CA2817524C - Pharmaceutical formulations containing corticosteroids for topical administration - Google Patents
Pharmaceutical formulations containing corticosteroids for topical administration Download PDFInfo
- Publication number
- CA2817524C CA2817524C CA2817524A CA2817524A CA2817524C CA 2817524 C CA2817524 C CA 2817524C CA 2817524 A CA2817524 A CA 2817524A CA 2817524 A CA2817524 A CA 2817524A CA 2817524 C CA2817524 C CA 2817524C
- Authority
- CA
- Canada
- Prior art keywords
- pharmaceutical composition
- concentration
- liquid oil
- oil component
- halobetasol
- 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.)
- Active
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 43
- 239000003246 corticosteroid Substances 0.000 title abstract description 124
- 229960001334 corticosteroids Drugs 0.000 title description 32
- 238000011200 topical administration Methods 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 136
- 239000007788 liquid Substances 0.000 claims abstract description 58
- -1 dicarboxylic acid ester Chemical class 0.000 claims abstract description 46
- 229940125379 topical corticosteroid Drugs 0.000 claims abstract description 5
- 239000003921 oil Substances 0.000 claims description 69
- BDSYKGHYMJNPAB-LICBFIPMSA-N ulobetasol propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]2(C)C[C@@H]1O BDSYKGHYMJNPAB-LICBFIPMSA-N 0.000 claims description 47
- 229950008396 ulobetasol propionate Drugs 0.000 claims description 30
- 239000006071 cream Substances 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 239000006210 lotion Substances 0.000 claims description 18
- 229940115747 halobetasol Drugs 0.000 claims description 15
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical group [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 230000000699 topical effect Effects 0.000 claims description 13
- 239000003995 emulsifying agent Substances 0.000 claims description 12
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 10
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical group O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 9
- 201000004681 Psoriasis Diseases 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 229940059904 light mineral oil Drugs 0.000 claims description 9
- 239000002562 thickening agent Substances 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 201000004624 Dermatitis Diseases 0.000 claims description 7
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical group FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims description 6
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 6
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 6
- 229960002216 methylparaben Drugs 0.000 claims description 6
- 235000011069 sorbitan monooleate Nutrition 0.000 claims description 6
- 239000001593 sorbitan monooleate Substances 0.000 claims description 6
- 229940035049 sorbitan monooleate Drugs 0.000 claims description 6
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical group [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 5
- 208000010668 atopic eczema Diseases 0.000 claims description 5
- 239000002738 chelating agent Substances 0.000 claims description 5
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000003906 humectant Substances 0.000 claims description 5
- 239000002480 mineral oil Substances 0.000 claims description 5
- 235000010446 mineral oil Nutrition 0.000 claims description 5
- 239000003755 preservative agent Substances 0.000 claims description 5
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 5
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 5
- 229960003415 propylparaben Drugs 0.000 claims description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
- 206010058898 Hand dermatitis Diseases 0.000 claims description 4
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- 206010012442 Dermatitis contact Diseases 0.000 claims description 3
- 208000010247 contact dermatitis Diseases 0.000 claims description 3
- 239000003002 pH adjusting agent Substances 0.000 claims description 3
- 208000002419 toxicodendron dermatitis Diseases 0.000 claims description 3
- 229940124274 edetate disodium Drugs 0.000 claims description 2
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 claims 3
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 claims 3
- 229940031954 dibutyl sebacate Drugs 0.000 claims 3
- 229940031578 diisopropyl adipate Drugs 0.000 claims 3
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims 2
- 230000002335 preservative effect Effects 0.000 claims 2
- 229960002903 benzyl benzoate Drugs 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 115
- 230000002829 reductive effect Effects 0.000 abstract description 14
- 235000019198 oils Nutrition 0.000 description 42
- 239000012071 phase Substances 0.000 description 16
- 230000003389 potentiating effect Effects 0.000 description 15
- 239000002674 ointment Substances 0.000 description 13
- 230000009885 systemic effect Effects 0.000 description 13
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- 239000000243 solution Substances 0.000 description 12
- CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 description 11
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- 230000000694 effects Effects 0.000 description 10
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- BOBLHFUVNSFZPJ-JOYXJVLSSA-N diflorasone diacetate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H](C)[C@@](C(=O)COC(C)=O)(OC(C)=O)[C@@]2(C)C[C@@H]1O BOBLHFUVNSFZPJ-JOYXJVLSSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000004615 ingredient Substances 0.000 description 8
- 229960002124 diflorasone diacetate Drugs 0.000 description 7
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- 239000000499 gel Substances 0.000 description 6
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 6
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 229960001102 betamethasone dipropionate Drugs 0.000 description 5
- CIWBQSYVNNPZIQ-XYWKZLDCSA-N betamethasone dipropionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CIWBQSYVNNPZIQ-XYWKZLDCSA-N 0.000 description 5
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- 208000017520 skin disease Diseases 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 230000001839 systemic circulation Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000012049 topical pharmaceutical composition Substances 0.000 description 5
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- 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
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- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- 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
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- 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
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- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA3055328A CA3055328C (en) | 2010-11-22 | 2011-11-09 | Pharmaceutical formulations containing corticosteroids for topical administration |
Applications Claiming Priority (3)
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|---|---|---|---|
| US45833910P | 2010-11-22 | 2010-11-22 | |
| US61/458,339 | 2010-11-22 | ||
| PCT/US2011/059861 WO2012087443A1 (en) | 2010-11-22 | 2011-11-09 | Pharmaceutical formulations containing corticosteroids for topical administration |
Related Child Applications (1)
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| CA3055328A Division CA3055328C (en) | 2010-11-22 | 2011-11-09 | Pharmaceutical formulations containing corticosteroids for topical administration |
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| CA2817524A1 CA2817524A1 (en) | 2012-06-28 |
| CA2817524C true CA2817524C (en) | 2019-11-05 |
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| CA3055328A Active CA3055328C (en) | 2010-11-22 | 2011-11-09 | Pharmaceutical formulations containing corticosteroids for topical administration |
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|---|---|---|---|
| CA3055328A Active CA3055328C (en) | 2010-11-22 | 2011-11-09 | Pharmaceutical formulations containing corticosteroids for topical administration |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11957753B2 (en) | 2010-11-22 | 2024-04-16 | Bausch Health Ireland Limited | Pharmaceutical formulations containing corticosteroids for topical administration |
| US8809307B2 (en) | 2010-11-22 | 2014-08-19 | Dow Pharmaceutical Sciences, Inc. | Pharmaceutical formulations containing corticosteroids for topical administration |
| CN103705440B (zh) * | 2012-10-08 | 2017-05-10 | 天津金耀集团有限公司 | 一种哈西奈德乳膏 |
| CN103705441B (zh) * | 2012-10-08 | 2017-06-23 | 天津金耀集团有限公司 | 一种丙酸倍氯米松乳膏 |
| US8962028B2 (en) * | 2012-10-18 | 2015-02-24 | MiCal Pharmaceuticals LLC—H Series, a Series of MiCal Pharmaceuticals LLC, a Multi-Division Limited Liability Company | Topical steroid composition and method |
| US10111956B2 (en) | 2013-06-03 | 2018-10-30 | Tolmar, Inc. | Corticosteroid compositions |
| CN104095805B (zh) * | 2014-01-02 | 2016-08-24 | 江苏知原药业有限公司 | 地奈德乳膏及其制备方法 |
| US20160184431A1 (en) * | 2014-03-11 | 2016-06-30 | Promius Pharma Llc | Topical compositions comprising a corticosteroid |
| RS60672B1 (sr) * | 2015-06-18 | 2020-09-30 | Bausch Health Ireland Ltd | Topikalne kompozicije koje sadrže kortikosteroide i retinoid za lečenje psorijaze |
| US20190133943A1 (en) * | 2015-06-18 | 2019-05-09 | Valeant Pharmaceuticals North America | Topical compositions and methods for treating skin diseases |
| CN106474052B (zh) * | 2016-12-16 | 2019-10-25 | 重庆华邦制药有限公司 | 二丙酸阿氯米松乳膏及其制备方法 |
| US11311482B2 (en) | 2017-05-12 | 2022-04-26 | Bausch Health Us, Llc | Topical compositions and methods for treating skin diseases |
| US10653656B2 (en) | 2018-04-05 | 2020-05-19 | Bausch Health Ireland Limited | Topical pharmaceutical compositions for treating skin conditions |
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| EP4103151A1 (en) * | 2020-02-11 | 2022-12-21 | Taro Pharmaceutical Industries Ltd. | Compositions comprising desoximetasone and tazarotene |
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2011
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