CA2503722A1 - Fentanyl suspension-based silicone adhesive formulations and devices for transdermal delivery of fentanyl - Google Patents

Fentanyl suspension-based silicone adhesive formulations and devices for transdermal delivery of fentanyl Download PDF

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Publication number
CA2503722A1
CA2503722A1 CA002503722A CA2503722A CA2503722A1 CA 2503722 A1 CA2503722 A1 CA 2503722A1 CA 002503722 A CA002503722 A CA 002503722A CA 2503722 A CA2503722 A CA 2503722A CA 2503722 A1 CA2503722 A1 CA 2503722A1
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CA
Canada
Prior art keywords
fentanyl
solvated
adhesive layer
patch
silicone
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.)
Granted
Application number
CA002503722A
Other languages
French (fr)
Other versions
CA2503722C (en
Inventor
Kenneth J. Ii Miller
Sharad K. Govil
Kuljit Singh Bhatia
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.)
Mylan Pharmaceuticals Inc
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2503722A1 publication Critical patent/CA2503722A1/en
Application granted granted Critical
Publication of CA2503722C publication Critical patent/CA2503722C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7069—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • Y10T156/00—Adhesive bonding and miscellaneous chemical manufacture
    • Y10T156/10—Methods of surface bonding and/or assembly therefor

Abstract

Silicone adhesive formulations are provided, in which fentanyl particles are suspended one or more a solvated silicone adhesives. The formulations can be used for manufacturing improved, matrix-type transdermal devices for administering fentanyl.

Claims (54)

