CA1333769C - Adhesive dressing containing a pharmaceutically active ingredient - Google Patents

Adhesive dressing containing a pharmaceutically active ingredient

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Publication number
CA1333769C
CA1333769C CA000576790A CA576790A CA1333769C CA 1333769 C CA1333769 C CA 1333769C CA 000576790 A CA000576790 A CA 000576790A CA 576790 A CA576790 A CA 576790A CA 1333769 C CA1333769 C CA 1333769C
Authority
CA
Canada
Prior art keywords
adhesive layer
adhesive
mineral oil
active ingredient
pharmaceutically active
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.)
Expired - Fee Related
Application number
CA000576790A
Other languages
French (fr)
Inventor
Rodolfo Dominic Cilento
Margaret Ann Frank
Frank Michael Freeman
John Esam Fairbrother
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.)
ER Squibb and Sons LLC
Original Assignee
ER Squibb and Sons LLC
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 ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC
Application granted granted Critical
Publication of CA1333769C publication Critical patent/CA1333769C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • A61K9/7038—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
    • 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
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/44—Medicaments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/58—Adhesives
    • A61L15/585—Mixtures of macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/41—Anti-inflammatory agents, e.g. NSAIDs
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S602/00—Surgery: splint, brace, or bandage
    • Y10S602/90—Method of making bandage structure
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/14—Layer or component removable to expose adhesive
    • Y10T428/1452—Polymer derived only from ethylenically unsaturated monomer

Abstract

A dressing comprising a flexible backing member and a pressure sensitive adhesive layer.
The adhesive layer comprises one or more poly-isobutylenes, elastomers, and one or more moistrue absorbing, moisture transmitting, water soluble and/or water swellable agents. A dispersion of the active ingredient in a medium compatible with the adhesive layer is laminated to the skin contacting surface.

Description

ADHESIVE DRESSINGS CONTAINING A
PHA~'~CEUTICALLY ACTIVE INGREDIENT

This invention is directed to a pressure sensitive, adhesive dressing containing a pharma-ceutically active ingredient and to the method of preparing such dressing. The adhesive layer of the dressing is capable of releasing the active ingredient to the surface of the skin covered by the dressing over a period of time of from several hours to one or more days. The surface of the adhesive layer opposite the skin contacting surface is attached to a flexible backing member.
The adhesive layer comprises a homogeneous blend of one or more polyisobutylenes or mixture of one or more polyisobutylenes and an elastomer such as butyl rubber and/or styrene radial or block type copolymers and one or more moisture absorbing, moisture transmitting, water soluble or water swellable agents.
The adhesive may contain other optional ingredients such as mineral oil, tackifiers, antioxidants, etc.
The pharmaceutically active ingredient is incorporated into the adhesive layer so that it resides at the skin contacting surface and in the strata of the adhesive layer closest to the skin contacting surface. This is accomplished by forming t 333769 a suspension of the active ingredient in a material which is compatible with the composition of the adhesive layer. This suspension is then cast onto a sheet of silicone coated release paper which is then laminated to the skin contacting surface of the adhesive layer.

