CA2483774A1 - Formulations containing amiodarone and sulfoalkyl ether cyclodextrin - Google Patents

Formulations containing amiodarone and sulfoalkyl ether cyclodextrin Download PDF

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CA2483774A1
CA2483774A1 CA002483774A CA2483774A CA2483774A1 CA 2483774 A1 CA2483774 A1 CA 2483774A1 CA 002483774 A CA002483774 A CA 002483774A CA 2483774 A CA2483774 A CA 2483774A CA 2483774 A1 CA2483774 A1 CA 2483774A1
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amiodarone
sae
formulation
agent
independently
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CA2483774C (en
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Gerold L. Mosher
Karen T. Johnson
Atef A. Gayed
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Cydex Pharmaceuticals Inc
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    • 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
    • A61K31/716—Glucans
    • A61K31/724—Cyclodextrins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/0004—Screening or testing of compounds for diagnosis of disorders, assessment of conditions, e.g. renal clearance, gastric emptying, testing for diabetes, allergy, rheuma, pancreas functions
    • A61K49/0006—Skin tests, e.g. intradermal testing, test strips, delayed hypersensitivity
    • 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
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • 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
    • A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
    • A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/08—Solutions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • 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
    • A61K47/06—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
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids

Abstract

The present invention provides aqueous parenteral formulations containing an antiarrhythmic agent, such as amiodarone, and a sulfoalkyl ether cyclodextri n. The liquid formulations are clear, sterilizable, and chemically and physical ly stable. The liquid formulations do not require a surfactant and do not precipitate upon dilution with distilled water or other pharmaceutically acceptable liquid carrier. The sulfoalkyl ether cyclodextrin-containing formulation provides significant advantages over other cyclodextrin-containi ng formulations of amiodarone. The formulation can be prepared in acidic, neutr al and slightly basic medium while providing acceptable concentrations of amiodarone suitable for parental administration. An SAE-CD-containing formulation of amiodarone can be provided in liquid form or as a reconstitutable powder. Moreover, highly concentrated solutions exceeding 20 0 mg of amiodarone per mL can be prepared. Solutions can be made either dilutable or non-dilutable with water at room temperature or under condition s typically encountered in the clinic.

Claims (51)

