(5R,5aR,8aR,9S)-9-[[4,6-O-(1R)-Ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one 4'-去甲基表鬼臼毒素-beta-D-乙叉吡喃葡萄糖甙

CAS 33419-42-0 MFCD00869325

化学结构图

33419-42-0
SMILES: COc1cc([C@@H]2c3cc4c(cc3C(O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O

化学属性

Mol. FormulaC29H32O13
Mol. Weight589
Melting Point236-251
SolubilitySoluble in DMSO, not in water
Appearance White to off-white solid powder

别名和识别编码

Chemical Name(5R,5aR,8aR,9S)-9-[[4,6-O-(1R)-Ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
CAS Number33419-42-0
Synonym (5R,5aR,8aR,9S)- 4'-Demethyl 4'-Demethylepipodophyllotoxin 9-(4,6-O-Ethylidene--D-glucopyranoside) 4'-Demethylepipodophyllotoxin 9-(4,6-O-Ethylidene-β-D-glucopyranoside) 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside) 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside) VP-16-213 4'-Demethylepipodophyllotoxin ethylidene-beta-D-glucoside 4'-O-Demethyl-1-O-(4,6-O-ethylidene-beta-D-glucopyranosyl)epipodophyllotoxin 4'-去甲表鬼臼9 -（4,6-O-亚乙基-β-e-吡喃葡萄糖苷）VP-16-213 4-Demethyl-epipodophyllotoxin-beta-D-ethylidene-glucoside 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside Demethyl Epipodophyllotoxin Ethylidine Glucoside. epipodophyllotoxin. US brand names: Toposar. VePesid. Foreign brand name: Lastet. Abbreviation: EPEG Code names: VP16; VP16213. Demethyl-epipodophyllotoxin ethylidene glucoside EPE {h
PubChem Substance ID24278178
EC Number251-509-1
MDL NumberMFCD00869325
Reaxys-RN365969
Merck Number3886
Beilstein Registry Number365969
Chemical Name Translation4'-去甲基表鬼臼毒素-beta-D-乙叉吡喃葡萄糖甙
LabNetwork Molecule IDLN01327181
FormulaC29H32O13
IUPAC Name(5R,5aR,8aR)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
InChIKeyVJJPUSNTGOMMGY-YLLUJYJTSA-N
InChIInChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26?,27-,29+/m1/s1
Canonical SMILESO=C1OC[C@]2([H])C(O[C@H]3[C@H](O)[C@@H](O)[C@]4([H])O[C@H](C)OC[C@@]4([H])O3)C5=C(C=C6OCOC6=C5)[C@@H](C7=CC(OC)=C(O)C(OC)=C7)[C@]21[H]
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分类

  • Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics, Antitumor Agents, Apoptosis and Cell Cycle, Application Index, Approved Therapeutics/Drug Candidates, Bioactive Small Molecules, Biochemicals and Reagents, Cancer Research, Cell Biology, Cell Signaling Enzymes, Cell Signaling and Neuroscience, Culture, DNA Repair Regulators, DNA metabolism, E, Enzyme Inhibitors, Enzymes, Inhibitors, and Substrates, Enzymes, Substrates, Inhibitors &, Modulators for Stem Cell Biology, General Stem Cell Biology, Inhibito

产品应用

  • Etoposide is a semisynthetic derivative of podophyllotoxin and a substance extracted from the mandrake root Podophyllum peltatum. Possessing potent antineoplastic properties, etoposide binds to and inhibits topoisomerase II and its function in ligating cleaved DNA molecules, resulting in the accumulation of single- or double-strand DNA breaks, the inhibition of DNA replication and transcription, and apoptotic cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

相关文献及参考

  • Burden, D.A., et al.: J. Biol. Chem., 271, 29238 (1996),
  • Joel, S., et al.: Cancer Treat. Rev., 22, 179 (1996),
  • Davies JH, Evans BA, Jenney ME, Gregory JW, Effects of chemotherapeutic agents on the function of primary human osteoblast-like cells derived from children. J. Clin. Endocrinol. Metab. , 6088-97, (2003) 摘要
  • Abbas T, White D, Hui L, Yoshida K, Foster DA, Bargonetti J, Inhibition of human p53 basal transcription by down-regulation of protein kinase Cdelta. J. Biol. Chem. , 9970-7, (2004) 摘要
  • Humphries MJ, Limesand KH, Schneider JC, Nakayama KI, Anderson SM, Reyland ME, Suppression of apoptosis in the protein kinase Cdelta null mouse in vivo. J. Biol. Chem. , 9728-37, (2005)
  • Soane L, Rus H, Niculescu F, Shin ML, Inhibition of oligodendrocyte apoptosis by sublytic C5b-9 is associated with enhanced synthesis of bcl-2 and mediated by inhibition of caspase-3 activation. J. Immunol. , 6132-8, (2008) 摘要
  • Li X, Choi JS, Effects of quercetin on the pharmacokinetics of Etoposide after oral or intravenous administration of etoposide in rats. Anticancer Res. , 1411-5, (2009) 摘要
  • Ferecatu, I., et al., Evidence For A Mitochondrial Localization Of The Retinoblastoma Protein. BMC Cell Biol. 10 , 50, (2009) 摘要
  • Chung, J.W., et al., Pseudomonas Aeruginosa Eliminates Natural Killer Cells Via Phagocytosis-induced Apoptosis. PLoS Pathog. 5 , e1000561, (2009) 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
  • Edgar, C.E., et al., CAML Regulates Bim-dependent Thymocyte Death. Cell Death Differ. 17 , 1566-76, (2010) 摘要
  • Mandriota, S.J., et al., Ataxia Telangiectasia Mutated