1. A monolithic patch for administering fentanyl transdermally to an individual, comprising:
(a) a backing layer substantially impervious to the fentanyl to be administered transdermally;
(b) a fentanyl-containing adhesive layer in contact with at least a portion of the backing layer, the adhesive layer being cast from a formulation comprising a blend of fentanyl particles suspended in one or more solvated silicone adhesives; and (c) a removable release liner in contact with the adhesive layer.
2. The patch of claim 1, wherein the one or more solvated silicone adhesives is a heptane-solvated silicone adhesive.
3. The patch of claim 2, wherein the adhesive layer comprises about 1% to about 10% w/w fentanyl.
4. The patch of claim 3, wherein the adhesive layer comprises about 3% to about 7% w/w fentanyl.
5. The patch of claim 4, wherein the adhesive layer comprises about 4% w/w fentanyl.
6. The patch of claim 2, wherein the adhesive layer comprises about 5% to about 15% w/w fentanyl.
7. The patch of claim 6, wherein the adhesive layer comprises about 8% to about 12% w/w fentanyl.
8. The patch of claim 7, wherein the adhesive layer comprises about 9.5% w/w fentanyl.
9. The patch of claim 8, wherein the adhesive layer comprises about 9.1% w/w fentanyl.
10. The patch of claim 1, wherein the fentanyl is the fentanyl free base.
11. The patch of claim 1, wherein the backing layer is a polyolefin.
12. The patch of claim 1, wherein the fentanyl is suspended uniformly in the solvated silicone adhesives as small particles.
13. The patch of claim 1, wherein the fentanyl-containing adhesive layer is cast from a formulation comprising a blend of a slurry of fentanyl in a silicone fluid blended with one or more solvated silicone adhesives.
14. The patch of claim 13, wherein the fentanyl-containing layer comprises up to about 25% w/w silicone fluid.
15. The patch of claim 14, wherein the fentanyl-containing layer comprises about 2% to about 10% w/w silicone fluid.
16. The patch of claim 15, wherein the fentanyl-containing layer comprises about 6.5% w/w silicone fluid.
17. The patch of claim 13, wherein the silicone fluid comprises polydimethylsiloxane.
18. The patch of claim 1, which further comprises a fentanyl-free adhesive layer between and in contact with said backing layer and said fentanyl-containing adhesive layer which extends at least partially beyond said fentanyl-containing adhesive layer.
19. The patch of claim 18, wherein the fentanyl-containing adhesive layer is cast from a formulation comprising a blend of a slurry of fentanyl in a silicone fluid blended with one or more solvated silicone adhesives.
20. The patch of claim 19, wherein the fentanyl-containing layer comprises up to about 25o w/w silicone fluid.
21. A method for making a laminate, which is useful for making a monolithic patch for transdermal administration of fentanyl, comprising:
a) selecting a solvent that can substantially or fully solvate a silicone adhesive while keeping fentanyl, when blended with the solvated adhesive, suspended in the solvated adhesive;
b) blending fentanyl particles with one or more silicone adhesives which are solvated with the above solvent, to form a blend formulation in which fentanyl particles are suspended in the solvated adhesives;
c) casting the blend formulation onto a support material; and d) removing the solvent, to produce a laminate containing the support material and a fentanyl suspension-containing adhesive layer.
22. The method of claim 21, wherein the support material is a backing layer or release liner.
23. The method of claim 21, wherein the blend formulation is treated prior to the casting step to disperse the fentanyl throughout the formulation and particle size is maintained by passing the formulation through a high shear colloid mill, homogenizer, or other mixing device.
24. The method of claim 21, wherein the solvent is heptane.
25. The method of claim 24, wherein the silicone adhesive is solvated in about 20% to about 50% heptane.
26. The method of claim 25, wherein the silicone adhesive is solvated in about 30% heptane.
27. The method of claim 21, wherein the fentanyl is the fentanyl free base.
28. The method of claim 21, wherein fentanyl particles are suspended uniformly in the solvated silicone adhesives as small particles.
29. A method for making a laminate, which is useful for making a monolithic patch for transdermal administration of fentanyl, comprising:
a) selecting a solvent that can substantially or fully solvate a silicone adhesive while keeping fentanyl particles, when blended with the solvated adhesive, suspended in the solvated adhesive;
b) solvating said silicone adhesive in said solvent;
c) forming a slurry of fentanyl particles in a silicone fluid;
d) blending the slurry from step c) with the solvated silicone adhesive of step b) so as to form a blend formulation in which fentanyl particles are suspended in the solvated adhesive;
e) casting the blend formulation onto a support material; and f) removing the solvent to produce a laminate containing the support material and a fentanyl suspension-containing adhesive layer.
30. The method of claim 29, wherein the support material is a backing layer or release liner.
31. The method of claim 29, wherein the solvated silicone adhesive is divided into a first portion and a second portion, the slurry of fentanyl particles is blended with a first portion of the solvated silicone adhesive, the resulting blend is passed through a mixing device to form a suspension, and the resulting suspension is blended with the second portion of the solvated silicone adhesive.
32. The method of claim 29, wherein the solvent is heptane.
33. The method of claim 32, wherein the silicone adhesive is solvated in about 20% to about 50% heptane.
34. The method of claim 29, wherein the fentanyl is fentanyl free base.
35. The method of claim 29, wherein fentanyl particles are suspended uniformly in the solvated silicone adhesive as small particles.
36. A method for administering fentanyl transdermally to an individual in need of such administration, comprising applying to the skin of the individual a monolithic patch comprising:
(a) a backing layer substantially impervious to the fentanyl to be administered transdermally; and (b) a fentanyl-containing adhesive layer in contact with the backing layer, the adhesive layer being cast from a formulation comprising a blend of fentanyl suspended in one or more solvated silicone adhesives.
37. The method of claim 36, wherein the solvated silicone adhesives are heptane-solvated silicone adhesives.
38. The method of claim 37, wherein the adhesive layer comprises about 1% to about 10% w/w fentanyl.
39. The method of claim 38, wherein the adhesive layer comprises about 3o to about 7% w/w fentanyl.
40. The method of claim 39, wherein the adhesive layer comprises about 4% w/w fentanyl.
41. The method of claim 40, wherein the fentanyl is administered transdermally for a period of about 3 days.
42. The method of claim 37, wherein the adhesive layer comprises about 5% to about 15% w/w fentanyl.
43. The method of claim 42, wherein the adhesive layer comprises about 8% to about 12% fentanyl.
44. The method of claim 43, wherein the adhesive layer comprises about 9.5% w/w fentanyl.
45. The method of claim 37, wherein the adhesive layer comprises about 9.1% w/w fentanyl.
46. The method of claims 44, wherein the fentanyl is administered transdermally for a period of about 7 days.
47. The method of claims 45, wherein the fentanyl is administered transdermally for a period of about 7 days.
48. The method of claim 36, wherein the fentanyl is the fentanyl free base.
49. The method of claim 36, wherein the fentanyl-containing adhesive layer is cast from a formulation comprising a blend of a slurry of fentanyl in silicone fluid blended with one or more solvated silicone adhesives.
50. The method of claim 49, wherein the fentanyl-containing adhesive layer comprises up to about 25% w/w silicone fluid.
51. The method of claim 50, wherein the fentanyl-containing adhesive layer comprises about 2% to about 100 w/w silicone fluid.
52. The method of claim 51, wherein the fentanyl containing adhesive layer comprises about 6.5% w/w silicone fluid.
53. The method of claim 48, wherein fentanyl particles are suspended uniformly in the solvated silicone adhesives as small particles.
54. The method of claim 36, wherein the backing layer is a polyolefin.
CA2503722A 2002-10-30 2003-10-29 Fentanyl suspension-based silicone adhesive formulations and devices for transdermal delivery of fentanyl Expired - Fee Related CA2503722C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/283,355 2002-10-30
US10/283,355 US20040086551A1 (en) 2002-10-30 2002-10-30 Fentanyl suspension-based silicone adhesive formulations and devices for transdermal delivery of fentanyl
PCT/US2003/034403 WO2004041324A2 (en) 2002-10-30 2003-10-29 Transdermal delivery of fentanyl