1. A dilutable clear liquid formulation comprising amiodarone and a sulfoalkyl ether cyclodextrin (SAE-CD), wherein the molar ratio of SAE-CD to amiodarone is greater than or equal to about 1.1~0.01, and the liquid formulation is dilutable with a pharmaceutically acceptable aqueous liquid carrier at ambient temperature with insignificant precipitation of amiodarone.
2. The formulation of claim 1, wherein the amiodarone concentration is in the range of less than or equal to about 3 mg/ml, the SAE-CD concentration is less than or equal to about 0.9% wt., and the pH of the liquid approximates or is less than the pKa of amiodarone.
3. The formulation of claim 1, wherein the amiodarone concentration is greater than or equal to about 34 mg/mL, the SAE-CD concentration is greater than or equal to about 55 mM, and the pH of the liquid approximates or is less than the pKa of amiodarone.
4. The formulation of claim 1, wherein the SAE-CD is a compound or mixture of compounds of the Formula 1 wherein: n is 4, 5, or 6;
R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each, independently, -O- or a -O-(C2 - C6 alkylene)-SO3 group, wherein at least one of R1-R9 is independently a -O-(C2 -alkylene)-SO3 group; and S1, S2, S3, S4, S5, S6, S7, S8, and S9 are each, independently, a pharmaceutically acceptable cation.
5. The formulation of claim 4, wherein the compound of Formula 1 has a degree of substitution of about 4 or 7.
6. The formulation of claim 1 further comprising a solubilizing agent, antioxidant, buffering agent, acidifying agent, complexation enhancing agent, saline, dextrose, lyophilizing aid, bulking agent, stabilizing agents, electrolyte, another therapeutic agent, alkalizing agent, antimicrobial agent, antifungal agent or a combination thereof.
7. The formulation of claim 6, wherein the buffering agent is an organic or inorganic acid, organic or inorganic base, or salt thereof.
8. The formulation of claim 7, wherein the buffering agent is selected from the group consisting of acetic acid, citric acid, phosphoric acid, boric acid, or a salt thereof.
9. The formulation of claim 6, wherein the total ionic strength of charged species in solution, excluding amiodarone and SAE-CD, is less than about 0.5 M.
10. The formulation of claim 1, wherein the formulation has a surface tension greater than about 50 dynes/cm when the concentration of amiodarone is less than or equal to about 10 mg/mL.
11. The formulation of claim 1, wherein the formulation has a tonicity between about 280 to 500 mOsm when the concentration of amiodarone is less than or equal to about 10 mg/mL.
12. A dilutable clear liquid formulation comprising amiodarone and an SAE-CD, wherein a. the molar ratio of SAE-CD to amiodarone is greater than or equal to about 1.1~0.01;
b. the liquid formulation is dilutable with a pharmaceutically acceptable aqueous liquid carrier at ambient temperature with insignificant precipitation of amiodarone;
c. the amiodarone concentration is in the range of less than or equal to about mg/ml;
d. the SAE-CD concentration is less than or equal to about 4.5 mM;
e. the pH of the liquid approximates or is less than the pKa of amiodarone;
and f. the sulfoalkyl ether cyclodextrin is a compound or mixture of compounds of the Formula 1 wherein: n is 4, 5, or 6;
R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each, independently, -O- or a -O-(C2 - C6 alkylene)-SO3 group, wherein at least one of R1-R9 is independently a -O-(C2 -alkylene)-SO3 group; and S1, S2, S3, S4, S5, S6, S7, S8, and S9 are each, independently, a pharmaceutically acceptable cation.
