CA1156552A - Aging resistant aluminum ibuprofen pharmaceutical suspensions - Google Patents
Aging resistant aluminum ibuprofen pharmaceutical suspensionsInfo
- Publication number
- CA1156552A CA1156552A CA000380223A CA380223A CA1156552A CA 1156552 A CA1156552 A CA 1156552A CA 000380223 A CA000380223 A CA 000380223A CA 380223 A CA380223 A CA 380223A CA 1156552 A CA1156552 A CA 1156552A
- Authority
- CA
- Canada
- Prior art keywords
- ibuprofen
- aluminum
- suspension
- composition according
- salt
- 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.)
- Expired
Links
- QAZIXAUMDFPQRW-UHFFFAOYSA-K aluminum;2-[4-(2-methylpropyl)phenyl]propanoate;hydroxide Chemical compound [Al+2]O.CC(C)CC1=CC=C(C(C)C([O-])=O)C=C1.CC(C)CC1=CC=C(C(C)C([O-])=O)C=C1 QAZIXAUMDFPQRW-UHFFFAOYSA-K 0.000 title claims abstract description 67
- 230000032683 aging Effects 0.000 title description 17
- 239000007971 pharmaceutical suspension Substances 0.000 title description 15
- 239000000203 mixture Substances 0.000 claims abstract description 102
- 239000000725 suspension Substances 0.000 claims abstract description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 45
- 229930006000 Sucrose Natural products 0.000 claims abstract description 38
- 239000005720 sucrose Substances 0.000 claims abstract description 38
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims abstract description 37
- 239000000375 suspending agent Substances 0.000 claims abstract description 23
- 229910001868 water Inorganic materials 0.000 claims abstract description 23
- 229930091371 Fructose Natural products 0.000 claims abstract description 9
- 239000005715 Fructose Substances 0.000 claims abstract description 9
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims abstract description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 9
- 239000008103 glucose Substances 0.000 claims abstract description 9
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 claims abstract description 8
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract description 6
- 239000002245 particle Substances 0.000 claims abstract description 6
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 46
- 229960001680 ibuprofen Drugs 0.000 claims description 46
- 239000006194 liquid suspension Substances 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 22
- 239000008213 purified water Substances 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 18
- 239000004334 sorbic acid Substances 0.000 claims description 18
- 235000010199 sorbic acid Nutrition 0.000 claims description 18
- 229940075582 sorbic acid Drugs 0.000 claims description 18
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 17
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 17
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 17
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 16
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 14
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 13
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 235000010210 aluminium Nutrition 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 11
- WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 claims description 9
- -1 ethyleneoxy groups Chemical group 0.000 claims description 9
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 9
- 229960001462 sodium cyclamate Drugs 0.000 claims description 7
- 239000000796 flavoring agent Substances 0.000 claims description 6
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000008371 vanilla flavor Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 238000010979 pH adjustment Methods 0.000 claims 2
- 239000003086 colorant Substances 0.000 claims 1
- 238000004090 dissolution Methods 0.000 abstract description 37
- 230000009467 reduction Effects 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 abstract 1
- 229940085605 saccharin sodium Drugs 0.000 abstract 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 48
