JPS59104326A - マクロライド抗生物質の安定な経口用製剤および安定化法 - Google Patents
マクロライド抗生物質の安定な経口用製剤および安定化法Info
- Publication number
- JPS59104326A JPS59104326A JP57212942A JP21294282A JPS59104326A JP S59104326 A JPS59104326 A JP S59104326A JP 57212942 A JP57212942 A JP 57212942A JP 21294282 A JP21294282 A JP 21294282A JP S59104326 A JPS59104326 A JP S59104326A
- Authority
- JP
- Japan
- Prior art keywords
- salt
- acid
- curve
- aqueous solution
- shows
- 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
- 239000003120 macrolide antibiotic agent Substances 0.000 title claims abstract description 71
- 239000000126 substance Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims description 30
- 230000000087 stabilizing effect Effects 0.000 title claims description 13
- 239000007864 aqueous solution Substances 0.000 claims abstract description 58
- 239000003381 stabilizer Substances 0.000 claims abstract description 38
- 239000002253 acid Substances 0.000 claims abstract description 28
- -1 carboxylic acid basic salt Chemical class 0.000 claims abstract description 22
- 230000002378 acidificating effect Effects 0.000 claims abstract description 19
- 230000001747 exhibiting effect Effects 0.000 claims abstract description 16
- 150000001447 alkali salts Chemical class 0.000 claims abstract description 14
- 150000001413 amino acids Chemical class 0.000 claims abstract description 12
- 230000007935 neutral effect Effects 0.000 claims abstract description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims abstract description 4
- 229940069428 antacid Drugs 0.000 claims abstract description 4
- 239000003159 antacid agent Substances 0.000 claims abstract description 4
- 230000001458 anti-acid effect Effects 0.000 claims abstract description 4
- 229910017053 inorganic salt Inorganic materials 0.000 claims abstract 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 130
- 230000006641 stabilisation Effects 0.000 claims description 85
- 238000011105 stabilization Methods 0.000 claims description 85
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 30
- 235000002639 sodium chloride Nutrition 0.000 claims description 29
- 239000000243 solution Substances 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 19
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 18
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 15
- 238000009472 formulation Methods 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 14
- 229910019142 PO4 Inorganic materials 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 239000010452 phosphate Substances 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 13
- 235000001014 amino acid Nutrition 0.000 claims description 12
- 229940024606 amino acid Drugs 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
- 229910052791 calcium Inorganic materials 0.000 claims description 10
- 239000011575 calcium Substances 0.000 claims description 10
- 239000004471 Glycine Substances 0.000 claims description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 5
- 230000003115 biocidal effect Effects 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 239000004220 glutamic acid Substances 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- HWPKGOGLCKPRLZ-UHFFFAOYSA-M monosodium citrate Chemical compound [Na+].OC(=O)CC(O)(C([O-])=O)CC(O)=O HWPKGOGLCKPRLZ-UHFFFAOYSA-M 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 101100228210 Caenorhabditis elegans gly-7 gene Proteins 0.000 claims description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 3
- 235000004279 alanine Nutrition 0.000 claims description 3
- 235000013922 glutamic acid Nutrition 0.000 claims description 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002524 monosodium citrate Substances 0.000 claims description 3
- 235000018342 monosodium citrate Nutrition 0.000 claims description 3
- 235000019321 monosodium tartrate Nutrition 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 239000000661 sodium alginate Substances 0.000 claims description 3
- 235000010413 sodium alginate Nutrition 0.000 claims description 3
- 229940005550 sodium alginate Drugs 0.000 claims description 3
- 239000001433 sodium tartrate Substances 0.000 claims description 3
- NKAAEMMYHLFEFN-ZVGUSBNCSA-M sodium;(2r,3r)-2,3,4-trihydroxy-4-oxobutanoate Chemical compound [Na+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O NKAAEMMYHLFEFN-ZVGUSBNCSA-M 0.000 claims description 3
