DEB0023108MA

DEB0023108MA -

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Publication number: DEB0023108MA
Authority: DE; Germany
Prior art keywords: amphomycin; solutions; solution; water; aqueous
Prior art date
Legal status : Active

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German (de)

English (en)

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XBNDESPXQUOOBQ-LSMLZNGOSA-N (2R,3S)-4-[[(2S)-1-[[2-[[(2S)-1-[[2-[[(2R,3S)-1-[[(2S)-1-[(2S)-2-[[(1S)-1-[(3S,9aR)-1,4-dioxo-3,6,7,8,9,9a-hexahydro-2H-pyrido[1,2-a]pyrazin-3-yl]ethyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-amino-1-oxobutan-2-yl]amino]-2-oxoethyl]am Chemical compound CCC(C)CCCCC\C=C\CC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)C(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@H]([C@H](C)N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)[C@H]1C(=O)N2CCCC[C@@H]2C(=O)N1 XBNDESPXQUOOBQ-LSMLZNGOSA-N 0.000 claims description 55
108010079465 amphomycin Proteins 0.000 claims description 55
239000000243 solution Substances 0.000 claims description 47
230000003115 biocidal Effects 0.000 claims description 41
LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
235000015097 nutrients Nutrition 0.000 claims description 20
OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 15
239000007864 aqueous solution Substances 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 14
241000187747 Streptomyces Species 0.000 claims description 13
239000011780 sodium chloride Substances 0.000 claims description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
230000002378 acidificating Effects 0.000 claims description 11
244000005700 microbiome Species 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
239000003242 anti bacterial agent Substances 0.000 claims description 10
238000000605 extraction Methods 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
230000000844 anti-bacterial Effects 0.000 claims description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
GXUDINOISGOIAV-UHFFFAOYSA-O Reinecke's salt Chemical compound [NH4+].O.S=C=N[Cr-3]([NH3+])([NH3+])(N=C=S)(N=C=S)N=C=S GXUDINOISGOIAV-UHFFFAOYSA-O 0.000 claims description 3
150000003863 ammonium salts Chemical class 0.000 claims description 3
239000012535 impurity Substances 0.000 claims description 3
AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 3
239000012454 non-polar solvent Substances 0.000 claims description 3
CPIVYSAVIPTCCX-UHFFFAOYSA-N 4-methylpentan-2-yl acetate Chemical compound CC(C)CC(C)OC(C)=O CPIVYSAVIPTCCX-UHFFFAOYSA-N 0.000 claims description 2
239000003929 acidic solution Substances 0.000 claims description 2
238000005273 aeration Methods 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
150000001720 carbohydrates Chemical class 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
238000005755 formation reaction Methods 0.000 claims description 2
150000001447 alkali salts Chemical class 0.000 claims 1
CLFAPTXAJGBEMW-UHFFFAOYSA-J azane;chromium(3+);tetrathiocyanate Chemical compound N.N.[Cr+3].[S-]C#N.[S-]C#N.[S-]C#N.[S-]C#N CLFAPTXAJGBEMW-UHFFFAOYSA-J 0.000 claims 1
239000007788 liquid Substances 0.000 description 18
230000002401 inhibitory effect Effects 0.000 description 14
239000000047 product Substances 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000126 substance Substances 0.000 description 12
238000000855 fermentation Methods 0.000 description 11
230000004151 fermentation Effects 0.000 description 11
229920001817 Agar Polymers 0.000 description 10
239000008272 agar Substances 0.000 description 10
235000002639 sodium chloride Nutrition 0.000 description 10
229940064005 Antibiotic throat preparations Drugs 0.000 description 9
229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 9
229940042052 Antibiotics for systemic use Drugs 0.000 description 9
229940042786 Antitubercular Antibiotics Drugs 0.000 description 9
229940093922 Gynecological Antibiotics Drugs 0.000 description 9
229940049954 Penicillin Drugs 0.000 description 9
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 9
229940024982 Topical Antifungal Antibiotics Drugs 0.000 description 9
229960000626 benzylpenicillin Drugs 0.000 description 9
229940079866 intestinal antibiotics Drugs 0.000 description 9
229940005935 ophthalmologic Antibiotics Drugs 0.000 description 9
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
238000010790 dilution Methods 0.000 description 8
239000002609 media Substances 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
238000009792 diffusion process Methods 0.000 description 7
239000000284 extract Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
229960001031 Glucose Drugs 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000007853 buffer solution Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000001963 growth media Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
WQZGKKKJIJFFOK-VFUOTHLCSA-N β-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 description 6
239000006286 aqueous extract Substances 0.000 description 5
239000012531 culture fluid Substances 0.000 description 5
238000011081 inoculation Methods 0.000 description 5
238000002955 isolation Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
210000004215 spores Anatomy 0.000 description 5
229960003563 Calcium Carbonate Drugs 0.000 description 4
FEMOMIGRRWSMCU-UHFFFAOYSA-N Ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 4
235000019764 Soybean Meal Nutrition 0.000 description 4
LWIHDJKSTIGBAC-UHFFFAOYSA-K Tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
238000007792 addition Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
230000001488 breeding Effects 0.000 description 4
229910000019 calcium carbonate Inorganic materials 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