- 229960004793 sucrose Drugs 0.000 description 34
- 235000011187 glycerol Nutrition 0.000 description 24
- 229960005150 glycerol Drugs 0.000 description 24
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 22
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 22
- 235000010356 sorbitol Nutrition 0.000 description 22
- 239000000600 sorbitol Substances 0.000 description 22
- 229960002920 sorbitol Drugs 0.000 description 22
- 235000003599 food sweetener Nutrition 0.000 description 21
- 239000003765 sweetening agent Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 18
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 17
- 229940068968 polysorbate 80 Drugs 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 229920000053 polysorbate 80 Polymers 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- 238000009472 formulation Methods 0.000 description 13
- 230000000694 effects Effects 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 229960000443 hydrochloric acid Drugs 0.000 description 10
- 235000011167 hydrochloric acid Nutrition 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 10
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 description 9
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 description 9
- 239000000499 gel Substances 0.000 description 9
- 238000004062 sedimentation Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000003814 drug Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229940079593 drug Drugs 0.000 description 7
- 235000013305 food Nutrition 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 230000003679 aging effect Effects 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 235000019631 acid taste sensations Nutrition 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000000306 component Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000015424 sodium Nutrition 0.000 description 3
- 229940083542 sodium Drugs 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241000167854 Bourreria succulenta Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- RKFMOTBTFHXWCM-UHFFFAOYSA-M [AlH2]O Chemical compound [AlH2]O RKFMOTBTFHXWCM-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000019693 cherries Nutrition 0.000 description 2
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- 230000003247 decreasing effect Effects 0.000 description 2
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- 239000002552 dosage form Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
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- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- 239000001074 1-methoxy-4-[(E)-prop-1-enyl]benzene Substances 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
- TUZRJGVLAFMQEK-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1.CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 TUZRJGVLAFMQEK-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- 244000037364 Cinnamomum aromaticum Species 0.000 description 1
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- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 description 1
- HDIFHQMREAYYJW-XGXNLDPDSA-N Glyceryl Ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(O)CO HDIFHQMREAYYJW-XGXNLDPDSA-N 0.000 description 1
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- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- PTTPUWGBPLLBKW-UHFFFAOYSA-M sodium;2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound [Na+].CC(C)CC1=CC=C(C(C)C([O-])=O)C=C1 PTTPUWGBPLLBKW-UHFFFAOYSA-M 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 125000000185 sucrose group Chemical class 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16159980A | 1980-06-20 | 1980-06-20 | |
| US161,599 | 1980-06-20 | ||
| US259,232 | 1981-05-11 | ||
| US06/259,232 US4361580A (en) | 1980-06-20 | 1981-05-11 | Aluminum ibuprofen pharmaceutical suspensions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1156552A true CA1156552A (en) | 1983-11-08 |
