JP2013529632A5 - - Google Patents
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- JP2013529632A5 JP2013529632A5 JP2013516553A JP2013516553A JP2013529632A5 JP 2013529632 A5 JP2013529632 A5 JP 2013529632A5 JP 2013516553 A JP2013516553 A JP 2013516553A JP 2013516553 A JP2013516553 A JP 2013516553A JP 2013529632 A5 JP2013529632 A5 JP 2013529632A5
- Authority
- JP
- Japan
- Prior art keywords
- composition
- sodium
- chloride
- ionizable species
- combinations
- 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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- 239000000203 mixture Substances 0.000 claims description 61
- 241000894007 species Species 0.000 claims description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 16
- 239000000230 xanthan gum Substances 0.000 claims description 9
- 229920001285 xanthan gum Polymers 0.000 claims description 9
- 229940082509 xanthan gum Drugs 0.000 claims description 9
- 235000010493 xanthan gum Nutrition 0.000 claims description 9
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L MgCl2 Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 8
- NLVFBUXFDBBNBW-PBSUHMDJSA-N Tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims description 8
- 229960000707 Tobramycin Drugs 0.000 claims description 8
- LWIHDJKSTIGBAC-UHFFFAOYSA-K Tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 8
- 201000009910 diseases by infectious agent Diseases 0.000 claims description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 8
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 8
- 235000011152 sodium sulphate Nutrition 0.000 claims description 8
- 238000000338 in vitro Methods 0.000 claims description 6
- 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 claims description 5
- 229960003957 Dexamethasone Drugs 0.000 claims description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 4
- 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
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-Mannitol Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 4
- QEEAPRPFLLJWCF-UHFFFAOYSA-K Potassium citrate Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 claims description 4
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K Trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000004327 boric acid Substances 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 4
- 239000001110 calcium chloride Substances 0.000 claims description 4
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 4
- 235000011148 calcium chloride Nutrition 0.000 claims description 4
- 239000003792 electrolyte Substances 0.000 claims description 4
- 230000004968 inflammatory condition Effects 0.000 claims description 4
- 230000003993 interaction Effects 0.000 claims description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 4
- 235000011147 magnesium chloride Nutrition 0.000 claims description 4
- 239000000594 mannitol Substances 0.000 claims description 4
- 235000010355 mannitol Nutrition 0.000 claims description 4
- 239000001103 potassium chloride Substances 0.000 claims description 4
- 235000011164 potassium chloride Nutrition 0.000 claims description 4
- 239000001508 potassium citrate Substances 0.000 claims description 4
- 229960002635 potassium citrate Drugs 0.000 claims description 4
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- 235000002639 sodium chloride Nutrition 0.000 claims description 4
- 239000001509 sodium citrate Substances 0.000 claims description 4
- 239000001488 sodium phosphate Substances 0.000 claims description 4
