CA2913336C - Use of sustained release dexamethasone in post-cataract surgery inflammation - Google Patents
Use of sustained release dexamethasone in post-cataract surgery inflammation Download PDFInfo
- Publication number
- CA2913336C CA2913336C CA2913336A CA2913336A CA2913336C CA 2913336 C CA2913336 C CA 2913336C CA 2913336 A CA2913336 A CA 2913336A CA 2913336 A CA2913336 A CA 2913336A CA 2913336 C CA2913336 C CA 2913336C
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- CA
- Canada
- Prior art keywords
- dexamethasone
- dosage form
- unit dosage
- days
- formulation
- 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.)
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- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone 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)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 title claims abstract description 131
- 238000001356 surgical procedure Methods 0.000 title claims abstract description 59
- 206010061218 Inflammation Diseases 0.000 title claims description 30
- 230000004054 inflammatory process Effects 0.000 title claims description 29
- 208000002177 Cataract Diseases 0.000 title abstract description 47
- 229960003957 dexamethasone Drugs 0.000 claims abstract description 120
- 239000002552 dosage form Substances 0.000 claims abstract description 43
- 239000000203 mixture Substances 0.000 claims description 74
- 238000009472 formulation Methods 0.000 claims description 59
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 claims description 50
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 37
- 206010053781 Anterior chamber cell Diseases 0.000 claims description 27
- 238000002347 injection Methods 0.000 claims description 18
- 239000007924 injection Substances 0.000 claims description 18
- 238000000386 microscopy Methods 0.000 claims description 7
- 229940071643 prefilled syringe Drugs 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 abstract description 19
- 210000002159 anterior chamber Anatomy 0.000 abstract description 15
- 238000013268 sustained release Methods 0.000 abstract description 13
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
- 150000001860 citric acid derivatives Chemical class 0.000 description 5
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 5
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- 206010054765 Anterior chamber inflammation Diseases 0.000 description 4
- WYQPLTPSGFELIB-JTQPXKBDSA-N Difluprednate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2CC[C@@](C(=O)COC(C)=O)(OC(=O)CCC)[C@@]2(C)C[C@@H]1O WYQPLTPSGFELIB-JTQPXKBDSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 229960003655 bromfenac Drugs 0.000 description 4
- ZBPLOVFIXSTCRZ-UHFFFAOYSA-N bromfenac Chemical compound NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1 ZBPLOVFIXSTCRZ-UHFFFAOYSA-N 0.000 description 4
- -1 citric acid ester Chemical class 0.000 description 4
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- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical class CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 3
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- 229940125396 insulin Drugs 0.000 description 3
- 229960004752 ketorolac Drugs 0.000 description 3
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
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- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 2
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- 241000282412 Homo Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000010398 acute inflammatory response Effects 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 229960001798 loteprednol Drugs 0.000 description 2
- YPZVAYHNBBHPTO-MXRBDKCISA-N loteprednol Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)OCCl)[C@@H]4[C@@H]3CCC2=C1 YPZVAYHNBBHPTO-MXRBDKCISA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229960001002 nepafenac Drugs 0.000 description 2
- QEFAQIPZVLVERP-UHFFFAOYSA-N nepafenac Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N QEFAQIPZVLVERP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
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- 150000003431 steroids Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 241000288673 Chiroptera Species 0.000 description 1
- OMPIYDSYGYKWSG-UHFFFAOYSA-N Citronensaeure-alpha-aethylester Natural products CCOC(=O)CC(O)(C(O)=O)CC(O)=O OMPIYDSYGYKWSG-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000006424 Flood reaction Methods 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
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- 108091006629 SLC13A2 Proteins 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
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- FPVRUILUEYSIMD-RPRRAYFGSA-N [(8s,9r,10s,11s,13s,14s,16r,17r)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] acetate 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)CO)(OC(C)=O)[C@@]1(C)C[C@@H]2O FPVRUILUEYSIMD-RPRRAYFGSA-N 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000001384 anti-glaucoma Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
