ETOPOSIDE TONIRIBATE

Details

Stereochemistry	EPIMERIC
Molecular Formula	C36H42O17
Molecular Weight	746.7085
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(=CC(OC)=C1OC(=O)OCC2COC(C)(C)O2)[C@H]3[C@@H]4[C@H](COC4=O)[C@H](O[C@@H]5O[C@@H]6CO[C@@H](C)O[C@H]6[C@H](O)[C@H]5O)C7=C3C=C8OCOC8=C7

InChI

InChIKey=FCWSQAKOPTZCOD-SQYSSJHTSA-N

InChI=1S/C36H42O17/c1-15-43-13-25-32(49-15)28(37)29(38)34(50-25)51-30-19-9-22-21(46-14-47-22)8-18(19)26(27-20(30)12-44-33(27)39)16-6-23(41-4)31(24(7-16)42-5)52-35(40)45-10-17-11-48-36(2,3)53-17/h6-9,15,17,20,25-30,32,34,37-38H,10-14H2,1-5H3/t15-,17?,20+,25-,26-,27+,28-,29-,30-,32-,34+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C36H42O17
Molecular Weight	746.7085
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	10 / 11
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 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16101488	Inhibitor 8504		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 8583	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 8583	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	unhealthy, 1.1-17 Health Status: unhealthy Age Group: 1.1-17 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8021737	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
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	unhealthy, 1.1-17 Health Status: unhealthy Age Group: 1.1-17 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8021737	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 4, 14%) Sources: https://pubmed.ncbi.nlm.nih.gov/8021737
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	unhealthy, 39-72 Health Status: unhealthy Age Group: 39-72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7799021	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 4, 28.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/7799021
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	unhealthy, 39-72 Health Status: unhealthy Age Group: 39-72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7799021	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 3, 14.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/7799021
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	unhealthy, 39-72 Health Status: unhealthy Age Group: 39-72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7799021	DLT: Neutropenia, Neutropenia... Dose limiting toxicities: Neutropenia (grade 3, 25%) Neutropenia (grade 4, 25%) Sources: https://pubmed.ncbi.nlm.nih.gov/7799021
60 mg/m2 1 times / day multiple, oral 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	unhealthy, 39-83 Health Status: unhealthy Age Group: 39-83 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9469322	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
100 mg/m2 1 times / day multiple, intravenous 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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf	Disc. AE: Myelosuppression... AEs leading to discontinuation/dose reduction: Myelosuppression (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP2 499	OATP1B1 503 P-gp 2052 CYP2E1 729 CYP1A2 1197 CYP3A5 446 CYP2B6 776 CYP2A6 626 UGT1A1 479 UGT1A8 323 UGT1A3 470 UGT1A4 399 UGT1A6 343 UGT1A7 249 UGT1A9 423 UGT1A10 331 UGT2B4 278 UGT2B7 456 UGT2B15 236 UGT2B17 237 Abcc2 3 Abcc3 3 MRP2 252 MRP3 58	CYP3A5 92

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A5 201	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	slight
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12134946/	weak [Ki 756 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1946	substrate 4014 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 479	substrate 4014 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 1197	substrate 4014 Sources: https://jpet.aspetjournals.org/content/286/3/1294.long	minor
CYP2E1 729	substrate 4014 Sources: https://jpet.aspetjournals.org/content/286/3/1294.long	minor
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	minor
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	minor
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	no
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
Abcc2 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20028753/	yes
Abcc3 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20028753/	yes	ETOPOSIDE GLUCURONIDE 3
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	yes
MRP2 252	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3372834/	yes
MRP3 58	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11581266/	yes	ETOPOSIDE GLUCURONIDE 3
OATP1B1 503	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3372834/	yes
P-gp 2052	substrate 4014 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
eMolecules	32278021	https://www.emolecules.com/cgi-bin/more?vid=32278021
eMolecules	537894	https://www.emolecules.com/cgi-bin/more?vid=537894
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

