WO2011031402A1 - Stable hyaluronan/steroid formulation - Google Patents
Stable hyaluronan/steroid formulation Download PDFInfo
- Publication number
- WO2011031402A1 WO2011031402A1 PCT/US2010/044975 US2010044975W WO2011031402A1 WO 2011031402 A1 WO2011031402 A1 WO 2011031402A1 US 2010044975 W US2010044975 W US 2010044975W WO 2011031402 A1 WO2011031402 A1 WO 2011031402A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- harc
- tah
- control
- syringe
- Prior art date
Links
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
- A61K31/58—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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
- A61K31/728—Hyaluronic acid
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- 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
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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]
Definitions
- This invention is in the general field of compositions and methods comprising hyaluronic acid (HA) or an HA-related component (collectively "HARC”), for example pharmaceutical compositions, devices and methods for treating various medical conditions.
- HA hyaluronic acid
- HAC HA-related component
- Hyaluronic acid has many medical uses, and various HARCs have been developed.
- HARC includes hyaluronic acid itself (including HA from living sources such as avian or bacterial sources), as well as hyaluronic acid salts and derivatives of the foregoing, including polymerized gels, cross-linked gels, and derivatized hyaluronic acid.
- HARCs may be administered by themselves, for example to provide relief from arthritis. They also may be mixed with anti-inflammatory steroids. Lyons
- US2006/0141049 discloses pharmaceutical compositions containing triamcinolone acetonide and hyaluronate. Yu et al., Osteoarthritis and Cartilage vol. 12, Supp. B, P350 at page SI 44 (2004) discloses an in vitro evaluation of hylan G-F 20 diluted with a corticosteroid (triamcinolone acetonide) suspension.
- HARCs When used in a medical product HARCs typically are sterilized by heating, autoclaving, chemical treatment or filtration. Often it is important to maintain the viscoelastic properties of the HARC. Sterilization techniques may alter viscoelastic properties or make it difficult to control or maintain the stability of those properties. Sterilization may decrease the shelf life of the product.
- HARCs are heat sterilized before forming a steroid/HARC mixture. Sterility of the final mixture may be achieved by filtration of the steroid solution before it is mixed with the HARC.
- TAH triamcinolone hexacetonide
- composition comprising in admixture a hyaluronic acid related component (HARC) and a pharmaceutically effective amount of triamcinolone hexacetonide (TAH).
- HAC hyaluronic acid related component
- TAH triamcinolone hexacetonide
- the % change of one or more viscoelastic properties should be no more than ⁇ 10% as compared to the comparable change in the control HARC (without TAH);
- the change in the composition pH should be no more than 0.5 pH unit;
- the change in osmolarity should be less than 10% (more preferably less than 5%) different from the change in osmolarity of the control HARC;
- the steroid should retain at least 90% (more preferably at least 95%) of its chemical integrity— i.e., there is less than 10% (more preferably less than 5%) chemical degradation— as determined by recovery data. Examples of suitable protocols for shelf- life and other tests are provided below.
- the composition can be heat sterilized.
- the composition is stable in a simulated autoclave conditions with approximate 30 F 0 , in which the composition is heated at 121°C for 30 min in a oil bath.
- the %> change of G ⁇ viscosity ( ⁇ ) or phase angle ( ⁇ ) should be no more than 20% different (more preferably no more than 15% different) from the control (HARC without TAH);
- the HARC component includes both a cross- linked HARC gel and an HARC fluid component.
- the combination has a gel: fluid ratio between 80% and 20%, more preferably between 65% and 35%.
- HARCs may be used, including Orthovisc®, Mono viseTM, CingalTM, and ElevessTM dermal filler (all from Anika Therapeutics), Adant, Arthrease, Arthrum, Durolane, Fermathron, Go-on, Hya-ject, Hyalgan/Hyalart, Hyalubrix, Hy-GAG, Ostenil, Sinovial, Supartz/Artz, Suplasyn, Synochrom, Viscorneal, Enflexxa, and Gel-eo.
