymer solution mixture is heated to 80 "C to dissolve the reactants completely, and is cooled to room temperature to coagulate the polymer solution mixture.
  • agar forms a crosslinked gel networks and polyacylic acid entangles through crosslinked gel network resulting in IPNs.
  • the role of agar is to provide a crosslinked gel networks and that of polyacrylic acid is to increase the ion concentration in gel networks.
  • the polyelectrolyte gel matrix prepared by the methods described above is immersed into nicotine solution as model drug to form ionic bond between nicotine and carboxyl group of polyelectrolyte gel at pH 4 - 5. Then, nicotine-loaded gel is prepared within a short time, which can be used as matrix for the transdermal drug delivery system as shown in Fig. 3.
  • the transdermal drug delivery system of the present invention is an advanced form of drug delivery system which has the additional advantage of controlling the drug release rate by ionic bond between the ionic functional group in polyelectrolyte gel matrix and drug, as well as the diffusion of in the gel matrix.
  • the drug delivery system of the present invention has a strong advantage of controlling the drug loading amount and the drug release rate because the system of the present invention has higher concentration of ionic group than that of EP patent application of 91 306 457.2 mentioned above.
  • aqueous polymer solution was prepared from sodium alginate selected as polysaccharide and -2 wt % aqueous polymer solution was prepared from polyacrylic acid selected as polyacrylic acid.
  • Two prepared aqueous polymer solutions were mixed with the ratio of 50 : 50 by weight to prepare aqueous polymer mixture solution, which was cast on glass plate with gadner film knife in thickness of 3 mm, and it was added to calcium chloride, and then it was coagulated in the form of paper.
  • the disc-type polyelectrolyte gel matrix was obtained using a punch of 1 cm radius and immersed into nicotine solution to form ionic bond between carboxylic group of polyelectrolyte gel and nicotine at pH 4 - 5. After 12 hours, nicotine-leaded gel matrix was obtained.
  • the nicotine release experiment was performed using diffusion cell as illustrated in Fig. 4. Phosphate buffer solution was used in the receiving compartment.
  • EXAMPLE 2 2 g of acrylamide, instead of sodium alginate used in EXAMPLE 1, was added to 100 g of water to prepare aqueous monomer solution, and 2 g of polyacrylic acid as polyelectrolyte was mixed with 100 g of water to prepare aqueous polyelectrolyte solution. Two obtained aqueous solutions were mixed with the ratio of 50 : 50 by weight to prepare aqueous polymer solution mixture solution, and 0.1 g of N,N'-methylene bisacrylamide as cross- linking agent and ammonium persulfate as polymerization initiator was added, and then UV was irradiated for 15 minutes.
  • acrylamide was polymerized to polymer gel, polyacrylic acid entangled through the crosslinked gel networks resulting in IPNs.
  • the disc ⁇ type polyelectrolyte gel matrix was obtained using a punch of 1 cm radius and immersed into nicotine solution to form ionic bond between carboxylic group of polyelectrolyte gel and nicotine at pH 4 - 5. After 12 hours, nicotine-leaded gel matrix was obtained. The nicotine release experiment was performed using diffusion cell as illustrated in Fig. 4. Phosphate buffer solution was used in the receiving compartment.
  • agar instead of sodium alginate used in EXAMPLE 1, was added to 100 g of water to prepare aqueous polymer solution, and 2 g of polyacrylic acid as polyelectrolyte was mixed with 100 g of water to prepare aqueous polyelectrolyte solution.
  • Two obtained aqueous solutions were mixed with the ratio of 50 : 50 by weight to prepare aqueous polymer solution mixture solution, and it was heated at 80 "C to dissolve the mixed materials completely, and then cooled at room temperature to solidify agar.
  • the coagulated agar formed crosslinked gel networks, and polyacrylic acid entangled through the crosslinked gel network resulting in IPNs.
  • the disc-type polyelectrolyte gel matrix was obtained using a punch of 1 cm radius and immersed into nicotine solution to form ionic bond between carboxylic group of polyelectrolyte gel and nicotine at pH 4 - 5. After 12 hours, nicotine-leaded gel matrix was obtained. The nicotine release experiment was performed using diffusion cell as illustrated in Fig. 4. Phosphate buffer solution was used in the receiving compartment.
  • the experiment was performed by the same method as that of EXAMPLE 1 except that the polyelectrolyte was not used.
  • the experiment was performed by the same method as that of EXAMPLE 2 except that the polyelectrolyte was not used.
  • the experiment was performed by the same method as that of EXAMPLE 3 except that the polyelectrolyte was not used.
  • FIG. 5 shows release experiment using nicotine- loaded polymer matrices obtained in the above EXAMPLE 1 and COMPARATIVE EXAMPLE 1.
  • High loading of nicotine could be accomplished using IPNs composite composed of sodium alginate and polyacylic acid which was prepared according to EXAMPLE 1.
  • This system showed excellent loading efficiency comparing with the matrix prepared by sodium alginate only according to COMPARATIVE EXAMPLE 1 as described in European Patent Application No. 91306457.2.
  • the precisely regulated drug release could be achieved by the polymer matrix of EXAMPLE 1. This was because the drug release could be controlled by the dissociated of ionic bond between gel matrix and drug as well as the diffusion of drug in the matrix.
  • FIG. 6 shows the release experiment using nicotine- loaded polymer matrices obtained in the above EXAMPLE 2 and COMPARATIVE EXAMPLE 2. High loading of nicotine could be accomplished using IPNs composite composed of acrylamide and polyacrylic acid which was prepared according to EXAMPLE 2.
  • This system showed excellent loading efficiency comparing with the matrix prepared by acrylamide only according to COMPARATIVE EXAMPLE 2.
  • the precisely regulated drug release * could be achieved by the polymer matrix of EXAMPLE 2. This was because drug release could be controlled by the dissociation of ionic bond between gel matrix and drug as well as the diffusion of drug in the matrix.
  • FIG. 7 shows the release experiment using nicotine- loaded polymer matrices obtained in the above EXAMPLE 3 and COMPARATIVE EXAMPLE 3.
  • High loading of nicotine could be accomplished using IPNs composite composed of agar and polyacylic acid which was prepared according to EXAMPLE 3.
  • This system showed excellent loading efficiency comparing with the matrix prepared by agar only according to COMPARATIVE EXAMPLE 3.
  • the precisely regulated drug release could be achieved by the polymer matrix of EXAMPLE 3. This was because the drug release could be controlled by the dissociation ionic bond between gel matrix and drug as well as the diffusion of drug in the matrix.

