WO1992019271A1 - Percutaneous administration and absorption promoter composition and external preparation for percutaneous administration - Google Patents

Percutaneous administration and absorption promoter composition and external preparation for percutaneous administration Download PDF

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Publication number
WO1992019271A1
WO1992019271A1 PCT/JP1992/000194 JP9200194W WO9219271A1 WO 1992019271 A1 WO1992019271 A1 WO 1992019271A1 JP 9200194 W JP9200194 W JP 9200194W WO 9219271 A1 WO9219271 A1 WO 9219271A1
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WO
WIPO (PCT)
Prior art keywords
composition
weight
water
pharmacologically active
present
Prior art date
Application number
PCT/JP1992/000194
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Syuji Sato
Katsuya Mukae
Yoshinobu Higashi
Tatsuaki Suzuki
Mitsuhiro Mizumachi
Hirofumi Sakaguchi
Original Assignee
Hisamitsu Pharmaceutical Co., Inc.
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 Hisamitsu Pharmaceutical Co., Inc. filed Critical Hisamitsu Pharmaceutical Co., Inc.
Priority to JP4504703A priority Critical patent/JP2945140B2/ja
Publication of WO1992019271A1 publication Critical patent/WO1992019271A1/ja

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions

Definitions

  • Transdermal absorption absorption composition and transdermal topical composition
  • the present invention relates to a composition for external use for transdermal administration for obtaining a therapeutic effect by transdermally administering a pharmacologically active substance, and a composition for promoting absorption for transdermal administration for promoting transdermal absorption of a pharmacologically active substance.
  • Oral administration and injection-based administration are widely used as administration methods of pharmaceuticals, but such administration methods have side effects such as gastrointestinal disorders and shock.
  • the absorbed drug does not pass through the liver during the first circulation in the body.
  • the metabolism in the liver does not significantly reduce the efficacy.
  • by controlling the absorbability of the drug it is possible to reduce the side effects caused by the absorption of a large amount of the drug in a short time. .
  • a constant drug concentration in the blood can be maintained over a long period of time, the number of drug administrations can be reduced.
  • the drug does not easily penetrate the skin, and the bioavailability often decreases. Absorption and transmission of drugs is relatively low, especially since the stratum corneum of the skin has a barrier function that prevents foreign substances from entering the body. It is a difficult one. Therefore, even if the drug is administered alone or in the form of conventional ointments, creams, gels, or patches, the skin of the drug is sufficient to achieve the desired pharmacological effect. It is difficult to obtain the amount of transmission.
  • Japanese Patent Application Laid-Open No. 61-249934 discloses an attempt to increase the absorption promoting effect by adding fatty acid hydrocarbons to water Z lower alcohol, The effect of promoting absorption of the drug is not sufficiently high, and there is no description about improvement in permeability by adjusting pH.
  • Japanese Patent Application Laid-Open Nos. Sho 63-126268 and European Patent No. 2555485 disclose linoleic acid, propylene glycol or i.
  • a method is disclosed in which a mixed solution of sopropanol and an ester compound is used, and this method is used.
  • the effect of promoting absorption of the drug is not sufficiently high, and there is no description regarding the water / alcohol composition or description regarding the improvement of permeability by adjusting the pH.
  • Japanese Patent Application Laid-Open No. 63-122263 discloses a method of adding an azole or oleic acid to an ethanol solution.
  • Japanese Patent Application Laid-Open Publication No. Sho 63-3-21 1241 discloses a low-alcohol force and ophthalic acid and glycerol monopoly.
  • the present invention solves the drawbacks of the conventional methods and provides a novel absorption promoting composition having an excellent transdermal absorption promoting effect on a drug, and a composition containing the composition and a pharmacologically active substance.
  • the purpose of the present invention is to provide a composition for external use for transdermal application.
