US20040234472A1 - Micellar drug delivery systems for hydrophobic drugs - Google Patents

Micellar drug delivery systems for hydrophobic drugs Download PDF

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US20040234472A1
US20040234472A1 US10/475,453 US47545304A US2004234472A1 US 20040234472 A1 US20040234472 A1 US 20040234472A1 US 47545304 A US47545304 A US 47545304A US 2004234472 A1 US2004234472 A1 US 2004234472A1
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composition
molecular weight
water soluble
hydrophobic
polymer
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John Jackson
Jason Zastre
Helen Burt
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University of British Columbia
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Assigned to UNIVERSITY OF BRITISH COLUMBIA, THE reassignment UNIVERSITY OF BRITISH COLUMBIA, THE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ZASTRE, JASON, BURT, HELEN M., JACKSON, JOHN K.
Publication of US20040234472A1 publication Critical patent/US20040234472A1/en
Priority to US11/296,184 priority patent/US20060189785A1/en
Priority to US12/193,648 priority patent/US7875677B2/en
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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
    • A61K9/0012—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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
    • 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
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • 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
    • 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
    • A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • This invention relates to micellar compositions for drug formulation and drug delivery.
  • micellar formulations are expected to achieve some level of circulation concentration of the drug without precipitation of the drug in the bloodstream.
  • the principle behind micelle formation is that amphiphatic molecules can form aggregates in an aqueous environment whereby hydrophobic components of the molecules come together to exclude water and make up the inner core of the micelle.
  • the hydrophilic components of the molecules are orientated towards the outside of the micelle. This aggregation occurs above the critical micelle concentration (CMC) of the molecules in water.
  • CMC critical micelle concentration
  • hydrophobic drugs may be solubilized in the inner hydrophobic core of micelles during their formation.
  • hydrophobic drugs such as methotrexate, indomethacin, paclitaxel and doxorubicin into micelles made from biocompatible, amphipathic polymeric molecules (e.g. U.S. Pat. No. 6,322,805; Kim S Y et al. J. Controlled Release (1998) 56:13-22; Inoue T et al. J. Controlled Release (1998) 51:221; and, Kataoka K. J Controlled Release (2000) 64:143-153).
  • hydrophobic drugs such as methotrexate, indomethacin, paclitaxel and doxorubicin into micelles made from biocompatible, amphipathic polymeric molecules
  • micellar compositions are typically made by dissolving a hydrophobic drug in a water miscible organic solvent in which the drug is soluble, combining the resulting solution with a micellar composition in an aqueous solution with mixing by vigorous stirring, agitation, or sonication. For example, the mixture might be stirred for up to about 24 hours and any remaining drug not incorporated into micelles then removed.
  • micellar solution may then be used directly for administration or freeze-dried into nanoparticles (which may be resuspended in water at a later time) providing the solvent is biocompatible and/or is capable of being removed by freeze-drying or other methods.
  • These methods are complicated, expensive, and expose potentially water labile drugs to long periods in aqueous media.
  • U.S. Pat. No. 4,745,160 (Churchill J. R. et al.) teaches a process for manufacturing micelle compositions from biodegradable amphipathic copolymers.
  • the patent teaches that in order to incorporate a hydrophobic drug it is necessary to dissolve the drug in a water miscible organic solvent such as dioxan, acetic acid, acetonitrile, methanol or ethanol.
  • U.S. Pat. No. 5,510,103 (Yokoyama M. et al.) and U.S. Pat. No. 5,939,453 (Heller J. et al.) describe micelles made of block copolymers in which hydrophobic drugs are physically trapped.
  • the disclosed methods of trapping require heating, ultrasonication, and/or the use of organic solvents and dialysis.
  • U.S. Pat. No. 6,136,846 (Rubinfeld J. et al.) describes incorporation of paclitaxel into micelles made from amphipathic block copolymers in which the hydrophobic block is a lipid tail.
