JPS58148816A - 低刺激性チアムリン注射剤 - Google Patents
低刺激性チアムリン注射剤Info
- Publication number
- JPS58148816A JPS58148816A JP57031506A JP3150682A JPS58148816A JP S58148816 A JPS58148816 A JP S58148816A JP 57031506 A JP57031506 A JP 57031506A JP 3150682 A JP3150682 A JP 3150682A JP S58148816 A JPS58148816 A JP S58148816A
- Authority
- JP
- Japan
- Prior art keywords
- injection
- thiamulin
- cyclodextrin
- fumarate
- tiamulin
- 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
- 239000007924 injection Substances 0.000 title claims abstract description 44
- 238000002347 injection Methods 0.000 title claims abstract description 44
- 239000002085 irritant Substances 0.000 title abstract description 4
- 231100000021 irritant Toxicity 0.000 title abstract description 4
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 42
- UURAUHCOJAIIRQ-QGLSALSOSA-N tiamulin Chemical compound CCN(CC)CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 UURAUHCOJAIIRQ-QGLSALSOSA-N 0.000 claims description 16
- 229960004885 tiamulin Drugs 0.000 claims description 16
- 229940049920 malate Drugs 0.000 claims description 8
- 230000000774 hypoallergenic effect Effects 0.000 claims description 3
- 229940080345 gamma-cyclodextrin Drugs 0.000 abstract description 22
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 abstract description 19
- 230000007794 irritation Effects 0.000 abstract description 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract description 11
- 230000008961 swelling Effects 0.000 abstract description 10
- 239000000725 suspension Substances 0.000 abstract description 8
- 239000000243 solution Substances 0.000 abstract description 7
- 241000282898 Sus scrofa Species 0.000 abstract description 6
- 210000000601 blood cell Anatomy 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 230000003115 biocidal effect Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 208000014085 Chronic respiratory disease Diseases 0.000 abstract description 2
- 206010035664 Pneumonia Diseases 0.000 abstract description 2
- 241000271566 Aves Species 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- 208000035473 Communicable disease Diseases 0.000 abstract 1
- 241000606790 Haemophilus Species 0.000 abstract 1
- 230000001629 suppression Effects 0.000 abstract 1
- YXQXDXAHCSEVSD-GCYNEOGWSA-N dynamutilin Chemical compound OC(=O)\C=C\C(O)=O.CCN(CC)CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 YXQXDXAHCSEVSD-GCYNEOGWSA-N 0.000 description 30
- 229940092292 tiamulin fumarate Drugs 0.000 description 30
- 238000012360 testing method Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 11
- 239000012153 distilled water Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000003814 drug Substances 0.000 description 8
- 206010018910 Haemolysis Diseases 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 230000008588 hemolysis Effects 0.000 description 7
- 210000003205 muscle Anatomy 0.000 description 7
- 241000283690 Bos taurus Species 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 238000010587 phase diagram Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000004455 differential thermal analysis Methods 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 241000204031 Mycoplasma Species 0.000 description 3
- 241000282887 Suidae Species 0.000 description 3
- 210000001217 buttock Anatomy 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 2
- 206010020565 Hyperaemia Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 230000017074 necrotic cell death Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 239000001116 FEMA 4028 Substances 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 206010061190 Haemophilus infection Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000029549 Muscle injury Diseases 0.000 description 1
- 241000204022 Mycoplasma gallisepticum Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- OBUUFWIMEGVAQS-UHFFFAOYSA-N Pleuromutenol Natural products CC1C(O)C(C)(C=C)CC(O)C2(C)C(C)CCC31C2C(=O)CC3 OBUUFWIMEGVAQS-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 210000003314 quadriceps muscle Anatomy 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- STZYTFJPGGDRJD-NHUWBDDWSA-N retapamulin Chemical compound C([C@H]([C@@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CS[C@@H]3C[C@H]4CC[C@H](N4C)C3)C)C[C@]32[C@H]1C(=O)CC3 STZYTFJPGGDRJD-NHUWBDDWSA-N 0.000 description 1
- 229960002771 retapamulin Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57031506A JPS58148816A (ja) | 1982-02-27 | 1982-02-27 | 低刺激性チアムリン注射剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57031506A JPS58148816A (ja) | 1982-02-27 | 1982-02-27 | 低刺激性チアムリン注射剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58148816A true JPS58148816A (ja) | 1983-09-05 |
| JPH0149125B2 JPH0149125B2 (enrdf_load_stackoverflow) | 1989-10-23 |
Family
ID=12333100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57031506A Granted JPS58148816A (ja) | 1982-02-27 | 1982-02-27 | 低刺激性チアムリン注射剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58148816A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT400674B (de) * | 1991-07-24 | 1996-02-26 | Biochemie Gmbh | Pharmazeutische pleuromutilin-zubereitung |
| WO1998003162A1 (fr) * | 1996-07-18 | 1998-01-29 | Yoshitomi Pharmaceutical Industries, Ltd. | Compositions medicinales |
| WO1999036065A1 (fr) * | 1998-01-19 | 1999-07-22 | Yoshitomi Pharmaceutical Industries, Ltd. | Compositions medicinales |
| US6476004B1 (en) | 1996-07-18 | 2002-11-05 | Mitsubishi Pharma Corporation | Pharmaceutical composition |
| JP2005523243A (ja) * | 2001-11-28 | 2005-08-04 | ノバルティス アクチエンゲゼルシャフト | プレウロムチリン誘導体を含有する微小球体 |
-
1982
- 1982-02-27 JP JP57031506A patent/JPS58148816A/ja active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT400674B (de) * | 1991-07-24 | 1996-02-26 | Biochemie Gmbh | Pharmazeutische pleuromutilin-zubereitung |
| US5578585A (en) * | 1991-07-24 | 1996-11-26 | Biochemie Gesellschaft M.B.H. | Pleuromutilin derivative complexes |
| WO1998003162A1 (fr) * | 1996-07-18 | 1998-01-29 | Yoshitomi Pharmaceutical Industries, Ltd. | Compositions medicinales |
| US6476004B1 (en) | 1996-07-18 | 2002-11-05 | Mitsubishi Pharma Corporation | Pharmaceutical composition |
| WO1999036065A1 (fr) * | 1998-01-19 | 1999-07-22 | Yoshitomi Pharmaceutical Industries, Ltd. | Compositions medicinales |
| JP4434486B2 (ja) * | 1998-01-19 | 2010-03-17 | 田辺三菱製薬株式会社 | 医薬組成物 |
| JP2005523243A (ja) * | 2001-11-28 | 2005-08-04 | ノバルティス アクチエンゲゼルシャフト | プレウロムチリン誘導体を含有する微小球体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0149125B2 (enrdf_load_stackoverflow) | 1989-10-23 |
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