  • the present inventors have conducted intensive studies to solve the above problems, and as a result, by appropriately mixing water, a lower alcohol and a hydrophobic substance, and preferably adjusting the pH. It has also been found that a novel absorption-enhancing composition capable of realizing an excellent transdermal absorption-enhancing effect on drugs can be obtained.
  • the inventors have found that binary systems of water and lower alcohols or hydrophobic substances alone do not significantly enhance the skin permeability of drugs.
  • these compositions are combined and formulated as a ternary system, and the skin permeability of the drug is remarkably promoted only when the blending ratio and the pH are adjusted, preferably.
  • the inventors have found that the object can be achieved, and have completed the present invention.
  • composition for promoting absorption through transdermal administration of the present invention is characterized by comprising a hydrophobic substance, water and lower alcohol.
  • composition for topical administration for transdermal administration of the present invention is characterized by comprising a pharmacologically active substance, a hydrophobic substance, water and a lower alcohol.
  • composition for promoting absorption through transdermal administration of the present invention will be described more specifically.
  • the hydrophobic substance used in the present invention is palmitic acid. Cethyl, methyl cetyl citrate, getyl sebacate, sorbitan sodium oleate, polystyrene monophosphate, polyethylene glycol, Butyl hydroxy anisol and chlorazole are listed as being preferred. These hydrophobic substances are preferably contained in an amount of 0.1 to 0.1% by weight based on the total amount of 100% by weight of the composition, and more preferably 1 to 5% by weight. Is
  • lower alcohol used in the present invention those having 1 to 4 carbon atoms are preferably used, and those having 2 to 3 carbon atoms are particularly preferable. .
  • methyl alcohol, ethyl alcohol, n-propyl alcohol, iso-propyl alcohol, n-butyl alcohol, iso-butyl alcohol Reile, sec-butyl alcohol, etc. are preferred, and are listed as those of particular preference, particularly preferred are ethyl alcohol, n-butamate pirualcohol, isobropiruasolco. It is a rule.
  • These lower alcohols are preferably from 1 to 70% by weight, more preferably from 20 to 40% by weight, based on 100% by weight of the total composition. It is blended. Further, it is particularly preferable to appropriately determine the mixing ratio according to the type of alcohol to be used.
  • purified water or the like is appropriately used as water used in the present invention.
  • the water is preferably contained in an amount of 1 to 90% by weight, more preferably 60 to 80% by weight, based on 100% by weight of the total composition.
  • the combined It is particularly preferable to appropriately determine the mixing ratio of water according to the type of the roll.
  • the water according to the present invention may contain a salt and a buffer used for adjusting pH, and may be contained in the composition of the present invention as a physiological saline, a buffer or the like.
  • composition for external use for transdermal administration of the present invention will be described more specifically.
  • hydrophobic substance, water, and lower alcohol used in the composition for transdermal administration of the present invention are as described above.
  • the pharmacologically active substance that can be contained in the composition for external use for transdermal administration of the present invention is not particularly limited as long as it is a drug that can be absorbed transdermally, but it may be a general anesthetic, a hypnotic / sedative, and an anti-inflammatory drug.
  • hypnosis sedatives, antipyretic analgesics, mental nerve agents, local anesthetics, skeletal muscle relaxants, autonomic nerve agents, Analgesic, anti-parkinson, anti-histamine, cardiotonic, antihypertensive, vasoconstrictor, coronary vasodilator, peripheral vasodilator, cholagogue, antithyroid Lumons, narcotics, adrenal cortical hormones, follicular luteal hormones, agents for parasitic skin diseases, gout remedies, diabetes drugs, etc. are preferred.