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
Nitroso-urea-cisplatin-based chemotherapy associated with valproate: increase of haematologic toxicity.	2001 Feb	11300327
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
Metastatic placental site trophoblastic tumor. Report of a case with complete response to chemotherapy.	2001 Mar	11304870
High-dose chemotherapy as a consolidation approach in advanced ovarian cancer: long-term results.	2001 May	11438815
Langerhans cell histiocytosis.	2001 Nov	11903153
Chemoresistant or aggressive lymphoma predicts for a poor outcome following reduced-intensity allogeneic progenitor cell transplantation: an analysis from the Lymphoma Working Party of the European Group for Blood and Bone Marrow Transplantation.	2002 Dec 15	12393626
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
Relapse in the skull after myeloablative therapy for high-risk neuroblastoma.	2003 Jan-Feb	12687750
Inhibition of telomerase activity in malignant glioma cells correlates with their sensitivity to temozolomide.	2003 Sep 1	12942127
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
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
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
Sequential oral 9-nitrocamptothecin and etoposide: a pharmacodynamic- and pharmacokinetic-based phase I trial.	2006 Aug	16928835
Local control in pelvic Ewing sarcoma: analysis from INT-0091--a report from the Children's Oncology Group.	2006 Aug 20	16921035
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
Resveratrol at high doses acts as an apoptotic inducer in endothelial cells.	2006 Feb	19771259
Prevalence and rupture rate of cerebral aneurysms discovered during intra-arterial chemotherapy of brain tumors.	2006 Feb	16484396
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
BRCA1- and BRCA2-deficient cells are sensitive to etoposide-induced DNA double-strand breaks via topoisomerase II.	2007 Aug 1	17671173
Modulation of topoisomerase IIalpha expression by a DNA sequence-specific polyamide.	2007 Jan	17237293
[Bilateral lung masses: the same aetiology?].	2007 Mar-Apr	17492239
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
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
Impaired DNA double-strand break repair contributes to chemoresistance in HIF-1 alpha-deficient mouse embryonic fibroblasts.	2008 Dec	18842680
Treatment experiences of testicular cancer in Hispanic patients with Down's syndrome at the National Cancer Institute of Mexico.	2008 Nov	19015076
Haematopoietic stem cell transplantation for autoimmune disorders.	2008 Nov	18832930
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
Clinical aspects and therapy of sporadic burkitt lymphoma.	2009 Dec 28	21416007
2-Arylbenzimidazoles as antiviral and antiproliferative agents--Part 2.	2009 Nov	19534676
Palonosetron in prevention of nausea and vomiting after highly emetogenic chemotherapy before haematopoietic stem cell transplantation-single center experience.	2009 Oct	19857722
Helicobacter pylori counteracts the apoptotic action of its VacA toxin by injecting the CagA protein into gastric epithelial cells.	2009 Oct	19798427
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
Bevacizumab in combination with sequential high-dose chemotherapy in solid cancer, a feasibility study.	2010 Dec	20228848
A novel podophyllotoxin derivative (YB-1EPN) induces apoptosis and down-regulates express of P-glycoprotein in multidrug resistance cell line KBV200.	2010 Feb 10	19879873
Preclinical pharmacology of BA-TPQ, a novel synthetic iminoquinone anticancer agent.	2010 Jul 13	20714427
Reduced-dose craniospinal radiotherapy followed by high-dose chemotherapy and autologous stem cell rescue for children with newly diagnosed high-risk medulloblastoma or supratentorial primitive neuroectodermal tumor.	2010 Jun	21120191

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 `Tue Apr 01 18:44:14 GMT 2025` Edited by `admin` on `Tue Apr 01 18:44:14 GMT 2025`
Record UNII	A59HL2Q48U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETOPOSIDE TONIRIBATE

Official Name

English

(4-((5S,5AR,8AR,9R)-5-(((2R,4AR,6R,7R,8R,8AS)-7,8-DIHYDROXY-2-METHYL-4,4A,6,7,8,8A-HEXAHYDROPYRANO(3,2-D)(1,3)DIOXIN-6-YL)OXY)-8-OXO-5A,6,8A,9-TETRAHYDRO-5H-ISOBENZOFURO(5,6-F)(1,3)BENZODIOXOL-9-YL)-2,6-DIMETHOXY-PHENYL) (2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)M

Preferred Name

English

CARBONIC ACID, (2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)METHYL 4-((5R,5AR,8AR,9S)-9-((4,6-O-(1R)-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSYL)OXY)-5,5A,6,8,8A,9-HEXAHYDRO-6-OXOFURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-5-YL)-2,6-DIMETHOXYPHENYL ESTER

Systematic Name

English

PROVP-16I

Common Name

English

((4RS)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)METHYL4-((5R,5AR,8AR,9S)-9-((4,6-O-((1R)-ETHANE-1,1-DIYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-6-OXO-5,5A,6,8,8A,9-HEXAHYDRO-2H-FURO(3',4':6,7)NAPHTHO(2,3-D)(1,3)DIOXOL-5-YL)-2,6-DIMETHOXYPHENYL CARBONATE

Systematic Name

English

etoposide toniribate [INN]

Common Name

English

CAP-7.1

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

671318