AU727811B2 - Composition for the transdermal administration of steroid drugs - Google Patents

Composition for the transdermal administration of steroid drugs Download PDF

Info

Publication number: AU727811B2
Authority: AU; Australia
Prior art keywords: composition; drug; diethylene glycol; absorption promoter; layer
Prior art date: 1997-01-27
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.): Ceased

Application number

AU58820/98A

Other languages

English (en)

Other versions

AU5882098A (en

Inventor

Jong Kun Choi

Mi Suk Choi

Cheol Moon

Je Phil Ryoo

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.)

LG Corp

Original Assignee

LG Chemical Co Ltd

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.)

1997-01-27

Filing date

1998-01-23

Publication date

2000-12-21

1998-01-23 Application filed by LG Chemical Co Ltd filed Critical LG Chemical Co Ltd

1998-08-18 Publication of AU5882098A publication Critical patent/AU5882098A/en

2000-12-21 Application granted granted Critical

2000-12-21 Publication of AU727811B2 publication Critical patent/AU727811B2/en

2018-01-23 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims description 81
229940079593 drug Drugs 0.000 title claims description 67
239000003814 drug Substances 0.000 title claims description 67
150000003431 steroids Chemical class 0.000 title claims description 21
229940124532 absorption promoter Drugs 0.000 claims description 38
239000010410 layer Substances 0.000 claims description 27
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 24
238000009472 formulation Methods 0.000 claims description 17
-1 sorbitan ester Chemical class 0.000 claims description 17
239000011159 matrix material Substances 0.000 claims description 13
XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical group CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 claims description 11
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical group CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 11
229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims description 11
229930182833 estradiol Natural products 0.000 claims description 11
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 10
229960005309 estradiol Drugs 0.000 claims description 10
229940035044 sorbitan monolaurate Drugs 0.000 claims description 10
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 9
IMONTRJLAWHYGT-ZCPXKWAGSA-N Norethindrone Acetate Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@](C#C)(OC(=O)C)[C@@]1(C)CC2 IMONTRJLAWHYGT-ZCPXKWAGSA-N 0.000 claims description 9
239000000853 adhesive Substances 0.000 claims description 9
230000001070 adhesive effect Effects 0.000 claims description 9
229960001652 norethindrone acetate Drugs 0.000 claims description 9
230000001681 protective effect Effects 0.000 claims description 9
229960003604 testosterone Drugs 0.000 claims description 5
239000012790 adhesive layer Substances 0.000 claims description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
239000003098 androgen Substances 0.000 claims description 3
239000000262 estrogen Substances 0.000 claims description 3
229940011871 estrogen Drugs 0.000 claims description 3
229920000058 polyacrylate Polymers 0.000 claims description 3
239000000583 progesterone congener Substances 0.000 claims description 3
WWYNJERNGUHSAO-XUDSTZEESA-N (+)-Norgestrel Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 WWYNJERNGUHSAO-XUDSTZEESA-N 0.000 claims description 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims description 2
GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 claims description 2
BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 claims description 2
GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 claims description 2
229920002367 Polyisobutene Polymers 0.000 claims description 2
PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 claims description 2
229960004976 desogestrel Drugs 0.000 claims description 2
RPLCPCMSCLEKRS-BPIQYHPVSA-N desogestrel Chemical compound C1CC[C@@H]2[C@H]3C(=C)C[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 RPLCPCMSCLEKRS-BPIQYHPVSA-N 0.000 claims description 2
229960002568 ethinylestradiol Drugs 0.000 claims description 2
229960004400 levonorgestrel Drugs 0.000 claims description 2
229960002985 medroxyprogesterone acetate Drugs 0.000 claims description 2
PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 claims description 2
229960001566 methyltestosterone Drugs 0.000 claims description 2
229940053934 norethindrone Drugs 0.000 claims description 2
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 claims description 2
229920002379 silicone rubber Polymers 0.000 claims description 2
239000001593 sorbitan monooleate Substances 0.000 claims description 2
235000011069 sorbitan monooleate Nutrition 0.000 claims description 2
229940035049 sorbitan monooleate Drugs 0.000 claims description 2
HPFVBGJFAYZEBE-ZLQWOROUSA-N testosterone cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(CCC(=O)C=C4CC3)C)CC[C@@]21C)C(=O)CCC1CCCC1 HPFVBGJFAYZEBE-ZLQWOROUSA-N 0.000 claims description 2
229960000921 testosterone cypionate Drugs 0.000 claims description 2