Publications (2)

Publication Number Publication Date
CA2503722A1 true CA2503722A1 (en) 2004-05-21
CA2503722C CA2503722C (en) 2012-05-22

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CA2503722A Expired - Fee Related CA2503722C (en) 2002-10-30 2003-10-29 Fentanyl suspension-based silicone adhesive formulations and devices for transdermal delivery of fentanyl

Country Status (14)

Country Link
US (8) US20040086551A1 (en)
EP (1) EP1585470B1 (en)
JP (1) JP5069402B2 (en)
AT (1) ATE511393T1 (en)
AU (1) AU2003288977A1 (en)
CA (1) CA2503722C (en)
CY (1) CY1112582T1 (en)
DE (1) DE03781469T1 (en)
DK (1) DK1585470T3 (en)
ES (1) ES2249197T3 (en)
HK (1) HK1075816A1 (en)
PT (1) PT1585470E (en)
SI (1) SI1585470T1 (en)
WO (1) WO2004041324A2 (en)

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Publication number Publication date
ES2249197T3 (en) 2011-09-06
ES2249197T1 (en) 2006-04-01
US20060210617A1 (en) 2006-09-21
JP2006513160A (en) 2006-04-20
WO2004041324A2 (en) 2004-05-21
US20070259027A1 (en) 2007-11-08
AU2003288977A8 (en) 2004-06-07
EP1585470B1 (en) 2011-06-01
HK1075816A1 (en) 2005-12-30
US8449907B2 (en) 2013-05-28
DE03781469T1 (en) 2006-08-10
DK1585470T3 (en) 2011-06-27
JP5069402B2 (en) 2012-11-07
US7556823B2 (en) 2009-07-07
CY1112582T1 (en) 2016-02-10
SI1585470T1 (en) 2011-10-28
EP1585470A4 (en) 2008-06-18
PT1585470E (en) 2011-08-25
US20120145320A1 (en) 2012-06-14
US20130319595A1 (en) 2013-12-05
US20040086551A1 (en) 2004-05-06
WO2004041324A3 (en) 2004-07-22
US20090041831A1 (en) 2009-02-12
ATE511393T1 (en) 2011-06-15
EP1585470A2 (en) 2005-10-19
AU2003288977A1 (en) 2004-06-07
US20090238861A1 (en) 2009-09-24
US20070166365A1 (en) 2007-07-19
CA2503722C (en) 2012-05-22

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