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33419-42-0 molecular structure
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(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1(9),2,7-trien-12-one

ChemBase ID: 653
Molecular Formular: C29H32O13
Molecular Mass: 588.55658
Monoisotopic Mass: 588.18429108
SMILES and InChIs

SMILES:
O([C@H]1[C@@H]2[C@@H]([C@@H](c3c1cc1OCOc1c3)c1cc(OC)c(O)c(OC)c1)C(=O)OC2)[C@@H]1O[C@H]2[C@@H](O[C@@H](OC2)C)[C@H](O)[C@H]1O
Canonical SMILES:
COc1cc(cc(c1O)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@@H](c2c1cc1OCOc1c2)O[C@@H]1O[C@@H]2CO[C@H](O[C@H]2[C@@H]([C@H]1O)O)C
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
InChIKey:
VJJPUSNTGOMMGY-MRVIYFEKSA-N

Cite this record

CBID:653 http://www.chembase.cn/molecule-653.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1(9),2,7-trien-12-one
(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one
(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one
(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one
IUPAC Traditional name
etoposide
Brand Name
Eposin
Etopophos
Lastet
Toposar
Vepesid
Vepesid J
Zuyeyidal
Synonyms
(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
EPEG
P 16-213
Vepesid J
Zuyeyidal
(-)-Etoposide
Etoposidum [INN-Latin]
trans-Etoposide
Etoposide
4′-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside)
VP-16-213
Etoposide
EPA
Demethyl-epiodophyllotoxin ethylidene glucoside
Eposin
Vepesid
VP-16
Toposar
CAS Number
33419-42-0
EC Number
251-509-1
MDL Number
MFCD00869325
PubChem SID
46505434
24278178
160964116
PubChem CID
36462

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.329948  H Acceptors 12 
H Donor LogD (pH = 5.5) 1.1603667 
LogD (pH = 7.4) 1.155394  Log P 1.1604304 
Molar Refractivity 139.0212 cm3 Polarizability 55.93246 Å3
Polar Surface Area 160.83 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 0.73  LOG S -2.78 
Solubility (Water) 9.78e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
58.7 mg/L expand Show data source
DMSO: soluble30 mg/mL expand Show data source
Methanol expand Show data source
Apperance
white powder expand Show data source
White Solid expand Show data source
Melting Point
236-251 °C(lit.) expand Show data source
254-256°C expand Show data source
Hydrophobicity(logP)
1 expand Show data source
pKa
9.8 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer, Under Inert Atmosphere expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
KC0190000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
45-22 expand Show data source
R:22-45-36/37/38 expand Show data source
Safety Statements
53-45 expand Show data source
S:28-29-36/37/39-45-53 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H302-H350 expand Show data source
GHS Precautionary statements
P201-P308 + P313 expand Show data source
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 expand Show data source
Target
Topoisomerase expand Show data source
Gene Information
human ... ABCB1(5243), CYP3A4(1576), TOP2A(7153)mouse ... Abcb1a(18671), Abcb1b(18669)rat ... Top2a(360243) expand Show data source
Purity
≥98% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Biological Source
synthetic expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00773 external link
Item Information
Drug Groups approved
Description A semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. [PubChem]
Indication For use in combination with other chemotherapeutic agents in the treatment of refractory testicular tumors and as first line treatment in patients with small cell lung cancer. Also used to treat other malignancies such as lymphoma, non-lymphocytic leukemia, and glioblastoma multiforme.
Pharmacology Etoposide is an antineoplastic agent and an epipodophyllotoxin (a semisynthetic derivative of the podophyllotoxins). It inhibits DNA topoisomerase II, thereby ultimately inhibiting DNA synthesis. Etoposide is cell cycle dependent and phase specific, affecting mainly the S and G2 phases. Two different dose-dependent responses are seen. At high concentrations (10 µg/mL or more), lysis of cells entering mitosis is observed. At low concentrations (0.3 to 10 µg/mL), cells are inhibited from entering prophase. It does not interfere with microtubular assembly. The predominant macromolecular effect of etoposide appears to be the induction of DNA strand breaks by an interaction with DNA-topoisomerase II or the formation of free radicals.
Toxicity Side effects include alopecia, constipation, diarrhea, nausea and vomiting and secondary malignancies (leukemia).
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic (through O-demethylation via the CYP450 3A4 isoenzyme pathway) with 40% excreted unchanged in the urine.
Absorption Absorbed well, time to peak plasma concentration is 1-1.5 hrs. Mean bioavailability is 50%.
Half Life 4-12 hours
Protein Binding 97%
Elimination Etoposide is cleared by both renal and nonrenal processes, i.e., metabolism and biliary excretion. Glucuronide and/or sulfate conjugates of etoposide are also excreted in human urine. Biliary excretion of unchanged drug and/or metabolites is an important route of etoposide elimination as fecal recovery of radioactivity is 44% of the intravenous dose. Only 8% or less of an intravenous dose is excreted in the urine as radiolabeled metabolites of 14C-etoposide.
Clearance * 33 - 48 mL/min [IV administration]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1225 external link
Research Area: Cancer
Biological Activity:
Two subclones of the OCI/AML-2 cell line, etoposide-sensitive (ES) and etoposide-resistant (ER) were used to investigate whether the Fas pathway is involved in etoposide-induced apoptosis in acute myeloblastic leukemia (AML). Both of the studied subclones expressed the Fas receptor (FasR), but only the ER cell line expressed the Fas ligand (FasL). Etoposide caused an increase in the mean fluorescence intensity of FasR in both subclones, and an induction of FasL in the ES subclone. However, no change in the numbers of apoptotic cells induced by etoposide was observed when FasR was blocked by an antagonist anti-Fas antibody, nor was an agonist anti-Fas antibody alone cytotoxic to the subclones or enhanced the cytotoxic effect of etoposide. [1]Etoposide phosphate is rapidly absorbed and converted to etoposide. Bioavailability averages 68% at doses up to 150 mg/m2/day. [3]
Sigma Aldrich - E1383 external link
Biochem/physiol Actions
Etoposide is an antitumor agent that complexes with topoisomerase II and DNA to enhance double-strand and single-strand cleavage of DNA and reversibly inhibit religation. Blocks the cell cycle in in S-phase and G2-phase of the cell cycle; induces apoptosis in normal and tumor cell lines; inhibits synthesis of the oncoprotein Mdm2 and induces apoptosis in tumor lines that overexpress Mdm2.
Toronto Research Chemicals - E933750 external link
A DNA topoisomerase II inhibitor. Semi-synthetic derivative of podophyllotoxin, related structurally to Teniposide. Antineoplastic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Siitonen T et al. Leuk Res. 2000 Apr;24(4):281-8
  • • Burden, D.A., et al.: J. Biol. Chem., 271, 29238 (1996)
  • • Joel, S., et al.: Cancer Treat. Rev., 22, 179 (1996)
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PATENTS

PATENTS

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INTERNET

INTERNET

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