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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Abstract

Système d'administration de médicaments par voie transdermique, préparé par utilisation d'une matrice de gel polyélectrolytique à concentration ionique maximale suivant le concept des réseaux interconnectés (IPN), et par chargement d'un médicament ionisable dans la matrice de gel polyélectrolytique par liaison ionique. Il s'agit d'un système perfectionné d'administration de médicaments par voie transdermique dans lequel la quantité chargée est maximisée grâce à l'augmentation du groupe fonctionnel ionique dans la matrice de gel polyélectrolytique, et le taux de libération du médicament est régulé par la dissociation de la liaison ionique entre le groupe fonctionnel ionique de la matrice de gel polyélectrolytique et le médicament ionisable, ainsi que par la diffusion du médicament dans la matrice.
PCT/KR1995/000051 1994-05-09 1995-05-09 Systeme d'administration de medicaments par voie transdermique, possedant des reseaux polymeres ioniques WO1995030411A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP7528850A JPH09506110A (ja) 1994-05-09 1995-05-09 イオン性高分子ネットワークを持つ皮膚薬物伝達体系
EP95918203A EP0719135A1 (fr) 1994-05-09 1995-05-09 Systeme d'administration de medicaments par voie transdermique, possedant des reseaux polymeres ioniques

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KR1019940010116A KR0121127B1 (ko) 1994-05-09 1994-05-09 이온성 고분자 네트웍을 갖는 피부약물전달체계
KR1994/10116 1994-05-09