  • the drug (pharmacologically active substance) according to the present invention is preferably water-soluble, and when the drug is acidic, the drug is ionically dissociated in the composition. It is possible to adjust the pH of the above composition or a preparation containing the composition to an alkaline region more than pK a that can be present, that is, pH 6 to 8. I like it. On the other hand, when the drug is basic, the composition is more acidic than pKa at which the drug can exist as the ionic dissociated form in the composition, that is, the pH is about 3 to 6. In addition, it is preferable to adjust the pH of the composition or a preparation containing the composition.
  • the pH adjusting agent used for the above-mentioned pH adjustment includes acids (for example, inorganic acids such as hydrochloric acid, sulfuric acid, and acetic acid, succinic acid, maleic acid, and triethanol).
  • Organic acids such as amines), alkalines (hydroxy hydradium, potassium hydroxide, etc.), and various buffers, etc., which are commonly used. It is appropriately selected from the pH adjusters and the like to be used.
  • the above-mentioned drugs are used alone or in a mixture of two or more kinds, and are compounded in the range of 0.001 to 20% by weight based on 100% by weight of the whole composition. This is preferred.
  • composition of the present invention may further contain additives such as an ultraviolet absorbent, an antioxidant, and a preservative, if necessary.
  • an ultraviolet absorber known P-amino benzoic acid derivatives, anthranilic acid derivatives, salicylic acid derivatives, coumarin derivatives, amino acid compounds, Benzotriazole derivative, tetrazol derivative, imidazoline derivative, pyrimidin derivative, dioxane derivative, fran derivative, pyrone derivative, down off ⁇ over derivatives, nucleic acid derivatives, ⁇ run-preparative Lee emissions derivatives, two co Chi phosphate derivatives, have in co two emissions may include Vita Mi emissions B 6 derivatives, Tokunibe emission zone off two Roh down Derivatives, for example, 2-hydroxy-4-methoxenbenzophenone derivatives are preferably used.
  • antioxidants examples include ascorbic acid, ester stearate, sodium ascorbate, and tocopherol ( ⁇ -tocolate).
  • preservatives include benzoic acid, sodium benzoate, ethyl benzoate, ethyl benzoate pill, butyl parabenzoate, and the like. Is preferably used.
  • Said UV absorber or antioxidant is preferably from 0.01 to 5% by weight, more preferably from 0.1 to 100% by weight of the total amount of each composition.
  • ⁇ : L weight% is blended.
  • the above-mentioned preservative is preferably contained in an amount of 0.01 to 5% by weight, more preferably 0.05 to 1% by weight, based on 100% by weight of the whole composition. .
  • the composition for promoting absorption for transdermal administration of the present invention contains water, alcohol, and a hydrophobic substance, and preferably has a compounding ratio and pH adjustment. By doing so, the pharmacologically active substance has high skin permeability.
  • the composition for external application for transdermal administration of the present invention comprises the above-mentioned composition for enhancing percutaneous administration for absorption by absorption as a percutaneously absorbable pharmacologically active substance as an active ingredient.
  • the skin permeability of the pharmacologically active substance is extremely high.
  • composition for external use for transdermal administration of the present invention is applied to the transdermal skin as it is or by adding a known pharmaceutically acceptable third component or the like as an external preparation. Further, if necessary, an ultraviolet absorbent, an antioxidant, a preservative and the like may be added.
  • a known pharmaceutically acceptable third component or the like as an external preparation.
  • an ultraviolet absorbent, an antioxidant, a preservative and the like may be added.
  • the dosage form of the external preparation include gels, gel creams, liniments, aerosols, reservoir-type patches, patches, and the like.
  • the gel preparation according to the present invention comprises the above-mentioned water, lower alcohol and hydrophobic substance (for example, cetyl palmitate, getyl separate) according to the present invention together with a pharmacologically active substance in a gel base.
  • a gel base Etc.
  • the gel base may be a conventionally known gel base.
  • gel base examples include gelling agents (for example, carboxyvinyl polymer, hydroxyshethyl cellulose, hydroxyxyl bilcellulose, Carreboxyl methylcellulose, etc.), neutralizing agents (for example, triethanolamine, diisobromobanolamine, sodium hydroxide, etc.), surfactants (for example, sodium hydroxide) Sorbitan lioleate, Sorbitan monooleate, Sorbitan monostearate, Sorbitan monolaurate, Polyoxyethylene Examples thereof include those appropriately mixed with a base selected from ensetyl ether, polyoxyethylene lauryl ether, and the like.
