23214-92-8

• 常用中文名：阿霉素
• 常用英文名：Doxorubicin hydrochloride
• CAS号：23214-92-8
• 分子式：C₂₇H₂₉NO₁₁
• 分子量：543.52
• 相关类别： 原料药 抗肿瘤药 抗生素类抗肿瘤药
• 发布时间：2018-09-07 17:58:31
• 更新时间：2026-07-01 11:30:42
• Doxorubicin 是一种有细胞毒性的蒽环类抗生素,用于治疗多种癌症。 Doxorubicin 在癌细胞中起作用的可能机制是嵌入 DNA 和破坏 topoisomerase-II 介导的DNA修复。

名称

• 中文名: 阿霉素
• 英文名: doxorubicin
• 中文别名: 10-((3-氨基-2,3,6-三去氧-ALPHA-L-来苏-己吡喃基)氧)-7,8,9,10-四氢-6,8,11-三羟基-8-羟乙酰基-1-甲氧基-5,12-萘二酮/羟基红比霉素/羟基柔红霉素/亚法里亚霉素/多柔比星/14-羟正定霉素/14-羟柔红霉素/阿得里亚霉素/亚德里亚霉素; PE标记的前动力蛋白2抗体; CY7标记的前动力蛋白2抗体; 多柔比星(阿霉素)/盐酸表柔比星杂质C/盐酸柔红霉素齐杂质D; 羟正定霉素; PKM 多克隆抗体-E-AB-13771; 阿霉素 游离态; PE-CY5标记的前动力蛋白2抗体; 羟基红比霉素; PE-CY7标记的前动力蛋白2抗体; DOXORUBICIN阿霉素; (8S,10S)-10-(((2R,4S,5S,6S)-4-氨基-5-羟基-6-甲基四氢-2H-吡喃-2-基)氧基)-6,8,11-三羟基-8-(2-羟基乙酰基)-1-甲氧基-7,8,9,10-四氢并四苯-5,12-二酮; 羟柔红霉素; BF405标记的前动力蛋白2抗体; CY5.5标记的前动力蛋白2抗体; 重组人 PKM2蛋白 (His标签)-PDEH100880; CY5标记的前动力蛋白2抗体; 阿霉; PACIFIC BLUE标记的前动力蛋白2抗体; BF555标记的前动力蛋白2抗体; BF594标记的前动力蛋白2抗体; APC-CY7标记的前动力蛋白2抗体; 表柔比星(表阿霉素)杂质3(表柔比星(表阿霉素)杂质C); BF700标记的前动力蛋白2抗体; APC-CY5.5标记的前动力蛋白2抗体; PKM 多克隆抗体-E-AB-10004; APC标记的前动力蛋白2抗体; PER标记的前动力蛋白2抗体; CY3标记的前动力蛋白2抗体; 多柔比星; 10-((3-氨基-2,3,6-三去氧-alpha-L-来苏-己吡喃基)氧)-7,8,9,10-四氢-6,8,11-三羟基-8-羟乙酰基-1-甲氧基-5,12-萘二酮; PKM2 多克隆抗体-D-AB-10309L; BF750标记的前动力蛋白2抗体; PER-CY5.5标记的前动力蛋白2抗体; 柔红霉素杂质D; 盐酸表阿霉素杂质C; BF647标记的前动力蛋白2抗体; HRP标记的前动力蛋白2抗体; PER-CY7标记的前动力蛋白2抗体; (8S,10S)-1-甲氧基-6,8,11-三羟基-8-(2-羟基乙酰基)-10-[[(2R,4S,5S,6S)-4-氨基-5-羟基-6-甲基-2-四氢吡喃基]氧基]-7,8,9,10-四氢并四苯-5,12-二酮; 阿霉素 -13C-D3; BF680标记的前动力蛋白2抗体; PE-CY5.5标记的前动力蛋白2抗体; 羟基柔红霉素; Doxorubicin 多柔比星/阿霉素; BF350标记的前动力蛋白2抗体; BIOTIN标记的前动力蛋白2抗体; 亚法里亚霉素; Adriamycin阿霉素; 盐酸多柔比星 标准品; 多柔比星杂质; RBITC标记的前动力蛋白2抗体; BF488标记的前动力蛋白2抗体; AP标记的前动力蛋白2抗体; Doxorubicin :阿霉素,多柔比星
• 英文别名: Adriamycin RDF (hydrochloride salt); (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside hydrochloride; 5,12-naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-, hydrochloride; ADRIAMYCINSEMIQUINONE; Doxorubicin hydrochloride (hydrochloride salt); (1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside hydrochloride (1:1); (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-Methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-Methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione; Doxorubincine; 5,12-naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-, hydrochloride (1:1); NCI-C-01514; Doxolem; Adriblastina (hydrochloride salt); EINECS 245-495-6; Biotransdox; ADRIAMYCIN; adriablatina (hydrochloride salt); PROK2; (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranoside hydrochloride (1:1); adiblastine (hydrochloride