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000021572A2 (fr) * 1998-10-09 2000-04-20 The University Of Michigan Hydrogels et supports polymeres solubles dans l'eau pour administration de medicaments
JP2000505430A (ja) * 1996-02-09 2000-05-09 メイヨー・ファウンデーション・フォー・メディカル・エデュケーション・アンド・リサーチ ニコチンの結腸送達による炎症性腸疾患の治療
WO2001037660A1 (fr) * 1999-11-19 2001-05-31 Nof Corporation Preparation du type dispersion aqueuse a liberation prolongee, et procede de production correspondant
EP1327442A1 (fr) * 2000-10-16 2003-07-16 Sekisui Kaseihin Kogyo Kabushiki Kaisha Technique de production de feuille de gel pour application a un corps vivant, feuille de gel pour application a un corps vivant obtenue par cette technique de production, et procede de soins de la peau a l'aide de cette feuille de gel
WO2004058211A1 (fr) * 2002-12-23 2004-07-15 Beiersdorf Ag Matrice polymere autocollante contenant un extrait de sel marin
JP2007176945A (ja) * 1997-05-02 2007-07-12 Kobo Products Inc 局所的に施される活性剤用の日焼け止め組成物
EP1938809A1 (fr) * 2005-09-20 2008-07-02 Hisamitsu Pharmaceutical Co., Inc. Patch adhésif sur la peau
EP1579854B1 (fr) * 2004-03-10 2011-08-03 Acino AG Système thérapeutique dermal ou transdermal comprénant une matrice constituée par un matériau recroissant
US7993654B2 (en) 2002-12-23 2011-08-09 Beiersdorf Ag Self-adhesive polymer matrix containing sea algae extract
WO2021127097A3 (fr) * 2019-12-19 2021-09-10 Juul Labs, Inc. Compositions de gel de nicotine à base organique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ302789B6 (cs) 2009-11-25 2011-11-09 Zentiva, K. S. Zpusob zvýšení rozpustnosti farmaceuticky aktivních látek a cílený (kontrolovaný) transport do streva

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EP0562445A2 (fr) * 1992-03-25 1993-09-29 MEDPROJECT PHARMA-ENTWICKLUNGS- UND VERTRIEBSGESELLSCHAFT mbH Gel opththalmique
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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000505430A (ja) * 1996-02-09 2000-05-09 メイヨー・ファウンデーション・フォー・メディカル・エデュケーション・アンド・リサーチ ニコチンの結腸送達による炎症性腸疾患の治療
JP2007176945A (ja) * 1997-05-02 2007-07-12 Kobo Products Inc 局所的に施される活性剤用の日焼け止め組成物
US7186413B2 (en) 1998-10-09 2007-03-06 The Regents Of The University Of Michigan Hydrogels and water soluble polymeric carriers for drug delivery
WO2000021572A3 (fr) * 1998-10-09 2000-11-30 Univ Michigan Hydrogels et supports polymeres solubles dans l'eau pour administration de medicaments
WO2000021572A2 (fr) * 1998-10-09 2000-04-20 The University Of Michigan Hydrogels et supports polymeres solubles dans l'eau pour administration de medicaments
WO2001037660A1 (fr) * 1999-11-19 2001-05-31 Nof Corporation Preparation du type dispersion aqueuse a liberation prolongee, et procede de production correspondant
EP1327442A1 (fr) * 2000-10-16 2003-07-16 Sekisui Kaseihin Kogyo Kabushiki Kaisha Technique de production de feuille de gel pour application a un corps vivant, feuille de gel pour application a un corps vivant obtenue par cette technique de production, et procede de soins de la peau a l'aide de cette feuille de gel
EP1327442A4 (fr) * 2000-10-16 2006-07-26 Sekisui Plastics Technique de production de feuille de gel pour application a un corps vivant, feuille de gel pour application a un corps vivant obtenue par cette technique de production, et procede de soins de la peau a l'aide de cette feuille de gel
WO2004058211A1 (fr) * 2002-12-23 2004-07-15 Beiersdorf Ag Matrice polymere autocollante contenant un extrait de sel marin
US7820177B2 (en) 2002-12-23 2010-10-26 Beiersdorf Ag Self-adhesive polymer matrix containing a seaweed extract
US7993654B2 (en) 2002-12-23 2011-08-09 Beiersdorf Ag Self-adhesive polymer matrix containing sea algae extract
EP1579854B1 (fr) * 2004-03-10 2011-08-03 Acino AG Système thérapeutique dermal ou transdermal comprénant une matrice constituée par un matériau recroissant
EP1938809A1 (fr) * 2005-09-20 2008-07-02 Hisamitsu Pharmaceutical Co., Inc. Patch adhésif sur la peau
EP1938809A4 (fr) * 2005-09-20 2012-05-16 Hisamitsu Pharmaceutical Co Patch adhésif sur la peau
WO2021127097A3 (fr) * 2019-12-19 2021-09-10 Juul Labs, Inc. Compositions de gel de nicotine à base organique
CN115135175A (zh) * 2019-12-19 2022-09-30 尤尔实验室有限公司 有机基尼古丁凝胶组合物

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KR0121127B1 (ko) 1997-11-13
EP0719135A1 (fr) 1996-07-03
JPH09506110A (ja) 1997-06-17
KR950031053A (ko) 1995-12-18

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