WO1997026015A1 - Sustained release drug formulations - Google Patents
Sustained release drug formulations Download PDFInfo
- Publication number
- WO1997026015A1 WO1997026015A1 PCT/IB1997/000014 IB9700014W WO9726015A1 WO 1997026015 A1 WO1997026015 A1 WO 1997026015A1 IB 9700014 W IB9700014 W IB 9700014W WO 9726015 A1 WO9726015 A1 WO 9726015A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- polymer
- drug
- formulation according
- formulation
- Prior art date
Links
Classifications
-
- 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
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- 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
- 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
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
Definitions
- Biodegradable polymer sustained release formulations have been used to administer drugs over a prolonged period of time. See, e.g., U.S. Patent Nos. 3,773,919 and 4,767,628. These formulations are generally in the form of solid cylindrical implants, microcapsules, or microspheres. Solid implants require incisions in the patient which often are quite painful, resulting in poor patient compliance. Solid microcapsules and microspheres, which are injected into the patient, are often difficult to reproducibly manufacture and, thus, can give varying release profiles. Also, microcapsules and microspheres require lyophilization in order to avoid agglomerization of the particles during storage and large needles for injection.
- the invention features a sustained release drug formulation which includes: a drug; a biodegradable polymer insoluble in water (i.e., less than 0.01 mg/ml at
- an oil vehicle containing 10-100% by volume a pharmaceutically acceptable and biodegradable oil and 0- 90% by volume a pharmaceutically acceptable liquid carrier.
- the drug and the biodegradable polymer are dissolved in the oil vehicle.
- the amount of a drug dissolved in an oil vehicle depends on its solubility, and may range from 1 to 500 mg per ml of the oil vehicle.
- the drug can be a peptide, e.g., somatostatin, luteinizing hormone-releasing hormone
- LHRH growth hormone releasing peptide
- bo besin growth hormone releasing peptide
- gastrin releasing peptide gastrin releasing peptide
- calcitonin bradykinin
- CONFIRMATIONCOPT galanin melanocyte stimulating hormone, growth hormone releasing factor, amylin, adrenomedullin, tachykinins, secretin, parathyroid hormone, enkephalin, endotheiin, calcitonin gene releasing peptide, neuromedins, parathyroid hormone related protein, glucagon, neurotensin, adrenocorticotrophic hormone, peptide YY, glucagon releasing peptide, vasoactive intestinal peptide, pituitary adenylated cyclase activating peptide, motilin, substance P, neuropeptide Y, thyrotropin stimulating hormone, and analogs and fragments thereof.
- the drug can also be a steroid. Examples of a steroid drug include, but are not limited to, 17-?-hydroxy oestradiol and progesterone.
- the drug can be provided in the form of pharmaceutically acceptable salts.
- such salts include, but are not limited to, those formed with organic acids (e.g., acetic, lactic, maleic, citric, malic, ascorbic, succinic, benzoic, methanesulfonic, toluenesulfonic, or pamoic acid) , inorganic acids (e.g. , hydrochloric acid, sulfuric acid, or phosphoric acid) , polymeric acids (e.g., tannic acid, carboxymethyl cellulose, polylactic, polyglycolic, or copolymers of polylactic-glycolic acids) .
- organic acids e.g., acetic, lactic, maleic, citric, malic, ascorbic, succinic, benzoic, methanesulfonic, toluenesulfonic, or pamoic acid
- inorganic acids e.g. , hydrochloric acid, sulfuric acid, or
- a suitable biodegradable polymer to be used to practice this invention is a polyester.
- monomers used to form such a polyester include, but are not limited to, e-caprolactone, lactic acid, glycolic acid, e-caprolic acid, p-dioxanone, e-caprionic acid, l,5-dioxepan-2-one, l,4-dioxepan-2-one, alkylene oxylate, cycloalkylene, cycloalkylene oxylate, alkylene succinate, and 3-hydroxy butyrate, .
- any optically active isomers or racemates can be used.
- the polyester can be a copolymers prepared from two or more different monomers.
- the biodegradable polymer may be a liquid, or have a glass transition temperature or a melting temperature up to 200°C. It may have a molecular weight (averaged) of 500-150,000 daltons, preferably, 1,000-75,000 daltons. Polymers with higher molecular weights slow down the release of the drug from the formulation. Generally speaking, 1-500 mg (preferably, 15-300 mg) of the polymer can be dissolved in 1 ml of the oil vehicle.
- Examples of a biodegradable oil, an essential component of the oil vehicle include oils derived from plants (e.g., corn oil, coconut oil, linseed oil, olive oil, palm oil, sunflower seed oil, cottonseed oil, peanut oil, sesame oil, or castor oil), animals (e.g., sardine oil, cod-liver oil, whale oil, sperm oil), paraffin oil, or triglyceride derivatives such as miglyol (Labafac, Gattefusse, Lyon, France) , or mixtures thereof.