Family
ID=26857961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000380223A Expired CA1156552A (en) | 1980-06-20 | 1981-06-19 | Aging resistant aluminum ibuprofen pharmaceutical suspensions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4361580A (show.php) |
| CA (1) | CA1156552A (show.php) |
| DE (1) | DE3124014A1 (show.php) |
| FR (1) | FR2484834A1 (show.php) |
| GB (1) | GB2079600B (show.php) |
| IT (1) | IT1136671B (show.php) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58126810A (ja) * | 1981-12-24 | 1983-07-28 | Kaken Pharmaceut Co Ltd | 抗炎症眼科用液剤およびその製法 |
| IT1175941B (it) * | 1984-02-16 | 1987-08-12 | Stabil Bioterapico Farmachim | Sali d'alluminio mono, bi e trisostituiti degli acidi aril-alcanoici e composizioni farmaceutiche che li contengono |
| US4609675A (en) * | 1984-08-17 | 1986-09-02 | The Upjohn Company | Stable, high dose, high bulk density ibuprofen granulations for tablet and capsule manufacturing |
| DE3437599C2 (de) * | 1984-10-13 | 1987-04-16 | Dolorgiet GmbH & Co KG, 5205 St Augustin | Ibuprofen enthaltende Weichgelatinekapseln |
| IE58110B1 (en) * | 1984-10-30 | 1993-07-14 | Elan Corp Plc | Controlled release powder and process for its preparation |
| US4761274A (en) * | 1986-03-27 | 1988-08-02 | Warner-Lambert Company | Medicament adsorbates of analgesics with complex magnesium aluminum silicate and their preparation |
| GB8623557D0 (en) * | 1986-10-01 | 1986-11-05 | Boots Co Plc | Therapeutic agents |
| US5071643A (en) * | 1986-10-17 | 1991-12-10 | R. P. Scherer Corporation | Solvent system enhancing the solubility of pharmaceuticals for encapsulation |
| GB8629567D0 (en) * | 1986-12-10 | 1987-01-21 | Boots Co Plc | Therapeutic agents |
| NL194638C (nl) * | 1986-12-19 | 2002-10-04 | Novartis Ag | Hydrosol die vaste deeltjes van een farmaceutisch actieve stof bevat en farmaceutisch preparaat dat deze hydrosol bevat. |
| GB8701392D0 (en) * | 1987-01-22 | 1987-02-25 | Boots Co Plc | Therapeutic agents |
| US4788220A (en) * | 1987-07-08 | 1988-11-29 | American Home Products Corporation (Del.) | Pediatric ibuprofen compositions |
| US4861797A (en) * | 1987-10-15 | 1989-08-29 | Oratech Pharmaceutical Development Corporation | Liquid ibuprofen compositions and methods of making them |
| US4859704A (en) * | 1987-10-15 | 1989-08-22 | Oratech Pharmaceutical Development Corporation | Water soluble ibuprofen compositions and methods of making them |
| US5013716A (en) * | 1988-10-28 | 1991-05-07 | Warner-Lambert Company | Unpleasant taste masking compositions and methods for preparing same |
| US4975465A (en) * | 1989-03-28 | 1990-12-04 | American Home Products Corporation | Orally administrable ibuprofen compositions |
| NZ234143A (en) * | 1989-06-28 | 1991-10-25 | Mcneil Ppc Inc | Aqueous pharmaceutical suspension formulation for administering substantially insoluble pharmaceutical agents |
| DE3938227C1 (en) * | 1989-11-17 | 1991-05-02 | Dolorgiet Gmbh & Co Kg, 5205 St Augustin, De | Oral antiinflammatory and analgetic pharmaceutical compsn. - comprises magnesium ibuprofen dissolved in mixt. of water, propane-1,2-diol and glycerol |
| US5024997A (en) * | 1990-06-22 | 1991-06-18 | American Home Products Corporation | Palatable ibuprofen solutions |
| US5272137A (en) * | 1992-02-14 | 1993-12-21 | Mcneil-Pfc, Inc. | Aqueous pharmaceutical suspension for pharmaceutical actives |
| IL108366A (en) * | 1993-03-11 | 1999-11-30 | Taro Vit Ind Ltd | Semi-solid pharmaceutical compounds and a device for their use |
| EP0620001A1 (en) * | 1993-04-16 | 1994-10-19 | McNEIL-PPC, INC. | Aqueous pharmaceutical suspension and process for preparation thereof |
| US5466865A (en) * | 1993-07-02 | 1995-11-14 | Ibah, Inc. | Neomorphic ibuprofen and methods of using same |
| US5310961A (en) * | 1993-07-02 | 1994-05-10 | Affinity Biotech, Inc. | Neomorphic ibuprofen |
| US5310960A (en) * | 1993-07-02 | 1994-05-10 | Affinity Biotech, Inc. | Low temperature process for preparing neomorphic ibuprofen |