13. The formulation of claim 12, wherein the compound of Formula 1 has a degree of substitution of about 4 or 7.
14. The formulation of claim 12, wherein the total ionic strength of charged species in solution, excluding amiodarone and SAE-CD, is less than about 0.5 M.
15. The formulation of claim 12, wherein the formulation has a surface tension greater than about 50 dynes/cm and a tonicity between about 280 to 500 mOsm.
16. A dilutable clear liquid formulation comprising amiodarone and an SAE-CD, wherein a. the molar ratio of SAE-CD to amiodarone is greater than or equal to about 1.1~0.01;
b. the liquid formulation is dilutable with a pharmaceutically acceptable aqueous liquid carrier at ambient temperature with insignificant precipitation of amiodarone;
c. the amiodarone concentration is greater than or equal to about 50 mM;
d. the SAE-CD concentration is greater than or equal to about 55 mM;
e. the pH of the liquid medium approximates or is less than the pKa of amiodarone; and f. the sulfoalkyl ether cyclodextrin is a compound or mixture of compounds of the Formula 1 wherein: n is 4, 5, or 6;
R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each, independently, -O- or a -O-(C2 - C6 alkylene)-SO3 group, wherein at least one of R1-R9 is independently a -O-(C2 -alkylene)-SO3 group; and S1, S2, S3, S4, S5, S6, S7, S8, and S9 are each, independently, a pharmaceutically acceptable cation.
17. The formulation of claim 16, wherein the compound of Formula 1 has a degree of substitution of about 4 or 7.
18. A clear liquid formulation comprising amiodarone, SAE-CD and an aqueous liquid carrier, wherein the molar ratio of SAE-CD to amiodarone is less than or equal to about 1.09~0.01.
19. The formulation of claim 18, wherein the molar ratio of amiodarone to SAE-CD is greater than or equal to about 0.3 and the liquid formulation has been exposed to a temperature of greater than or equal to about 45°C thereby rendering the liquid formulation clear.
20. The formulation of claim 18, wherein the pH of the liquid formulation approximates or is less than the pKa of amiodarone.
21. The formulation of claim 20, wherein the liquid formulation is dilutable with a heated pharmaceutically acceptable aqueous liquid carrier, an aqueous liquid comprising SAE-CD or an aqueous liquid comprising a solubilizing agent, soap, detergent, surfactant, or complexation enhancing agent to form a clear diluted liquid formulation.
22. The formulation of claim 19, wherein the SAE-CD is a compound or mixture of compounds of the Formula 1 wherein: n is 4, 5, or 6;
R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each, independently, -O- or a -O-(C2 - C6 alkylene)-SO3 group, wherein at least one of R1-R9 is independently a -O-(C2 -alkylene)-SO3 group; and S1, S2, S3, S4, S5, S6, S7, S8, and S9 are each, independently, a pharmaceutically acceptable cation.
23. A reconstitutable solid comprising SAE-CD and amiodarone, wherein the molar ratio of SAE-CD to amiodarone is greater than or equal to about 1.1~0.01, and the reconstitutable solid forms a dilutable clear reconstituted liquid formulation when mixed with water at a temperature of about 20°C to about 28°C.
24. The formulation of claim 23, wherein the SAE-CD is a compound or mixture of compounds of the Formula 1 wherein: n is 4, 5, or 6;