- the oil vehicle may also contain one or more pharmaceutically acceptable liquid carriers, e.g., solvents of either the drug or the polymer such as water and ethanol.
- a pharmaceutically acceptable liquid ester or polyether may be added to the oil vehicle to aid in the dissolution of the drug or the polymer into the oil vehicle.
- suitable esters include benzyl benzoate (which can assist the dissolution of the polymer such as a polyester), or polyethylene glycol, e.g., PEG 400 (which can assist the dissolution of the drug such as a peptide).
- the ester or polyether may constitute 0.1- 90% by volume of the oil vehicle.
- the oil vehicle may also include a pharmaceutically acceptable surfactant in order to clarify the formulation.
- suitable surfactants include polysorbates (e.g., TWEEN 80 or SPAN 80) .
- an oil vehicle herein is a water-immiscible medium in which a drug and a biodegradable polymer are dissolved. It contains at least an oil and may also contain a liquid carrier for the drug or polymer, a liquid ester or polyether, or a surfactant. Sterilization of formulations may be assured by microfiltration. This specialized technique, which is for low viscosity liquid formulations labile to heat or other sterilization methods, depends upon the physical removal of microorganisms by adsorption onto a filter or sieve mechanism. The separation of microorganisms from the filtrate may involve interactions associated with electrostatic forces or mechanical sieving by the size, shape, and tortuousness of the voids. Examples of filters for achieving sterility have a nominal porosity of 0.22 ⁇ m.
- the formulations of the invention may be stored at 4°C sheltered from sunlight.
- compositions of the present invention may be distributed into the systemic circulation by parenteral, e.g. , intramuscular or subcutaneous, administration, oral, ophthalmic, nasal, or pulmonary administration.
- parenteral e.g. , intramuscular or subcutaneous, administration, oral, ophthalmic, nasal, or pulmonary administration.
- the biodegradable polymer was a copolymer comprising 50% by weight D, -lactic acid and 50% by weight glycolic acid (“50/50 PLGA”) and having an average molecular weight between 20,000 and 30,000 daltons, and was synthesized using standard methods known in the art. See, e.g., U.S. Patent Nos. 2,703,316 or 2,758,987.
- Example 2 The formulation prepared by the procedures described above in Example 1 was poured into a vial containing 20 ml of saline. Again, the dye was contained within the congealed globules, and was slowly released into the surrounding saline upon the addition of 3 ml of methylene chloride.
- the formulation was dispersed into a vial containing distilled water, and the vial was agitated.
- the formulation emulsified as globules in the vial.
- the globules had a mean diameter of 60 nM.
- High performance liquid chromatography revealed virtually no degradation of the LHRH agonist during the formulation process.
- Example 3 The formulation described in Example 3 was injected into Wistar rats (IFFA Credo, St. Germain Sur L'Arbesle, France) at a dose of 400 ⁇ g of peptide per kg weight of rat.
- Plasma levels of testosterone were determined from blood samples collected at different days by sinus retroorbital taking. 50 ⁇ l of blood sample, 200 ⁇ l of ⁇ 125 testosterone, and 200 ⁇ l of antiserum were poured into tubes which were shaken and incubated during 24 hours at 37°C.
- the immuno- precipitant reagent propanol (1 ml) was added in each tube, and all the tubes were incubated 15 minutes at room temperature. The supernatant was eliminated after centrifugation, and radioactivity was measured with a multigamma counter LKB-WALLAC Model 1261 (LKB, Les Ulis, France) .
- Example 3 The above synthetic protocol in Example 3 was performed with the exception that 62 mg of the insoluble pamoate salt of TriptorelinTM dissolved in 1 ml of ethanol was used instead of 51 mg of the acetate salt of TriptorelinTM dissolved in 0.1 ml of water and 0.9 ml of - 8 - ethanol.
- the resulting formulation was injected into Wistar rats at a concentration of 400 ⁇ g/kg as performed in Example 4.
- the data is presented in Table II.
- the formulation slowly released the LHRH agonist over a period of at least 17 days.
- Example 6 The formulation described in Example 6 was intramuscularly injected into Wistar rats at a dose of 6 g of peptide per kg weight of rat. Blood for peptide analysis was collected into aprotinine tubes to avoid any peptide degradation (Laboratoire CHOAY, Gentilly, France) . Samples were centrifuged immediately and the plasma separated and stored at -20°C until radioimmunoassay ("RIA") to determine the amounts of the drug (ng/ml) . RIA had been developed after immunization of rabbits with peptide conjugated to bovine serum albumin to obtain a specific antibody. Iodine 125 has been used to label LANREOTIDE.