  • Organic solvents are used but the patent also teaches that polyethylene glycol (PEG) of 300-400 molecular weight may be used as the “solubilizer”.
  • PEG polyethylene glycol
  • This aspect of the invention provides a micelle forming composition comprising:
  • a second aspect of the invention results from the discovery that a micellar composition comprising a biocompatible micelle forming polymer; a biocompatible, low molecular weight water soluble polymer; and, a hydrophobic drug, may be formulated as a semi-solid material (e.g. a wax like substance or a paste) capable of being injected into a patient and which will spontaneously form drug containing micelles at the site of deposition of the material in the patient.
  • the water soluble polymer may be one that is liquid or semi-solid at about room temperature (e.g. at about 20-30° C.).
  • This aspect of the invention has the advantage of providing short to medium term localization of a drug at a specific site of injection in a patient, with the drug being released inside micelles to the physiological environment of the site and ultimately to the bloodstream.
  • This aspect of the invention includes compositions comprising a hydrophobic drug, a biocompatible micelle forming polymer and a sufficient amount of a biocompatible low molecular weight water soluble polymer such that the composition is a semi-solid (e.g. a “paste”) at temperatures at or about room temperature and is injectable through a syringe.
  • This aspect of the invention provides a micelle forming composition comprising:
  • This invention also provides methods for using the aforementioned compositions to form micelles in vitro and in vivo.
  • In vivo methodologies include injection of the composition to a site in a patient's body where drug containing micelles are formed at the site.
  • This invention also provides injection devices such as a syringe containing a micelle forming composition according to this invention.
  • FIG. 1 is a graph showing size distribution micelles with a peak at a particle size diameter of approximately 10 nm. Size distribution was measured on a Zetasizer 3000HS at a temperature of 25 C, at a count rate of 12.0 kCps, with a detector angle of 90.00 and at a wavelength of 633.0.
  • “Micelle forming polymer” as used herein refers to an amphipathic polymer that is comprised of both a hydrophilic and a hydrophobic component and which is capable of forming micelles in water. Numerous examples are known and are disclosed in the art. Micelle forming polymers include block (e.g. diblock) copolymers comprising a hydrophobic block and a hydrophilic block such as are disclosed in the prior art documents referred to above and in WO01/87345. The micelle forming polymers known in the art that are employed in this invention are those that are biocompatible and thus pharmaceutically suitable. Such is the case for the specific polymers disclosed herein.
  • a “hydrophobic drug,” is a water insoluble drug.
  • a “drug” is a therapeutically active substance which is delivered to a living subject to produce a desired effect, such as to treat a condition of the subject.
  • a drug is also provided to a subject prophylactically to prevent the development of a condition or to decrease the severity of a condition that the subject may develop.
  • a “water insoluble drug” has a solubility of less than 0.1 mg/mL in distilled water at 250C.
  • a “slightly soluble drug” (solubility: 1-10 mg/mL) and a “very slightly soluble drug” (solubility: 0.1-1 mg/mL) may also be referred to.
  • hydrophobic drugs include the following agents including their water soluble derivatives and analogs:
  • Amphotericin used for the treatment or prevention of infection of an open wound by topical administration or for the treatment or prevention of an infection in an exposed wound after surgery by local application.
  • Amphotericin is an antifungal and is insoluble in water at pH 6 to 7 (The Merck Index.).
  • Anthralin used for the treatment of “wet” psoriasis by topical application.
  • Anthralin is an agent for psoriasis therapy and is practically insoluble in water (The Merck Index).
  • Beclomethasone used for the reduction of local inflammation by peri-ophthalmic and inside the eyelid or intranasal (e.g., for the treatment of rhinitis) application.
  • Beclomethasone is a corticosteroid and is very slightly soluble in water. See, for example, Gennaro, (ed.), Remington's Pharmaceutical Sciences. 17th Edition, (Mack Publishing Company 1985).
