WO2009119992A2 - Préparation percutanée comprenant du fentanyl - Google Patents

Préparation percutanée comprenant du fentanyl Download PDF

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Publication number
WO2009119992A2
WO2009119992A2 PCT/KR2009/001399 KR2009001399W WO2009119992A2 WO 2009119992 A2 WO2009119992 A2 WO 2009119992A2 KR 2009001399 W KR2009001399 W KR 2009001399W WO 2009119992 A2 WO2009119992 A2 WO 2009119992A2
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WO
WIPO (PCT)
Prior art keywords
acrylate polymer
fentanyl
polyethylene glycol
absorbent
adhesive
Prior art date
Application number
PCT/KR2009/001399
Other languages
English (en)
Korean (ko)
Other versions
WO2009119992A3 (fr
Inventor
최후균
Original Assignee
조선대학교산학협력단
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 조선대학교산학협력단 filed Critical 조선대학교산학협력단
Publication of WO2009119992A2 publication Critical patent/WO2009119992A2/fr
Publication of WO2009119992A3 publication Critical patent/WO2009119992A3/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
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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

Definitions

  • the present invention relates to a preparation containing fentanyl as an active ingredient as a transdermal absorbent in matrix form in which the active ingredient is dissolved or dispersed in a high molecular material.
  • Fentanyl is known to have about 80 times more potent effects than morphine, so fentanyl citrate in the form of fentanyl citrate is used to relieve pain in cancer patients or surgery patients. buccal) or the like is administered through the transdermal (transdermal) in the form of fentanyl base (fentanyl base).
  • transdermal transdermal
  • fentanyl base fentanyl base
  • transdermal absorbents can maintain a constant blood concentration due to the nature of the formulation, which can minimize side effects that may occur due to initial high concentrations during intravenous administration, and because of the simple method of administration and easy removal of the formulation. The advantage is that you can simply stop taking the drug in an emergency.
  • the method of delivering drugs through the skin can be divided into active methods of delivering drugs using energy such as electricity and passive methods of delivering drugs by passive transport of drugs without using energy.
  • the active method works well, but has the disadvantage of being expensive and simple to apply to the patient compared to the passive method.
  • the passive method can be divided into a reservoir form and a matrix form. Since the reservoir form supports the drug on a gel carrier, the drug can be loaded at a high concentration and the permeation rate control membrane is provided. Although it has the advantage of controlling the penetration rate of the drug through, but because the manufacturing process is complex and thick compared to the matrix form, you may feel a little heterogeneity when applied to the skin.
  • the matrix form directly dissolves or disperses the drug in the polymer adhesive, the rate of diffusion into the skin can be controlled by the solubility in the carrier of the drug according to the characteristics of the polymer adhesive used as the carrier of the drug.
  • This simple, formulation is thinner and more flexible than the reservoir form, thus increasing patient preference.
  • Korean Patent Laid-Open Publication No. 10-2003-0021418 uses fentanyl and a permeation accelerator having a boiling point of 120 ° C. or less, using a single-layer matrix type transdermal absorbent in which an adhesive is used. Formulations have been proposed that increase the permeability and shorten the delay time.
  • a solvent that evaporates relatively easily is used as a permeation accelerator, so that the permeation accelerator is evaporated and absorbed into a dried adhesive instead of a method of preparing a conventional matrix type transdermal absorbent preparation.
  • the formulation should be prepared by addition by the method.
  • the delayed time can be shortened by increasing the initial permeability when the formulation prepared by the above method is applied, the permeation rate of the latter part is drastically decreased due to the complicated manufacturing method and the rapid increase of the amount of drug permeated at the beginning. Therefore, continuous drug delivery may be rather difficult, and by using a permeation accelerator having a boiling point of 120 ° C. or less, it may cause a decrease in permeability due to evaporation of the permeation accelerator during storage.
  • 10-2001-0036685 uses a silicone adhesive having a low solubility of fentanyl in the lower layer to increase the initial transmittance, and an upper layer using an acrylic adhesive having a high solubility of fentanyl in the upper layer.