201000009910 diseases by infectious agent Diseases 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
239000004455 soybean meal Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
241000194106 Bacillus mycoides Species 0.000 description 3
235000014469 Bacillus subtilis Nutrition 0.000 description 3
229950007432 Endomycin Drugs 0.000 description 3
241000192125 Firmicutes Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
239000002021 butanolic extract Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000008121 dextrose Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
239000002054 inoculum Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000012265 solid product Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
OJCKRNPLOZHAOU-RSXXJMTFSA-N (1R,2R)-2-[(2S,4E,6E,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid Chemical compound O1C(=O)C[C@H](O)[C@@H](C)C[C@@H](C)C[C@@H](C)C[C@H](C)[C@@H](O)\C(C#N)=C\C=C\C[C@H]1[C@H]1[C@H](C(O)=O)CCC1 OJCKRNPLOZHAOU-RSXXJMTFSA-N 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
PGMYKACGEOXYJE-UHFFFAOYSA-N Amyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
229940089206 Anhydrous Dextrose Drugs 0.000 description 2
240000008371 Bacillus subtilis Species 0.000 description 2
229940075615 Bacillus subtilis Drugs 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
229960004475 Chlortetracycline Drugs 0.000 description 2
CYDMQBQPVICBEU-XRNKAMNCSA-N Chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 description 2
BJHIKXHVCXFQLS-UYFOZJQFSA-N Fructose Natural products OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 2
108010068370 Glutens Proteins 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
GUBGYTABKSRVRQ-YOLKTULGSA-N Maltose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@H]1CO)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 GUBGYTABKSRVRQ-YOLKTULGSA-N 0.000 description 2
239000001888 Peptone Substances 0.000 description 2
108010080698 Peptones Proteins 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N Sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
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239000005862 Whey Substances 0.000 description 2
SRBFZHDQGSBBOR-SQOUGZDYSA-N Xylose Natural products O[C@@H]1CO[C@@H](O)[C@@H](O)[C@@H]1O SRBFZHDQGSBBOR-SQOUGZDYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
229940072049 amyl acetate Drugs 0.000 description 2
244000052616 bacterial pathogens Species 0.000 description 2
239000002585 base Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
235000019365 chlortetracycline Nutrition 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
235000005824 corn Nutrition 0.000 description 2
230000034994 death Effects 0.000 description 2
231100000517 death Toxicity 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
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239000012530 fluid Substances 0.000 description 2
235000021312 gluten Nutrition 0.000 description 2
238000011031 large scale production Methods 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
235000019319 peptone Nutrition 0.000 description 2
239000008055 phosphate buffer solution Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910000160 potassium phosphate Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
238000005507 spraying Methods 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
239000010959 steel Substances 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
235000019798 tripotassium phosphate Nutrition 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
235000021307 wheat Nutrition 0.000 description 2
BBBFYZOJHSYQMW-LGDQNDJISA-N (2S)-2,4-diamino-4-oxobutanoic acid;(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC(=O)[C@@H](N)CC(N)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O BBBFYZOJHSYQMW-LGDQNDJISA-N 0.000 description 1
241000186361 Actinobacteria <class> Species 0.000 description 1
VTIKDEXOEJDMJP-WYUUTHIRSA-N Actinorhodin Chemical compound C([C@@H](CC(O)=O)O[C@@H]1C)C(C(C2=C(O)C=3)=O)=C1C(=O)C2=C(O)C=3C(C(=C1C2=O)O)=CC(O)=C1C(=O)C1=C2[C@@H](C)O[C@H](CC(O)=O)C1 VTIKDEXOEJDMJP-WYUUTHIRSA-N 0.000 description 1
229940064004 Antiseptic throat preparations Drugs 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000193738 Bacillus anthracis Species 0.000 description 1
229960003071 Bacitracin Drugs 0.000 description 1
108010001478 Bacitracin Proteins 0.000 description 1
241000546721 Bruchidius aureus Species 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
229940041514 Candida albicans extract Drugs 0.000 description 1
229940077731 Carbohydrate nutrients Drugs 0.000 description 1
240000001817 Cereus hexagonus Species 0.000 description 1
HAWPXGHAZFHHAD-UHFFFAOYSA-N Chlormethine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
GZCGUPFRVQAUEE-KCDKBNATSA-N D-(+)-Galactose Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-KCDKBNATSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N D-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 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L Dipotassium phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
235000019749 Dry matter Nutrition 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
235000019733 Fish meal Nutrition 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
229960003082 Galactose Drugs 0.000 description 1
229940015001 Glycerin Drugs 0.000 description 1
229960004905 Gramicidin Drugs 0.000 description 1
108010026389 Gramicidin Proteins 0.000 description 1
IUAYMJGZBVDSGL-XNNAEKOYSA-N Gramicidin S Chemical compound C([C@@H]1C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CCCN)C(=O)N[C@H](C(N[C@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CCCN)C(=O)N[C@@H](CC(C)C)C(=O)N1)C(C)C)=O)CC(C)C)C(C)C)C1=CC=CC=C1 IUAYMJGZBVDSGL-XNNAEKOYSA-N 0.000 description 1
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