  • Betamethasone used for the reduction of local inflammation by oral (e.g., canker sore), intravaginal, and intrarectal application. Betamethasone is a corticosteroid and has a solubility of 190 ⁇ g/mL water. See, for example, Gennaro, (ed.), Remington's Pharmaceutical Sciences, 17th Edition, (Mack Publishing Company 1985).
  • Camptothecin used for the treatment of diseases involving cellular proliferation such as cancer, arthritis, psoriasis, restenosis, surgical adhesions. Camptothecin has a water solubility of 1-2 ⁇ g/mL.
  • Curcumin a potent antioxidant and potential antiarthritic drug. Curcumin is practically insoluble in water.
  • Dexamethasone used for the reduction of local inflammation by oral application (e.g., post wisdom tooth removal).
  • Dexamethasone is a corticosteroid and has a solubility of 10 ⁇ g/mL in water (The Merck Index).
  • Genistein a tyrosine kinase inhibitor and potentially used for the treatment of diseases involving cellular proliferation. Genistein is practically insoluble in water.
  • Indomethacin used for the treatment of symptoms of gout by intraarticular or intramuscular injection or for the reduction of local inflammation by peri-ophthalmic and inside the eyelid, oral, intranasal, intravaginal and intrarectal application.
  • Indomethacin is a non-steroidal anti-inflammatory (NSAID) and is practically insoluble in water (The Merck Index).
  • Lidocaine provides local anesthesia by intramuscular injection, or administration by application to mucus membranes, including periophthalmic and inside the eyelid, oral, intranasal, intravaginal and intrarectal. Lidocaine is a local anesthetic and is practically insoluble in water. See, for example, Gennaro, (ed.), Remington's Pharmaceutical Sciences, 17th Edition, (Mack Publishing Company 1985).
  • Taxol e.g. Paclitaxel
  • Paclitaxel used for the treatment of angiogenic related diseases such as arthritis, cancer, restenosis, psoriasis, or surgical adhesions.
  • Paclitaxel has a water solubility of 1-2, ⁇ g/mL.
  • Tetracycline used for the treatment of eye infections by periophthalmic and inside the eyelid application. Tetracycline is an antibacterial and has a solubility of 400 pg/mL water. See, e.g., Gennaro, (ed.), Remington's Pharmaceutical Sciences, 17th Edition, (Mack Publishing Company 1985).
  • Therapeutic proteins proteins that are practically insoluble in water, such as insulin, are contemplated for use in this presently described polymeric drug delivery system.
  • organic solvent as used herein with reference to this invention means a non-polymeric solvent, such as an aromatic hydrocarbon, ester, ether, ketone, amine, alcohol, nitrated hydrocarbon and chlorinated hydrocarbon, which non-polymeric solvents include: acetone, ethanol, tetrahydrofuran, acetonitrile and pyrrolidones.
  • organic solvents are not biocompatible and organic solvents are not suitable for injection into various areas of the patient's body, particularly the eye, blood vessels, or the synovial joint.
  • This invention makes use of a biocompatible, low molecular weight, water soluble polymer in place of an organic solvent as defined above. This obviates the need to remove an organic solvent and permits the formation of hydrophobic drug containing micelles without heating, agitation, vigorous stirring or sonication. It also makes possible the preparation of a semi-solid capable of forming micelles in vivo, for administration by injection to a patient.
  • composition comprises none, or essentially none of the ingredient.
  • ingredient may be present in such small amounts in the composition that do not affect the properties or pharmaceutical utility of the composition.
  • Injection devices such as syringes may be prepared so as to contain micelle forming compositions of this invention by using any technique whereby the composition is placed within the injection device in a manner that the composition becomes injectable by the device.
  • a composition of this invention may be placed within the barrel of a syringe by mechanical means or extrusion.
  • compositions of this invention may be placed in sterile containers for subsequent pharmaceutical formulation.
  • a container may be a sealed vial which preferably will contain sufficient space for the subsequent addition of an aqueous, physiologically acceptable carrier.
