ETOPOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H32O13
Molecular Weight	588.5566
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12COC(=O)[C@]1([H])[C@H](C3=CC(OC)=C(O)C(OC)=C3)C4=CC5=C(OCO5)C=C4[C@H]2O[C@]6([H])O[C@]7([H])CO[C@@H](C)O[C@@]7([H])[C@H](O)[C@H]6O

InChI

InChIKey=VJJPUSNTGOMMGY-MRVIYFEKSA-N

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

HIDE SMILES / InChI

Molecular Formula	C29H32O13
Molecular Weight	588.5566
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16101488
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf

Etoposide (trade name Etopophos) is a semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. It has been in clinical use for more than two decades and remains one of the most highly prescribed anticancer drugs in the world. The primary cytotoxic target for etoposide is topoisomerase II. This ubiquitous enzyme regulates DNA under- and over winding, and removes knots and tangles from the genome by generating transient double-stranded breaks in the double helix. Etoposide kills cells by stabilizing a covalent enzyme-cleaved DNA complex (known as the cleavage complex) that is a transient intermediate in the catalytic cycle of topoisomerase II. The accumulation of cleavage complexes in treated cells leads to the generation of permanent DNA strand breaks, which trigger recombination/repair pathways, mutagenesis, and chromosomal translocations. If these breaks overwhelm the cell, they can initiate death pathways. Thus, etoposide converts topoisomerase II from an essential enzyme to a potent cellular toxin that fragments the genome. Although the topoisomerase II-DNA cleavage complex is an important target for cancer chemotherapy, there also is evidence that topoisomerase II-mediated DNA strand breaks induced by etoposide and other agents can trigger chromosomal translocations that lead to specific types of leukemia. Etopophos (etoposide phosphate) is indicated in the management of the following neoplasms: Refractory Testicular Tumors-and for Small Cell Lung Cancer. The in vitro cytotoxicity observed for etoposide phosphate is significantly less than that seen with etoposide, which is believed due to the necessity for conversion in vivo to the active moiety, etoposide, by dephosphorylation. The mechanism of action is believed to be the same as that of etoposide.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II 65 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16101488	Inhibitor 8146		0.8 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Refractory testicular tumors 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf	Primary		Approved 8307	ETOPOPHOS PRESERVATIVE FREE Approved Use ETOPOPHOS for Injection is indicated in the management of the following neoplasms: Refractory Testicular Tumors-ETOPOPHOS for Injection in combination therapy with other approved chemotherapeutic agents in patients with refractory testicular tumors who have already received appropriate surgical, chemotherapeutic, and radiotherapeutic therapy. Small Cell Lung Cancer-ETOPOPHOS for Injection in combination with other approved chemotherapeutic agents as first-line treatment in patients with small cell lung cancer. Launch Date 4.37270413E11
Small-cell lung cancer 41 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf	Primary		Approved 8307	ETOPOPHOS PRESERVATIVE FREE Approved Use ETOPOPHOS for Injection is indicated in the management of the following neoplasms: Refractory Testicular Tumors-ETOPOPHOS for Injection in combination therapy with other approved chemotherapeutic agents in patients with refractory testicular tumors who have already received appropriate surgical, chemotherapeutic, and radiotherapeutic therapy. Small Cell Lung Cancer-ETOPOPHOS for Injection in combination with other approved chemotherapeutic agents as first-line treatment in patients with small cell lung cancer. Launch Date 8.3229121E11