- Orthovisc® Mono viseTM
- CingalTM CingalTM
- ElevessTM dermal filler all from Anika Therapeutics
- Adant Adant
- Arthrease Arthrum
- Durolane Fermathron
- Go-on Hya-ject
- Hyalgan/Hyalart Hyalubrix
- Hy-GAG Hy-GAG
- Ostenil Sinovial
- Supartz/Artz Suplasyn
- one ml of the composition includes at least 5 mg HA, when measured by standard procedures such as acid degradation followed by a determination of the HA free acid.
- the composition has a viscosity and an extrusion force that enable its use in a syringe. For example, it is delivered from a 5cc syringe with a needle size of 20G-1.5" with an extrusion force of less than 30 Newtons.
- the viscosity is between 20 Pas and 100 Pas.
- the gel component may be divinyl sulfone (DVS) cross-linked hyaluronic acid.
- DVD divinyl sulfone
- composition may be packaged in a syringe for delivery to a patient and it has a sterility assurance level (SAL) suitable for human administration.
- SAL sterility assurance level
- the composition includes a surfactant, such as Polysorbate 80, Polysorbate 20, Pluronic F-127, Pluronic F-68 or other physiologically suitable surfactants.
- a surfactant such as Polysorbate 80, Polysorbate 20, Pluronic F-127, Pluronic F-68 or other physiologically suitable surfactants.
- the stability provided by the invention enables a longer shelf life at room temperature so that the mixture may be stored after heat sterilization.
- the sterilized mixture can be packaged and stored (e.g., in a syringe) for later use.
- another aspect of the invention features a package containing a syringe filled with the sterilized pharmaceutical composition.
- the invention also provides more efficient manufacturing methods, and another aspect of the invention can be generally stated as a method of making the above described sterilized pharmaceutical composition by mixing the HARC with the TAH, and subjecting the mixture to heat sterilization. The sterilized mixture is then stored under sterile conditions.
- the invention may be used in a method of treating a patient for joint disease by using the syringe to administer the pharmaceutical composition into a joint of the patient.
- Administration may be by standard injection, by introduction on-site during arthroscopic surgery or open-knee surgery.
- FIG. 1 shows the structure of TAH.
- FIGS. 2a and 2b plot the change in elastic modulus after an accelerated shelf-life test (2a) and after sterilization (2b) for various HA / steroid formulations.
- FIGS. 3a and 3b show the relative % of steroid recovery after heat treatment of various formulations.
- One embodiment of the invention combines: a) a cross linked HA-gel; b) a modified or unmodified HA fluid and c) the insoluble steroid triamcinolone hexacetonide (TAH).
- TAA insoluble steroid triamcinolone hexacetonide
- formaldehyde, glutaraldehyde, glyoxal (US 4,713,448); 1,4 butane diol diglycidylether (BDDE) 1,4-butane diol diglycidylether (BDDE), 1 ,2-ethandioldiglycidylether (EDDE), l-(2,3-epoxypropyl)- 2,3,epoxycyclohexane, ⁇ , ⁇ -diglycidylaniline, epoxysubstituted pentaerythritol (US Pat. No.
- Formulations according to the invention are stable to an autoclave sterilization process. Additionally, the formulations are stable when subjected to accelerated stability tests such as a simulated two-year room temperature storage condition. Stability (as determined by rheology) of triamcinolone hexacetonide / viscosupplement combinational formulations compare favorably with formulations that replace the triamcinolone hexacetonide with a very similar steroid, triamcinolone acetonide (TAA). These two steroids are very similar chemically and a significant difference in stability would not be predicted.
- TAA triamcinolone acetonide
- Formulations were also evaluated after heating at 80°C for 24 hours (simulated two year room temperature shelf-life).
- Viscosupplements containing triamcinolone hexacetonide generally exhibited stability comparable to a viscosupplement control (the same formulation with no steroid) within the limits described.
- Other steroid / viscosupplement combinations we tested demonstrated a decrease in HA stability as determined by rheology.
- ⁇ %X heat (HARC/Steroid) - %X heat (HARC/Ctrl);
- TAH formulations behaved comparably to control formulations having no steroid.