R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each, independently, -O- or a -O-(C2 - C6 alkylene)-SO3- group, wherein at least one of R1-R9 is independently a -O-(C2 -alkylene)-SO3- group; and S1, S2, S3, S4, S5, S6, S7, S8, and S9 are each, independently, a pharmaceutically acceptable cation.
25. The solid of claim 24 further comprising a solubilizing agent, antioxidant, buffering agent, acidifying agent, complexation enhancing agent, saline, dextrose, lyophilizing aid, bulking agent, stabilizing agents, electrolyte, another therapeutic agent, alkalizing agent, antimicrobial agent, antifungal agent or a combination thereof.
26. The solid of claim 24 further comprising a buffering agent such that the pH of the reconstituted liquid formulation approximates or is less than the pKa of amiodarone.
27. The solid of claim 24, wherein the SAE-CD and amiodarone are in admixture and a major portion of the amiodarone is not complexed with the SAE-CD prior to reconstitution.
28. The solid of claim 24, wherein a major portion of the amiodarone is complexed with the SAE-CD prior to reconstitution.
29. A reconstitutable solid comprising SAE-CD and amiodarone, wherein the molar ratio of SAE-CD to amiodarone is less than about 1.09~0.01, and the reconstitutable solid forms a clear reconstituted liquid formulation when mixed with a pharmaceutically acceptable liquid carrier at a temperature of greater than or equal to about 30°C.
30. The formulation of claim 29, wherein the SAE-CD is a compound or mixture of compounds of the Formula 1 wherein: n is 4, 5, or 6;
R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each, independently, -O- or a -O-(C2 - C6 alkylene)-SO3- group, wherein at least one of R1-R9 is independently a -O-(C2 -alkylene)-SO3- group; and S1, S2, S3, S4, S5, S6, S7, S8, and S9 are each, independently, a pharmaceutically acceptable cation.
31. The solid of claim 30 further comprising a solubilizing agent, antioxidant, buffering agent, acidifying agent, complexation enhancing agent, saline, dextrose, lyophilizing aid, bulking agent, stabilizing agents, electrolyte, another therapeutic agent, alkalizing agent, antimicrobial agent, antifungal agent or a combination thereof.
32. The solid of claim 30 further comprising a buffering agent such that the pH of the reconstituted liquid formulation approximates or is less than the pKa of amiodarone.
33. The solid of claim 30, wherein the SAE-CD and amiodarone are in admixture and a major portion of the amiodarone is not complexed with the SAE-CD prior to reconstitution.
34. The solid of claim 30, wherein a major portion of the amiodarone is complexed with the SAE-CD prior to reconstitution.
35. The solid of claim 30, wherein the molar ratio of SAE-CD to amiodarone is greater than about 0.3.
36. The solid of claim 30, wherein the solid has been prepared from a sterile liquid formulation by spray-drying, freeze-drying, spray-freeze-drying, antisolvent precipitation, solvent evaporation, or by a process utilizing a supercritical or near supercritical fluid.
37. A clear dilutable concentrated liquid formulation comprising SBE7-.beta.-CD and amiodarone, wherein the amiodarone is present in amount of greater than about mg/mL, and the SBE7-.beta.-CD to amiodarone ratio is greater than or equal to about 1.1~0.01, wherein the liquid formulation can be diluted with water at about 20°C
to 30°C to form a clear diluted liquid formulation.
38. A clear ready-to-inject sterile liquid formulation comprising SBE7-.beta.-CD and amiodarone, wherein the SBE7-.beta.-CD is present in an amount of at least about 0.3% wt. and the amiodarone is present in amount of 1-2 mg/mL.
39. A method of increasing the solubility of an acid-ionizable agent comprising the steps of:
a. providing an aqueous liquid comprising an SAE-CD and an acid-ionizable agent, wherein the pH of the liquid approximates or is less than the pKa of the acid-ionizable agent, and the agent binds to the SAE-CD predominantly by one or more non-covalent ionic bonds.
40. The method of claim 39, wherein the sulfoalkyl ether cyclodextrin is a compound or mixture of compounds of the Formula 1 wherein: n is 4, 5, or 6;
R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each, independently, -O- or a -O-(C2 - C6 alkylene)-SO3- group, wherein at least one of R1-R9 is independently a -O-(C2 -alkylene)-SO3- group; and S1, S2, S3, S4, S5, S6, S7, S8, and S9 are each, independently, a pharmaceutically acceptable cation.
41. The method of claim 40, wherein the acid-ionizable compound is amiodarone and the concentration of SAE-CD is less than about 0.025 M.
42. The method of claim 40, wherein the aqueous liquid further comprises a salt or buffering agent present at a concentration of less than about 0.5 M.
43. The method of claim 40, wherein the pH of the liquid is at least 0.1 pH
units less than the pKa of the acid-ionizable agent.
44. The method of claim 40, wherein the acid-ionizable agent comprises at least one acid-ionizable functional group selected from the group consisting of primary amine, secondary amine, tertiary amine, quaternary amine, aromatic amine, unsaturated amine, enol, primary thiol, secondary thiol, sulfonium, and hydroxyl.
45. The method of claim 40, wherein the pH of the liquid is no more than 0.5 pH units greater that the pKa of the acid-ionizable agent.
46. The method of claim 40, wherein the compound of Formula 1 has a degree of substitution of about 4 or 7.
47. A method of preparing a clear liquid formulation comprising the steps of:
a. providing amiodarone, SAE-CD and a pharmaceutically acceptable liquid carrier to form a mixture, wherein the molar ratio of SAE-CD to amiodarone is less than about 1.09~0.1; and b. heating the liquid carrier and/or liquid formulation thereby forming the clear liquid formulation.
48. The method of claim 47, wherein the heating step is conducted at a temperature of at least about 45°C.
49. The method of claim 48, wherein the molar ratio of amiodarone to SAE-CD is greater than or equal to about 0.3.
50. The method of claim 47, wherein the SAE-CD is a compound or mixture of compounds of the Formula 1 wherein: n is 4, 5, or 6;
R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each, independently, -O- or a -O-(C2 - C6 alkylene)-SO3- group, wherein at least one of R1-R9 is independently a -O-(C2 -alkylene)-SO3- group; and S1, S2, S3, S4, S5, S6, S7, S8, and S9 are each, independently, a pharmaceutically acceptable cation.
51. The solid of claim 24, wherein the solid has been prepared from a sterile liquid formulation by spray-drying, freeze-drying, spray-freeze-drying, antisolvent precipitation, solvent evaporation, or by a process utilizing a supercritical or near supercritical fluid.
CA2483774A 2002-05-04 2003-04-29 Formulations containing amiodarone and sulfoalkyl ether cyclodextrin Expired - Lifetime CA2483774C (en)