The pressure sensitive adhesive dressing of this invention consists of an adhesive layer formulated from materials suitable for use on human skin and a flexible backing layer. The adhesive layer must be capable of bonding to the skin for from several hours to several days.
Suitable pressure sensitive adhesive composi-tions for use as the skin contacting adhesive layerof the dressing of this invention are homogeneous blends of one or more polyisobutylenes or mixtures of one or more polyisobutylenes and an elastomer such as butyl rubber, medium or high molecular weight polyisobutylene and/or styrene radial or block type copolymers and one or more moisture absorbing, moisture transmitting, water soluble and/or water swellable agents. The adhesive compo-sitions may contain other optional ingredients such as mineral oil, tackifiers, antioxidants, etc.
The polyisobutylene component of the pressure sensitive adhesive compositions function to provide adhesion to dry body surfaces, i.e., dry tack, and along with the flexible backing layer maintain the structural integrity of the dressing. Preferably, the polyisobutylenes employed are one or more low molecular weight polyisobutylenes having a viscosity average molecular weight of from about 8,700 to about _3_ SA38 11,700 (Staudinger). Such polyisobutylenes are commercially available under the trademark Vistanex from Exxon as grades LM - MS and LM - MH.
The polyisobutylene can be combined with one or more elastomers. These materials function to increase the elasticity, tear resistance, and cohesiveness of the adhesive compositions. Suitable elastomers include butyl rubber which is a copolymer of isobutylene with a minor amount of isoprene having a viscosity average molecular weight of from about 350,000 to about 450,000 (Florey), medium and high molecular weight polyisobutylene such as Vistanex MM L-100 having a viscosity average molecular weight of from about 81,000 to about 99,000 (Staudinger) and styrene radial or block copolymers. Particularly suitable styrene copolymers include styrene-butadiene-styrene (S-B-S) and styrene-isoprene-styrene (S-I-S) block type copolymers both of which are commercially available, for example, from Shell Chemical Co. under their tradename Kraton 1100, 1101, 1102, 1107, etc.
The moisture absorbing, moisture transmitting, water soluble or water swellable agents permit the adhesive compositions to adhere to moist body surfaces, i.e., wet tack. In addition, while not being limited in attempting to explain the mechanism by which the pharmaceutical ingredient is released from the dressing, it is believed that the absorption of moisture from the surface of the skin into the adhesive layer results in a dynamic change in the microenvironment at the adhesive layer-skin inter-face caused by hydration of these agents at the adhesive surface and gradually throughout the entire adhesive layers. This results in the continuous release of the topically active pharmaceutical agent from the adhesive layer. Suitable water * Trade-mark ~'~

1 s~376q ` 4 SA38 soluble agents for incorporation within the adhesive compositions are hydrocolloid gums including sodium carboxymethylcellulose, potassium carboxymethyl-cellulose, pectin, gelatin, guar gum, locust bean gum, gum karaya, xanthan gum, mixed sodium/calcium salts of alginic acid, carrageenan, etc., and mixtures thereof. Suitable water swellable agents include substantially water insoluble cross-linked sodium carboxymethylcellulose such as that commer-cially available under the trademarks AcDiSol orAqualon or that described in U.S. Patent 3,589,364, substantially water insoluble starch-acrylonitrile graft copolymer such as that in U.S. Patent 3,661,815 and that commercially available from Grain Processing Corp. under their Water-Lock trademark, and substantially water insoluble cross-linked dextran such as that commercially available under the trademark Sephadex.
Mineral oil can be included within the adhesive layer both as a component of the pressure sensitive adhesive formulation and, as explained below, as the preferred agent for incorporating or depositing the pharmaceutically active agent at the skin contacting surface and in the strata of the adhesive layer closest to the skin contacting surface.
Tackifiers can also be included within the adhesive layer. Suitable tackifiers include the pentaerythritol esters of rosin commercially available from Hercules under the trademark Pentalyn H, trimethylol propane ester of rosin commercially available from Hercules under the tradename Staybelite Ester 10, and the beta pinine resins such as Piccolyte S115 or the cyclopentadiene * Trade-mark ~c I ~`3 3 769 resins commercially available from Exxon such as *