  • gelling agents for example, carboxyvinyl polymer, hydroxyshethyl cellulose, hydroxyxyl bilcellulose, Carreboxyl methylcellulose, etc.
  • neutralizing agents for example, triethanolamine, diisobromobanolamine, sodium hydroxide, etc.
  • surfactants for example, sodium hydroxide
  • the gel agent is added to water and allowed to swell.
  • the pharmacologically active substance is dissolved or suspended in an appropriate amount of the dissolving agent, and then the mixture is mixed with the above-mentioned hydrophobic substance and a lower alcohol, or the above-mentioned hydrophobic substance.
  • Dissolved in a mixture of the three components of the substance, lower alcohol and glycols Let me do it.
  • the obtained solution is applied to the gelling agent swelled with water as described above, and a neutralizing agent is further added to the gelling agent to adjust the pH to 3 to 8, thereby obtaining the present invention.
  • a neutralizing agent is further added to the gelling agent to adjust the pH to 3 to 8, thereby obtaining the present invention.
  • this production example is merely an example, and it goes without saying that the above-mentioned gel agent is appropriately produced by a known or similar method and formulation.
  • the gel cream according to the present invention includes the above-mentioned water, lower alcohol and water-phobic substance according to the present invention in addition to a cream base and a pharmacologically active substance. It can be obtained by blending antioxidants, ultraviolet absorbers and preservatives as needed.
  • the above-mentioned cream base may be a conventionally known cream base, for example, white petrolatum, liquid paraffin, higher fatty acid esters (for example, Esters such as ester titanate, ester palmitate, hexyl laurate, and ethyl isooctanoate), emulsifiers (eg, polyoxyethylene alkyl ether) Ters, fatty acid esters, etc.), gelling agents (for example, carboxyl polymer, hydroxyshethylcellulose, hydroxypropyl propylcellulose, methylcellulose) , Carboxymethylcellulose, etc.) and neutralizing agents (for example, triurea noramine, diisobromononolamine, sodium hydroxide, etc.) Examples include those in which the base selected from the above is appropriately blended.
  • fatty acid esters for example, Esters such as ester titanate, ester palmitate, hexyl laurate, and ethyl isooctanoate
  • the regenerating agent according to the present invention includes lower alcohols (for example, ethanol, isopropanol, etc.), water, and hydrophobic substances (for example, cetyl palmitate,
  • the compound can be obtained by adding a pharmacologically active substance to a mixture such as getylsebacate and, if necessary, adding an ultraviolet absorber, an antioxidant, and a preservative.
  • a viscosity-imparting agent can be added. It should be noted that this production example is merely an example, and it cannot be overemphasized that the above-mentioned liniment is appropriately produced by a known or similar method and formulation.
  • the azole agent according to the present invention includes lower alcohols (for example, ethanol, Add a pharmacologically active substance to a mixture of isopropanol, a hydrophobic substance (for example, cetyl palmitate, getylsebacate, etc.) and water. Filling an aerosol container with LPG under pressure with added inorganic materials such as talc, ultraviolet absorbers, antioxidants, preservatives, dimethyl ether, etc. You can get it by It should be noted that this production example is merely an example, and it goes without saying that the above-mentioned aerosol is appropriately produced by a known or similar method and formulation.
  • the patch according to the present invention includes lower alcohols (for example, ethanol, isopropanol, etc.), water-soluble polyhydric alcohol, water, and ethanol.
  • lower alcohols for example, ethanol, isopropanol, etc.
  • water-soluble polyhydric alcohol for example, water, and ethanol.
  • a water-phobic substance for example, cetyl palmitate, getyl sebacate, etc.
  • a pharmacologically active ingredient are added to a mixture of the unsaturated unsaturated monomer, methacrylate and the crosslinking component.
  • a water-phobic substance for example, cetyl palmitate, getyl sebacate, etc.