  • a matrix transdermal absorption formulation consisting of a multi-layer) is provided.
  • US Pat. No. 5,186,939 also proposed a matrix transdermal absorption formulation using propylene glycol monolaurate as a silicone adhesive and a permeation accelerator to reduce the initial delay of fentanyl.
  • solubility of fentanyl in silicon is not sufficient to support a large amount of the drug in the pressure-sensitive adhesive layer, but it can increase the initial permeability and shorten the delay time, but most drugs are released within 24 hours. It is not preferable as a preparation for maintaining long-term efficacy, and when a silicone adhesive is used, it can raise a manufacturing cost more when an acrylic adhesive is used.
  • U.S. Patent No. 4,588,580 discloses a matrix transdermal absorption preparation in which fentanyl is supported on a silicone or polyisobutylene pressure-sensitive adhesive.
  • silicone used as the pressure-sensitive adhesive
  • the fentanyl solubility in silicon is low.
  • high diffusion coefficient (diffusivity) of the fentanyl in the pressure-sensitive adhesive is able to permeate most drugs in a short time is not preferable as a formulation for maintaining the long-term drug efficacy.
  • the use of polyisobutylene as a pressure sensitive adhesive is undesirable because it may not have sufficient adhesion to be applied to a formulation for long-term drug delivery.
  • a matrix transdermal sorbent has been developed that allows for sustained drug release. Accordingly, it is an object of the present invention to provide a transdermal absorbent which increases the skin absorption rate of fentanyl used as an active ingredient and enables long-term sustained drug release.
  • the present invention is a transdermal absorbent containing fentanyl, a narcotic analgesic component excellent in pain relief, and is characterized by high skin absorption rate, long-term sustained drug release, and simple composition of fentanyl as an active ingredient.
  • the content of fentanyl used as the active ingredient is 2 to 20% by weight, more preferably 4 to 18% by weight in the dried composition.
  • the drug content is 2% by weight or less, it is difficult to continuously deliver the drug amount corresponding to the effective blood concentration for a long time, and at 20% by weight or more, recrystallization of the drug in the formulation may reduce the permeability and decrease the adhesive strength.
  • Permeation accelerators may be used for the purpose of improving the skin absorption rate of fentanyl.
  • the permeation accelerator that can be used at this time is polyglyceryl-3 oleate (Plurol oleique cc497 ® Polyethyleneglycol-20 Almond Glyceride (Crovol PK40 ® ), Polyethylene glycol-12 palm kernel glycerides, (Crovol A40 ® Isopropyl myristate Crodamol IPM ® ), Isopropyl Palmitate Crodamol IPP ® ), Sorbitan mono oleate (Span 80 ® ), Oleyl alcohol (Oleyl alcohol ® ), Polyethylene glycol 300 (Polyethylene glycol 300 ® ), Polyoxyglycerides (Labrafil 1944 ® It is preferable to use at least one permeation promoter selected from the group consisting of The content of the permeation accelerator used in the present invention is 1 to 30% by weight, more preferably 2 to
  • the amount of the permeation accelerator is less than 1% by weight, the effect of enhancing the skin permeation of the drug is insignificant, and the adhesion of the agent may be reduced at 30% by weight or more, and the cold flow, that is, when the agent is applied to the affected part Slippage can occur and reduce patient preference.
  • one or more pressure-sensitive adhesives selected from the group consisting of acrylate polymers having hydroxyl groups as a pressure-sensitive adhesive which functions as a carrier of the skin and the components of the formulation.
  • a mixed adhesive in which an acrylate polymer having no functional group is mixed with an acrylate polymer having a hydroxyl group may be used.
  • the proportion of the acrylate polymer having a hydroxyl group is 20% by weight or more, more preferably 50% by weight or more. When the proportion of the acrylate polymer having a hydroxyl group is lowered, the skin permeability or adhesion of the drug may be lowered.
  • the back layer is a commercially available polymer membrane composed of polyester, polypropylene, polyethylene, polyurethane, ethylenevinylacetate copolymer, etc. A permeable one can be used.
  • the release paper is a commercially available polymer film coated with silicone, and when the transdermal absorbent is applied to the skin, the matrix adhesive should be easily separated without remaining on the release paper.
  • FIG. 1 is a view showing the structure of the transdermal absorbent of the present invention.
  • Example 1 a patch was prepared in the same manner except that 8 ⁇ l of polyglyceryl-3 oleate (Plurol oleique cc497 ® ) was used instead of 20 ⁇ l of polyethylene glycol-20 almond glyceride (Crovol PK40 ® ).