Escorez 5300 or the Arakawa cyclic tackifiers namely the Arkon products. The adhesive layer can also contain small aounts, i.e., less than about 2% by weight of an antioxidant such as zinc dibutyldithiocarbamate (commercially available from R.T. Vanderbilt Co. under the tradename Butyl Zimate) or those available from Ciba Geigy such as Irganox 1010, tetrakis [methylene-(3,5-ditert-butyl-4-hydroxyhydrocinnamate] or Irganox 1076, octadecyl 3-[3,5-ditert-butyl-4'-hydroxy-phenyl]-propionate, etc.
The thickness of the adhesive layer can be varied. In general, the adhesive layer will be from about 20 to about 100 mils. Thicknesses greater than 100 mils are undesirable as being uncomfortable to wear and more prone to accidental removal.
Preferably, the composition of the adhesive layer prior to incorporation of the pharmaceutically active ingredient contains from about 15% to about 50% by weight of polyisobutylenes or blends of polyisobutylenes and one or more elastomers, from about 20% to about 70% by weight of one or more moisture absorbing, moisture transmitting, water soluble and/or water swellable agents, up to about 25% by weight of mineral oil, and up to about 20% by weight of tackifiers.
The surface of the adhesive layer that does not contact the skin has a flexible backing member affixed to it. Suitable backing members include polymeric films, woven and nonwoven fabric backings, and polymeric foams which themselves have a film or skin on the outer surface opposite the adhesive layer.

* Trade-mark l^ 3376q Suitable commercially available polymeric films include films made from polyethylene, polyurethane, polyether polyamide block copolymers, etc. Suitable commercially available nonwoven fabric backings include materials made from polyester fibers, polypropylene fibers, nylon fibers, composite olefin fibers, or cellulosic fibers. Suitable woven fabric backings include cotton, cotton blends, etc. Suitable polymeric foams include semi-open cell polyurethane foam as described by Chen in U.S. Patent 3,972,328. The skin contacting pressure sensitive adhesive layer can be affixed to the polyurethane foam by means of a secondary adhesive layer as taught by Pawelchak et al. in U.S. Patent 4,538,603.
When the flexible backing member is a polymeric film or fabric, it will vary in thickness from about 1 to about 5 mils. When the flexible backing member is a polymeric foam, it will vary in thickness from about 20 to about 100 mils.
The pharmaceutically active ingredient is incorporated into the adhesive layer so that it resides at the skin contacting surface and in the strata of the adhesive layer closest to the skin contacting surface. This is accomplished by forming a suspension of the pharmaceutically active ingredient in a material or medium which is compatible with the composition of the adhesive layer, i.e., able to be absorbed or intermixed or dissolved in the surface of the adhesive layer without impairing its adhesive characteristics. Of course, this material must be inert with respect to the active ingredient and capable of dispersing or dissolving it. This material must also be non-irritating, non-sensitizing, non-allergenic, and non-toxic. The resulting suspension is then cast onto a sheet of silicone coated release paper which is laminated to the skin contacting surface of the adhesive layer.
Various classes of pharmaceutically active ingredients can be incorporated into the dressing of this invention. Among the classes are topical anti-inflammatory agents and antipruritics including steroids such as triamcinolone acetonide, halcinonide, betamethasone valerate, hydrocortisone, tipredane, etc., and non-steroidal agents such as bufexamac, camphor, aspirin, etc., antipsoriatrics such as di-thranol, coal tar extracts, etc., keratolytics suchas salicylic acid, urea, etc., local anaesthetics such as lidocaine, benzocaine, etc., antibacterials such as benzalkonium chloride, fusidic acid, chlorhexidine, etc. antifungals such as nystatin, dithranol, ampho-tericin, econazole, etc., anti-viral agents, anti-acne agents such as benzoyl peroxide, vitamin A derivatives, etc., biological factors such as urokinase, tissue plaminogen activator, angiogenesis factor, etc., wart removers such as salicylic acid, lactic acid, etc., and enzymes such as fibrinolytic or proteolytic enzymes.
The preferred material for forming the suspension of the active ingredient is mineral oil and particularly mineral oil thickened by mixing with a polyethylene and liquid petrolatum base, i.e., Plastibase, the mineral oil and 1 7`3376q Plastibase being mixed on a 1:1 basis. The active ingredient is suspended in the mineral oil in an amount up to about 15% by weight with about 10% by weight being preferred. Other agents such as surfactants, suspending agents, skin penetration enhancers, thickeners, etc., can optionally be added in small ~uantities to the suspension.
The adhesive layer can also contain various optional ingredients. For example, the adhesive layer can contain up to about 10% by weight of the pharmaceutically active ingredient blended directly into the mixture of polyisobutylenes, elastomers, water soluble and/or water swellable agents. While such blended pharmaceutically active material is not released from the adhesive layer in an amount and at a rate to be useful by itself, it is released in a sufficient amount to augment the release of the pharma-ceutically active material contained at and adjacent the skin contacting surface of the adhesive layer.
Alternatively, the dressing can include a reservoir containing the pharmaceutically active material as described, for example, in the Zaffaroni patents and this reservoir can be employed to augment the release of the pharmaceutically active material contained at and adjacent the surface of the adhesive layer. In addition, the adhesive layer can contain up to about 10% by weight of one or more agents to enhance the i ~3376~

