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33419-42-0 (Etoposide)

1

Identification

Etoposide Etoposide
Name Etoposide
Formula C29H32O13
MW 588.56
CAS No. 33419-42-0
EINECS 251-509-1
Smiles O=C1OC[[email protected]]2([H])[[email protected]](O[[email protected]]3[[email protected]@H]([[email protected]]([[email protected]@H]4O[[email protected]](C)OC[[email protected]]4O3)O)O)C5=C(C=C6OCOC6=C5)[[email protected]@H](C7=CC(OC)=C(O)C(OC)=C7)[[email protected]]21[H]
Synonyms VP-16;VP-16-213; (5R,5aR,8aR,9S)-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
InChI InChI=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
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Introduction

Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. Target: Topoisomerase Approved: 1983 Etoposide inhibits the growth of murine angiosarcoma cell line (ISOS-1) in a 5 days-period with IC50 of 0.25 μg/mL.

Background Information

Topoisomerase II inhibitor, blocking the cell cycle in in S-phase and G2-phase of the cell cycle, inducing apoptosis in normal and tumor cell line ......by AOBIOUS INC
Etoposide is a semisynthetic derivative of podophyllotoxin, which inhibits DNA synthesis via topoisomerase II inhibition activity. Etoposide caused an increase in the mean fluorescence intensity of FasR in both subclones, and an induction of FasL in the ES subclone. Etoposide phosphate is rapidly absorbed and converted to etoposide. Bioavailability averages 68% at doses up to 150 mg/m2/day. ......by AbMole BioScience
Potent anti-cancer compound. Induces apoptosis in normal and tumor cell lines [1, 5]. DNA Topoisomerase II activity inhibitor. Increases Topo II-mediated DNA breakage primarily by inhibiting the ability of the enzyme to religate cleaved nucleic acid molecules. Does not lead to immediate block of DNS synthesis, induces a progressive inhibition of DNA replication [2, 4, 6]. p53 activator [3]. Blocks the cell cycle between the end of the S phase and the early G2 phase [2, 8]. Oncoprotein Mdm2 synthesis inhibitor [7]. Apoptosis inducer through the cytochrome c/Apaf-1/caspase-9 pathway and the Fas-mediated death signaling pathway [9, 10]. Cell cycle checkpoint activator. Affects gene expression at different levels (chromatin remodeling, transcription and alternative splicing) [11, 14, 15]. Chemotherapeutic compound used in cancers [12, 13]. Used in conditioning regimen prior to a bone marrow or blood stem cell transplantation [16]. Highly effective in mobilizing stem cells [17] ......by Adipogen Corporation
Etoposide forms a ternary complex with DNA and the topoisomerase II enzyme (which aids in DNA unwinding), prevents re-ligation of the DNA strands, and by doing so causes DNA strands to break. Therefore, this causes errors in DNA synthesis and promotes apoptosis of the cancer cell. ......by AdooQ BioScience, LLC
A topoisomerase II inhibitor. A derivative of podophyllotoxin that has major activity against a number of tumors, including germ cell neoplasms, small cell lung cancer, and malignant lymphoma. Induces apoptosis in human T cells, mouse thymocytes, and HL-60 human leukemia cells ......by BioVision, Inc.,
This product is etoposide itself; please see Etoposide 4'-Phosphate, Free Acid, Cat. No. E-4444, for further technical information. Both etoposide and etoposide 4'-phosphate are used in formulations for use in humans. ......by LC Laboratoies
Etoposide is a topoisomerase II inhibitor, inhibiting DNA synthesis. ......by MedChemexpress Co., Ltd.
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). ......by MedKoo Biosciences, Inc.
Etoposide is a semisynthetic derivative of podophyllotoxin, which inhibits DNA synthesis via topoisomerase II inhibition activity. ......by Selleck Chemicals LLC
Etoposide is a semisynthetic derivative of podophyllotoxin, which inhibits DNA synthesis via topoisomerase II inhibition activity. ......by Target Molecule Corp.
Topoisomerase II inhibitor (IC50 = 59.2 μM). ......by Tocris Bioscience Inc.
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Protocol(Only for Reference)

Cell Experiment

Animal Experiment

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Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000016363

Storage condition

Store at or below -20 oC. by LC Laboratoies

Solubility

Soluble in DMSO at 100 mg/mL; very poorly soluble in ethanol; very poorly soluble in water; maximum solubility in plain water is estimated to be 20-50 μM; buffers, serum or other additives may increase or decrease the aqueous solubility. by LC Laboratoies
DMSO 100 mg/mL;Water <1 mg/mL by MedChemexpress Co., Ltd.
DMSO 100 mg/mL (169 mM) ; Water <1 mg/mL (<1 mM) ; Ethanol <1 mg/mL (<1 mM) by Selleck Chemicals LLC
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Mechanism and Indication