C_max

Value	Dose	Co-administered	Analyte	Population
14.7 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8431968	80 mg/m² other, intravenous dose: 80 mg/m² route of administration: Intravenous experiment type: OTHER co-administered:		ETOPOSIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
18.66 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8431968	95 mg/m² other, intravenous dose: 95 mg/m² route of administration: Intravenous experiment type: OTHER co-administered:		ETOPOSIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2707 μg × min/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8431968	80 mg/m² other, intravenous dose: 80 mg/m² route of administration: Intravenous experiment type: OTHER co-administered:		ETOPOSIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
5806 μg × min/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8431968	95 mg/m² other, intravenous dose: 95 mg/m² route of administration: Intravenous experiment type: OTHER co-administered:		ETOPOSIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.37 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8431968	80 mg/m² other, intravenous dose: 80 mg/m² route of administration: Intravenous experiment type: OTHER co-administered:		ETOPOSIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.32 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8431968	95 mg/m² other, intravenous dose: 95 mg/m² route of administration: Intravenous experiment type: OTHER co-administered:		ETOPOSIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
3% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf			ETOPOSIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
25 mg/m2 3 times / day multiple, oral Highest studied dose Dose: 25 mg/m2, 3 times / day Route: oral Route: multiple Dose: 25 mg/m2, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8021737 Page: p.1455	unhealthy, 1.1-17 n = 8 Health Status: unhealthy Condition: Cancer Age Group: 1.1-17 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/8021737 Page: p.1455	DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 25%) Thrombocytopenia (grade 4, 12.5%) Leukopenia (grade 4, 12.5%) Diarrhea (grade 3, 12.5%) Diarrhea (grade 4, 12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/8021737 Page: p.1455
20 mg/m2 3 times / day multiple, oral MTD Dose: 20 mg/m2, 3 times / day Route: oral Route: multiple Dose: 20 mg/m2, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8021737 Page: p.1455	unhealthy, 1.1-17 n = 7 Health Status: unhealthy Condition: Cancer Age Group: 1.1-17 Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/8021737 Page: p.1455	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 4, 14%) Sources: https://pubmed.ncbi.nlm.nih.gov/8021737 Page: p.1455
175 mg/m2 1 times / day multiple, intravenous MTD Dose: 175 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 175 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7799021 Page: p.203	unhealthy, 39-72 n = 7 Health Status: unhealthy Condition: Cancer Age Group: 39-72 Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/7799021 Page: p.203	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 4, 28.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/7799021 Page: p.203
175 mg/m2 1 times / day multiple, intravenous MTD Dose: 175 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 175 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7799021 Page: p.203	unhealthy, 39-72 n = 7 Health Status: unhealthy Condition: Cancer Age Group: 39-72 Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/7799021 Page: p.203	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 3, 14.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/7799021 Page: p.203
220 mg/m2 1 times / day multiple, intravenous MTD Dose: 220 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 220 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7799021 Page: p.203	unhealthy, 39-72 n = 8 Health Status: unhealthy Condition: Cancer Age Group: 39-72 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/7799021 Page: p.203	DLT: Neutropenia, Neutropenia... Dose limiting toxicities: Neutropenia (grade 3, 25%) Neutropenia (grade 4, 25%) Sources: https://pubmed.ncbi.nlm.nih.gov/7799021 Page: p.203
60 mg/m2 1 times / day multiple, oral (max) Recommended Dose: 60 mg/m2, 1 times / day Route: oral Route: multiple Dose: 60 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9469322 Page: p.407	unhealthy, 39-83 n = 97 Health Status: unhealthy Condition: Ovarian carcinoma Age Group: 39-83 Sex: F Population Size: 97 Sources: https://pubmed.ncbi.nlm.nih.gov/9469322 Page: p.407	DLT: Leukopenia, Neutropenia... Disc. AE: Nausea and vomiting, Fatigue... Dose limiting toxicities: Leukopenia (grade 4, 12%) Neutropenia (grade 4, 25%) Leukopenia (grade 3, 29%) Neutropenia (grade 3, 20%) Thrombocytopenia (grade 4, 4%) AEs leading to discontinuation/dose reduction: Nausea and vomiting (3%) Fatigue (1%) Neutropenic sepsis (grade 5, 2%) Bleeding (grade 5, 1%) Sources: https://pubmed.ncbi.nlm.nih.gov/9469322 Page: p.407
100 mg/m2 1 times / day multiple, intravenous (max) Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Testicular cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf Page: p.1	Disc. AE: Myelosuppression... AEs leading to discontinuation/dose reduction: Myelosuppression (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf Page: p.1

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1670

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP2 363	OATP1B1 389 P-gp 1491 CYP2E1 633 CYP1A2 1013 CYP3A5 383 CYP2B6 648 CYP2A6 510 UGT1A1 417 UGT1A8 282 UGT1A3 421 UGT1A4 345 UGT1A6 306 UGT1A7 235 UGT1A9 378 UGT1A10 289 UGT2B4 248 UGT2B7 387 UGT2B15 202 UGT2B17 212 Abcc2 3 Abcc3 3 MRP2 196 MRP3 50	CYP3A5 76