  • Example 1 a patch was prepared in the same manner except that polyethylene glycol-20 almond glyceride (Crovol PK40 ® ) was used as isopropyl myristate (Crodamol IPM ® ).
  • Example 1 a patch was prepared in the same manner except that polyethylene glycol-20 almond glyceride (Crovol PK40 ® ) was used as isopropyl palmitate (Crodamol IPP ® ).
  • Example 1 a patch was prepared in the same manner except that 40 ⁇ l of sorbitan mono oleate (Span 80 ® ) was used instead of 20 ⁇ l of polyethylene glycol-20 almond glyceride (Crovol PK40 ® ).
  • Example 1 except that the oleyl alcohol (Oleyl alcohol ®) in 60 ⁇ l instead of polyethylene glycol -20 almond glycerides (Crovol PK40 ®) in 20 ⁇ l were prepared in the same manner paechwije.
  • Oleyl alcohol ® oleyl alcohol
  • Cisco PK40 ® polyethylene glycol -20 almond glycerides
  • Example 1 a patch was prepared in the same manner except that 20 ⁇ l of polyethylene glycol-20 almond glyceride (Crovol PK40 ® ) was used instead of 12 ⁇ l of polyethylene glycol-12 palm kernel glyceride (Crovol A40 ® ).
  • Example 1 a patch was prepared in the same manner except that polyethylene glycol-20 almond glyceride (Crovol PK40 ® ) was used as polyethylene glycol 300 ® .
  • Example 1 a patch was prepared in the same manner except that polyethylene glycol-20 almond glyceride (Crovol PK40 ® ) was used instead of propylene glycol sorbitan monooleate (Tween 80 ® ).
  • Polyethylene glycol-20 almond glyceride (Crovol PK40 ® ) was used instead of propylene glycol sorbitan monooleate (Tween 80 ® ).
  • Example 1 a patch was prepared in the same manner except that polyethylene glycol-20 almond glyceride (Crovol PK40 ® ) was used instead of polyoxyethylene 4 lauryl ether (Brij ® ).
  • Example 1 except for using, instead of polyethylene glycol -20 almond glycerides (Crovol PK40 ®) in cine ol (Cineole ®) was prepared in the same manner paechwije.
  • Example 1 polyethylene glycol-20 almond glycerides (Crovol PK40 ® ) Instead propylene glycol laurate (Lauroglycol ® A patch was prepared in the same manner except that was used.
  • Example 1 polyethylene glycol-20 almond glycerides (Crovol PK40 ® Propylene Glycol Dicaprylocaprate Instead (Labrafac PG ® A patch was prepared in the same manner except that was used.
  • Hairless mouse skin was used to determine the skin permeability of the prepared fentanyl.
  • the final experimental example specified in another patent was used as a comparative example.
  • the skin of hairless mouse (6 ⁇ 8 weeks old) is taken just before the experiment, and the product to be tested is cut in a circle so that its area becomes 2cm 2 and attached to the skin, and clamped with Flow Through Diffusion Cell.
  • the samples were fixed for 72 hours at intervals of 4 hours, and quantified by high-performance liquid chromatography.
  • isotonic phosphate buffer (pH 6) was added and maintained at 37 ° C., followed by constant stirring with a magnetic stirrer. Analysis conditions are as follows.
  • Comparative Example 5 Comparative Example 6, and Comparative Example 7 did not show an excellent effect on the skin permeability of fentanyl, Comparative Example 3, Comparative Example 4 showed an excellent permeability enhancement effect, but showed a problem in adhesion In Examples 1 to 9, excellent permeability enhancement effects and appropriate adhesive strengths could be obtained.
  • the present invention by increasing the skin absorption rate of fentanyl used as the active ingredient and by providing a transdermal absorbent in the form of a matrix capable of long-term continuous drug release, it is possible to reduce the discomfort to alleviate pain to increase patient compliance Expect.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne une préparation percutanée sous forme matricielle qui comprend du fentanyl et au moins un type d'agent améliorant la pénétration destiné à augmenter l'absorptivité du fentanyl, laquelle préparation permet de soulager la douleur d'un patient de manière prolongée. L'agent améliorant la pénétration est choisi dans le groupe composé de l'oléate de polyglycéryle-3 (Plurol oléique cc497®), du glycéride polyéthylèneglycol-20 d'huile d'amande douce (Crovol PK40®), du glycéride polyéthylèneglycol-12 d'huile de palmiste (Crovol A40®), du myristate d'isopropyle (Crodamol IPM®), du palmitate d'isopropyle (Crodamol IPP®), du monoolétate de sorbitan (Span 80®), de l'alcool d'oléyle (Oleyl alcohol®), du polyéthylène glycol 300 (Polyéthylène glycol 300®), et du polyoxyglycéride (Labrafil 1944®).
PCT/KR2009/001399 2008-03-24 2009-03-19 Préparation percutanée comprenant du fentanyl WO2009119992A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020080026795A KR20090101579A (ko) 2008-03-24 2008-03-24 펜타닐을 함유한 경피 흡수제
KR10-2008-0026795 2008-03-24

