(+)-Camptothecin 喜树碱

CAS 7689-03-4 MFCD00081076

化学结构图

7689-03-4
SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3ccccc3nc2-1

化学属性

Mol. FormulaC20H16N2O4
Mol. Weight348.35
Density1.51
Melting Point260°C
Appearance Light yellow solid powder solid 淡黄色针状结晶。熔点259-263℃（分解），亦有报道为275-277℃及287-288℃。微溶于乙醇、氯仿，难溶于水。与酸不能生成稳定的盐，与氢氧化钠溶液加热反应可生成钠盐而溶于水。钠盐水溶液黄色澄明具蓝色荧光。
SolubilitySoluble in DMSO, not in water
Boiling Point757°C at 760 mmHg

别名和识别编码

Chemical Name(+)-Camptothecin
CAS Number7689-03-4
Alfabeta NameCAMPTOTHECIN
MDL NumberMFCD00081076
EC Number444-280-6
Beilstein Registry Number631069
PubChem Substance ID24360
Synonym Camptothecin {LY} Camptothecin {} {LY} Camptothecin {} {} {LY} Camptothecin {} {} {} {LY} (S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione (Irinotecan Impurity) {} {} {} {} {Chemicalbook} (S)-4-ETHYL-4-HYDROXY-1H-PYRANO-[3',4':6,7]INDOLIZINO[1,2-B]QUINOLINE-3,14(4H,12H)-DIONE {} {} {} {} {} {Chemicalbook} (S)-4-ETHYL-4-HYDROXY-1,12-DIHYDRO-4H-2-OXA-6,12A-DIAZA-DIBENZO[B,H]FLUORENE-3,13-DIONE {} {} {} {} {} {} {Chemicalbook} (S)-(+)-喜树碱 {} {} {} {} {} {} {} {Chemicalbook} (S)-(+)-CAMPTOTHECIN {} {} {} {} {} {} {} {} {Chemicalbook} (20S)-CAMPTOTHECIN {} {} {} {} {} {} {} {} {} {Chemicalbook} (+)-喜树碱 {} {} {} {} {} {} {} {} {} {} {Chemicalbook} (+)-CAMPTOTHECIN {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
Chemical Name Translation喜树碱
Merck Number1735
Reaxys-RN6075662
InChIInChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1
LabNetwork Molecule IDLN00173166
FormulaC20H16N2O4
IUPAC Name(S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
InChIKeyVSJKWCGYPAHWDS-FQEVSTJZSA-N
Canonical SMILESO=C1C2=C([C@@](O)(CC)C(OC2)=O)C=C(N1C3)C(C3=C4)=NC5=C4C=CC=C5
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分类

  • {SNA} Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics, Apoptosis and Cell Cycle, Bioactive Small Molecule Alphabetical Index, C-CH, DNA Repair Regulators, DNA metabolism, Enzyme Inhibitors, Inhibits an Enzyme, Interferes with DNA Synthesis, Mechanism of Action, Other Apoptosis Related Reagents, Phytochemicals in Herbal Medicine or Traditional Chinese Medicine (TCM), 抗生素, 抗肿瘤药物, 生化试剂, 生物活性小分子, 癌症研究, 细胞信号转导和神经科学, 细胞生物学, 营

产品应用

  • Camptothecin (CPT) is a cytotoxic quinoline alkaloid which inhibits the DNA enzyme topoisomerase I (topo I). It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic screening of natural products for anticancer drugs. It was isolated from the bark and stem of Camptotheca acuminata (Camptotheca, Happy tree), a tree native to China used as a cancer treatment in Traditional Chinese Medicine. CPT showed remarkable anticancer activity in preliminary clinical trials but also low solubility and (high) adverse drug reaction. Because of these disadvantages synthetic and medicinal chemists have developed numerous syntheses of Camptothecin and various derivatives to increase the benefits of the chemical, with good results. Two CPT analogues have been approved and are used in cancer chemotherapy today, topotecan and irinotecan.