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A5 130	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	slight
MRP2 452	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/12134946/	weak [Ki 756 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1670	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf	major		weak (co-administration study) Comment: Ketoconazole increased the area under the plasma concentration-time curve (AUC) of oral etoposide by a median of 20% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf
UGT1A1 417	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	major		yes (pharmacogenomic study) Comment: UGT1A128 and UGT1A16 mutations might be regarded as predictors for etoposide-induced grade 4 neutropenia. Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/
CYP1A2 1013	substrate 3264 Sources: https://jpet.aspetjournals.org/content/286/3/1294.long	minor
CYP2E1 633	substrate 3264 Sources: https://jpet.aspetjournals.org/content/286/3/1294.long	minor
UGT1A3 421	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	minor
UGT1A8 282	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	minor
CYP2A6 510	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	no
CYP2B6 648	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	no
UGT1A10 289	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A4 345	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A6 306	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A7 235	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A9 378	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B15 202	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B17 212	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B4 248	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B7 387	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
Abcc2 3	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/20028753/	yes
Abcc3 3	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/20028753/	yes	ETOPOSIDE GLUCURONIDE 3
CYP3A5 383	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	yes
MRP2 196	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3372834/	yes
MRP3 50	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/11581266/	yes	ETOPOSIDE GLUCURONIDE 3
OATP1B1 389	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3372834/	yes
P-gp 1491	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/7850926/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4911	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4911
MolPort	MolPort-006-069-121	https://www.molport.com/shop/molecule-link/MolPort-006-069-121
Selleck Chemicals	Etopophos	http://www.selleckchem.com/products/Etopophos.html
ZINC	ZINC000003938684	http://zinc15.docking.org/substances/ZINC000003938684
eMolecules	32278021	https://www.emolecules.com/cgi-bin/more?vid=32278021
eMolecules	537894	https://www.emolecules.com/cgi-bin/more?vid=537894