penetration of the pharmaceutically active agent into the skin of the user. Suitable penetration enhancers include oleic acid and other unsaturated acids, methyl-2-pyrrolidone, 2-pyrrolidone, lactic acid, phosphatidol choline and other phospholipids, dimethylisosorbide, dimethyl sulfoxide, Azone, etc.
The pharmaceutically active adhesive dressings of this invention can be prepared as follows. The process will vary somewhat depending upon the par-ticular polyisobutylenes and/or mixtures of polyiso-butylenes and elastomers employed in the adhesive layer. However, in general, these viscous materials along with the mineral oil and tackifiers are combined and blended in a sigma blade type mixer at room temperature or with heating. A blend of the powdery water soluble or swellable agents along with any other optional ingredients are added gradually and mixing is continued until a homogeneous mass is obtained as described in the Doyle et al. and Pawelchak et al.
patents discussed above. The adhesive mass is layered onto a sheet of silicone coated release paper, flattened to the desired thickness by either calendering or extruding, and a flexible backing member is laminated to the other surface of the adhesive layer.
A dispersion or suspension of the pharmaceuti-cally active ingredient in a medium compatible with the adhesive layer is formed. This dispersion is cast onto a sheet of silicone coated release paper as a thin uniform layer using a knife-over-roller, Meyer Rods, a transfer roll coater, etc.

1 }337hq The release paper is stripped off the adhesive layer and the adhesive layer is laminated to the silicone release paper coated with the dis-persion of the pharmaceutically active material.
The adhesive dressings of this invention can be sterilized by means of gamma radiation.
The following examples are illustrative of the invention.

1 33376~

Example 1 A pressure sensitive adhesive is prepared consisting of the following ingredients:
Ingredient Weight percent within the adhesive mass Polyisobutylene (Vistanex LM - MH) 8 Styrene-isoprene-styrene copolymer (Kraton D1107) 6 Butyl rubber (Grade 065-Exxon) 16.25 Tackifier (Pentalyn H) 12.75 Mineral oil 11.50 Antioxidant (Irganox 1010)0.50 Sodium carboxymethyl-cellulose 15.00 Pectin 15.00 Gelatin 15.00 The mineral oil (40.83 kg.), polyisobutylene (28.40 kg.), Kraton D1107 (21.30 kg.), Irganox 1010 (1.80 kg.) and butyl rubber (57.68 kg.) are combined in a sigma blade mixer with heating (about 115C) and ~ 333769 agitating for approximately 1 to 2.5 hours. The mixture is cooled to about 100C and after another 30 minutes of blending, sodium carboxymethylcellulose (53.25 kg.), pectin (53.25 kg.), gelatin (53.25 kg.), and Pentalyn H (45.26 kg.) are added. Mixing is continued at about 100C. for 30 minutes to give 355 kg. of a homogeneous adhesive mass.
The mass is allowed to cool and is flattened into an adhesive layer of the desired thickness of about 35 mils. A sheet of polyethylene is laminated to one surface and silicone coated release paper to the other.
Powdered triamcinolone acetonide ( 10.0 g.) is dispersed in a mixture of mineral oil and Plastibase 50W
at a 1:1 ratio (90.0 g). The dispersion is cast onto silicone coated release paper by means of a Meyer rod (#2) to give a uniform layer of dispersion of 7 to 8 mg./in.2.
The release paper is removed from the adhesive layer and this layer is laminated on the triamcinolone acetonide dispersion layer. In a few hours the dispersion is absorbed into the adhesive surface creating a smooth, glossy, tacky surface.
The resulting dressing contains at its surface 0.75 mg./in.2 of triamcinoline acetonide.
Example 2 Following the procedure of Example 1 but dispersing ( 2 g.) of triamcinolone acetonide in the thickened mineral oil, the resulting dressing contains 0.15 mg./in.2 of triamcinolone acetonide at its surface.