salt); (8S-cis)-10-(3-Amino-2,3,6-Trideoxy-alpha-L-Lyxo-Hexopyranosyl)Oxy-7,8,9,10-Tetrahydro-6,8,11-Trihydroxy-8-(Hydroxyacetyl)-1-Methoxy-5,12-Naphthacenedione; Hydroxydaunorubicin hydrochloride (hydrochloride salt); Adriamycin PFS (hydrochloride salt); (8S-cis)-10-((3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione hydrochloride; Adriacin (hydrochloride salt); (1S,3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranoside hydrochloride; Rubex (hydrochloride salt); Protein Bv8 homolog; Adriamycin PFS; Adriblastin; Adriamycin Adriamycin; 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S); (8S-cis)-10-[(3-Amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione hydrochloride; AdriaMycin, 14-HydroxydaunoMycin, FI 106, K 1039, KW 125, NSC; (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride; Doxorubicin Free Base; 10-((3-amino-2,3,6-trideoxy-alpha-l-lyso-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione; ADM hydrochloride; 5,12-Naphthacenedione, 10-(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S); Adriamycin hydrochloride; Adriamycin; Evacet; [14C]-Doxorubicin; [3H]-Doxorubicin; 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-, hydrochloride (1:1); (85-Cis)-10-Tetrahydro-6,8,11-Trihydroxy-8-(Hydroxyacetyl)-1-methoxy-5,12-Naphthacenedione; etrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione; (1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside hydrochloride (1:1); 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis); adriamycine; Fmablastina (hydrochloride salt); 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S); Prokineticin-2 human; adriablastine (hydrochloride salt); Doxorubicin hydrohloride; 10-((3-Amino-2,3,6-trideoxy-α-L-lyso-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-Methoxy-5,12-naphthacenedione; ADRIAMYCIN, PHMA; Rubidox; (8S)-10-((4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione; HydroxydaunoMycin; DOXOPINHYDROCHLORIDE; (1s,3s)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranoside; Doxil; Adriamycin HCl; DOXORUBICIN; (85-cis)-10-[(3-amino-2,3,6-trideoxy-alpha-l-lyxohexapyranosyl)oxy]-7,8,9,10- t; PK 2; Rubex; Adriamycin RDF; (8S,10S)-10-((3-Amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione hydrochloride; Adriamycin, hydrochloride; 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S); (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione; Hydroxydaunomycin hydrochloride (hydrochloride salt); Doxorubicin base; (8S,10S)-10-((3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione hydrochloride; adriblatina (hydrochloride salt); 14-Hydroxydaunomycin

物化性质

• 密度: 1.61 g/cm3
• 熔点: 205ºC
• 分子式: C₂₇H₂₉NO₁₁
• 分子量: 543.52
• 闪点: 443.8ºC
• PSA: 206.07000
• LogP: 1.50360
• 外观性状: 橙色至红色粉末
• 蒸汽压: 9.64E-28mmHg at 25°C
• 折射率: 1.709
• 储存条件: 库房通风低温干燥,与食品原料分开存放
• 水溶解性: Soluble

生物活性

• 描述: Doxorubicin 是一种有细胞毒性的蒽环类抗生素,用于治疗多种癌症。 Doxorubicin 在癌细胞中起作用的可能机制是嵌入 DNA 和破坏 topoisomerase-II 介导的DNA修复。
• 相关类别:
  信号通路 >> 抗体- 药物偶联物 >> ADC细胞毒素
  信号通路 >> 自噬 >> 自噬
  信号通路 >> 自噬 >> 自噬
  研究领域 >> 癌症
  天然产物 >> 其他
• 靶点:

  Topoisomerase II

• 体外研究: 在最高测试浓度(2μM和10μM,分别)中阿霉素和辛伐他汀的组合杀死了97％的Hela细胞[2]。
• 体内研究: 携带PC3异种移植物的小鼠注射2,4或8mg/kg多柔比星,并随时间测量肿瘤体积。 2mg/kg的剂量不影响肿瘤生长,而较高剂量最初延迟肿瘤生长(第18天和第22天p <0.05),4mg/kg或8mg/kg阿霉素显着降低PC3异种移植物中c-FLIP的水平。 [3]。单次腹膜内注射10mg/kg(多柔比星1)在大鼠中给药,每天10次腹膜内注射1mg/kg(多柔比星2),或每周5次腹膜内注射2mg/kg(多柔比星3)。在阿霉素1中第28天观察到80％的死亡率,而在第107天和第98天,阿霉素2和阿霉素3分别达到80％的死亡率。在多柔比星DOX1中,第2周的分数缩短减少30％,在阿霉素2中第13周减少55％,在阿霉素3中第13周减少42％[4]。
• 细胞实验: 将160μLHela细胞悬浮液（3×10 4细胞/ mL）分配到三个96孔U形底微量培养板中，并在37℃，5％CO 2的完全湿润气氛中孵育24小时。在板1中，加入多柔比星（20μL;终浓度，0.1-2μM）和辛伐他汀（20μL;终浓度，0.25-2μM）的连续稀释液至终体积200μL并再孵育72小时。在板2和3中，加入每种药物（辛伐他汀或多柔比星，40μL）的连续稀释液。在24小时的温育期后，吸出培养基并在PBS中洗涤细胞。然后，加入其他药物（40μL）的连续稀释液并补充培养基至终体积为200μL，并孵育48小时。多柔比星和辛伐他汀单独用作阳性对照（每孔40μL），仅用溶剂处理的细胞被认为是阴性对照。为了评估细胞存活，向每个孔中加入20μLMTT溶液（PBS中5mg / mL）并孵育3小时。然后用150μLDMSO代替培养基，并通过重复移液溶液实现甲crystals晶体的完全溶解。然后通过ELISA板读数器在540nm测定吸光度。在4或8个孔中测定每种药物浓度并重复3次。阿霉素的细胞毒性/细胞抑制作用表示为相对存活率（％对照）并计算。阴性对照中细胞存活的百分比假定为100.相对存活率=（实验吸光度 - 背景吸光度）/（未处理对照的吸光度 - 背景吸光度）×100％[2]。
• 动物实验: 小鼠[3]使用无胸腺雄性裸鼠（3-4周龄）。将PC3细胞（4×106）皮下注射到小鼠的侧腹中。将携带肿瘤的动物随机分配到治疗组（每组5或6只小鼠），并且当异种移植物达到约100mm 3的体积时开始治疗。使用数字卡尺测量肿瘤并使用以下公式计算体积：体积=宽度2×长度×0.52，其中宽度表示肿瘤的较短尺寸。如所示使用载体（含有0.1％BSA的PBS），阿霉素（2-8mg / kg），Apo2L / TRAIL（500μg/动物）或4mg / kg多柔比星的组合然后500μgApo2L/的施用来施用处理。落后。全身施用阿霉素，而在肿瘤内或全身施用Apo2L / TRAIL。所有治疗都给予一次。每天监测小鼠的不良反应迹象（无精打采和邋app的外观）。治疗似乎很好耐受。计算每个数据点的平均值±SEM。通过学生t检验分析治疗组之间的差异。当P <0.05时，差异被认为是显着的。大鼠[4]将30只雄性Sprague-Dawley大鼠（体重250-300g）随机分配到3个实验组中的1个：阿霉素方案1（多柔比星1，n = 10），阿霉素方案2（多柔比星2，n = 10），或阿霉素方案3（多柔比星3，n = 10）。对于所有阿霉素治疗方案，阿霉素的累积剂量为10mg / kg。附表1涉及以10mg / kg单次推注腹膜内注射阿霉素。附表2涉及以1mg / kg连续10天腹膜内注射多柔比星10次。附表3涉及5次腹膜内注射2mg / kg的阿霉素，每周一次，持续5周。在第一次阿霉素治疗之前和开始阿霉素治疗后每周一次，在所有存活的动物中评估血压和心脏功能，只要每组至少有3只大鼠。
• 参考文献:

  [1]. Nitiss JL, et al. Targeting DNA topoisomerase II in cancer chemotherapy.Nat Rev Cancer. 2009 May;9(5):338-50.

  [2]. Sadeghi-Aliabadi H, et al. Cytotoxic evaluation of doxorubicin in combination with simvastatin against human cancer cells. Res Pharm Sci. 2010 Jul;5(2):127-33.

  [3]. El-Zawahry A, et al. Doxorubicin increases the effectiveness of Apo2L/TRAIL for tumor growth inhibition of prostate cancerxenografts. BMC Cancer. 2005 Jan 7;5:2.

  [4]. Hayward R, et al. Doxorubicin cardiotoxicity in the rat: an in vivo characterization. J Am Assoc Lab Anim Sci. 2007 Jul;46(4):20-32.

  [5]. Zhang D, et al. Co-delivery nanoparticles with characteristics of intracellular precision release drugs for overcoming multidrug resistance. Int J Nanomedicine. 2017 Mar 16;12:2081-2108.

  [6]. Majumder S, et al. Shifts in podocyte histone H3K27me3 regulate mouse and human glomerular disease. J Clin Invest. 2018 Jan 2;128(1):483-499.

MSDS

Material Safety Data Sheet Section1. Identification of the substance Product Name: Adriamycin Synonyms: Section2. Hazards identification Harmful by inhalation, in contact with skin, and if swallowed. Section3. Composition/information on ingredients. Ingredient name:Adriamycin CAS number:23214-92-8 Section4. First aid measures Skin contact:Immediately wash skin with copious amounts of water for at least 15 minutes while removing contaminated clothing and shoes. If irritation persists, seek medical attention. Eye contact:Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical attention. Inhalation:Remove to fresh air. In severe cases or if symptoms persist, seek medical attention. Ingestion:Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention. Section5. Fire fighting measures In the event of a fire involving this material, alone or in combination with other materials, use dry powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus should be worn. Section6. Accidental release measures Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national standards. Respiratory precaution:Wear approved mask/respirator Hand precaution:Wear suitable gloves/gauntlets Skin protection:Wear suitable protective clothing Eye protection:Wear suitable eye protection Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container for disposal. See section 12. Environmental precautions: Do not allow material to enter drains or water courses. Section7. Handling and storage Handling:This product should be handled only by, or under the close supervision of, those properly qualified in the handling and use of potentially hazardous chemicals, who should take into account the fire, health and chemical hazard data given on this sheet. Store in closed vessels, refrigerated. Storage: Section8. Exposure Controls / Personal protection Engineering Controls: Use only in a chemical fume hood. Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles. General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse. Section9. Physical and chemical properties Appearance:Not specified Boiling point:No data No data Melting point: Flash point:No data Density:No data Molecular formula:C27H29NO11 Molecular weight:543.5 Section10. Stability and reactivity Conditions to avoid: Heat, flames and sparks. Materials to avoid: Oxidizing agents. Possible hazardous combustion products: Carbon monoxide, nitrogen oxides. Section11. Toxicological information No data. Section12. Ecological information No data. Section13. Disposal consideration Arrange disposal as special waste, by licensed disposal company, in consultation with local waste disposal authority, in accordance with national and regional regulations. Section14. Transportation information Non-harzardous for air and ground transportation. Section15. Regulatory information No chemicals in this material are subject to the reporting requirements of SARA Title III, Section 302, or have known CAS numbers that exceed the threshold reporting levels established by SARA Title III, Section 313. SECTION 16 - ADDITIONAL INFORMATION N/A

安全

• 危害码 (欧洲): Xn

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