Signaling Pathways Cell Cycle/DNA Damage Autophagy
Target Topoisomerase Autophagy
Research Area Cancer
Indications
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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Etoposide - Launched
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Safety Data of Etoposide

Hazard Symbols : T,Xi
Risk Statements : 45-22-36/37/38
Safety Statements : 53-45-36/37-26
RTECS : KC0190000
WGKGermany : 3
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Spectral Information

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Suppliers List

Company Price and Availability Country/Region
AOBIOUS INC USA
AbMole BioScience USA
Adipogen Corporation USA
AdooQ BioScience, LLC USA
Aladdin 100mg/RMB170();500mg/RMB629() China
Apexbio Technology LLC USA
BOC Sciences
BioVision, Inc., USA
Biochempartner Co., Ltd China
CHEMSCENE, LLC 100mg/USD60();200mg/USD84() USA
Cayman Chemical Company USA
Dimysh ( ShangHai ) Trading Co., Ltd. China
Jiangsu Zhongdan Group Co., Ltd. China
LC Laboratoies 100mg/USD44(In stock);250mg/USD87(In stock);500mg/USD136(In stock);1g/USD225(In stock);2g/USD414(In stock);5g/USD890(In stock) USA
Lianyungang Guike Pharmaceutical Co., ltd. China
Lianyungang Jinkang Pharmaceutical Technology Co., Ltd. China
MedChemexpress Co., Ltd. 100mg/USD60();200mg/USD84() USA
MedKoo Biosciences, Inc. USA
Selleck Chemicals LLC 100mg/USD70(In stock);10mM/1mLIn DMSO/USD91(In stock);500mg/USD280(In stock) USA
Shandong Kingnod Pharmaceuticals Co., Ltd. China
Shanghai Haoyuan Chemexpress Co., Ltd. 100mg/USD60();200mg/USD84() China
Shanghai Jinhe Bio-Technology Co., Ltd. China
Shanghai Orient Chemical Co., Ltd. China
Shanghai SPE Chemicals Co., Ltd. China
Suzhou Unite Pharmtech Co., Ltd. China
Taizhou Bolon Pharmachem Co., Ltd. China
Target Molecule Corp. 1mg/USD20();2mg/USD40();5mg/USD67();10mg/USD112() USA
Tocris Bioscience Inc. USA
Yancheng Hejia Chemical Co., Ltd. China
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Related Products

Other Forms of 33419-42-0

Name CAS No Formula MW
Etoposide Phosphate 117091-64-2 C29H33O16P 668.54

Recommended Compounds in Topoisomerase Autophagy

Name CAS No Formula MW
Pirarubicin (Hydrochloride) 95343-20-7 C32H38ClNO12 664.1
Exatecan (Mesylate) 169869-90-3 C25H26FN3O7S 531.55
Flumequine 42835-25-6 C14H12FNO3 261.25
Nemorubicin 108852-90-0 C32H37NO13 643.64
Amsacrine (hydrochloride) 54301-15-4 C21H20ClN3O3S 429.92
Ellipticine 519-23-3 C17H14N2 246.31
DOXO-EMCH 151038-96-9 C37H42N4O13 750.75
Topotecan (Hydrochloride) 119413-54-6 C23H24ClN3O5 457.91
Topotecan 123948-87-8 C23H23N3O5 421.45
Tirapazamine 27314-97-2 C7H6N4O2 178.15
Teniposide 29767-20-2 C32H32O13S 656.65
TAS-103 174634-08-3 C20H19N3O2 333.38
TAS-103 (dihydrochloride) 174634-09-4 C20H21Cl2N3O2 406.31
Pixantrone (dimaleate) 144675-97-8 C21H23N5O6 441.44
Pixantrone 144510-96-3 C17H19N5O2 325.37
Pirarubicin 72496-41-4 C32H37NO12 627.64
SN-38 86639-52-3 C22H20N2O5 392.4
Irinotecan (hydrochloride) 100286-90-6 C33H39ClN4O6 623.14
Exatecan 171335-80-1 C24H22FN3O4 435.45
Epirubicin (hydrochloride) 56390-09-1 C27H30ClNO11 579.98

Recommended Compounds in Same Indication

Name CAS No Formula MW
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Route of Synthesis

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References

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More Information

Etoposide

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