  • the compositions of this invention may be employed for production of drug containing micelles within the aforementioned container after introduction of the aqueous carrier. Dissolution of the composition in the carrier with concomitant formation of drug containing micelles may be accelerated by agitation (e.g. shaking) although the compositions of this invention will dissolve over time, without agitation. Long term or vigorous agitation or sonication is not necessary.
  • the composition will comprise one or more biocompatible micelle forming polymers.
  • micelle forming polymers may be any such polymer known in the art, including the references referred to above and in WO 01/87345.
  • one or more micelle forming polymers in compositions of this invention will be a diblock copolymer suitable for formation of micelles as taught in the art or as specifically described herein.
  • Hydrophobic portions of such diblock copolymers may comprise one or more hydrophobic polymers, such as polyesters, polyanhydrides, polyglycolic acids, polybutrylactones, polyhydroxybutyrates, polylactic acids and polylacaprolactones.
  • the hydrophobic portion of the copolymer may comprise one or more different hydrophobic polymers in random or block orientation.
  • the hydrophobic portion of a copolymer will have a molecular weight from about 200 to about 5000.
  • Preferred hydrophilic portions of micelle forming copolymers that may be used in this invention have a molecular weight of about 750 or greater up to about 8000.
  • the molecular weight will be in the range of about 1000 or 2000-3000 or 5000.
  • Most preferred is a molecular weight of polymer as the hydrophilic portion of the micelle forming polymer being about 2000.
  • Weight ratios of hydrophobic and hydrophilic components of micelle forming polymers used in this invention may be adjusted to provide for a desired CMC.
  • the amount of water soluble polymer employed in compositions of this invention may be adjusted to achieve a desired consistency of the resulting mixture of matrix.
  • the amount of water soluble polymer be such that the resulting mixture or matrix is injectable, as defined herein.
  • the amount of hydrophobic drug included in the composition will be such as to provide a desired amount of drug loaded micelles, preferably not exceeding an amount that can be sufficiently distributed within the micelle forming composition.
  • Methoxypolyethylene glycol (MePEG) oligomers of molecular weight 750 and 2000 and stannous octoate were obtained from Sigma-Aldrich (St. Louis, Mo.), while ⁇ -Caprolactone was obtained from Aldrich (Milwaukee, Wis.). Chloroform and dichloromethane (DCM) were BPLC grade (Fisher Scientific, Fair Lawn, N.J.).
  • Copolymers of methoxypolyethylene glycol (MePEG) and poly( ⁇ -caprolactone) were prepared as follows. MePEG oligomers with molecular weights of 750 and 2000 were combined with ⁇ -caprolactone in varying weight ratios to control the final molecular weight of the copolymer. The total weight of the two reagents was 50 g. The reagents were placed in a round bottom flask sealed with a ground glass stopper and immersed in a heavy mineral oil bath heated to 140° C. The temperature was controlled using a Dyna-Sense MK-1 controller (Scientific Instruments Inc., Skokie, Ill.).
  • the reagents were stirred using a teflon coated 2.5 cm magnetic stir bar. After the reagents were mixed for 30 minutes to produce a homogeneous liquid, 0.15 ml of stannous octoate was added to the flask. The polymerization reaction was allowed to proceed for 6 hours. Cooling the polymer to room temperature terminated the reaction.
  • paclitaxel Hauser chemicals
  • MePEG methoxypolyethylene glycol
  • 570 mg of poly-L-lactic acid-MePEG diblock copolymer Angiotech Pharmaceuticals, Vancouver Canada
  • the waxy material could be injected easily through a 21-gauge needle without compromise of the integrity of the composition.
  • 100 ⁇ l of the mixture was injected into 5 ml of water the mixture slowly dissolved. There was no precipitation of any of the components.
  • the formulation self assembled into micelles with a particle size of approximately 10 nm diameter, as shown in FIG. 1. This solution had a paclitaxel concentration of 1 mg/ml, almost 1000 fold greater than the free solubility of the drug in water.