PubMed

Title	Date	PubMed
Etoposide-induced hypersensitivity reactions. Report of two cases.	1985 Dec	3830414
Expression of p21 and bcl-2 proteins and p53 mRNA in surgically resected preparations of non-small cell lung cancer (stage IIIA) after etoposide and cisplatin chemotherapy.	2001	11820594
Bone morphogenetic protein-2 promotes osteoblast apoptosis through a Smad-independent, protein kinase C-dependent signaling pathway.	2001 Aug 3	11395480
Comparison of 'sequential' versus 'standard' chemotherapy as re-induction treatment, with or without cyclosporine, in refractory/relapsed acute myeloid leukaemia (AML): results of the UK Medical Research Council AML-R trial.	2001 Jun	11380463
High-dose chemotherapy as a consolidation approach in advanced ovarian cancer: long-term results.	2001 May	11438815
Langerhans cell histiocytosis.	2001 Nov	11903153
Expression of P-glycoprotein and multidrug resistance associated protein in Ehrlich ascites tumor cells after fractionated irradiation.	2001 Nov 15	11704330
Treatment of gestational trophoblastic tumors.	2002 Apr	12057074
Alpha-CD25 antibody treatment in a child with hemophagocytic lymphohistiocytosis.	2002 Feb	11813188
Estrogen receptor-dependent and estrogen receptor-independent pathways for tamoxifen and 4-hydroxytamoxifen-induced programmed cell death.	2002 Nov 22	12244117
Expression of p21 and bcl-2 proteins in paraffin-embedded preparations of non-small cell lung cancer in stage IIIA after Etoposide and Cisplatin induced chemotherapy.	2003	15314975
EBNA1 may prolong G(2)/M phase and sensitize HER2/neu-overexpressing ovarian cancer cells to both topoisomerase II-targeting and paclitaxel drugs.	2003 Aug 1	12893273
Relapse in the skull after myeloablative therapy for high-risk neuroblastoma.	2003 Jan-Feb	12687750
Oral melphalan as a treatment for platinum-resistant ovarian cancer.	2003 Jun 16	12799622
Phase I/II trial of weekly cisplatin, etoposide, and irinotecan chemotherapy for metastatic lung cancer: JCOG 9507.	2003 Mar 24	12644814
High-throughput technology: green fluorescent protein to monitor cell death.	2005	15901932
Long-term results of autologous stem cell transplantation for Hodgkin's disease (HD) and low-/intermediate-grade B non-Hodgkin's lymphoma (NHL): a report from the Austrian Stem Cell Transplantation Registry (ASCTR).	2005 Jul	15726362
Prognostic value of the age-adjusted International Prognostic Index in chemosensitive recurrent or refractory non-Hodgkin's lymphomas treated with high-dose BEAM therapy and autologous stem cell transplantation.	2005 Jun	16019530
Evaluation of the combined effect of p53 codon 72 polymorphism and hotspot mutations in response to anticancer drugs.	2005 Jun 15	15958617
HER-2/neu and CD117 (c-kit) overexpression in patients with pesticide exposure and extensive stage small cell lung carcinoma (ESSCLC).	2005 Jun 9	15946380
Pregnancy outcome after prenatal exposure to bleomycin, etoposide and cisplatin for malignant ovarian germ cell tumors: report of 2 cases.	2005 Mar-Apr	15749271
Use of preclinical models to improve treatment of retinoblastoma.	2005 Oct	16231976
Bcl-XL is qualitatively different from and ten times more effective than Bcl-2 when expressed in a breast cancer cell line.	2006 Aug 23	16928273
[Pulmonary and pleural manifestations of multiple myeloma].	2006 Dec	17163315
Randomized phase III trial comparing irinotecan/cisplatin with etoposide/cisplatin in patients with previously untreated extensive-stage disease small-cell lung cancer.	2006 May 1	16648503
Genotoxic risks to nurses from contamination of the work environment with antineoplastic drugs in Japan.	2006 Nov	17179646
BRCA1- and BRCA2-deficient cells are sensitive to etoposide-induced DNA double-strand breaks via topoisomerase II.	2007 Aug 1	17671173
Curative surgery after neoadjuvant chemotherapy in metastatic poorly differentiated neuroendocrine carcinoma.	2007 Dec	17350785
Dielectrophoretic detection of membrane morphology changes in Jurkat T-cells undergoing etoposide-induced apoptosis.	2007 Feb	17500582
The N-terminus and alpha-5, alpha-6 helices of the pro-apoptotic protein Bax, modulate functional interactions with the anti-apoptotic protein Bcl-xL.	2007 May 23	17519046
Effect of structural modification at the 4, 3', and 2' positions of doxorubicin on topoisomerase II poisoning, apoptosis, and cytotoxicity in human melanoma cells.	2007 May-Jun	17557149
Upregulation of bfl-1 is a potential mechanism of chemoresistance in B-cell chronic lymphocytic leukaemia.	2007 Sep 17	17726463
Glassy cell carcinoma of the uterine cervix responsive to neoadjuvant intraarterial chemotherapy.	2008 Dec	19093183
Interferonalpha enhances etoposide-induced apoptosis in human osteosarcoma U2OS cells by a p53-dependent pathway.	2008 Feb 13	18191951
Ifosfamide, epirubicin and etoposide rituximab in refractory or relapsed B-cell lymphoma: analysis of remission induction and stem cell mobilization.	2008 Jul	18604723
Haematopoietic stem cell transplantation for autoimmune disorders.	2008 Nov	18832930
[Production of reconstructed two-cell rat embryos after chemical inactivation of chromosomes in MII oocytes by etoposide].	2008 Sep-Oct	18959199
Primary sinonasal choriocarcinoma.	2009 Apr	19302957
[Diabetes insipidus followed, after 4 years, with dysarthria and mild right-sided hemiparesis--the first clinical signs of Erdheim-Chester disease. Description and depiction of a case with a review of information on the disease].	2009 Dec	20070034
Fasting and cancer treatment in humans: A case series report.	2009 Dec 31	20157582
Pegylated liposomal doxorubicin in ovarian cancer.	2009 Jun	19707541
No attenuation of the ATM-dependent DNA damage response in murine telomerase-deficient cells.	2009 Mar 1	19071232
Chemotherapy resistance in metastatic breast cancer: the evolving role of ixabepilone.	2010	21050423
Mitochondrial fission and cristae disruption increase the response of cell models of Huntington's disease to apoptotic stimuli.	2010 Dec	21069748
Cellular responses to etoposide: cell death despite cell cycle arrest and repair of DNA damage.	2010 Feb	20041303
The role of an all-oral chemotherapy containing lomustine (CCNU) in advanced,fs progressive Hodgkin lymphoma: a patient-friendly palliative option which can result in long-term disease control.	2010 Feb	19901016
Preclinical pharmacology of BA-TPQ, a novel synthetic iminoquinone anticancer agent.	2010 Jul 13	20714427
Role of dephosphorylation of FOXO1 on apoptosis induced by wortmannin for non-Hodgkin's lymphoma cells.	2010 Jun	19757185
Outpatient reduced-intensity allogeneic stem cell transplantation for patients with refractory or relapsed lymphomas compared with autologous stem cell transplantation using a simplified method.	2010 Oct	20490794
Management of non-gestational ovarian choriocarcinoma: laparoscopy can be essential. Report of two cases.	2010 Sep	20561742