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US10/139,620 US6869939B2 (en) 2002-05-04 2002-05-04 Formulations containing amiodarone and sulfoalkyl ether cyclodextrin
PCT/US2003/013250 WO2003092590A2 (en) 2002-05-04 2003-04-29 Formulations containing amiodarone and sulfoalkyl ether cyclodextrin

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8183230B2 (en) 2004-01-30 2012-05-22 Pfizer Inc. Antimicrobial preservatives to achieve multi-dose formulation using beta-cyclodextrins for liquid dosage forms

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101098678A (en) 2004-04-23 2008-01-02 锡德克斯公司 Dpi formulation containing sulfoalkyl ether cyclodextrin
WO2005113784A1 (en) 2004-05-12 2005-12-01 Luca Technologies, Llc Generation of hydrogen from hydrocarbon-bearing materials
US7426960B2 (en) 2005-05-03 2008-09-23 Luca Technologies, Inc. Biogenic fuel gas generation in geologic hydrocarbon deposits
US20100204178A1 (en) 2006-10-02 2010-08-12 James Cloyd Novel parenteral carbamazepine formulation
US7629331B2 (en) 2005-10-26 2009-12-08 Cydex Pharmaceuticals, Inc. Sulfoalkyl ether cyclodextrin compositions and methods of preparation thereof
US7416879B2 (en) 2006-01-11 2008-08-26 Luca Technologies, Inc. Thermacetogenium phaeum consortium for the production of materials with enhanced hydrogen content
CA2647348A1 (en) 2006-03-28 2007-10-04 Javelin Pharmaceuticals, Inc. Formulations of low dose diclofenac and beta-cyclodextrin
AU2007230718B2 (en) * 2006-03-28 2012-05-10 Javelin Pharmaceuticals, Inc. Formulations of low dose non-steroidal anti-inflammatory drugs and beta-cyclodextrin
US7977282B2 (en) 2006-04-05 2011-07-12 Luca Technologies, Inc. Chemical amendments for the stimulation of biogenic gas generation in deposits of carbonaceous material
US7696132B2 (en) 2006-04-05 2010-04-13 Luca Technologies, Inc. Chemical amendments for the stimulation of biogenic gas generation in deposits of carbonaceous material
EP2061458B1 (en) * 2006-09-15 2014-12-10 Regents of the University of Minnesota Topiramate compositions and methods for their use
US20090239942A1 (en) * 2006-09-15 2009-09-24 Cloyd James C Topiramate Compositions and Methods of Making and Using the Same
US20090270496A1 (en) * 2007-05-03 2009-10-29 Courchesne William E Antifungal compounds
US7635773B2 (en) 2008-04-28 2009-12-22 Cydex Pharmaceuticals, Inc. Sulfoalkyl ether cyclodextrin compositions
US8479813B2 (en) 2009-12-16 2013-07-09 Luca Technologies, Inc. Biogenic fuel gas generation in geologic hydrocarbon deposits
EP2335686A1 (en) 2009-12-21 2011-06-22 LEK Pharmaceuticals d.d. An aqueous intravenous nanosuspension with reduced adverse effects
NL2004260C2 (en) * 2010-02-18 2011-08-22 Univ Amsterdam Disinfectant composition and its use in dental treatment.
WO2011156481A2 (en) 2010-06-11 2011-12-15 Baxter International Inc. Formulations including amiodarone and salts thereof and methods of their manufacture and use
BR112014001335A2 (en) 2011-07-20 2017-02-21 Hospira Inc method for treating postoperative pain in a mammal and method for treating pain in a mammal
EP2785352B1 (en) * 2011-11-29 2020-03-11 Jurox Pty Ltd Stable injectable pharmaceutical compositions comprising 2-hydroxypropyl-beta-cyclodextrin and alfaxalone
US20130209444A1 (en) * 2012-01-30 2013-08-15 Baxter Healthcare S.A. Non-anticoagulant sulfated or sulfonated polysaccharides
PT2814849T (en) 2012-02-15 2020-03-04 Cydex Pharmaceuticals Inc Manufacturing process for cyclodextrin derivatives
JP2015508846A (en) 2012-02-28 2015-03-23 サイデックス・ファーマシューティカルズ・インコーポレイテッド Alkylated cyclodextrin compositions and methods for their preparation and use
US9004162B2 (en) 2012-03-23 2015-04-14 Transworld Technologies Inc. Methods of stimulating acetoclastic methanogenesis in subterranean deposits of carbonaceous material
KR20150070303A (en) * 2012-10-17 2015-06-24 자피오텍 게엠베하 Anthocyanidin complex for the treatment of multiple myeloma
WO2014066274A1 (en) 2012-10-22 2014-05-01 Cydex Pharmaceuticals, Inc. Alkylated cyclodextrin compositions and processes for preparing and using the same
JP6235603B2 (en) * 2012-11-15 2017-11-22 ザピオテック・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＳＡＰＩＯＴＥＣ ＧｍｂＨ Delphinidin complex as anti-inflammatory and / or immunosuppressive active ingredient
EP2773033B1 (en) 2013-02-28 2018-12-05 Dialog Semiconductor GmbH Divide by 2 and 3 charge pump methods
GB201312737D0 (en) 2013-07-17 2013-08-28 Univ Greenwich Cyclodextrin
HUE063851T2 (en) 2014-08-22 2024-02-28 Cydex Pharmaceuticals Inc Fractionated alkylated cyclodextrin compositions and processes for preparing and using the same
US10736891B2 (en) 2016-01-07 2020-08-11 Roy MADIGAN Composition and method for treating chagas disease
US11166911B2 (en) * 2016-03-04 2021-11-09 Sun Pharmaceutical Industries Limited Parenteral dosage form of amiodarone
CN107753439A (en) * 2016-08-22 2018-03-06 黑龙江迪龙制药有限公司 A kind of hydrochloride for injection amiodarone and preparation method thereof
TW201828938A (en) 2016-11-18 2018-08-16 德商艾庫里斯抗感染治療有限公司 Novel formulations of amidine substituted beta-lactam compounds on the basis of modified cyclodextrins and acidifying agents, their preparation and use as antimicrobial pharmaceutical compositions
CN114126596A (en) * 2019-05-15 2022-03-01 贝克森生物医药公司 Ketamine formulations for subcutaneous injection
US20230000997A1 (en) 2019-08-06 2023-01-05 L.E.A.F. Holdings Group Llc Processes of preparing polyglutamated antifolates and uses of their compositions
CN115969833A (en) * 2023-01-03 2023-04-18 上海上药第一生化药业有限公司 Amiodarone medicinal composition, injection, preparation method thereof and injector containing amiodarone medicinal composition and injection