  • an antioxidant and a preservative may be added as necessary, and a polymerization crosslinking reaction may be carried out in the presence of a polymerization initiator to obtain the compound.
  • This production example is merely an example, and it goes without saying that the above-mentioned patch is appropriately produced by a known or similar method
  • the reservoir used in this reservoir patch is a mixture of a pharmacologically active substance and the composition for promoting transdermal administration and absorption of the present invention.
  • the porous membrane or polymer membrane used as the control membrane used herein is, for example, polyethylene, polypropylene, polyestermethacrylate ester, or the like.
  • the support includes polypropylene, polyester, polychlorinated vinylidene, polyacrylyl, polyurethan, ethylene-pinyl acetate copolymer, Cloth, non-woven fabric, etc. are used.
  • the composition of the layer is constituted by an adhesive composition containing a pharmacologically active substance.
  • the present invention provides an adhesive layer based on an adhesive base containing no pharmacologically active substance on the outer side of the porous membrane or the molecular membrane as the release surface, and according to the present invention.
  • a formulation can be obtained.
  • This production example is only an example, and it goes without saying that the above-mentioned reservoir-type patch is appropriately produced by a known or similar method and formulation.
  • the topical composition for transdermal administration of the present invention is a conventional composition obtained by dissolving a drug in a two-component mixture of water and ethanol.
  • Enhanced drug absorption compared to It is very effective and can be absorbed by drugs of low transdermal absorbability (skin permeability) by the use of the composition of the present invention to the extent that there is no practical problem. It is possible to increase the performance.
  • transdermal composition for external use for transdermal administration of the present invention containing various hydrophobic substances and pharmacologically active substances (drugs) (Example), and a hydrophobic substance
  • a transdermal composition for external use for transdermal administration of the present invention containing various hydrophobic substances and pharmacologically active substances (drugs) (Example), and a hydrophobic substance
  • the permeability of various drugs to hairless skin was measured and compared.
  • each test was performed as follows.
  • the skin extirpated from the ventral part of the female hairless mouse is sandwiched between two horizontal chambers, and the cell is stratum corneum. 2.7 ml of the above sample solution, 2.7 ml of saline in the cell on the dermis side, and transfer from the supply tank side to the receiving tank side.
  • the composition for transdermal administration according to the present invention which contains the above-mentioned pharmacologically active substance, hydrophobic substance, water and lower alcohol, and is preferably adjusted to have a pH, comprises water and d.
  • a conventional composition in which a drug was dissolved in a two-component mixture with ethanol the permeability of the drug to the skin was very high, and the absorption efficiency of the drug was very high. Therefore, by employing the composition for transdermal administration for external use of the present invention, it is possible to increase the absorbability of a drug having a low transdermal absorbability to the extent that there is no practical problem. And are possible.
  • the transdermal composition of the present invention which contains the above-mentioned hydrophobic substance, water and lower alcohol, and is preferably adjusted in pH.
  • the administration absorption promotion composition has a remarkable effect on the absorption of drugs, and thus greatly contributes to the development of transdermal preparations for percutaneous absorption of poorly absorbable drugs. It is very useful in the pharmaceutical industry.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)
PCT/JP1992/000194 1991-05-02 1992-02-24 Percutaneous administration and absorption promoter composition and external preparation for percutaneous administration WO1992019271A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP4504703A JP2945140B2 (ja) 1991-05-02 1992-02-24 経皮投与吸収促進組成物及び経皮投与外用組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP13045791 1991-05-02
JP3/130457 1991-05-02