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 4
- 235000011008 sodium phosphates Nutrition 0.000 claims description 4
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- 239000011791 tripotassium citrate Substances 0.000 claims description 4
- 235000015870 tripotassium citrate Nutrition 0.000 claims description 4
- 235000019798 tripotassium phosphate Nutrition 0.000 claims description 4
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 claims description 4
- 239000011778 trisodium citrate Substances 0.000 claims description 4
- 235000019263 trisodium citrate Nutrition 0.000 claims description 4
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 4
- 230000000699 topical Effects 0.000 claims description 2
- 238000003381 deacetylation reaction Methods 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000850 deacetylating Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002708 enhancing Effects 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
Description
本発明はまた、部分的には、キサンタンガムは、少なくとも部分的に脱アセチル化されている場合、本発明の組成物において、粘度増強剤としてはるかにより有効であるという発見に基づく。より具体的には、キサンタンガムは、水溶液においてゆっくりと脱アセチル化を受ける。そのような脱アセチル化は、組成物のｐＨをさらに低下させ、それによってトブラマイシンおよびデキサメタゾンの間のイオン性相互作用を増加させることが決定された。これらの相互作用は、最初は粘度の喪失を引き起こし、そして最終的にキサンタンガムおよびトブラマイシンの集塊および／または沈殿を引き起こす。本発明者らは、本発明の組成物に含む前にキサンタンガムを脱アセチル化することによって、この問題を克服し得ることを決定した。
例えば、本発明は以下の項目を提供する。
（項目１）
局所用眼用組成物であって、該組成物は、
０．１から０．５ｗ／ｖ％のトブラマイシン；
０．０３から０．１ｗ／ｖ％のデキサメタゾン；
０．３から０．９％の濃度で脱アセチル化キサンタンガムを含む、水性の眼科学的に許容されるビヒクル；および
１つ以上のイオン化可能な種であって、該組成物のインビトロ粘度が６ｓｅｃ −１ のせん断速度および２５℃の温度において１０から７００ｃｐの範囲内に維持されるように、該トブラマイシンおよび該脱アセチル化キサンタンガムの間のイオン性相互作用を制限するのに十分な量の、１つ以上のイオン化可能な種
を含み、
５から６のｐＨを有する、組成物。
（項目２）
前記１つ以上のイオン化可能な種が、無機電解質、有機緩衝剤、およびその組み合わせからなる群より選択される、項目１に記載の組成物。
（項目３）
前記１つ以上のイオン化可能な種が、塩化ナトリウム、塩化カリウム、塩化カルシウム、塩化マグネシウム、硫酸ナトリウム、クエン酸ナトリウム、クエン酸カリウム、リン酸ナトリウム、リン酸カリウム、酢酸ナトリウム、ホウ酸ナトリウム、ホウ酸／マンニトール複合体、ホウ酸／ソルビトール複合体、およびその組み合わせからなる群より選択される、項目２に記載の組成物。
（項目４）
前記イオン化可能な種が、塩化ナトリウム、硫酸ナトリウム、およびその組み合わせからなる群より選択される、項目３に記載の組成物。
（項目５）
前記組成物のインビトロ粘度が、１０から３００ｃｐの範囲内にある、項目１に記載の組成物。
（項目６）
前記組成物が、２５から１７５ｃｐの初期粘度を有する、項目５に記載の組成物。
（項目７）
前記組成物が、０．０１から０．６５のインビトロ／インビボ粘度比を有する、項目６に記載の組成物。
（項目８）
前記１つ以上のイオン化可能な種が、無機電解質、有機緩衝剤、およびその組み合わせからなる群より選択される、項目７に記載の組成物。
（項目９）
前記１つ以上のイオン化可能な種が、塩化ナトリウム、塩化カリウム、塩化カルシウム、塩化マグネシウム、硫酸ナトリウム、クエン酸ナトリウム、クエン酸カリウム、リン酸ナトリウム、リン酸カリウム、酢酸ナトリウム、ホウ酸ナトリウム、ホウ酸／マンニトール複合体、ホウ酸／ソルビトール複合体、およびその組み合わせからなる群より選択される、項目８に記載の組成物。
（項目１０）
前記イオン化可能な種が、塩化ナトリウム、硫酸ナトリウム、およびその組み合わせからなる群より選択される、項目９に記載の組成物。
（項目１１）
前記組成物が、０．３ｗ／ｖ％の濃度のトブラマイシン、０．６ｗ／ｖ％の濃度のキサンタンガム、および０．０５ｗ／ｖ％の濃度のデキサメタゾンを含む、項目１〜１０のいずれか一項に記載の組成物。
（項目１２）
前記組成物のｐＨが、約５．７である、項目１１に記載の組成物。
（項目１３）
感染または感染のリスクのいずれかが存在する、眼の炎症性状態を処置する方法であって、治療上有効な量の項目１に記載の組成物を、罹患した眼に局所付与する工程を含む、方法。
（項目１４）
感染または感染のリスクのいずれかが存在する、眼の炎症性状態を処置する方法であって、治療上有効な量の項目１１に記載の組成物を、罹患した眼に付与する工程を含む、方法。
The invention is also based, in part, on the discovery that xanthan gum is much more effective as a viscosity enhancer in the compositions of the invention when it is at least partially deacetylated. More specifically, xanthan gum undergoes slow deacetylation in aqueous solution. Such deacetylation has been determined to further reduce the pH of the composition, thereby increasing the ionic interaction between tobramycin and dexamethasone. These interactions initially cause a loss of viscosity and ultimately agglomeration and / or precipitation of xanthan gum and tobramycin. The inventors have determined that this problem can be overcome by deacetylating xanthan gum prior to inclusion in the composition of the present invention.
For example, the present invention provides the following items.