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- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000005252 bulbus oculi Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
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- 210000000399 corneal endothelial cell Anatomy 0.000 description 1
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- 230000000881 depressing effect Effects 0.000 description 1
- 229960003657 dexamethasone acetate Drugs 0.000 description 1
- 229960002344 dexamethasone sodium phosphate Drugs 0.000 description 1
- PLCQGRYPOISRTQ-FCJDYXGNSA-L dexamethasone sodium phosphate Chemical compound [Na+].[Na+].C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COP([O-])([O-])=O)(O)[C@@]1(C)C[C@@H]2O PLCQGRYPOISRTQ-FCJDYXGNSA-L 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
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- BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
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- 229960004584 methylprednisolone Drugs 0.000 description 1
- 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 description 1
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- 230000002980 postoperative effect Effects 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[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 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
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Classifications
-
- 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
- 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
- A61K9/0048—Eye, e.g. artificial tears
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medical Preparation Storing Or Oral Administration Devices (AREA)
- Infusion, Injection, And Reservoir Apparatuses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361827091P | 2013-05-24 | 2013-05-24 | |
| US61/827,091 | 2013-05-24 | ||
| PCT/US2014/039319 WO2014190248A1 (en) | 2013-05-24 | 2014-05-23 | Use of sustained release dexamethasone in post-cataract surgery inflammation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2913336A1 CA2913336A1 (en) | 2014-11-27 |
| CA2913336C true CA2913336C (en) | 2020-12-15 |
Family
ID=51934201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2913336A Active CA2913336C (en) | 2013-05-24 | 2014-05-23 | Use of sustained release dexamethasone in post-cataract surgery inflammation |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US10028965B2 (enExample) |
| EP (2) | EP3003318B1 (enExample) |
| JP (1) | JP6530744B2 (enExample) |
| KR (1) | KR102245354B1 (enExample) |
| CN (2) | CN105407896B (enExample) |
| AU (1) | AU2014268434B2 (enExample) |
| CA (1) | CA2913336C (enExample) |
| ES (1) | ES2902951T3 (enExample) |
| WO (1) | WO2014190248A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2701773T3 (pl) | 2011-04-25 | 2019-09-30 | Icon Bioscience, Inc. | Prowadniki dawki do strzykawki iniekcyjnej |
| EP4566638A3 (en) | 2015-05-29 | 2025-08-27 | Allergan, Inc. | Implant for treatment of an ocular condition |
| US10682340B2 (en) | 2016-06-30 | 2020-06-16 | Durect Corporation | Depot formulations |
| BR112018077259A2 (pt) | 2016-06-30 | 2019-06-18 | Durect Corporation | formulações depot |
| JP2020059652A (ja) * | 2016-12-26 | 2020-04-16 | 参天製薬株式会社 | タフルプロストとクエン酸エステルとを含有するデポ剤 |
| AU2019218870B2 (en) | 2018-02-09 | 2024-05-23 | Icon Bioscience, Inc. | Systems, kits and methods for loading and delivering a small volume dose from a syringe |
| WO2020168106A1 (en) | 2019-02-13 | 2020-08-20 | Notable Labs, Inc. | Combinations of agonists of protein kinase c with steroids or retinoic acids for the treatment of cancer |
| IT201900003529A1 (it) * | 2019-03-11 | 2020-09-11 | Ntc S R L | Riduzione della posologia antibiotica in composizioni antibiotico/antinfiammatorio in associazione tra loro per uso oftalmico |
| US11911499B2 (en) | 2019-11-07 | 2024-02-27 | Resurge Therapeutics, Inc. | System and method for prostate treatment |
| US11957654B2 (en) | 2022-01-29 | 2024-04-16 | Resurge Therapeutics, Inc. | Treating benign prostatic hyperplasia |
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| US4211793A (en) | 1979-03-19 | 1980-07-08 | American Cyanamid Company | Triethyl citrate solutions of PGE-type compounds |
| DE3500103C2 (de) | 1985-01-04 | 1987-01-22 | R.P. Scherer GmbH, 6930 Eberbach | Pharmazeutische Zubereitung mit einem in Wasser und Verdauungssäften schwer löslichen Wirkstoff |
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| US20160095818A1 (en) | 2013-06-03 | 2016-04-07 | Mcneil Ab | Solid pharmaceutical dosage form for release of at least one active pharmaceutical ingredient in the oral cavity |
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| AU2014268434A1 (en) | 2015-12-10 |
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| US20230078906A1 (en) | 2023-03-16 |
| US20190105330A1 (en) | 2019-04-11 |
| JP6530744B2 (ja) | 2019-06-12 |
| US10028965B2 (en) | 2018-07-24 |
| CN105407896A (zh) | 2016-03-16 |
| WO2014190248A1 (en) | 2014-11-27 |
| CN105407896B (zh) | 2019-08-27 |
| CN110339153A (zh) | 2019-10-18 |
| CA2913336A1 (en) | 2014-11-27 |
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