ETOPOSIDE PHOSPHATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H33O16P
Molecular Weight	668.5365
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(OP(O)(O)=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=LIQODXNTTZAGID-OCBXBXKTSA-N

InChI=1S/C29H33O16P/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35)/t11-,15+,20-,21-,22+,23-,24-,25-,27-,29+/m1/s1

HIDE SMILES / InChI

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 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16101488	Inhibitor 8297		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 8429	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 1983
Small-cell lung cancer 41 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf	Primary		Approved 8429	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 1996

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 1737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP2 383	OATP1B1 406 P-gp 1537 CYP2E1 667 CYP1A2 1054 CYP3A5 395 CYP2B6 664 CYP2A6 543 UGT1A1 418 UGT1A8 283 UGT1A3 422 UGT1A4 347 UGT1A6 307 UGT1A7 236 UGT1A9 380 UGT1A10 291 UGT2B4 249 UGT2B7 389 UGT2B15 203 UGT2B17 213 Abcc2 3 Abcc3 3 MRP2 205 MRP3 50	CYP3A5 76

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A5 130	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	slight
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/12134946/	weak [Ki 756 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1737	substrate 3367 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 418	substrate 3367 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 1054	substrate 3367 Sources: https://jpet.aspetjournals.org/content/286/3/1294.long	minor
CYP2E1 667	substrate 3367 Sources: https://jpet.aspetjournals.org/content/286/3/1294.long	minor
UGT1A3 422	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	minor
UGT1A8 283	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	minor
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	no
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	no
UGT1A10 291	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A4 347	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A6 307	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A7 236	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A9 380	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B15 203	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B17 213	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B4 249	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
Abcc2 3	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20028753/	yes
Abcc3 3	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20028753/	yes	ETOPOSIDE GLUCURONIDE 3
CYP3A5 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	yes
MRP2 205	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3372834/	yes
MRP3 50	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11581266/	yes	ETOPOSIDE GLUCURONIDE 3
OATP1B1 406	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3372834/	yes
P-gp 1537	substrate 3367 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
High-dose chemotherapy with peripheral blood stem cell transplantation for patients with advanced ovarian cancer.	2001 Apr	11315259
Bone morphogenetic protein-2 promotes osteoblast apoptosis through a Smad-independent, protein kinase C-dependent signaling pathway.	2001 Aug 3	11395480
Adult Gaucher disease in association with primary malignant bone tumors.	2001 Feb 1	11169926
High-dose chemotherapy as a consolidation approach in advanced ovarian cancer: long-term results.	2001 May	11438815
Irinotecan: future directions in small-cell lung cancer.	2001 May	14725724
Langerhans cell histiocytosis.	2001 Nov	11903153
Pro-oxidant and antioxidant mechanisms of etoposide in HL-60 cells: role of myeloperoxidase.	2001 Nov 1	11691792
Expression of P-glycoprotein and multidrug resistance associated protein in Ehrlich ascites tumor cells after fractionated irradiation.	2001 Nov 15	11704330
Alpha-CD25 antibody treatment in a child with hemophagocytic lymphohistiocytosis.	2002 Feb	11813188
Coexisting true hermaphroditism and partial hydatidiform mole developing metastatic gestational trophoblastic tumors. A case report.	2002 Nov	12447683
Estrogen receptor-dependent and estrogen receptor-independent pathways for tamoxifen and 4-hydroxytamoxifen-induced programmed cell death.	2002 Nov 22	12244117
Detection of topoisomerase inhibitor-induced DNA strand breaks and apoptosis by the alkaline comet assay.	2002 Sep 26	12297143
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
Inhibition of telomerase activity in malignant glioma cells correlates with their sensitivity to temozolomide.	2003 Sep 1	12942127
Phase I dose escalation study of carboplatin to a fixed dose of irinotecan as first-line treatment of small cell lung cancer.	2004 Jun	15249718
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
Use of preclinical models to improve treatment of retinoblastoma.	2005 Oct	16231976
Adenine nucleotides inhibit proliferation of the human lung adenocarcinoma cell line LXF-289 by activation of nuclear factor kappaB1 and mitogen-activated protein kinase pathways.	2006 Aug	16911524
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
Signaling from p53 to NF-kappaB determines the chemotherapy responsiveness of neuroblastoma.	2006 Nov	17132229
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
Modulation of topoisomerase IIalpha expression by a DNA sequence-specific polyamide.	2007 Jan	17237293
Incidence and risk factors of central nervous system recurrence in aggressive lymphoma--a survey of 1693 patients treated in protocols of the German High-Grade Non-Hodgkin's Lymphoma Study Group (DSHNHL).	2007 Jan	17018708
Expression of CYP3A4 as a predictor of response to chemotherapy in peripheral T-cell lymphomas.	2007 Nov 1	17634410
A Contribution to solve the problem of the need for consolidative radiotherapy after intensive chemotherapy in advanced stages of Hodgkin's lymphoma--analysis of a quality control program initiated by the radiotherapy reference center of the German Hodgkin Study Group (GHSG).	2007 Nov 15	17703895
In vivo targeting of dead tumor cells in a murine tumor model using a monoclonal antibody specific for the La autoantigen.	2007 Sep 15	17875784
Therapy-associated genetic aberrations in patients treated for non-Hodgkin lymphoma.	2008 Apr	18324966
Interferonalpha enhances etoposide-induced apoptosis in human osteosarcoma U2OS cells by a p53-dependent pathway.	2008 Feb 13	18191951
[Production of reconstructed two-cell rat embryos after chemical inactivation of chromosomes in MII oocytes by etoposide].	2008 Sep-Oct	18959199
[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
Etoposide induces MLL rearrangements and other chromosomal abnormalities in human embryonic stem cells.	2009 Sep	19587093
Chemotherapy resistance in metastatic breast cancer: the evolving role of ixabepilone.	2010	21050423
Biological characteristics and treatment outcomes of metastatic or recurrent neuroendocrine tumors: tumor grade and metastatic site are important for treatment strategy.	2010 Aug 23	20731845
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

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.

Name

Type

Language

ETOPOSIDE PHOSPHATE

Official Name

English

ETOPOPHOS PRESERVATIVE FREE

Brand Name

English

ETOPOSIDE PHOSPHATE [USAN]

Common Name

English

ETOPOSIDE PHOSPHATE [USP-RS]

Common Name

English

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

Common Name

English

BMY-40481

Code

English

ETOPOSIDE PHOSPHATE [VANDF]

Common Name

English

VP-16

Code

English

VP16

Code

English

VEPESIDE

Common Name

English

Etoposide phosphate [WHO-DD]

Common Name

English

BMY 40481

Code

English

ETOPOPHOS

Brand Name

English

ETOPOSIDE PHOSPHATE [USP MONOGRAPH]

Common Name

English

ETOPOSIDE PHOSPHATE [MI]

Common Name

English

ETOPOSIDE PHOSPHATE [MART.]

Common Name

English

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

Common Name

English

ETOPOSIDE PHOSPHATE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1331