(Item 1)
A topical ophthalmic composition comprising:
0.1 to 0.5 w / v% tobramycin;
0.03 to 0.1 w / v% dexamethasone;
An aqueous ophthalmically acceptable vehicle comprising deacetylated xanthan gum at a concentration of 0.3 to 0.9%; and
One or more ionizable species , wherein the tobramycin and the deacetylated species such that the in vitro viscosity of the composition is maintained in the range of 10 to 700 cp at a shear rate of 6 sec −1 and a temperature of 25 ° C. One or more ionizable species in an amount sufficient to limit ionic interactions between the xanthane gum
Including
A composition having a pH of 5 to 6.
(Item 2)
2. The composition of item 1, wherein the one or more ionizable species is selected from the group consisting of an inorganic electrolyte, an organic buffer, and combinations thereof.
(Item 3)
The one or more ionizable species is sodium chloride, potassium chloride, calcium chloride, magnesium chloride, sodium sulfate, sodium citrate, potassium citrate, sodium phosphate, potassium phosphate, sodium acetate, sodium borate, boron Item 3. The composition according to Item 2, selected from the group consisting of acid / mannitol complex, boric acid / sorbitol complex, and combinations thereof.
(Item 4)
4. The composition of item 3, wherein the ionizable species is selected from the group consisting of sodium chloride, sodium sulfate, and combinations thereof.
(Item 5)
The composition of item 1, wherein the in vitro viscosity of the composition is in the range of 10 to 300 cp.
(Item 6)
6. The composition of item 5, wherein the composition has an initial viscosity of 25 to 175 cp.
(Item 7)
7. A composition according to item 6, wherein the composition has an in vitro / in vivo viscosity ratio of 0.01 to 0.65.
(Item 8)
8. The composition of item 7, wherein the one or more ionizable species is selected from the group consisting of an inorganic electrolyte, an organic buffer, and combinations thereof.
(Item 9)
The one or more ionizable species is sodium chloride, potassium chloride, calcium chloride, magnesium chloride, sodium sulfate, sodium citrate, potassium citrate, sodium phosphate, potassium phosphate, sodium acetate, sodium borate, boron 9. The composition of item 8, selected from the group consisting of acid / mannitol complex, boric acid / sorbitol complex, and combinations thereof.
(Item 10)
10. The composition of item 9, wherein the ionizable species is selected from the group consisting of sodium chloride, sodium sulfate, and combinations thereof.
(Item 11)
Items 1-10, wherein the composition comprises tobramycin at a concentration of 0.3 w / v%, xanthan gum at a concentration of 0.6 w / v%, and dexamethasone at a concentration of 0.05 w / v%. A composition according to 1.
(Item 12)
Item 12. The composition according to Item 11, wherein the pH of the composition is about 5.7.
(Item 13)
A method of treating an inflammatory condition of the eye, wherein either an infection or a risk of infection exists, comprising topically applying a therapeutically effective amount of the composition of item 1 to the affected eye. ,Method.
(Item 14)
A method of treating an inflammatory condition of the eye, wherein either an infection or a risk of infection exists, comprising applying a therapeutically effective amount of the composition of item 11 to the affected eye. Method.
Claims (14)
０．１から０．５ｗ／ｖ％のトブラマイシン；
０．０３から０．１ｗ／ｖ％のデキサメタゾン；
０．３から０．９％の濃度で脱アセチル化キサンタンガムを含む、水性の眼科学的に許容されるビヒクル；および
１つ以上のイオン化可能な種であって、該組成物のインビトロ粘度が６ｓｅｃ−１のせん断速度および２５℃の温度において１０から７００ｃｐの範囲内に維持されるように、該トブラマイシンおよび該脱アセチル化キサンタンガムの間のイオン性相互作用を制限するのに十分な量の、１つ以上のイオン化可能な種
を含み、
５から６のｐＨを有する、組成物。 A topical ophthalmic composition comprising:
0.1 to 0.5 w / v% tobramycin;
0.03 to 0.1 w / v% dexamethasone;