Example 3 A pressure sensitive adhesive is prepared consisting of the following ingredients:
IngredientWeight percent within the adhesive mass Polyisobutylene (Vistanex LM - MH) 9.55 Styrene-isoprene-styrene copolymer (Kraton D1107) 20.55 Tackifier (Pentalyn H) 12.80 Mineral oil 20.45 Antioxidant (Irganox 1010)1.55 Sodium carboxymethyl-cellulose 25.70 Cross-linked sodium carboxy-methylcellulose (Ac-Di-Sol)9.40 The mineral oil (22.5 kg.), polyisobutylene (10.5 kg.), Kraton D1107 (22.6 kg.), and Irganox 1010 (1.7 kg.) are combined in a sigma blade mixer with heating (about 115C) and agitating for approximately 1 to 2.5 hours. After cooling with additional blending, the sodium carboxymethylcellulose (28.3 kg.), Ac-Di-Sol (10.3 kg.), and Pentalyn H (14.1 kg.) are added. Mixing is continued at about 100C. for 30 minutes to give 110 kg. of a homogeneous adhesive mass.

* Trade-mark The adhesive mass is allowed to cool and is flattened into an adhesive layer of the desired thickness of about 35 mils. A sheet of polyethylene is laminated to one surface and the triamcinolone acetonide-mineral oil dispersion described in Example 1 is laminated to the other adhesive surface.
The resulting dressing contains 0.75 mg./in.2 of triamcinolone acetonide at the adhesive surface.
Example 4 Following the procedure of Example 3 but employing the triamcinolone acetonide-mineral oil dispersion of Example 2, a dressing is obtained containing 0.15 mg./in.2 of triamcinolone acetonide at the adhesive surface.
Exam~le 5 A pressure sensitive adhesive is prepared consisting of the following ingredients:
Ingredient Weight percent within the adhesive mass Polyisobutylene (Vistanex LM - MH) ^ 9.5 Polyisobutylene (Vistanex MM - L100) 9.5 Mineral oil 14.4 Sodium carboxymethyl-cellulose 22.2 Pectin 22.2 Gelatin 22.2 1 s3376~

The Vistanex MM-L100 (5.7 kg.) is added to the mixer and agitated for several minutes. The Vistanex LM-MH (5.7 kg.) is added and mixing continued for about 5 minutes. The gelatin is then added (13.3 kg.) and mixing continued for another 5 minutes.
This is followed by addition of the mineral oil (8.7 kg.) over ~ period of several minutes followed by the sodium carboxymethylcellulose (13.3 kg.) and pectin (13.3 kg.). Mixing is continued for another 20 minutes to give 60 kg. of a homogeneous adhesive mass.
The adhesive mass is flattened into an adhesive layer of the desired thickness of about 35 mils. A
sheet of polyethylene is laminated to one surface and the triamcinolone acetonide-mineral oil dispersion described in Example 1 is laminated to the other adhesive surface.
The resulting dressing contains 0.75 mg./in.2 of triamcinolone acetonide at the adhesive surface.
Example 6 Following the procedure of Example 5 but employing the triamcinolone acetonide-mineral oil dispersion of Example 2, a dressing is obtained containing 0.15 mg./in. of triamcinolone acetonide at the adhesive surface.
Example 7 An adhesive dressing is prepared as described by Pawelchak et al. in Example 1 of U.S. Patent 4,538,603.
The dressing consists of a layer of open cell polyurethane foam of about 0.045 inches thickness having a skin formed on one surface and an adhesive layer of about 0.005 inches on the other surface.