  • the waxy material could be injected easily through a 21 gauge needle without compromising the integrity of the composition.
  • 100 ⁇ l of the mixture was injected into 5 ml of water and-water-acidified to pH 1, the mixture slowly dissolved and there was no precipitation of any of the components.
  • the formulation self assembled into micelles.
  • Wistar rats weighing 400 g to 500 g were anesthetized with halothane. A vertical incision was made over the trachea and the left external carotid artery was exposed. Connective tissue around the left common carotid artery was left untouched. Two ligatures were placed around the external carotid artery and an arteriotomy was made between them. A 2 French Fogarty balloon was introduced into the external carotid artery and pushed into the left common carotid artery and the balloon was inflated with saline. The balloon was passed up and down the entire length of the carotid artery three times to stretch the vessel and denude the endothelium.
  • the balloon was removed and the ligatures tied off on the external carotid artery.
  • a 3% paclitaxel loaded self-assembling micellar composition based on poly-L-lactic acid—MePEG blended with MePEG 350 in a 60/40 weight ratio (as described in Example 2A) was injected through a 24 G angiocatheter between a distal segment of the common carotid artery and the surrounding connective tissue.
  • 0.1 to 0.2 ml of paste was applied around the artery in 4 injections in order to cover the whole circumference of the vessel on a length of approximately 1 cm. The wound was then closed and the animals recovered.
  • paclitaxel (Hauser chemicals), 108 mg of methoxypolyethylene glycol (MePEG) (molecular weight 350) (Union Carbide Inc.) and 252 mg of poly-L-lactic acid—MePEG diblock copolymer (Angiotech Pharmaceuticals, Inc. Vancouver Canada) were weighed into a 20 ml glass vial and stirred at 50° C. using a spatula. The mixture formed a miscible composition in which all the drug was dissolved. The mixture was sucked up into a 1 ml syringe through an 18 gauge needle and allowed to cool to room temperature.
  • MePEG methoxypolyethylene glycol
  • Angiotech Pharmaceuticals, Inc. Vancouver Canada 252 mg
  • the mixture formed a miscible composition in which all the drug was dissolved.
  • the mixture was sucked up into a 1 ml syringe through an 18 gauge needle and allowed to cool to room temperature.
  • the waxy material could be injected easily through a 21 gauge needle without compromise of the integrity of the composition.
  • 100 ⁇ l of the mixture was injected into 5 ml of water the mixture slowly dissolved. There was no precipitation of any of the components.
  • the formulation self assembled into micelles.

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US10/475,453 US20040234472A1 (en) 2001-04-20 2002-04-22 Micellar drug delivery systems for hydrophobic drugs
US11/296,184 US20060189785A1 (en) 1998-12-17 2005-12-06 Micellar drug delivery systems for hydrophobic drugs
US12/193,648 US7875677B2 (en) 2001-04-20 2008-08-18 Micellar drug delivery systems for hydrophobic drugs

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KR100678790B1 (ko) 2006-01-31 2007-02-02 (주)아모레퍼시픽 자외선 차단용 수중유형 유화 화장료 조성물
WO2007036792A3 (en) * 2005-09-29 2007-08-30 Novachem S A Kit for parenteral administration of medicaments

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PT1392254E (pt) * 2001-04-20 2007-06-29 Univ British Columbia Sistemas de distribuição micelares de fármacos para fármacos hidrofóbicos.
DE20204258U1 (de) * 2002-03-16 2003-07-31 Ruebben Alexander Stent mit Beschichtung (Vitastent 2)
US7297348B2 (en) 2002-07-19 2007-11-20 Omeros Corporation Biodegradable triblock copolymers, synthesis methods therefore, and hydrogels and biomaterials made there from
US7968115B2 (en) 2004-03-05 2011-06-28 Board Of Regents, The University Of Texas System Liposomal curcumin for treatment of cancer
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