- WTWSHHITWMVLBX-DKWTVANSSA-M sodium;(2s)-2-aminobutanedioate;hydron Chemical compound [Na+].[O-]C(=O)[C@@H](N)CC(O)=O WTWSHHITWMVLBX-DKWTVANSSA-M 0.000 claims description 3
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 2
- 229960001230 asparagine Drugs 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 2
- 229940041033 macrolides Drugs 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 235000013923 monosodium glutamate Nutrition 0.000 claims description 2
- 239000004223 monosodium glutamate Substances 0.000 claims description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 2
- 210000003323 beak Anatomy 0.000 claims 2
- JXYWFNAQESKDNC-BTJKTKAUSA-N (z)-4-hydroxy-4-oxobut-2-enoate;2-[(4-methoxyphenyl)methyl-pyridin-2-ylamino]ethyl-dimethylazanium Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 JXYWFNAQESKDNC-BTJKTKAUSA-N 0.000 claims 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 claims 1
- 229940009827 aluminum acetate Drugs 0.000 claims 1
- VHGGKQHEVXANRV-UHFFFAOYSA-J aluminum sodium tetraacetate Chemical compound C(C)(=O)[O-].[Al+3].[Na+].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-] VHGGKQHEVXANRV-UHFFFAOYSA-J 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- RUJUQAPQALJUPC-UHFFFAOYSA-K bis[(2-aminoacetyl)oxy]alumanyl 2-aminoacetate Chemical compound [Al+3].NCC([O-])=O.NCC([O-])=O.NCC([O-])=O RUJUQAPQALJUPC-UHFFFAOYSA-K 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 claims 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 235000007686 potassium Nutrition 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 abstract description 19
- 238000004090 dissolution Methods 0.000 abstract description 19
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 7
- 230000001737 promoting effect Effects 0.000 abstract description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 2
- 230000009471 action Effects 0.000 abstract description 2
- 238000006462 rearrangement reaction Methods 0.000 abstract description 2
- 230000003139 buffering effect Effects 0.000 abstract 1
- 229940126701 oral medication Drugs 0.000 abstract 1
- 239000011734 sodium Substances 0.000 description 43
- 229960004106 citric acid Drugs 0.000 description 34
- 238000010828 elution Methods 0.000 description 31
- 239000008187 granular material Substances 0.000 description 26
- 230000008859 change Effects 0.000 description 23
- RTIXKCRFFJGDFG-UHFFFAOYSA-N chrysin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 RTIXKCRFFJGDFG-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical class [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 17
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical class OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 15
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 15
- 229960004144 josamycin Drugs 0.000 description 15
- XJSFLOJWULLJQS-NGVXBBESSA-N josamycin Chemical compound CO[C@H]1[C@H](OC(C)=O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 XJSFLOJWULLJQS-NGVXBBESSA-N 0.000 description 15
- 239000011975 tartaric acid Substances 0.000 description 15
- 235000002906 tartaric acid Nutrition 0.000 description 15
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical class OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 14
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 13
- 229940000593 crinone Drugs 0.000 description 13
- 239000002504 physiological saline solution Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- 229910052698 phosphorus Inorganic materials 0.000 description 12
- NYCXYKOXLNBYID-UHFFFAOYSA-N 5,7-Dihydroxychromone Natural products O1C=CC(=O)C=2C1=CC(O)=CC=2O NYCXYKOXLNBYID-UHFFFAOYSA-N 0.000 description 11
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- 235000015334 Phyllostachys viridis Nutrition 0.000 description 10
- 239000011574 phosphorus Substances 0.000 description 10
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- 235000013399 edible fruits Nutrition 0.000 description 8
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- 230000002496 gastric effect Effects 0.000 description 7
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- 239000003242 anti bacterial agent Substances 0.000 description 6
- 229940088710 antibiotic agent Drugs 0.000 description 6
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
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- 239000010931 gold Substances 0.000 description 4
- JYAQWANEOPJVEY-LYFYHCNISA-N mycarose Chemical compound C[C@H](O)[C@H](O)[C@](C)(O)CC=O JYAQWANEOPJVEY-LYFYHCNISA-N 0.000 description 4