An aqueous ophthalmically acceptable vehicle comprising deacetylated xanthan gum at a concentration of 0.3 to 0.9%; and one or more ionizable species, wherein the composition has an in vitro viscosity of 6 sec. An amount of 1 sufficient to limit the ionic interaction between the tobramycin and the deacetylated xanthan gum such that it is maintained in the range of 10 to 700 cp at a shear rate of −1 and a temperature of 25 ° C. Including one or more ionizable species,
A composition having a pH of 5 to 6.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2010/039618 WO2011162752A1 (en) | 2010-06-23 | 2010-06-23 | Topical ophthalmic suspensions containing tobramycin and dexamethasone |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013529632A JP2013529632A (en) | 2013-07-22 |
| JP2013529632A5 true JP2013529632A5 (en) | 2013-08-29 |
| JP5728082B2 JP5728082B2 (en) | 2015-06-03 |
Family
ID=44080140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013516553A Expired - Fee Related JP5728082B2 (en) | 2010-06-23 | 2010-06-23 | Topical ophthalmic suspension containing tobramycin and dexamethasone |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP2585037A1 (en) |
| JP (1) | JP5728082B2 (en) |
| KR (1) | KR20130094280A (en) |
| CN (1) | CN102946855B (en) |
| AU (1) | AU2010356098B2 (en) |
| BR (1) | BR112012033052A2 (en) |
| CA (1) | CA2801731A1 (en) |
| MX (1) | MX2012015051A (en) |
| WO (1) | WO2011162752A1 (en) |
| ZA (1) | ZA201209240B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201208080D0 (en) | 2012-05-09 | 2012-06-20 | Norton Healthcare Ltd | Tobramycin formulation |
| JP6527315B2 (en) * | 2014-08-08 | 2019-06-05 | Ｄｓｐ五協フード＆ケミカル株式会社 | Fast-dissolving thickener, thickener for people with dysphagia and dysphagia, food and drink for patients with dysphagia and dysphagia |
| CN109260219B (en) * | 2018-11-30 | 2021-03-09 | 山东省药学科学院 | Articular cavity injection preparation and application thereof |
| IT202000002296A1 (en) * | 2020-02-06 | 2021-08-06 | Sifi Spa | Topical ophthalmic formulations based on xanthan with reduced dosage |
| IT202200000821A1 (en) * | 2022-01-19 | 2023-07-19 | Sifi Spa | TOPICAL OPHTHALMIC FORMULATIONS BASED ON XANTHANE WITH REDUCED DOSAGE |
| CN115006412B (en) * | 2022-05-20 | 2023-11-10 | 北京诺康达医药科技股份有限公司 | Compound tobramycin eye drops and preparation method thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4136177A (en) | 1977-01-31 | 1979-01-23 | American Home Products Corp. | Xanthan gum therapeutic compositions |
| US5149694A (en) | 1988-03-09 | 1992-09-22 | Alcon Laboratories, Inc. | Combination of tobramycin and dexamethasone for topical ophthalmic use |
| CN1229110C (en) * | 1997-07-29 | 2005-11-30 | 阿尔康实验室公司 | Ophthalmic compositions containing galactomannan polymers and borate |
| ATE245451T1 (en) * | 1998-04-07 | 2003-08-15 | Alcon Lab Inc | YELLOW-FORMING OPHTHALMIC COMPOSITIONS CONTAINING XANTHANG GUM |
| US6174524B1 (en) | 1999-03-26 | 2001-01-16 | Alcon Laboratories, Inc. | Gelling ophthalmic compositions containing xanthan gum |
| US6261547B1 (en) | 1998-04-07 | 2001-07-17 | Alcon Manufacturing, Ltd. | Gelling ophthalmic compositions containing xanthan gum |
| EP1305033B1 (en) | 2000-07-28 | 2004-10-20 | Alcon, Inc | Pharmaceutical compositions containing tobramycin and xanthan gum |
-
2010
- 2010-06-23 CA CA2801731A patent/CA2801731A1/en not_active Abandoned
- 2010-06-23 BR BR112012033052A patent/BR112012033052A2/en not_active IP Right Cessation
- 2010-06-23 MX MX2012015051A patent/MX2012015051A/en active IP Right Grant
- 2010-06-23 CN CN201080067666.9A patent/CN102946855B/en not_active Expired - Fee Related
- 2010-06-23 EP EP10726406.1A patent/EP2585037A1/en not_active Withdrawn
- 2010-06-23 JP JP2013516553A patent/JP5728082B2/en not_active Expired - Fee Related
- 2010-06-23 AU AU2010356098A patent/AU2010356098B2/en not_active Ceased
- 2010-06-23 KR KR1020137000258A patent/KR20130094280A/en active IP Right Grant
- 2010-06-23 WO PCT/US2010/039618 patent/WO2011162752A1/en active Application Filing
-
2012
- 2012-12-06 ZA ZA2012/09240A patent/ZA201209240B/en unknown
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