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WO2009119992A2 true WO2009119992A2 (fr) 2009-10-01
WO2009119992A3 WO2009119992A3 (fr) 2009-12-03

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8569343B2 (en) 2007-03-12 2013-10-29 Nektar Therapeutics Oligomer-opioid agonist conjugates
US10512644B2 (en) 2007-03-12 2019-12-24 Inheris Pharmaceuticals, Inc. Oligomer-opioid agonist conjugates

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101353478B1 (ko) * 2011-11-04 2014-01-20 주식회사 동일팜텍 펜타닐을 함유하는 경피투여용 패취 제제

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001087276A1 (fr) * 2000-05-16 2001-11-22 Samyang Corporation Composition d'hydrogel pour administration transdermique de medicaments
WO2002026217A2 (fr) * 2000-09-29 2002-04-04 3M Innovative Properties Company Composition pour l'administration transcutanée de fentanyle
US20040234584A1 (en) * 2001-08-24 2004-11-25 Walter Muller Transdermal therapeutic system with fentanyl or related substances
US20060013865A1 (en) * 2002-10-18 2006-01-19 Hisamitsu Pharmaceutical Co., Inc. Transdermal patch for external use comprising fentanyl
US20060039960A1 (en) * 2002-05-28 2006-02-23 Cordes Guenter Plaster containing fentanyl

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001087276A1 (fr) * 2000-05-16 2001-11-22 Samyang Corporation Composition d'hydrogel pour administration transdermique de medicaments
WO2002026217A2 (fr) * 2000-09-29 2002-04-04 3M Innovative Properties Company Composition pour l'administration transcutanée de fentanyle
US20040234584A1 (en) * 2001-08-24 2004-11-25 Walter Muller Transdermal therapeutic system with fentanyl or related substances
US20060039960A1 (en) * 2002-05-28 2006-02-23 Cordes Guenter Plaster containing fentanyl
US20060013865A1 (en) * 2002-10-18 2006-01-19 Hisamitsu Pharmaceutical Co., Inc. Transdermal patch for external use comprising fentanyl

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8569343B2 (en) 2007-03-12 2013-10-29 Nektar Therapeutics Oligomer-opioid agonist conjugates
US8946285B2 (en) 2007-03-12 2015-02-03 Nektar Therapeutics Oligomer-opioid agonist conjugates
US8952032B2 (en) 2007-03-12 2015-02-10 Nektar Therapeutics Oligomer-opioid agonist conjugates
US9233168B2 (en) 2007-03-12 2016-01-12 Nektar Therapeutics Oligomer-opioid agonist conjugates
US9233167B2 (en) 2007-03-12 2016-01-12 Nektar Therapeutics Oligomer-opioid agonist conjugates
US9458166B2 (en) 2007-03-12 2016-10-04 Nektar Therapeutics Oligomer-opioid agonist conjugates
US9512135B2 (en) 2007-03-12 2016-12-06 Nektar Therapeutics Oligomer-opioid agonist conjugates
US9827239B2 (en) 2007-03-12 2017-11-28 Nektar Therapeutics Oligomer-opioid agonist conjugates
US10143690B2 (en) 2007-03-12 2018-12-04 Nektar Therapeutics Oligomer-opioid agonist conjugates
US10307416B2 (en) 2007-03-12 2019-06-04 Nektar Therapeutics Oligomer-opioid agonist conjugates
US10512644B2 (en) 2007-03-12 2019-12-24 Inheris Pharmaceuticals, Inc. Oligomer-opioid agonist conjugates

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KR20090101579A (ko) 2009-09-29
WO2009119992A3 (fr) 2009-12-03

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