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0491812A4 (en) 1989-09-14 1992-11-04 Australian Commercial Research & Development Limited Drug delivery compositions
KR0166088B1 (en) 1990-01-23 1999-01-15 . Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof
US5376645A (en) 1990-01-23 1994-12-27 University Of Kansas Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof
WO1991013100A1 (en) 1990-03-02 1991-09-05 Australian Commercial Research & Development Limited Cyclodextrin compositions and methods for pharmaceutical and industrial applications
US5234949A (en) 1992-04-01 1993-08-10 Academic Pharmaceuticals, Inc. Parenteral solutions containing amiodarone in acetate buffer solution
FR2735978B1 (en) * 1995-06-30 1997-09-19 Sanofi Sa PHARMACEUTICAL COMPOSITION OF AMIODARONE FOR PARENTERAL ADMINISTRATION
UA57734C2 (en) * 1996-05-07 2003-07-15 Пфайзер Інк. Arylheterocyclic inclusion complexes
US5916883A (en) * 1996-11-01 1999-06-29 Poly-Med, Inc. Acylated cyclodextrin derivatives
US6046177A (en) * 1997-05-05 2000-04-04 Cydex, Inc. Sulfoalkyl ether cyclodextrin based controlled release solid pharmaceutical formulations
US5874418A (en) * 1997-05-05 1999-02-23 Cydex, Inc. Sulfoalkyl ether cyclodextrin based solid pharmaceutical formulations and their use
EP1143796A4 (en) * 1999-01-21 2002-03-20 Bristol Myers Squibb Co Complex of ras-farnesyltransferase inhibitor and sulfobutylether-7-beta-cyclodextrin or 2-hydroxypropyl-beta-cyclodextrin and method
US6267985B1 (en) 1999-06-30 2001-07-31 Lipocine Inc. Clear oil-containing pharmaceutical compositions
US6294192B1 (en) 1999-02-26 2001-09-25 Lipocine, Inc. Triglyceride-free compositions and methods for improved delivery of hydrophobic therapeutic agents
GB9921958D0 (en) * 1999-09-16 1999-11-17 Pharmacia & Upjohn Spa Formulations for parenteral use of estramustine phosphate and sulfoalkylether-cyclodextrins
US6479541B1 (en) * 2000-03-30 2002-11-12 Baxter International Amiodarone-containing parenteral administration

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8183230B2 (en) 2004-01-30 2012-05-22 Pfizer Inc. Antimicrobial preservatives to achieve multi-dose formulation using beta-cyclodextrins for liquid dosage forms

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