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical class [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 3
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
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- 239000011780 sodium chloride Substances 0.000 description 3
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- 240000005979 Hordeum vulgare Species 0.000 description 2
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- PDSAKIXGSONUIX-UHFFFAOYSA-N hexaaluminum;dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Bi+3].[Bi+3] PDSAKIXGSONUIX-UHFFFAOYSA-N 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000000554 iris Anatomy 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- XJSFLOJWULLJQS-UHFFFAOYSA-N leucomycin A3 Natural products COC1C(OC(C)=O)CC(=O)OC(C)CC=CC=CC(O)C(C)CC(CC=O)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(OC(=O)CC(C)C)C(C)(O)C2)C(C)O1 XJSFLOJWULLJQS-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 210000002652 macrocyte Anatomy 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002757 midecamycin Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940127249 oral antibiotic Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000001175 peptic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 235000014786 phosphorus Nutrition 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000006041 probiotic Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960001170 rokitamycin Drugs 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 210000004894 snout Anatomy 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K47/02—Inorganic compounds
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57212942A JPS59104326A (ja) | 1982-12-04 | 1982-12-04 | マクロライド抗生物質の安定な経口用製剤および安定化法 |
| GB08331772A GB2132086B (en) | 1982-12-04 | 1983-11-29 | Stable oral preparation of macrolide antibiotics and method for stabilising the same |
| IT23956/83A IT1169476B (it) | 1982-12-04 | 1983-11-30 | Preparazione orale stabile di antibiotici macrolidi e procedimento di stabilizzazione |
| FR8319359A FR2541287B1 (fr) | 1982-12-04 | 1983-12-02 | Preparation stable administrable par voie orale de macrolides antibiotiques et procede pour les stabiliser |
| US06/900,231 US4716153A (en) | 1982-12-04 | 1986-08-25 | Stable oral preparation of macrolide antibiotics and method for stabilizing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57212942A JPS59104326A (ja) | 1982-12-04 | 1982-12-04 | マクロライド抗生物質の安定な経口用製剤および安定化法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59104326A true JPS59104326A (ja) | 1984-06-16 |
| JPS6411007B2 JPS6411007B2 (enExample) | 1989-02-23 |
Family
ID=16630843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57212942A Granted JPS59104326A (ja) | 1982-12-04 | 1982-12-04 | マクロライド抗生物質の安定な経口用製剤および安定化法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4716153A (enExample) |
| JP (1) | JPS59104326A (enExample) |
| FR (1) | FR2541287B1 (enExample) |
| GB (1) | GB2132086B (enExample) |
| IT (1) | IT1169476B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3524572A1 (de) * | 1985-07-10 | 1987-01-15 | Thomae Gmbh Dr K | Feste arzneimittelformen zur peroralen anwendung enthaltend 9-deoxo-11-deoxy-9,11-(imino(2-(2-methoxyethoxy)ethyliden)-oxy)-(9s)-erythromycin und verfahren zu ihrer herstellung |
| IT1222309B (it) * | 1987-07-08 | 1990-09-05 | Menarini Sas | Utilizzazione di forme farmaceutiche per uso topico contenenti miocamicina per la terapia delle infezione da germi sensibili alla miocamicina stessa |
| US4877615A (en) * | 1988-09-23 | 1989-10-31 | Microlife Technics, Inc. | Antifungal product |
| IL129547A (en) * | 1994-10-26 | 2001-01-11 | Novartis Ag | Pharmaceutical compositions comprising a macrolide and an acid |
| US7205279B2 (en) * | 1995-10-25 | 2007-04-17 | Novartis Ag | Pharmaceutical compositions |
| DE4444051A1 (de) * | 1994-12-10 | 1996-06-13 | Rhone Poulenc Rorer Gmbh | Pharmazeutische, oral anwendbare Zubereitung |
| AU6381201A (en) * | 2000-03-28 | 2001-10-08 | Biochemie Gmbh | Granulated particles with masked taste |
| US6514537B1 (en) | 2000-06-02 | 2003-02-04 | Cumberland Swan Holdings, Inc. | Magnesium citrate solution |
| ITMI20021725A1 (it) * | 2002-08-01 | 2002-10-31 | Zambon Spa | Composizioni farmaceutiche ad attivita' antibiotica. |
| GB0230034D0 (en) * | 2002-12-23 | 2003-01-29 | Biochemie Gmbh | Organic compounds |