1 3~3769 This adhesive layer consists of:

Ingredient Percent by weight in the adhesive laYer Polyisobutylene (Vistanex LM - ~H) 18.0 Polyisobutylene (Vistanex MM L-100) 20.0 Tackifier (Piccolyte) 20.0 Antioxidant (BHT) 0.5 Mineral oil 8.5 Sodium carboxymethyl-cellulose 18.00 Gelatin 15.0 A skin contacting adhesive layer of 0.04 inches thickness is laminated to the adhesive layer described above. The skin contacting adhesive layer consists of:

Ingredient Percent by weight in the skin skin contacting adhesive layer Polyisobutylene (Vistanex LM - MH) 40 Pectin 20 Gelatin 20 Sodium carboxymethyl-cellulose 20 1 33376'3 The triamcinolone acetonide - mineral disper-sion described in Example 1 is laminated to the skin contacting adhesive layer to give a dressing contain-ing 0.75 mg./in. of triamcinolone acetonide at the adhesive surface.
Example 8 Following the procedure of Example 7 but employ-ing the triamcinolone acetonide-mineral oil dispersion described in Example 2, a dressing is obtained contain-ing 0.15 mg./in.2 of triamcinole acetonide at the adhesivesurface.
Exam~le 9 Following the procedure of Example 1 but re-placing the triamcinolone acetonide with betamethasone valerate at a concentration of 0.1 mg. per 5.5 mg. of mineral oil-Plastibase-betamethasone valerate mixture and 1.0 mg. per 5.5 mg. of mineral oil-Plastibase-beta-methasone valerate mixture to give dressings having from about 0.075 to 0.093 mg./in2. and from about 0.85 to 1.0 mg./in2. of betamethasone valerate at the adhesive surface.
Example 10 Following the procedure of Example 1 but replac-ing the triamcinolone acetonide with dithranol at a concentration of 0.1 mg. per 5.5 mg. of mineral oil-Plastibase-dithranol mixture and l.0 mg. per 5.5 mg.
of milleral oil-Plastibase-dithranol mixture to give drescings having 0.075 mg./in2. and 0.95 mg./in2. of dithranol at the adhesive surface.
Examples 11 - 17 Following the procedures of Examples 1 to 10, pre-ssure sensitive adhesive layers are formed of the follow-ing ingredients and a pharmaceutically active agent dis-persed in thickened mineral oil is laminated to the skin contacting adhesive surface at varying concentrations.

1 3337hq EXAMPLE
Ingredient Il 12 13 14 Polyisobutylene (Vistanex LM-MH) 10.2 8.0 20.0 35.0 Polyisobutylene (Vistanex MM-L100) - - 20.0 Butyl rubber - 16.25 Styrene-isoprene stryrene copolymer (Kraton D1107) 12.6 6.0 Tackifier 8.9512.75 20.0 Mineral Oil 25.111.50 19.5 9.5 Antioxidant 0.050.50 0.5 0.5 Sodium carboxymethylcellulose 31.020.0 Calcium carboxymethylcellulose - - - 15.0 Pectin Gelatin Guar gum - 15.0 Gum karaya - 10.0 Xanthan gum - - - 15.0 Mixed Sodium/Calcium alginate - - - 15.0 Carrageenan Water insoluble cross-linked sodium carboxymethylcellulose (Ac-Di-Sol) 12.1 Water insoluble starch-acryloni-trile graft copolymer (Water Lock A-100) Water insoluble cross-linked dextran - - - 10.0 Concentration of pharmaceutically active ingredient at skin contacting adhesive surface 0.65 2 0 55 2 0 45 2 0.25 2 mg/in mg/in mg/inmg/in EXAMPLE
Ingredient 15 16 17 Polyisobutylene (Vistanex LM-MH)10.0 10.0 30.0 Polyisobutylene (Vistanex MM-L100) Butyl rubber - 15.0 10.0 Styrene-isoprene stryrene copolymer (Kraton D1107) 15.0 8.0 Tackifier 5.0 7.95 Mineral Oil 9.5 20.0 15.0 Antioxidant 0.5 0.05 Sodium carboxymethylcellulose 20.0 15.0 Calcium carboxymethylcellulose Pectin - 12.0 Gelatin - 12.0 Guar gum Gum karaya Xanthan gum Mixed Sodium/Calcium alginate - - 15.0 Carrageenan 20.0 Water insoluble cross-linked sodium carboxymethylcellulose (Ac-Di-Sol) Water insoluble starch-acryloni-trile graft copolymer (Water Lock A-100) - - 10.0 Water insoluble cross-linked dextran Concentration of pharmaceutically active ingredient at skin contacting adhesive surface 7 2 0 50 2 0 30 2 mg/in mg/in mg/in