Publications (1)

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WO1992019271A1 true WO1992019271A1 (en) 1992-11-12

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PCT/JP1992/000194 WO1992019271A1 (en) 1991-05-02 1992-02-24 Percutaneous administration and absorption promoter composition and external preparation for percutaneous administration

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AU (1) AU1205792A (en, 2012)
TW (1) TW213418B (en, 2012)
WO (1) WO1992019271A1 (en, 2012)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999055332A1 (fr) * 1998-04-27 1999-11-04 Fujisawa Pharmaceutical Co., Ltd. Compositions medicinales
US6299900B1 (en) 1996-02-19 2001-10-09 Monash University Dermal penetration enhancers and drug delivery systems involving same
US6916487B2 (en) 1996-02-19 2005-07-12 Acrux Dds Pty Ltd Transdermal delivery of antiemetics
US6916486B2 (en) 1996-02-19 2005-07-12 Acrux Dds Pty Ltd Transdermal delivery of analgesics
US6923983B2 (en) 1996-02-19 2005-08-02 Acrux Dds Pty Ltd Transdermal delivery of hormones
US6929801B2 (en) 1996-02-19 2005-08-16 Acrux Dds Pty Ltd Transdermal delivery of antiparkinson agents
US6998138B2 (en) 1996-02-19 2006-02-14 Acrux Dds Pty. Ltd. Topical delivery of anti-alopecia agents
US7094422B2 (en) 1996-02-19 2006-08-22 Acrux Dds Pty Ltd. Topical delivery of antifungal agents

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5948413A (ja) * 1982-09-14 1984-03-19 Grelan Pharmaceut Co Ltd クリダナクを含有する消炎鎮痛外用剤
JPS61148117A (ja) * 1984-12-21 1986-07-05 Sekisui Chem Co Ltd 貼付剤およびその製造方法
JPS63258817A (ja) * 1987-04-02 1988-10-26 チバ−ガイギー　アクチェンゲゼルシャフト 活性成分の組合せのための経皮的治療システム
JPS6468327A (en) * 1987-09-08 1989-03-14 Teisan Seiyaku Kk Warming type insulin-containing plaster

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5948413A (ja) * 1982-09-14 1984-03-19 Grelan Pharmaceut Co Ltd クリダナクを含有する消炎鎮痛外用剤
JPS61148117A (ja) * 1984-12-21 1986-07-05 Sekisui Chem Co Ltd 貼付剤およびその製造方法
JPS63258817A (ja) * 1987-04-02 1988-10-26 チバ−ガイギー　アクチェンゲゼルシャフト 活性成分の組合せのための経皮的治療システム
JPS6468327A (en) * 1987-09-08 1989-03-14 Teisan Seiyaku Kk Warming type insulin-containing plaster

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6299900B1 (en) 1996-02-19 2001-10-09 Monash University Dermal penetration enhancers and drug delivery systems involving same
US6818226B2 (en) 1996-02-19 2004-11-16 Acrux Dds Pty. Ltd. Dermal penetration enhancers and drug delivery systems involving same
US6916487B2 (en) 1996-02-19 2005-07-12 Acrux Dds Pty Ltd Transdermal delivery of antiemetics
US6916486B2 (en) 1996-02-19 2005-07-12 Acrux Dds Pty Ltd Transdermal delivery of analgesics
US6923983B2 (en) 1996-02-19 2005-08-02 Acrux Dds Pty Ltd Transdermal delivery of hormones
US6929801B2 (en) 1996-02-19 2005-08-16 Acrux Dds Pty Ltd Transdermal delivery of antiparkinson agents
US6964777B2 (en) 1996-02-19 2005-11-15 Acrux Dds Pty Ltd Transdermal delivery of antianxiety agents
US6998138B2 (en) 1996-02-19 2006-02-14 Acrux Dds Pty. Ltd. Topical delivery of anti-alopecia agents
US7094422B2 (en) 1996-02-19 2006-08-22 Acrux Dds Pty Ltd. Topical delivery of antifungal agents
US7387789B2 (en) 1996-02-19 2008-06-17 Acrux Dds Pty. Ltd. Transdermal delivery of non-steroidal anti-inflammatory drugs
US7438203B2 (en) 1996-02-19 2008-10-21 Acrux Dds Pty Ltd Dermal penetration enhancers and drug delivery systems involving same
WO1999055332A1 (fr) * 1998-04-27 1999-11-04 Fujisawa Pharmaceutical Co., Ltd. Compositions medicinales

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TW213418B (en, 2012) 1993-09-21

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