- Other steroid formulations we tested either: a) (in the case of triamcinolone acetonide, methyl prednisolone acetate, and betamethasone phosphate) exacerbated degradation of HARC properties after heat treatment, or b) (in the case of betamethasone acetate) interacted with HARC.
- the change in elastic modulus for different HA viscosupplement / steroid formulations are plotted in Figures 2a & 2b. Based on these experiments, we conclude that the TAH/HARC composition generally maintains a suitable level of stability when compared to the nonsteroidal control. pH and Osmolality
- ⁇ %X hea t(HARC/Steroid) - %X hea t(HARC/Ctrl)
- %X heat 100% * X(post-heat) / X(pre-heat);
- Table 3b Steroids' stability study for hylastan SGL-80/steroid formulations (heat treatment)
- viscosuplement combinational formulations are stable while the triamcinolone acetonide / viscosupplement formulations are not stable based on the rheology evaluation. These two steroids are very similar chemically and large difference in stability would not be predicted.
- composition will be a homogeneous colloidal suspension of triamcinolone hexacetonide, USP combined with an HA-based viscosupplement.
- the physical appearance will be a milky white viscous fluid.
- Product will be supplied sterile in a prefilled syringe (e.g, 5 mL with a 5 mL product fill).
- Gen-S 1023-75 is a mixture of TAH (Triamcinolone Hexacetonide) with a HA based viscosupplement.
- the viscosupplement was made with DVS modified HA gel (AVS-gel) and unmodified HA fluid at 65 :35 ratio of fluid.
- Gen-S 1023-75 contained about 8 mg/ml TAH (lot#2196), 0.35 mg/ml Tween-80 (Lot#E35595), 6.5mg/ml of HA/DVS gel (lot#EX0848) and 3.5mg/ml of unmodified HA.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Infusion, Injection, And Reservoir Apparatuses (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10815804.9A EP2475251B1 (en) | 2009-09-10 | 2010-08-10 | Stable hyaluronan/steroid formulation |
CN201080043915.0A CN102573468B (en) | 2009-09-10 | 2010-08-10 | Stable hyaluronan/steroid formulation |
MX2012002830A MX2012002830A (en) | 2009-09-10 | 2010-08-10 | Stable hyaluronan/steroid formulation. |
EP19186507.0A EP3622820A1 (en) | 2009-09-10 | 2010-08-10 | Stable hyaluronan/steroid formulation |
JP2012528801A JP6121717B2 (en) | 2009-09-10 | 2010-08-10 | Stable hyaluronan / steroid combination |
BR112012005423-6A BR112012005423B1 (en) | 2009-09-10 | 2010-08-10 | PHARMACEUTICAL COMPOSITION COMPRISING A COMPONENT RELATED TO HYALURONIC ACID, SYRINGE AND METHOD FOR ITS MANUFACTURING |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/556,869 US8273725B2 (en) | 2009-09-10 | 2009-09-10 | Stable hyaluronan/steroid formulation |
US12/556,869 | 2009-09-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2011031402A1 true WO2011031402A1 (en) | 2011-03-17 |
Family
ID=43648224
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2010/044975 WO2011031402A1 (en) | 2009-09-10 | 2010-08-10 | Stable hyaluronan/steroid formulation |
Country Status (8)
Country | Link |
---|---|
US (2) | US8273725B2 (en) |
EP (2) | EP3622820A1 (en) |
JP (2) | JP6121717B2 (en) |
CN (1) | CN102573468B (en) |
AR (1) | AR078281A1 (en) |
BR (1) | BR112012005423B1 (en) |
MX (1) | MX2012002830A (en) |
WO (1) | WO2011031402A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014110454A1 (en) * | 2013-01-11 | 2014-07-17 | Carbylan Biosurgery, Inc. | Stabilized compositions comprising hyaluronic acid |
US8946305B2 (en) | 2011-12-22 | 2015-02-03 | Industrial Technology Research Institute | Method for crosslinking a colloid, and crosslinked colloid therefrom |