相关文献及参考

  • Merck: 14,1735

安全信息

Warnings IRRITANT
Signal word Danger Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
  • 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）；
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R25 Toxic if swallowed 吞咽有毒
Precautionary statements
  • P301+P310+P330
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P332+P313
  • P405 Store locked up. 上锁保管。
  • 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。
RTECSUQ0492000
Hazard statements
  • H302 Harmful if swallowed 吞食有害
  • H301 Toxic if swallowed 吞食有毒
Personal Protective Equipment Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes T T,Xi
Storage condition 2-8°C, protect from light {LY} 2-8°C, protect from light Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). {} {LY} 2-8°C, protect from light {} {} {LY} 2-8°C, protect from light {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {Chemicalbook} 2-8°C 储存温度2-8℃ 贮存温度2-8℃
UN Number 1544 UN 1544 6.1/PG 3
Hazard Class6.1
Packing GroupIII

其他信息

  • 用途一:用于治疗胃癌、肠癌、慢性粒细胞型和急性白血病等
  • MOL 文件:7689-03-4.mol
  • 灭火剂:水, 二氧化碳, 泡沫, 干粉
  • color:yellow
  • Hazard Note:Irritant
  • Sigma Aldrich:7689-03-4(sigmaaldrich)
  • 储运特性:库房低温通风干燥; 与食品原料分开存放
  • Acros Organics:5,6,7-三羟黄酮-7-葡萄糖醛酸酯 (+)-Camptothecin, 98%(7689-03-4)
  • 微溶于乙醇、氯仿，难溶于水。与酸不能生成稳定的盐，与氢氧化钠溶液加热反应可生成钠盐而溶于水。钠盐水溶液黄色澄明具蓝色荧光
  • 急性毒性:口服-大鼠 LD50: 153 毫克/公斤; 口服-小鼠 LD50: 50.1 毫克/公斤
  • 可燃性危险特性:热分解排出有毒氮氧化物烟雾; 与酸反应分解
  • 类别:有毒物质
  • 用途二:抗癌药。用于胃癌、结肠癌、直肠癌、头颈部圆柱瘤型癌和膀胱癌。
  • 用途三:抗癌药。用于胃癌、结肠癌、直肠癌、头颈部圆柱瘤型癌和膀胱癌
  • 下游产品:伊立替康
  • TCI Shanghai:(S)-(+)-喜树碱 (S)-(+)-Camptothecin,>;95.0%(LC)(T)(7689-03-4)
  • 检测方法:HPLC
  • 方法一:本品是由珙桐科旱莲属植物喜树的根、皮、果实提取制得的生物碱。也可合成生产。将喜树果粗粉用10倍量80%乙醇浸泡24小时，收集渗漉液，减压浓缩回收乙醇。浓缩液静置取清液，用氯仿提取，提取液蒸馏回收氯仿至干，再加甲醇溶液，冷却过滤，滤饼为喜树碱粗品，粗品用甲醇-氯仿混合溶剂重结晶，得喜树碱。对生药喜树果汁，总收率0.03-0.04%.
  • 刺激数据:皮肤-小鼠 0.3%/6周 轻度
  • 毒性分级:高毒
  • 喜树碱价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 C1495 (S)-(+)-喜树碱 (S)-(+)-Camptothecin 1G 765元 2014/06/02 C1495 (S)-(+)-喜树碱 (S)-(+)-Camptothecin 100MG 105元 2010/06/21 276721000 喜树碱 (+)-Camptothecin 98% 100 MG 943元
  • 上游原料:甲醇溶液

系列性分类

  1. Life Science 生命科学
  2. Antibiotics 抗生素
  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. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Apoptosis and Cell Cycle - Cell Signaling and Neuroscience
  5. DNA metabolism - Apoptosis and Cell Cycle
  6. DNA Repair Regulators - DNA metabolism
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Alkaloids
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Antibiotics by Application
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Mechanism of Action
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Mechanism of Action
  5. Interferes with Cell Wall Synthesis
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Apoptosis and Cell Cycle
  5. DNA metabolism
  6. DNA Intercalators and Crosslinkers
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Peptides and Proteins
  5. Apoptosis and Cell Cycle Proteins
  6. Cell Cycle
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Proteins and Derivatives
  4. Proteins for Cell Biology
  5. Apoptosis and Cell Cycle Proteins
  6. Cell Cycle
  1. Medical Research Areas
  2. DNA Damage
  3. Topoisomerase

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