- the data is presented in Table III.
- the formulation slowly released LANREOTIDE over a period of at least 12 days.
- Example 6 The above synthetic protocol in Example 6 was performed with the exception that 365 mg of the acetate salt of LANREOTIDE dissolved in 0.1 ml of water and 0.9 ml of ethanol was used instead of 388 mg of the pamoate salt of LANREOTIDE dissolved in 1 ml of ethanol.
- This formulation was injected into Wistar rats at a dose of 6 ⁇ g/kg and RIA performed in the manners as described in Example 7. The data is presented in Table IV. The formulation slowly released the peptide over a period of at least 14 days.
- Example 9 10 ml of PEG 400 and 8 ml of benzyl benzoate were added to and mixed within a 100 ml beaker. l g of 50/50 PLGA copolymer having an average molecular weight of 40,000 to 50,000 was added to the same beaker and dissolved by heating the beaker to 60°C while stirring. The beaker was then cooled. 200 mg of the steroid 179- hydroxy-oestradiol was then added to and mixed within the beaker. 4 ml of castor oil was then slowly added to and mixed within the same beaker.
- Example 10 10 ml of PEG 400 and 8 ml of benzyl benzoate were added to and mixed within a 100 ml beaker. l g of 50/50 PLGA copolymer having an average molecular weight of 40,000 to 50,000 was added to the same beaker and dissolved by heating the beaker to 60°C while stirring. The beaker was then cooled.
- Example 9 The formulation described in Example 9 was intramuscularly injected into Wistar rats at a dose of 4 mg/kg.
- the concentration of the steroid was determined using an EIA (enzymoimmunoassay) kit (Cayman Chemical, SPI-BIO, Massay, France) .
- the data is presented in Table V.
- the formulation slowly released the 17?-hydroxy- oestradiol over a period of at least 11 days.
- Example 12 The formulation in Example 12 was injected into Wistar rats at a dose of 4 ⁇ g/kg.
- concentration of the steroid (ng/ml plasma) was determined using an EIA kit (Cayman Chemical, SPI-BIO, Massay, France) .
- the data is presented in Table VI.
- the formulation slowly released progesterone over a period of at least 11 days.
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU12064/97A AU1206497A (en) | 1996-01-16 | 1997-01-15 | Sustained release drug formulations |
DE69721481T DE69721481T2 (en) | 1996-01-16 | 1997-01-15 | DELAYED RELEASE ACTIVE SUBSTANCE FORMULATIONS |
EP97900072A EP0874642B1 (en) | 1996-01-16 | 1997-01-15 | Sustained release drug formulations |
CA002242986A CA2242986C (en) | 1996-01-16 | 1997-01-15 | Sustained release drug formulations |
DK97900072T DK0874642T3 (en) | 1996-01-16 | 1997-01-15 | Delayed-release drug formulations |
AT97900072T ATE238813T1 (en) | 1996-01-16 | 1997-01-15 | SUSTAINED RELEASE ACTIVE FORMULATIONS |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/584,320 | 1996-01-16 | ||
US08/584,320 US5980945A (en) | 1996-01-16 | 1996-01-16 | Sustained release drug formulations |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997026015A1 true WO1997026015A1 (en) | 1997-07-24 |
Family
ID=24336839
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB1997/000014 WO1997026015A1 (en) | 1996-01-16 | 1997-01-15 | Sustained release drug formulations |
Country Status (10)
Country | Link |
---|---|
US (1) | US5980945A (en) |
EP (1) | EP0874642B1 (en) |
AT (1) | ATE238813T1 (en) |
AU (1) | AU1206497A (en) |
CA (1) | CA2242986C (en) |
DE (1) | DE69721481T2 (en) |
DK (1) | DK0874642T3 (en) |
ES (1) | ES2197982T3 (en) |
PT (1) | PT874642E (en) |
WO (1) | WO1997026015A1 (en) |
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Also Published As
Publication number | Publication date |
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EP0874642B1 (en) | 2003-05-02 |
EP0874642A1 (en) | 1998-11-04 |
PT874642E (en) | 2003-09-30 |
CA2242986A1 (en) | 1997-07-24 |
CA2242986C (en) | 2004-09-21 |
ES2197982T3 (en) | 2004-01-16 |
AU1206497A (en) | 1997-08-11 |
DE69721481T2 (en) | 2004-04-15 |
DK0874642T3 (en) | 2003-08-11 |
DE69721481D1 (en) | 2003-06-05 |
US5980945A (en) | 1999-11-09 |
ATE238813T1 (en) | 2003-05-15 |
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