CA2364610A1 - Pharmaceutical solubilized in aerosol propellant - Google Patents
Pharmaceutical solubilized in aerosol propellant Download PDFInfo
- Publication number
- CA2364610A1 CA2364610A1 CA002364610A CA2364610A CA2364610A1 CA 2364610 A1 CA2364610 A1 CA 2364610A1 CA 002364610 A CA002364610 A CA 002364610A CA 2364610 A CA2364610 A CA 2364610A CA 2364610 A1 CA2364610 A1 CA 2364610A1
- Authority
- CA
- Canada
- Prior art keywords
- ingredient
- intermediate formulation
- acid
- formulation
- pharmaceutical agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003380 propellant Substances 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 abstract 9
- 238000009472 formulation Methods 0.000 abstract 7
- 239000004615 ingredient Substances 0.000 abstract 7
- 239000008177 pharmaceutical agent Substances 0.000 abstract 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract 2
- -1 sodium oxo-cholanyl glycines Chemical class 0.000 abstract 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 abstract 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 abstract 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 abstract 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- 240000008067 Cucumis sativus Species 0.000 abstract 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 abstract 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004472 Lysine Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- 229920001363 Polidocanol Polymers 0.000 abstract 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract 1
- 108010039918 Polylysine Proteins 0.000 abstract 1
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 1
- 244000028344 Primula vulgaris Species 0.000 abstract 1
- 235000016311 Primula vulgaris Nutrition 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 abstract 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 150000005215 alkyl ethers Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 abstract 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 abstract 1
- 235000021324 borage oil Nutrition 0.000 abstract 1
- 229940119217 chamomile extract Drugs 0.000 abstract 1
- 235000020221 chamomile extract Nutrition 0.000 abstract 1
- 229940009025 chenodeoxycholate Drugs 0.000 abstract 1
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 abstract 1
- 229940009976 deoxycholate Drugs 0.000 abstract 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 abstract 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 abstract 1
- 229960004275 glycolic acid Drugs 0.000 abstract 1
- 229920002674 hyaluronan Polymers 0.000 abstract 1
- 229960003160 hyaluronic acid Drugs 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 235000014655 lactic acid Nutrition 0.000 abstract 1
- 239000004310 lactic acid Substances 0.000 abstract 1
- 229960000448 lactic acid Drugs 0.000 abstract 1
- 229960004488 linolenic acid Drugs 0.000 abstract 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 210000004072 lung Anatomy 0.000 abstract 1
- 229960003646 lysine Drugs 0.000 abstract 1
- 229940074096 monoolein Drugs 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 235000021313 oleic acid Nutrition 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- ONJQDTZCDSESIW-UHFFFAOYSA-N polidocanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO ONJQDTZCDSESIW-UHFFFAOYSA-N 0.000 abstract 1
- 229960002226 polidocanol Drugs 0.000 abstract 1
- 229920000570 polyether Polymers 0.000 abstract 1
- 229920000656 polylysine Polymers 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 abstract 1
- 229940117972 triolein Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/28—Insulins
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Otolaryngology (AREA)
- Pulmonology (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
A formulation with a pharmaceutical agent solubilized in a propellant can be administered buccally or into the lungs using a metered dose spray applicator. The pharmaceutical agent is dispensed from a pressurized container containing a stable solubilized mixture of propellant which is liquid under pressure and an intermediate formulation.
The intermediate formulation comprises the proteinic pharmaceutical agent, water, first ingredient, second ingredient and at least one third ingredient. The first ingredient is glycerin and/or polyglycerin in an amount of from 1-50 wt./wt.% of the intermediate formulation. The second ingredient is phenol and/or methyl phenol in an amount of from 1-20 wt./wt.% of the intermediate formulation. Each third ingredient is selected from the group consisting of alkali metal C8 to C22 alkyl sulphate, polidocanol C6 to C40 alkyl ethers, trihydroxy sodium oxo-cholanyl glycines, polyoxyethylene sorbitanethers, alkyl-aryl polyether alcohols, hyaluronic acid and pharmaceutically suitable salts thereof, monoolein, triolein, lysine, polylysine, oleic acid, linoleic acid, linolenic acid, monooleates and laurates, glycolic acid, lactic acid, chenodeoxycholate, deoxycholate, chamomile extract, cucumber extract, borage oil and evening of primrose oil and mixtures thereof, in an amount of from 1-50 wt./wt.% of the intermediate formulation. The total concentration of first, second and third ingredients is less than 90 wt./wt.% of the intermediate formulation.