| US7803817B2 (en) * | 2005-05-11 | 2010-09-28 | Vecta, Ltd. | Composition and methods for inhibiting gastric acid secretion |
| US7981908B2 (en) * | 2005-05-11 | 2011-07-19 | Vecta, Ltd. | Compositions and methods for inhibiting gastric acid secretion |
| WO2007120544A2 (en) * | 2006-04-12 | 2007-10-25 | Alexander Rayna L | Compositions comprising pyruvate alkyl esters and uses thereof |
| AU2007278986B2 (en) * | 2006-07-25 | 2010-09-16 | Vecta, Ltd. | Compositions and methods for inhibiting gastric acid secretion using derivatives of small dicarboxylic acids in combination with PPI |
| AU2008316830B2 (en) | 2007-10-25 | 2016-03-17 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| US12403095B2 (en) | 2008-05-30 | 2025-09-02 | Veloxis Pharmaceuticals, Inc. | Stabilized tacrolimus composition |
| WO2011100975A2 (en) * | 2010-02-17 | 2011-08-25 | Lifecycle Pharma A/S | Stabilized tacrolimus composition |
| US8604078B2 (en) * | 2011-04-06 | 2013-12-10 | Carlos Picornell Darder | Fosfomycin pharmaceutical composition |
| WO2013148891A1 (en) * | 2012-03-27 | 2013-10-03 | Cempra Pharmaceuticals, Inc. | Parenteral formulations for administering macrolide antibiotics |
| WO2025111352A1 (en) * | 2023-11-21 | 2025-05-30 | Veterinary Pharmacy Corporation | Formulations of penicillin and methods for stabilizing penicillin |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4064230A (en) * | 1966-04-25 | 1977-12-20 | Schmid Laboratories, Inc. | Polyenic macrolide compositions |
| GB1375986A (en) * | 1966-04-25 | 1974-12-04 | Schmid Inc Julius | Polyenic macrolide composition |
| US3891752A (en) * | 1966-04-25 | 1975-06-24 | Schmid Lab | Polyenic macrolide compositions and methods of use |
| GB1380741A (en) * | 1971-02-05 | 1975-01-15 | Squibb & Sons Inc | Antibiotic compositions and their preparation |
| GB1322306A (en) * | 1971-04-15 | 1973-07-04 | Meiji Seika Co | Stabilized antibiotic preparation and manufacturing process therefor |
| JPS531328B2 (enExample) * | 1971-12-13 | 1978-01-18 | ||
| US4137307A (en) * | 1973-11-15 | 1979-01-30 | The Green Cross Corporation | Process for preparing haptoglobin aqueous solution using strong anion exchanger |
| US4102999A (en) * | 1975-02-10 | 1978-07-25 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Process for producing stable macromomycin powder |
| US4127647A (en) * | 1975-04-08 | 1978-11-28 | Meiji Seika Kaisha, Ltd. | Process for preparation of stable amorphous macrolide antibiotic solids |
| GB1550359A (en) * | 1975-08-07 | 1979-08-15 | Beecham Group Ltd | Antibiotic compositions for oral administration |
| GB1511852A (en) * | 1975-09-11 | 1978-05-24 | Beecham Group Ltd | Reconstitutable powders |
| AU514992B2 (en) * | 1976-06-18 | 1981-03-12 | Rockwell International Corporation | Flexible tube, axial flow valve |
| ZA786259B (en) * | 1977-11-09 | 1979-10-31 | Procter & Gamble | Therapeutic composition |
| JPS54115389A (en) * | 1978-02-27 | 1979-09-07 | Meiji Seika Kaisha Ltd | Novel macrolide antibiotic derivative and its preparation |
| AU529422B2 (en) * | 1978-10-20 | 1983-06-09 | Eli Lilly And Company | Stable erythromycin solution |
| ZA795508B (en) * | 1978-10-23 | 1981-05-27 | Schering Corp | Derivatives of polyene macrolide antibiotics containing an amino sugar moiety, process for the preparation thereof, and pharmaceutical compositions containing them |
| US4338335A (en) * | 1980-02-05 | 1982-07-06 | Merck & Co., Inc. | Vaccine stabilizer containing L-glutamic acid and L-arginine |
| JPS56135418A (en) * | 1980-03-27 | 1981-10-22 | Green Cross Corp:The | Heat treatment of aqueous solution containing 8 factor of coagulation of blood derived from human |
| US4340582A (en) * | 1981-01-15 | 1982-07-20 | Abbott Laboratories | Erythromycin base tablets |
-
1982
- 1982-12-04 JP JP57212942A patent/JPS59104326A/ja active Granted
-
1983
- 1983-11-29 GB GB08331772A patent/GB2132086B/en not_active Expired
- 1983-11-30 IT IT23956/83A patent/IT1169476B/it active
- 1983-12-02 FR FR8319359A patent/FR2541287B1/fr not_active Expired
-
1986
- 1986-08-25 US US06/900,231 patent/US4716153A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2541287A1 (fr) | 1984-08-24 |
| FR2541287B1 (fr) | 1987-08-07 |
| GB2132086A (en) | 1984-07-04 |
| US4716153A (en) | 1987-12-29 |
| GB8331772D0 (en) | 1984-01-04 |
| IT1169476B (it) | 1987-05-27 |
| IT8323956A0 (it) | 1983-11-30 |
| GB2132086B (en) | 1986-05-21 |
| JPS6411007B2 (enExample) | 1989-02-23 |
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