安全信息

GHS Symbol
WGK Germany3
Hazard Codes T
Hazard statements
  • H350 May cause cancer 可能致癌
  • H302 Harmful if swallowed 吞食有害
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
RTECSKC0190000
Precautionary statements
  • P308+P313
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • 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。
  • P308+P311
  • 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。
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P301+P312+P330
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • 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。
  • 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。
  • P263 Avoid contact during pregnancy/while nursing. 怀孕/哺乳期间避免接触。
Signal word
Safety Statements
Risk Statements
  • R45 May cause cancer 可能致癌
  • R22 Harmful if swallowed 吞咽有害
{h

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 15070 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            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human
DOSE/DURATION           : 16 mg/kg/5D-I
TOXIC EFFECTS :
   Blood - agranulocytosis
   Blood - aplastic anemia
   Blood - changes in bone marrow (not otherwise specified)
REFERENCE :
   CANCAR Cancer (Philadelphia).  (Lippincott/Harper, Journal Fulfillment
   Dept., 2350 Virginia Ave., Hagerstown, MD 21740)  V.1-    1948-
   Volume(issue)/p

{

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1784 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Gastrointestinal - hypermotility, diarrhea
   Nutritional and Gross Metabolic - body temperature decrease
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: 19,3473,1985

TYPE OF T

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 58 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: -,230,1995

TYPE OF TEST

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Human Cells - not otherwise specified
DOSE/DURATION           : 2 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Human Cells - not otherwise specified
DOSE/DURATION           : 20 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 311,21,1994

{h

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 1 umol/L
REFERENCE :
   BCPCA6 Biochemical Pharmacology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.1-    1958-  Volume(issue)/page/year:
   37,1883,1988

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Rodent - mouse Leukocyte
DOSE/DURATION           : 5 mg/L
REFERENCE :
   CYLPDN Zhongguo Yaoli Xuebao.  Acta Pharmacologica Sinica.  Chinese Journal
   of Pharmacology.  (China International Book Trading Corp., POB 2820,
   Beijing, Peop. Rep. China)  V.1-    1980-  Volume(issue)/page/year:
   10,377,1989

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Human Cells - not otherwise specified
DOSE/DURATION           : 100 nmol/L/1H
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human HeLa cell
DOSE/DURATION           : 20 umol/L
REFERENCE :
   BICHAW Biochemistry.  (American Chemical Soc., Distribution Office Dept.
   223, POB 57136, West End Stn., Washington, DC 20037)  V.1-    1962-
   Volume(issue)/page/year: 15,5435,1976

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 1 mg/kg
SEX/DURATION            : female 8 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - Central Nervous System
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 18,31,1978

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 44 mg/kg
SEX/DURATION

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 14 mg/kg
SEX/DURATION            : male 5 week(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: 19,3561,1985

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROU

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 45 mg/kg
SEX/DURATION            : male 90 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - testes, epididymis, sperm duct
REFERENCE :
   TOLED5 Toxicology Letters.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1977-  Volume(issue)/page/year: 45,185,1989

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

Storage condition Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

其他信息

  • 依托泊苷是一种抗肿瘤剂，它与拓扑异构酶Ⅱ及DNA结合成复合物，以增强双链和单链DNA的裂解，并可逆地抑制再连接。在细胞周期S期和G2期阻断细胞周期，在正常和肿瘤细胞系中诱导细胞凋亡，抑制癌蛋白Mdm2的合成，在过渡表达Mdm2的肿瘤细胞系中诱发细胞凋亡。

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. Cell Biology 细胞生物学
  3. Stem Cell Biology - Cell Biology
  4. General Stem Cell Biology - Stem Cell Biology
  5. Stem Cell Expansion - General Stem Cell Biology
  6. Culture - Stem Cell Expansion
  7. Antibiotics - Culture
  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. Medical Research Areas
  2. DNA Damage
  3. Topoisomerase

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