Claims (12)

1. A method of preparing an adhesive dressing containing a pharmaceutically active ingredient compris-ing:
a) forming a pressure sensitive adhesive mass comprising:
i) one or more low molecular weight poly-isobutylenes, and ii) one or more moisture absorbing, mois-ture transmitting, water soluble and/or water swellable agents;
b) blending said pressure sensitive adhesive mass from step a) until homogeneous;
c) layering said blended adhesive mass from step b) onto a first release coated surface and flattening said mass to form an adhesive layer of desired thickness having a skin con-tacting surface and an adjacent strata;
d) laminating a flexible backing member to the exposed surface of said adhesive layer from step c);
e) dispersing a pharmaceutically active ingred-ient into a mineral oil or thickened mineral oil medium which itself is not an adhesive but is compatible with the composition of said skin contacting adhesion layer;
f) coating or casting said dispersion from step e) as a uniform layer onto a second release paper; and g) removing said first release coated surface from said adhesive layer in step d) and lam-inating said coated or cast-on second release paper from step f) to said adhesive layer so that said dispersion of pharmaceutically ac-tive ingredient contacts the now exposed sur-face of said adhesive layer and is absorbed therein to give an adhesive dressing wherein said pharmaceutically active ingredient is present at both said skin contacting surface and said adjacent strata of said adhesive layer.
2. The process of claim 1 wherein said pressure sensitive adhesive means in step a) comprises from about 15% to about 50% by weight of one or more low molecular weight polyisobutylenes, from about 20% to about 70% by weight of one or more moisture absorbing, moisture trans-mitting, water soluble and/or water swellable agents, up to about 25% by weight of mineral oil, and up to about 20% by weight of tackifiers.
3. The process of claim 2 wherein said moisture absorbing, moisture transmitting, water soluble agents are selected from the group consisting of sodium carboxy-methylcellulose, calcium carboxymethylcellulose, pectin, gelatin, guar gum, locust bean gum, gum karaya, xanthan gum, mixed sodium/calcium salts of alginic acid, and carrageenan and said moisture absorbing, moisture trans-mitting water swellable agents are selected from the group consisting of a water insoluble cross-linked sod-ium carboxymethylcellulose, water insoluble starch ac-rylonitrile graft copolymers, and water insoluble cross-linked dextran.
4. A method of preparing an adhesive dressing containing a pharmaceutically active ingredient compris-ing:
a) forming a pressure sensitive adhesive mass comprising:
i) one or more low molecular weight poly-isobutylenes and one or more elasto-mers, and ii) one or more moisture absorbing, mois-ture transmitting, water soluble and/or water swellable agents;
b) blending said pressure sensitive adhesive mass from step a) until homogeneous;
c) layering said blended adhesive mass from step b) onto a first release coated surface and flattening said mass to form an adhesive layer of desired thickness having a skin contacting adhesive surface and an adjacent strata;
d) laminating a flexible backing member to the exposed surface of said adhesive layer from step c);
e) dispersing a pharmaceutically active ingred-ient into a mineral oil or thickened mineral oil medium which itself is not an adhesive but is compatible with the composition of said skin contacting adhesive layer;