VOCBWIIFXDYGNZ-IXKNJLPQSA-N testosterone enanthate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCC)[C@@]1(C)CC2 VOCBWIIFXDYGNZ-IXKNJLPQSA-N 0.000 claims description 2
229960003484 testosterone enanthate Drugs 0.000 claims description 2
229960001712 testosterone propionate Drugs 0.000 claims description 2
241001559589 Cullen Species 0.000 claims 1
FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 claims 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 claims 1
229960002847 prasterone Drugs 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
210000003491 skin Anatomy 0.000 description 39
229940100515 sorbitan Drugs 0.000 description 8
YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 7
230000001186 cumulative effect Effects 0.000 description 7
238000000034 method Methods 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
239000013078 crystal Substances 0.000 description 6
230000036962 time dependent Effects 0.000 description 6
230000037317 transdermal delivery Effects 0.000 description 6
BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 4
PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 4
229940031439 squalene Drugs 0.000 description 4
TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 4
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
ARIWANIATODDMH-AWEZNQCLSA-N 1-lauroyl-sn-glycerol Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)CO ARIWANIATODDMH-AWEZNQCLSA-N 0.000 description 2
BHIZVZJETFVJMJ-UHFFFAOYSA-N 2-hydroxypropyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(C)O BHIZVZJETFVJMJ-UHFFFAOYSA-N 0.000 description 2
ARIWANIATODDMH-UHFFFAOYSA-N Lauric acid monoglyceride Natural products CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 2
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
230000004907 flux Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229960004063 propylene glycol Drugs 0.000 description 2
235000013772 propylene glycol Nutrition 0.000 description 2
229940026235 propylene glycol monolaurate Drugs 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 1
WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-UHFFFAOYSA-N 0.000 description 1
AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 description 1
206010070840 Gastrointestinal tract irritation Diseases 0.000 description 1
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
239000000006 Nitroglycerin Substances 0.000 description 1
239000004349 Polyvinylpyrrolidone-vinyl acetate copolymer Substances 0.000 description 1
MWQCHHACWWAQLJ-UHFFFAOYSA-N Prazepam Chemical compound O=C1CN=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CC1CC1 MWQCHHACWWAQLJ-UHFFFAOYSA-N 0.000 description 1
239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229940030486 androgens Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
229960005233 cineole Drugs 0.000 description 1
239000005331 crown glasses (windows) Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
229960002986 dinoprostone Drugs 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
229960003575 estradiol acetate Drugs 0.000 description 1
229960004756 ethanol Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
229960003711 glyceryl trinitrate Drugs 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000003475 lamination Methods 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
235000020778 linoleic acid Nutrition 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000019448 polyvinylpyrrolidone-vinyl acetate copolymer Nutrition 0.000 description 1
239000013641 positive control Substances 0.000 description 1
229960004856 prazepam Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 1
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
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230000001839 systemic circulation Effects 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1

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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/569—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone substituted in position 17 alpha, e.g. ethisterone
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
- 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
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- 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

Landscapes

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

AU58820/98A 1997-01-27 1998-01-23 Composition for the transdermal administration of steroid drugs Ceased AU727811B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
KR97/2233		1997-01-27
KR1019970002233A KR100215027B1 (ko)	1997-01-27	1997-01-27	스테로이드계 약물의 경피흡수투여용 조성물 및 이를 포함하는 경피흡수투여용 제형
PCT/KR1998/000013 WO1998032465A1 (en)	1997-01-27	1998-01-23	Composition for the transdermal administration of steroid drugs

Publications (2)

Publication Number	Publication Date
AU5882098A AU5882098A (en)	1998-08-18
AU727811B2 true AU727811B2 (en)	2000-12-21

Family

ID=19495561

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU58820/98A Ceased AU727811B2 (en)	1997-01-27	1998-01-23	Composition for the transdermal administration of steroid drugs

Country Status (12)