The intermediate formulation comprises the proteinic pharmaceutical agent, water, first ingredient, second ingredient and at least one third ingredient. The first ingredient is glycerin and/or polyglycerin in an amount of from 1-50 wt./wt.% of the intermediate formulation. The second ingredient is phenol and/or methyl phenol in an amount of from 1-20 wt./wt.% of the intermediate formulation. Each third ingredient is selected from the group consisting of alkali metal C8 to C22 alkyl sulphate, polidocanol C6 to C40 alkyl ethers, trihydroxy sodium oxo-cholanyl glycines, polyoxyethylene sorbitanethers, alkyl-aryl polyether alcohols, hyaluronic acid and pharmaceutically suitable salts thereof, monoolein, triolein, lysine, polylysine, oleic acid, linoleic acid, linolenic acid, monooleates and laurates, glycolic acid, lactic acid, chenodeoxycholate, deoxycholate, chamomile extract, cucumber extract, borage oil and evening of primrose oil and mixtures thereof, in an amount of from 1-50 wt./wt.% of the intermediate formulation. The total concentration of first, second and third ingredients is less than 90 wt./wt.% of the intermediate formulation.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/272,563 US6350432B1 (en) | 1999-03-19 | 1999-03-19 | Pressurized container having an aerosolized pharmaceutical composition |
| US09/272,563 | 1999-03-19 | ||
| US09/388,344 US6315984B1 (en) | 1999-03-19 | 1999-09-03 | Pressurized container having an aerosolized pharmaceutical composition |
| US09/388,344 | 1999-09-03 | ||
| PCT/CA2000/000260 WO2000056291A1 (en) | 1999-03-19 | 2000-03-10 | Pharmaceutical solubilized in aerosol propellant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2364610A1 true CA2364610A1 (en) | 2000-09-28 |
| CA2364610C CA2364610C (en) | 2006-12-19 |
Family
ID=26955601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002364610A Expired - Fee Related CA2364610C (en) | 1999-03-19 | 2000-03-10 | Pharmaceutical solubilized in aerosol propellant |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1162958A1 (en) |
| AU (1) | AU766745B2 (en) |
| CA (1) | CA2364610C (en) |
| MX (1) | MXPA01009466A (en) |
| NZ (1) | NZ514319A (en) |
| WO (1) | WO2000056291A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060171899A1 (en) * | 1998-12-10 | 2006-08-03 | Akwete Adjei | Water-stabilized aerosol formulation system and method of making |
| US6375975B1 (en) * | 1998-12-21 | 2002-04-23 | Generex Pharmaceuticals Incorporated | Pharmaceutical compositions for buccal and pulmonary application |
| US6451286B1 (en) * | 1998-12-21 | 2002-09-17 | Generex Pharmaceuticals Incorporated | Pharmaceutical compositions for buccal and pulmonary administration comprising an alkali metal alkyl sulfate and at least three micelle-forming compounds |
| US7087215B2 (en) | 1998-12-21 | 2006-08-08 | Generex Pharmaceuticals Incorporated | Methods of administering and enhancing absorption of pharmaceutical agents |
| US20030035774A1 (en) * | 2001-07-18 | 2003-02-20 | Adjei Akwete L. | Salt/ion pair medicinal aerosol formulation |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9007052D0 (en) * | 1990-03-29 | 1990-05-30 | Skua Investments Ltd | Pharmaceutical formulations |
| US5230884A (en) * | 1990-09-11 | 1993-07-27 | University Of Wales College Of Cardiff | Aerosol formulations including proteins and peptides solubilized in reverse micelles and process for making the aerosol formulations |
| US6017545A (en) * | 1998-02-10 | 2000-01-25 | Modi; Pankaj | Mixed micellar delivery system and method of preparation |
-
2000
- 2000-03-10 AU AU31400/00A patent/AU766745B2/en not_active Ceased
- 2000-03-10 EP EP00908880A patent/EP1162958A1/en not_active Withdrawn
- 2000-03-10 NZ NZ514319A patent/NZ514319A/en not_active IP Right Cessation
- 2000-03-10 CA CA002364610A patent/CA2364610C/en not_active Expired - Fee Related
- 2000-03-10 MX MXPA01009466A patent/MXPA01009466A/en active IP Right Grant
- 2000-03-10 WO PCT/CA2000/000260 patent/WO2000056291A1/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ514319A (en) | 2002-11-26 |
| MXPA01009466A (en) | 2002-05-14 |
| WO2000056291A1 (en) | 2000-09-28 |
| EP1162958A1 (en) | 2001-12-19 |
| CA2364610C (en) | 2006-12-19 |
| AU3140000A (en) | 2000-10-09 |
| AU766745B2 (en) | 2003-10-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20180312 |