f) coating or casting said dispersion from step e) as a uniform layer onto a second release paper; and g) removing said first release coated surface from said adhesive layer in step d) and lam-inating said coated or cast-on second release paper from step f) to said adhesive layer so that said dispersion of pharmaceutically ac-tive ingredient contacts the now exposed sur-face of said adhesive layer and is absorbed therein to give an adhesive dressing wherein said pharmaceutically active ingredient is present at both said skin contacting surface and said adjacent strata of said adhesive layer.
5. The process of claim 4 wherein said pharma-ceutically active ingredient is a topically active anti-inflammatory agent.
6. The process of claim 5 wherein said anti-inflammatory agent is triamcinolone acetonide and said dispersing medium is thickened mineral oil.
7. The process of claim 5 wherein said skin con-tacting adhesive layer prior to incorporation of the pharmaceutically active ingredient comprises from about 15% to about 50% by weight of blends of one or more low molecular weight polyisobutylenes and one or more elas-tomers, from about 30% to about 70% by weight of one or more moisture absorbing, moisture transmitting, water soluble and/or water swellable agents, up to about 25%
by weight of mineral oil, and up to about 20% by weight of tackifiers.
8. The process of claim 7 wherein said elastomer is selected from the group consisting of butyl rubber, medium and high molecular weight polyisobutylenes, and styrene radial or block copolymers, and said moisture absorbing, moisture transmitting, water soluble agents are selected from the group consisting of sodium carboxy-methylcellulose, calcium carboxymethylcellulose, pectin, gelatin, guar gum, locust bean gum, gum karaya, xanthan gum, mixed sodium/calcium salts of alginic acid, and carrageenan and said moisture absorbing, moisture trans-mitting water swellable agents are selected from the group consisting of a water insoluble cross-linked so-dium carboxymethylcellulose, water insoluble starch acrylonitrile graft copolymers, and water insoluble cross-linked dextran.
9. The process of claim 8 wherein said flexible backing member is selected from the group consisting of polymeric films, woven and nonwoven fabrics, and polymeric foams.
10. The process of claim 1 wherein said pharmaceu-tically active ingredient is a topically active anti-inflammatory agent.
11. The process of claim 10 wherein said anti-inflammatory agent is triamcinolone acetonide and said dispersing medium is thickened mineral oil.
12. The process of claim 3 wherein said flexible backing member is selected from the group consisting of polymeric films, woven and nonwoven fabrics, and poly-meric foams.
CA000576790A 1987-09-08 1988-09-08 Adhesive dressing containing a pharmaceutically active ingredient Expired - Fee Related CA1333769C (en)

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US94,364 1987-09-08
US07/094,364 US5059189A (en) 1987-09-08 1987-09-08 Method of preparing adhesive dressings containing a pharmaceutically active ingredient

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JPH0199564A (en) 1989-04-18
IE68882B1 (en) 1996-07-24
JP2790290B2 (en) 1998-08-27
ES2073401T3 (en) 1995-08-16
GR3017511T3 (en) 1995-12-31
NO883972L (en) 1989-03-09
NO180323B (en) 1996-12-23
NO180323C (en) 1997-04-02
EP0307187A3 (en) 1989-10-25
DE3854068D1 (en) 1995-08-03
ZA886003B (en) 1989-04-26
US5059189A (en) 1991-10-22
EP0307187A2 (en) 1989-03-15
NZ225773A (en) 1990-07-26
ATE124270T1 (en) 1995-07-15
DK497588D0 (en) 1988-09-07
AU2069488A (en) 1989-03-09
NO883972D0 (en) 1988-09-07
DK497588A (en) 1989-03-09
EP0307187B1 (en) 1995-06-28
DE3854068T2 (en) 1995-12-07
AU610217B2 (en) 1991-05-16
IE882700L (en) 1989-03-08

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