Patents

Sample Use Guides

In Vivo Use Guide

50 to 100 mg/m2/day on days 1 through 5 to 100 mg/m2/day on days 1, 3, and 5 (testicular cancer) 35 mg/m2/day for 4 days to 50 mg/m2/day for 5 days (small cell lung cancer)

Route of Administration: Intravenous

In Vitro Use Guide

Apoptosis of thymocytes has been investigated by morphological, biochemical and cytometric techniques, both in non-perturbed conditions and after exposure to the topoisomerase-II inhibitor etoposide in vitro. At low (0.1 to 10 uM) etoposide concentrations apoptotic cells had cytoplasm patterns similar to naturally occurring apoptotic thymocytes, whereas at high (50 to 100 uM) concentrations extensive organelle damage took place.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 17:28:39 UTC 2022` Edited by `admin` on `Fri Dec 16 17:28:39 UTC 2022`
Record UNII	6PLQ3CP4P3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETOPOSIDE

Official Name

English

(5R,5AR,8AR,9S)-9-((4,6-O-((1R)-ETHANE-1,1-DIYL)-.ALPHA.-D-GLUCOPYRANOSYL)OXY)-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDRO(2)BENZOFURO(5,6-F)(1,3)BENZODIOXOL-6(5AH)-ONE

Systematic Name

English

ETOPOSIDE [MART.]

Common Name

English

ETOPOSIDE [HSDB]

Common Name

English

VEPESID

Brand Name

English

VP-16-213

Code

English

ETOPOSIDE [USP-RS]

Common Name

English

TOPOSAR

Brand Name

English

ETOPOSIDE [USP MONOGRAPH]

Common Name

English

ETOPOSIDUM [WHO-IP LATIN]

Common Name

English

NSC-141540

Code

English

Etoposide [WHO-DD]

Common Name

English

ETOPOSIDE [ORANGE BOOK]

Common Name

English

ETOPOSIDE [JAN]

Common Name

English

ETOPOSIDE [VANDF]

Common Name

English

ETOPOSIDE [MI]

Common Name

English

etoposide [INN]

Common Name

English

SINTOPOZID

Common Name

English

ETOPOSIDE [USP IMPURITY]

Common Name

English

ETOPOSIDE [USAN]

Common Name

English

FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE-, 9-((4,6-O-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSYL)OXY)5,8,8A,9-TETRAHYDRO-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL), (5R-(5.ALPHA.,5A.BETA.,8A.ALPHA.,9.BETA.(R*)))-

Common Name

English

ETOPOSIDE [WHO-IP]

Common Name

English

ETOPOSIDE [IARC]

Common Name

English

4'-DEMETHYLEPIPODOPHYLLOTOXIN 9-(4,6-O-(R)-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSIDE)

Common Name

English

ETOPOSIDE [EP IMPURITY]

Common Name

English

ETOPOSIDE [EP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175609