| EP0785783A1 (en) * | 1994-10-14 | 1997-07-30 | Janssen Pharmaceutica N.V. | Sabeluzole oral suspensions |
| US5563177A (en) * | 1995-01-30 | 1996-10-08 | American Home Products Corporation | Taste masking guaifenesin containing liquids |
| US6348216B1 (en) * | 1996-06-10 | 2002-02-19 | Knoll Pharmaceutical Company | Ibuprofen and narcotic analgesic compositions |
| US6361794B1 (en) | 1996-06-12 | 2002-03-26 | Basf Corporation | Method of making ibuprofen and narcotic analgesic composition |
| US6071523A (en) | 1998-06-03 | 2000-06-06 | Taro Pharmaceuticals Industries, Ltd. | Spill resistant pharmaceutical compositions in semi-solid form |
| US20030232097A1 (en) * | 2002-06-17 | 2003-12-18 | Strides Inc. | Oily wax matrix suspension formulation comprising ibuprofen free acid and potassium salt of ibuprofen |
| ES2379464T3 (es) * | 2002-06-17 | 2012-04-26 | Taro Pharmaceuticals U.S.A., Inc. | Suspensión de ibuprofeno |
| WO2004004705A2 (en) * | 2002-07-03 | 2004-01-15 | Shannon Biotechnology Ltd | Pharmaceutical formulations for preparing drink products |
| US20060093629A1 (en) * | 2004-10-29 | 2006-05-04 | Buehler Gail K | Dye-free pharmaceutical suspensions and related methods |
| MX2008011823A (es) * | 2006-03-16 | 2008-10-31 | Novartis Ag | Forma de dosificacion solida que contiene un agente activo de sabor encubierto. |
| CN113893227B (zh) * | 2021-11-18 | 2023-04-14 | 山东则正医药技术有限公司 | 布洛芬片的制备原料、制备方法和布洛芬片 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB971700A (en) * | 1961-02-02 | 1964-09-30 | Boots Pure Drug Co Ltd | Anti-Inflammatory Agents |
| US3600437A (en) * | 1969-05-28 | 1971-08-17 | Lilly Co Eli | Substituted phenylalkanoic acids and derivatives thereof |
| US3636200A (en) * | 1969-06-09 | 1972-01-18 | Hoffmann La Roche | Pharmaceutical suspension |
| US3865857A (en) * | 1972-03-20 | 1975-02-11 | Teikoku Hormone Mfg Co Ltd | Tri-substituted aluminum salts or di-substituted aluminum salts of carboxyl group-containing, pharmaceutically effective compounds, and process for preparation thereof |
| US3976674A (en) * | 1972-11-01 | 1976-08-24 | Eli Lilly And Company | Aluminum salts of substituted phenylalkanoic acids |
| SE419538B (sv) * | 1973-10-29 | 1981-08-10 | Eisai Co Ltd | Analogiforfaranden for framstellning av 2-(n-fenoxfenyl)-propionsyraderivat |
| BE811810A (en) * | 1974-03-04 | 1974-09-04 | 2-(3-phenoxy-phenyl)-propionyloxy-aluminium - mono-or di-basic salts which form aq. suspensions without objectionable taste | |
| US3993753A (en) * | 1974-08-26 | 1976-11-23 | American Home Products Corporation | Anhydrous ampicillin stabilization and resultant compositions |
| US4031243A (en) * | 1975-07-03 | 1977-06-21 | Juste, S.A. Quimico-Farmaceutica | 2-(4-Isobutyl phenyl)butyric acid, salts thereof, and pharmaceutical compositions containing the same |
| CA1062721A (en) * | 1975-12-15 | 1979-09-18 | Anthony A. Sinkula | Propionic acid derivatives |
| US4145440A (en) * | 1977-08-18 | 1979-03-20 | The Upjohn Company | Liquid suspension of an aluminum salt of ibuprofen |
| IE49218B1 (en) * | 1978-12-01 | 1985-08-21 | Merck & Co Inc | Methyldopa composition |
-
1981
- 1981-05-11 US US06/259,232 patent/US4361580A/en not_active Expired - Fee Related
- 1981-06-17 IT IT22391/81A patent/IT1136671B/it active
- 1981-06-19 DE DE19813124014 patent/DE3124014A1/de not_active Withdrawn
- 1981-06-19 CA CA000380223A patent/CA1156552A/en not_active Expired
- 1981-06-19 FR FR8112139A patent/FR2484834A1/fr active Granted
- 1981-06-19 GB GB8118919A patent/GB2079600B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2484834B1 (show.php) | 1983-12-02 |
| IT1136671B (it) | 1986-09-03 |
| US4361580A (en) | 1982-11-30 |
| FR2484834A1 (fr) | 1981-12-24 |
| DE3124014A1 (de) | 1982-03-11 |
| GB2079600A (en) | 1982-01-27 |
| GB2079600B (en) | 1984-03-07 |
| IT8122391A0 (it) | 1981-06-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |