Doxorubicin hydrochloride 阿霉素 盐酸盐

CAS 25316-40-9 MFCD00077757

化学结构图

25316-40-9
SMILES: COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl

化学属性

Mol. FormulaC27H30ClNO11
Mol. Weight580
Melting Point216
Solubility溶于水、DMSO、四氢呋喃和醇，不溶于丙酮、苯、氯仿、乙醚。水中溶解度: 10 mg/mL, 水溶液为橙红色透明溶液。,
Appearance 盐酸盐为桔红色针状结晶，熔点204-205℃。溶于水和醇，不溶于丙酮、苯、氯仿、乙醚。
Density1.422
Stability对光和湿度敏感

别名和识别编码

Chemical NameDoxorubicin hydrochloride
Synonym CAELYX 亚德里亚霉素,阿霉素(盐酸盐) Doxorubicin hydrochloride HYDROXYDAUNORUBICIN HYDROCHLORIDE 阿得里亚霉素 (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-methoxynaphthacene-5,12-dione hydrochloride 14-羟正定霉素 亚德里亚霉素盐酸盐 fi6804 (8S-cis)-10-((3-氨基-2,3,6-三去氧-a-L-来苏己吡喃基)-氧)-7, DOXORUBICIN HCL {hazard_c 10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-12-naphthacenedione {ALD Doxorubicin; 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; (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 盐酸柔红霉素 盐酸亚德里亚霉素 DOX 多柔比星® 盐酸盐 羟基柔红霉素 盐酸盐 14-HYDROXYDAUNOMYCIN HYDROCHLORIDE 盐酸多柔比星,阿霉素 Adriacin Adriamycin, hydrochloride 盐酸阿霉 admhydrochloride ADRIACIN 8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-xy)-hydroc ADRIAMYCIN HCL 阿霉素 盐酸盐 盐酸多柔比星 KW-125 (8S-cis)-10-[(3-氨基-2,3,6-三去氧-a-L-来苏己吡喃基)-氧]-7,8,9,10-四氢-6,8,11-三羟基-8-羟基乙酰基-1-甲氧基-5,12-并四苯二酮盐酸盐 Hydroxydaunorubicin hydrochloride DOXORUBICIN HYDROCHLORIDE 14-HYDROXYDAUNOMYCIN HCL 羟基柔红霉素盐酸盐 盐酸阿霉素 DOX HYDROCHLORIDE 阿霉素盐酸盐 DOX 多柔比星? 盐酸盐 FI 106 Ardriamycin ADRIAMYCIN HYDROCHLORIDE ADRIBLASTINA
CAS Number25316-40-9
PubChem Substance ID253660149
EC Number246-818-3
Beilstein Registry Number4229251
MDL NumberMFCD00077757
Chemical Name Translation阿霉素 盐酸盐
Merck Number3439
Reaxys-RN4229251
Wiswesser Line NotationL E6 C666 BV MVT&&&J DQ HV1Q HQ KQ RO1 FO- FT6OTJ B1CQ DZ &GH
LabNetwork Molecule IDLN00236131
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分类

  • {SNA} Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics, Antiviral, Apoptosis and Cell Cycle, Chemical Structure Class, Detection, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Fluorescent Labels, Fluorescent Stains, Interferes with DNA Synthesis, Mechanism of Action, Nucleic Acid Stains, Nucleic Acid Stains For Flow Cytometry, Other Apoptosis Related Reagents, Other Fluorescent Labels, R to Z, Reverse Transcriptase, AMV, Spectrum of Activity, Tetracyclines, Wavelength Index,
  • {SNA} Antibiotics,

产品应用

  • 抗肿瘤抗生素，在心脏线粒体DNA方面有阿霉素的效果。反相转录酶和RNA聚合酶的抑制剂，免疫抑制剂；可插入DNA链中。临床上是癌症化疗剂、主要用于急、慢性白血病、恶性淋巴瘤。

相关文献及参考

  • Cheng, J., et al., Poly(ethylene Glycol)-conjugated Multi-walled Carbon Nanotubes As An Efficient Drug Carrier For Overcoming Multidrug Resistance. Toxicol. Appl. Pharmacol. 250 , 184-93, (2011) 摘要
  • 2. R.J. White et al. Drugs Pharm. Sci. 22 , 569, (1984)
  • Park, J.Y., et al., Doxorubicin Enhances CD4(+) T-cell Immune Responses By Inducing Expression Of CD40 Ligand And 4-1BB. Int. Immunopharmacol. 9 , 1530-9, (2009) 摘要
  • Ahn, J., et al., Srg3, A Mouse Homolog Of BAF155, Is A Novel P53 Target And Acts As A Tumor Suppressor By Modulating P21(WAF1/CIP1) Expression. Oncogene 30 , 445-56, (2011) 摘要
  • Simpson, N.E., et al., High Levels Of Hsp90 Cochaperone P23 Promote Tumor Progression And Poor Prognosis In Breast Cancer By Increasing Lymph Node Metastases And Drug Resistance. Cancer Res. 70 , 8446-56, (2010) 摘要
  • Friesen, C., et al., Cytotoxic drugs and the CD95 pathway. Leukemia 13 , 1854, (1999)
  • Venkatachalam, K., et al., Neutralization Of Interleukin-18 Ameliorates Ischemia/reperfusion-induced Myocardial Injury. J. Thorac. Cardiovasc. Surg. 284 , 7853-65, (2009) 摘要
  • Merck: 14,3439
  • Benson, E.K., et al., Role Of Progerin-induced Telomere Dysfunction In HGPS Premature Cellular Senescence. J. Cell Biol. 123 , 2605-12, (2010) 摘要
  • Rajagopal, A., and Simon, S.M. Mol. Biol. Cell 14 , 3389-3399, (2003) 摘要

安全信息

GHS Symbol
WGK Germany3
Hazard Codes T,Xi T,T+ T
Hazard statements
  • H302 Harmful if swallowed 吞食有害
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H350 May cause cancer 可能致癌
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
RTECSQI9295900
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P312+P330
  • P305+P351+P338
  • P308+P313
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
Storage condition 0-10°C 2-8°C 储存温度：2-8°C
Safety Statements
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R36/38 Irritating to eyes and skin 对眼睛和皮肤有刺激性
  • R45 May cause cancer 可能致癌
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Primate - monkey
DOSE/DURATION           : 27 mg/kg/2Y-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Blood - leukemia
REFERENCE :
   PHMGBN Pharmacology: International Journal of Experimental and Clinical
   Pharmacology.  (S. Karger AG, Postfach CH-4009 Basel, Switzerland)  V.1-
   1968-  Volume(issue)/page/year: 20,9,1980

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 2571 ug/kg/3W-I
TOXIC EFFECTS :
   Kidney, Ureter, Bladder - changes in tubules (including acute renal failure,
   acute tubular necrosis)
REFERENCE :
   AIMDAP Archives of Internal Medicine.  (AMA, 535 N. Dearborn St., Chicago,
   IL 60610)  V.1-    1908-  Volume(issue)/page/year: 137,385,1977

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1245 ug/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NCISP* National Cancer Institute Screening Program Data Summary,
   Developmental Therapeutics Program. (Bethesda, MD 20205)
   Volume(issue)/page/year: JAN1986

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 5980 ug/kg
TOXIC EFFECTS :
   Behavioral - food intake (animal)
   Behavioral - muscle weakness
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 7,1052,1973

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPO

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 16030 ug/kg
TOXIC EFFECTS :
   Gastrointestinal - hypermotility, diarrhea
   Skin and Appendages - dermatitis, allergic (after topical exposure)
   Nutritional and Gross Metabolic - weight loss

TYPE OF TEST            : Phage inhibition capacity
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 350 ug/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 77,197,1980

TYPE OF TEST            : DNA repair
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/D

TYPE OF TEST            : Sex chromosome loss and nondisjunction
TEST SYSTEM             : Non-mammalian species Testis
DOSE/DURATION           : 2 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 247,29,1991

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 700 ng/plate
REFERENCE :
   AJHPA9 A

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Non-mammalian species Cells - not otherwise specified
DOSE/DURATION           : 200 nmol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 247,29,1991

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Non-mammalian species Testis
DOSE/DURATION           : 2 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 247,29,1991

{hazar

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 100 nmol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 45,343,1977

TYPE OF TEST

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rabbit
DOSE                    : 30 mg/kg
SEX/DURATION            : male 30 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - testes, epididymis, sperm duct
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 7,1063,1973

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 6 mg/kg
SEX/DURATION            : male 2 week(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - spermatogenesis (incl. genetic material,
   sperm morphology, motility, and count)
   Reproductive - Paternal Effects - testes, epididymis, sperm duct
   Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland,
   accessory glands
REFERENCE :
   REPTED Reproductive Toxicology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.1-    1987-  Volume(issue)/page/year:
   2,117,1988

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 4500 ug/kg
SEX/DURATION            : male 5 week(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - spermatogenesis (incl. genetic material,
   sperm morphology, motility, and count)
   Reproductive - Paternal Effects - testes, epididymis, sperm duct
REFERENCE :
   ANDRDQ Andrologia.  (Grosse Verlag GmbH, Kurfuerstenstr. 112-113, D-1000
   Berlin 30, Fed. Rep. Ger.) V.6-    1974-  Volume(issue)/page/year:
   26,151,1994

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE

其他信息

  • MOL 文件:25316-40-9.mol
  • Doxorubicin (Adriamycin)是一种抗生素类试剂，抑制DNA拓扑异构酶II，且诱导DNA损伤和凋亡。
  • 上游原料:柔红霉素
  • EPA Substance Registry System:25316-40-9(EPA Substance)
  • 方法一:由松链丝菌浅灰色变株（Str.Peucetius var.Caesius）的培养液提取而得。本品化学结构与柔红霉素类似，因此可以由柔红霉素化学转化而制得。目前已可化学全合成。
  • 溶于水、DMSO、四氢呋喃和醇，不溶于丙酮、苯、氯仿、乙醚。水中溶解度: 10 mg/mL, 水溶液为橙红色透明溶液。
  • F:10-21
  • 用途一:癌症化疗剂、主要用于急、慢性白血病、恶性淋巴瘤。
  • 用途二:抗肿瘤抗生素，在心脏线粒体DNA方面有阿霉素的效果。反相转录酶和RNA聚合酶的抑制剂，免疫抑制剂；可插入DNA链中。临床上是癌症化疗剂、主要用于急、慢性白血病、恶性淋巴瘤。
  • 下游产品:吡柔比星

系列性分类

  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Antibiotics A to Z - Antibiotics
  4. Antibiotics A-F - Antibiotics A to Z
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Fluorescent Probes, Labels, Particles and Stains - Biochemicals and Reagents
  4. Fluorescent Labels - Fluorescent Probes, Labels, Particles and Stains
  5. Other Fluorescent Labels - Fluorescent Labels
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Enzyme Inhibitors - Enzymes, Inhibitors, and Substrates
  5. Enzyme Inhibitors by Enzyme - Enzyme Inhibitors
  6. R to Z - Enzyme Inhibitors by Enzyme
  7. Reverse Transcriptase, AMV - R to Z

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