58957-92-9 (伊达比星,Idarubicin)

CAS号:
58957-92-9
中文名称:
伊达比星
英文名称:
Idarubicin
分子式:
C26H27NO9
分子量:
497.493888139725
简介:
伊达比星(Idarubicin)为蒽环类细胞周期非特异性抗癌药,可抑制DNA合成,干扰RNA聚合酶,抑制拓扑异构酶Ⅱ。其效价强度为柔红霉素的8倍,阿霉素的4~5倍。

伊达比星(58957-92-9)名称与标识符

名称

中文别名:
伊达比星;依达比星;4-去甲氧基柔红霉素;伊达吡星;(1S,3S)-3-乙酰-1,2,3,4,6,11-六氢-3,15,12-三羟基-6,11-二氧代-L-丁炔基-3-氨基-2,3,6-三脱氧基-Α-L-来苏糖吡喃己糖苷;盐酸伊达比星;盐酸伊达比星 Idarubicin HCl;
英文别名:
Idarubicin;(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;4-demethoxydaunomycin;4-Demethoxydaunorubicin;5,12-naphthacenedione;Idamycin;Idarubicina;Idarubicine;Idarubicine [INN-French];Idarubicinum;Idarubicinum [INN-Latin];5,12-Naphthacenedione,9-acetyl-7-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-,(7S-cis)-;1-Demethoxydaunorubicin;4-DMD;Demethoxydaunorubicin;SR-01000075934;IDARUBICIN [WHO-DD];SMR000466355;(7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride;(7S,9S)-9-Acetyl-7-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione;BCP9000773;4-Desmethoxydaunorubicin;(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;Daunomycin, 4-demethoxy-;NCGC00093976-03;AB00698511-08;SDCCGSBI-0050582.P002;HY-17381A;SR-01000075934-1;4-DEMETHOXY-DAUNORUBICIN;NCGC00093976-02;DTXSID7023142;Tox21_500600;IDARUBICIN [VANDF];AKOS015895563;5,12-Naphthacenedione, 9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S-cis)-;UNII-ZRP63D75JW;MLS001401448;Lopac0_000600;NSC256439;Idarubicinum (INN-Latin);DTXCID503142;(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride;5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-;AB00698511-09;NCGC00093976-18;A935911;(1S,3S)-3-ACETYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSIDE;58957-92-9;(1S,3S)-3-Acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-6,11-dioxo-1-naphthacenyl-3-amino-2,3,6-trideoxy-alpha-L-hexopyranoside;GTPL7083;(7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione;AB00698511_11;Idarubicine (INN-French);(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-quinone;hydrochloride;L01DB06;EN300-7479233;DB01177;CS-0007534;(7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;Idarubicin, United States Pharmacopeia (USP) Reference Standard;D08062;A832088;AB00698511-06;Zavedos (TN);XDXDZDZNSLXDNA-TZNDIEGXSA-N;EU-0100600;HMS2089D05;NCGC00261285-01;(7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride;IDARUBICIN [MI];BCPP000207;NCGC00093976-01;NCGC00093976-05;BRD-K69650333-001-01-1;Idarubicin (INN);CHEMBL1117;5,12-NAPHTHACENEDIONE, 9-ACETYL-7-((3-AMINO-2,3,6-TRIDEOXY-alpha-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,9,11-TRIHYDROXY-, (7S,9S)-;AC-9384;Idarubicina [INN-Spanish];NSC 256439;(1S,3S)-3-ACETYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-alpha-L-LYXO-HEXOPYRANOSIDE;cid_636362;ZRP63D75JW;(7S,9S)-9-acetyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione;(7S,9S)-9-acetyl-7-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione;DM5;4 Desmethoxydaunorubicin;(1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside;Idarubicin [INN:BAN];Q1063862;Idarubicin hydrochloride, solid;CCG-204689;CCRIS 5083;BRD-K69650333-001-02-9;CHEBI:42068;NCGC00093976-04;5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-;HMS3261H22;4 Demethoxydaunorubicin;Idarubicina (INN-Spanish);5,12-NAPHTHACENEDIONE, 9-ACETYL-7-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,9,11-TRIHYDROXY-, (7S,9S)-;4-DMDR;(7S-cis)-9-Acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione;(1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside;Idarubicinhydrochloride;BDBM58490;I 1656;LP00600;AB00698511-10;KBioSS_002388;BRD-K69650333-003-14-0;SCHEMBL3750;IDARUBICIN [INN];NCGC00093976-12;5,12-Naphthacenedione,9-acetyl-7-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S,9S)-;BRD-K69650333-003-13-2;Idarubicin?;

标识符

MDL:
MFCD00897212
InChIKey:
XDXDZDZNSLXDNA-TZNDIEGXSA-N
Inchi:
1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1
SMILES:
O([C@H]1C[C@@H]([C@@H]([C@H](C)O1)O)N)[C@@H]1C2C(=C3C(C4C=CC=CC=4C(C3=C(C=2C[C@@](C(C)=O)(C1)O)O)=O)=O)O

伊达比星(58957-92-9)物化性质

实验特性

  • LogP : 1.72060
  • PSA : 176.61000
  • 折射率 : 1.6000 (estimate)
  • 沸点 : 725.435℃ at 760 mmHg
  • 熔点 : No data available
  • 蒸气压 : No data available
  • 闪点 : 392.5±32.9 °C
  • 颜色与性状 : No data avaiable
  • 密度 : 1.3477 (rough estimate)

计算特性

  • 精确分子量 : 497.16900
  • 氢键供体数量 : 5
  • 氢键受体数量 : 10
  • 可旋转化学键数量 : 3
  • 同位素质量 : 497.168581
  • 重原子数量 : 36
  • 复杂度 : 912
  • 同位素原子数量 : 0
  • 确定原子立构中心数量 : 6
  • 不确定原子立构中心数量 : 0
  • 确定化学键立构中心数量 : 0
  • 不确定化学键立构中心数量 : 0
  • 共价键单元数量 : 1
  • 疏水参数计算参考值(XlogP) : 无
  • 互变异构体数量 : 54
  • 表面电荷 : 0
  • 拓扑分子极性表面积 : 177

伊达比星(58957-92-9)国际标准相关数据

EINECS:
260-990-7

伊达比星(58957-92-9)生产方法和用途

用途:
抗肿瘤药。
生产方法:
-40℃和氩气保护下,将化合物((-)-Ⅱ)(159mg,0.29mmo1)和0.8g4A分子筛悬浮于12ml二氯甲烷和10ml乙醚的混合液中,加入TMSOTf(0.12ml,0.62mmo1)。在0℃下搅拌1h。冷却至-15℃,加入化合物(+)-(I)(85mg,0.23mm...

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