Country	Link
EP (1)	EP1001812A1 (es)
JP (1)	JP2000508349A (es)
KR (1)	KR100215027B1 (es)
CN (1)	CN1244806A (es)
AR (1)	AR011577A1 (es)
AU (1)	AU727811B2 (es)
BR (1)	BR9807009A (es)
CA (1)	CA2277970A1 (es)
ID (1)	ID19755A (es)
RU (1)	RU2176499C2 (es)
TW (1)	TW537899B (es)
WO (1)	WO1998032465A1 (es)

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AU2003296810A1 (en) *	2002-12-10	2004-07-09	Besins International Belgique	Pharmaceutical composition for transdermal or transmucous administration comprising a progestin or an estrogen, method for preparing same and uses thereof
FR2851470B1 (fr)	2003-02-20	2007-11-16	Besins Int Belgique	Composition pharmaceutique pour administration transdermique ou transmuqueuse
JP4422430B2 (ja) *	2003-05-14	2010-02-24	帝國製薬株式会社	エストロゲン及び／又はプロゲストゲン含有外用貼付剤
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DE102004059880A1 (de) *	2004-12-10	2006-06-14	Grünenthal GmbH	Stabiles, hormonhaltiges (Zwischen-)Produkt
JP4969050B2 (ja) *	2005-01-07	2012-07-04	ロート製薬株式会社	皮膚外用剤
JP2007045808A (ja) *	2005-01-07	2007-02-22	Rohto Pharmaceut Co Ltd	皮膚外用剤
US10080760B2 (en)	2009-10-27	2018-09-25	Besins Healthcare Luxembourg Sarl	Transdermal pharmaceutical compositions comprising active agents
JP6004364B2 (ja) *	2011-10-14	2016-10-05	大正製薬株式会社	皮膚外用剤
US9301920B2 (en)	2012-06-18	2016-04-05	Therapeuticsmd, Inc.	Natural combination hormone replacement formulations and therapies
EP3936133A1 (en)	2011-11-23	2022-01-12	TherapeuticsMD, Inc.	Natural combination hormone replacement formulations and therapies
US20150196640A1 (en)	2012-06-18	2015-07-16	Therapeuticsmd, Inc.	Progesterone formulations having a desirable pk profile
US10806740B2 (en)	2012-06-18	2020-10-20	Therapeuticsmd, Inc.	Natural combination hormone replacement formulations and therapies
US10806697B2 (en)	2012-12-21	2020-10-20	Therapeuticsmd, Inc.	Vaginal inserted estradiol pharmaceutical compositions and methods
US20130338122A1 (en)	2012-06-18	2013-12-19	Therapeuticsmd, Inc.	Transdermal hormone replacement therapies
US10537581B2 (en)	2012-12-21	2020-01-21	Therapeuticsmd, Inc.	Vaginal inserted estradiol pharmaceutical compositions and methods
US10471072B2 (en)	2012-12-21	2019-11-12	Therapeuticsmd, Inc.	Vaginal inserted estradiol pharmaceutical compositions and methods
US11266661B2 (en)	2012-12-21	2022-03-08	Therapeuticsmd, Inc.	Vaginal inserted estradiol pharmaceutical compositions and methods
US10568891B2 (en)	2012-12-21	2020-02-25	Therapeuticsmd, Inc.	Vaginal inserted estradiol pharmaceutical compositions and methods
JP5521025B2 (ja) *	2012-12-21	2014-06-11	日本精化株式会社	浸透促進剤
US9180091B2 (en)	2012-12-21	2015-11-10	Therapeuticsmd, Inc.	Soluble estradiol capsule for vaginal insertion
US11246875B2 (en)	2012-12-21	2022-02-15	Therapeuticsmd, Inc.	Vaginal inserted estradiol pharmaceutical compositions and methods
US10206932B2 (en)	2014-05-22	2019-02-19	Therapeuticsmd, Inc.	Natural combination hormone replacement formulations and therapies
US10328087B2 (en)	2015-07-23	2019-06-25	Therapeuticsmd, Inc.	Formulations for solubilizing hormones
CA3020153A1 (en)	2016-04-01	2017-10-05	Therapeuticsmd, Inc.	Steroid hormone pharmaceutical composition
US10286077B2 (en)	2016-04-01	2019-05-14	Therapeuticsmd, Inc.	Steroid hormone compositions in medium chain oils
KR101968873B1 (ko) *	2018-09-21	2019-04-29	아이큐어 주식회사	세포 침투 효과가 우수한 보툴리늄 유래 펩타이드를 포함하는 화장료 조성물