EP2699274B1 (en) | 2011-04-20 | 2015-03-04 | Carbylan Therapeutics, Inc. | In-situ gel forming compositions |
Families Citing this family (6)
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CA2633978A1 (en) | 2005-12-14 | 2007-06-21 | Anika Therapeutics, Inc. | Bioabsorbable implant of hyaluronic acid derivative for treatment of osteochondral and chondral defects |
EP2459239A1 (en) | 2009-07-30 | 2012-06-06 | Carbylan Biosurgery, Inc. | Modified hyaluronic acid polymer compositions and related methods |
IT201600075246A1 (en) * | 2016-07-19 | 2018-01-19 | Jointherapeutics S R L | Compositions comprising a polysaccharide matrix for the controlled release of active principles. |
CN106983733A (en) * | 2017-03-08 | 2017-07-28 | 江苏富泽药业有限公司 | Triamcinolone acetonide PLGA sustained-release microspheres injections, its preparation method and its application in treatment osteo-arthritic pain medicine is prepared |
KR20190038368A (en) | 2017-09-29 | 2019-04-08 | 주식회사 엘지화학 | Hyaluronic acid-based hydrogel pharmaceutical stablized composition and method for preparing the same |
CN118021719A (en) * | 2022-11-11 | 2024-05-14 | 北京华视诺维医疗科技有限公司 | Triamcinolone acetonide composition and preparation method thereof |
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-
2010
- 2010-08-10 JP JP2012528801A patent/JP6121717B2/en active Active
- 2010-08-10 WO PCT/US2010/044975 patent/WO2011031402A1/en active Application Filing
- 2010-08-10 EP EP19186507.0A patent/EP3622820A1/en active Pending
- 2010-08-10 EP EP10815804.9A patent/EP2475251B1/en active Active
- 2010-08-10 CN CN201080043915.0A patent/CN102573468B/en active Active
- 2010-08-10 MX MX2012002830A patent/MX2012002830A/en active IP Right Grant
- 2010-08-10 BR BR112012005423-6A patent/BR112012005423B1/en active IP Right Grant
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2012
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See also references of EP2475251A4 |
YU ET AL., OSTEOARTHRITIS AND CARTILAGE, vol. 12, 2004, pages SI44 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2699274B1 (en) | 2011-04-20 | 2015-03-04 | Carbylan Therapeutics, Inc. | In-situ gel forming compositions |
US9492383B2 (en) | 2011-04-20 | 2016-11-15 | Carbylan Therapeutics, Inc. | Rapid in-situ gel forming compositions prepared via reaction of vinyl sulfone derivatized hyaluronic acid with thiol derivatized polyethylene glycol at alkaline pH |
US8946305B2 (en) | 2011-12-22 | 2015-02-03 | Industrial Technology Research Institute | Method for crosslinking a colloid, and crosslinked colloid therefrom |
WO2014110454A1 (en) * | 2013-01-11 | 2014-07-17 | Carbylan Biosurgery, Inc. | Stabilized compositions comprising hyaluronic acid |
JP2016506909A (en) * | 2013-01-11 | 2016-03-07 | カービラン セラピューティクス, インコーポレイテッド | Stabilized composition comprising hyaluronic acid |
AU2014205213B2 (en) * | 2013-01-11 | 2017-09-21 | Carbylan Therapeutics, Inc. | Stabilized compositions comprising hyaluronic acid |
Also Published As
Publication number | Publication date |
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CN102573468B (en) | 2015-05-20 |
EP2475251A4 (en) | 2012-10-24 |
US8680073B2 (en) | 2014-03-25 |
US20110059918A1 (en) | 2011-03-10 |
EP2475251B1 (en) | 2019-07-17 |
JP2013504570A (en) | 2013-02-07 |
EP3622820A1 (en) | 2020-03-18 |
BR112012005423A2 (en) | 2017-07-04 |
EP2475251A1 (en) | 2012-07-18 |
CN102573468A (en) | 2012-07-11 |
US8273725B2 (en) | 2012-09-25 |
US20120316131A1 (en) | 2012-12-13 |
JP6121717B2 (en) | 2017-04-26 |
MX2012002830A (en) | 2012-04-10 |
BR112012005423B1 (en) | 2022-09-13 |
AR078281A1 (en) | 2011-10-26 |
JP2015172095A (en) | 2015-10-01 |
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