BE592400A - - Google Patents

Info

Publication number

BE592400A

BE592400A BE592400DA BE592400A BE 592400 A BE592400 A BE 592400A BE 592400D A BE592400D A BE 592400DA BE 592400 A BE592400 A BE 592400A

Authority

BE

Belgium

Prior art keywords

sep

kanamycin

glucuronate

solution

glucuronic acid

Prior art date

Links

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• Global Dossier
• Discuss

• SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims description 62
• 229960000318 kanamycin Drugs 0.000 claims description 61
• 229930027917 kanamycin Natural products 0.000 claims description 61
• 229930182823 kanamycin A Natural products 0.000 claims description 61
• AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 claims description 55
• 239000000243 solution Substances 0.000 claims description 47
• 229940097042 glucuronate Drugs 0.000 claims description 45
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
• IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 17
• 229940097043 glucuronic acid Drugs 0.000 claims description 17
• 239000007864 aqueous solution Substances 0.000 claims description 11
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 8
• -1 glucuronate ions Chemical class 0.000 claims description 8
• 239000000203 mixture Substances 0.000 claims description 6
• 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 claims description 5
• 229910052708 sodium Inorganic materials 0.000 claims description 5
• 239000011734 sodium Substances 0.000 claims description 5
• 239000007787 solid Substances 0.000 claims description 4
• 150000002500 ions Chemical class 0.000 claims description 3
• 239000002904 solvent Substances 0.000 claims 1
• 241001465754 Metazoa Species 0.000 description 11
• OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical compound OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 description 11
• 229960002064 kanamycin sulfate Drugs 0.000 description 11
• 239000000047 product Substances 0.000 description 8
• 239000012458 free base Substances 0.000 description 7
• 206010011878 Deafness Diseases 0.000 description 6
• WNFHGZLVUQBPMA-JSCKKFHOSA-M Sodium glucuronate Chemical compound [Na+].O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C([O-])=O WNFHGZLVUQBPMA-JSCKKFHOSA-M 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 239000002585 base Substances 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• 208000016354 hearing loss disease Diseases 0.000 description 4
• 230000001225 therapeutic effect Effects 0.000 description 4
• 241000700159 Rattus Species 0.000 description 3
• 239000003242 anti bacterial agent Substances 0.000 description 3
• 229940088710 antibiotic agent Drugs 0.000 description 3
• 231100000888 hearing loss Toxicity 0.000 description 3
• 230000010370 hearing loss Effects 0.000 description 3
• 206010033109 Ototoxicity Diseases 0.000 description 2
• 229910052788 barium Inorganic materials 0.000 description 2
• DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
• TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
• OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
• ILJIJWPWFKABMW-VAQXQGSJSA-L calcium;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxy-6-oxohexanoate Chemical compound [Ca+2].O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C([O-])=O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C([O-])=O ILJIJWPWFKABMW-VAQXQGSJSA-L 0.000 description 2
• 238000004108 freeze drying Methods 0.000 description 2
• 239000011259 mixed solution Substances 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• 231100000262 ototoxicity Toxicity 0.000 description 2
• OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 2
• 229910052939 potassium sulfate Inorganic materials 0.000 description 2
• 235000011151 potassium sulphates Nutrition 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 229940083542 sodium Drugs 0.000 description 2
• ICQRTPLATMRWJI-JLWXJWIASA-M sodium;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxy-6-oxohexanoate;hydrate Chemical compound O.[Na+].O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C([O-])=O ICQRTPLATMRWJI-JLWXJWIASA-M 0.000 description 2
• 239000012265 solid product Substances 0.000 description 2
• SBUJHOSQTJFQJX-HZKXJDKASA-N (2s,3r,4r,5s,6s)-2-(aminomethyl)-6-[(1r,2r,3s,4r,6s)-4,6-diamino-3-[(2r,3s,4r,5r,6s)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](CN)O[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@H]([C@H](N)[C@@H](O)[C@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-HZKXJDKASA-N 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• 230000002411 adverse Effects 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 231100000895 deafness Toxicity 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 235000021137 habitual diet Nutrition 0.000 description 1
• 238000000034 method Methods 0.000 description 1
• 230000003472 neutralizing effect Effects 0.000 description 1
• 230000002970 ototoxic effect Effects 0.000 description 1
• UVGZJJKEELPWRH-JSCKKFHOSA-M potassium (2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoate Chemical compound [K+].O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C([O-])=O UVGZJJKEELPWRH-JSCKKFHOSA-M 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 239000003440 toxic substance Substances 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1