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1997
- 1997-01-27 KR KR1019970002233A patent/KR100215027B1/ko not_active Expired - Fee Related
1998
- 1998-01-23 BR BR9807009-6A patent/BR9807009A/pt not_active Application Discontinuation
- 1998-01-23 JP JP10531848A patent/JP2000508349A/ja active Pending
- 1998-01-23 CA CA002277970A patent/CA2277970A1/en not_active Abandoned
- 1998-01-23 AU AU58820/98A patent/AU727811B2/en not_active Ceased
- 1998-01-23 CN CN98802010A patent/CN1244806A/zh active Pending
- 1998-01-23 WO PCT/KR1998/000013 patent/WO1998032465A1/en not_active Ceased
- 1998-01-23 EP EP98902269A patent/EP1001812A1/en not_active Withdrawn
- 1998-01-23 RU RU99118582/14A patent/RU2176499C2/ru not_active IP Right Cessation
- 1998-01-26 TW TW087101089A patent/TW537899B/zh active
- 1998-01-27 AR ARP980100352A patent/AR011577A1/es not_active Application Discontinuation
- 1998-01-27 ID IDP980113A patent/ID19755A/id unknown

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WO1993023083A1 (en) *	1992-05-11	1993-11-25	Agouron Pharmaceuticals, Inc.	Anhydrous formulations for administering lipophilic agents

Also Published As

Publication number	Publication date
AR011577A1 (es)	2000-08-30
CA2277970A1 (en)	1998-07-30
KR100215027B1 (ko)	1999-08-16
CN1244806A (zh)	2000-02-16
JP2000508349A (ja)	2000-07-04
AU5882098A (en)	1998-08-18
TW537899B (en)	2003-06-21
ID19755A (id)	1998-07-30
EP1001812A1 (en)	2000-05-24
RU2176499C2 (ru)	2001-12-10
WO1998032465A1 (en)	1998-07-30
BR9807009A (pt)	2000-03-14
KR19980066583A (ko)	1998-10-15

Publication	Publication Date	Title
AU727811B2 (en)	2000-12-21	Composition for the transdermal administration of steroid drugs
US20010023261A1 (en)	2001-09-20	Novel composition for the transdermal administration of drugs
CA2183543C (en)	2009-07-14	Sexual steroid-containing transdermal therapeutic systems
US9005653B2 (en)	2015-04-14	Transdermal delivery of hormones with low concentration of penetration enhancers
JP2001508070A (ja)	2001-06-19	ホルモン剤供給のための経皮吸収治療システム
CN1596105A (zh)	2005-03-16	含有甾类激素和含有丙二醇单辛酸酯的透皮治疗系统
EP1541137B1 (en)	2010-02-10	Transdermal delivery system of gestodene
WO1999062557A1 (en)	1999-12-09	Composition for the transdermal administration of non-steroidal anti-inflammatory drugs
JP4965263B2 (ja)	2012-07-04	浸透増強剤を必要としないホルモンの経皮送達
JP2001058961A (ja)	2001-03-06	経皮吸収促進剤及び経皮吸収型製剤
MXPA99006959A (es)	2000-01-01	Composicion para la administracion transdermica de drogas esteroidales
KR960013236B1 (ko)	1996-10-02	에스트로겐/프로게스틴 경피 전달 장치 및 이를 포함하는 키트
US8671945B2 (en)	2014-03-18	Low-dose transdermal patches with high drug release
HK1074801B (en)	2010-05-20	Transdermal delivery system of gestodene
HK1132682B (en)	2014-07-11	Transdermal delivery system of hormones without penetration enhancers

Legal Events

Date	Code	Title	Description
2001-04-26	FGA	Letters patent sealed or granted (standard patent)
2004-08-26	MK14	Patent ceased section 143(a) (annual fees not paid) or expired