TENIPOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H32O13S
Molecular Weight	656.654
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

COC1=CC(=CC(OC)=C1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@@H]5CO[C@H](O[C@H]5[C@H](O)[C@H]4O)C6=CC=CS6)C7=C2C=C8OCOC8=C7

InChI

InChIKey=NRUKOCRGYNPUPR-QBPJDGROSA-N

InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31+,32-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C32H32O13S
Molecular Weight	656.654
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Description

Teniposide is an inhibitor of topoisomerase II with anti-cancer activity. The drug was approved by FDA under the name Vumon for the treatment of children with acute lymphoblastic leukemia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II 66	Inhibitor 8,504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Refractory childhood acute lymphoblastic leukemia 1	Primary		Approved 8,583	VUMON

C_max

Value	Dose	Co-administered	Analyte	Population
7083.9 ng/mL	30 mg/m² single, intravenous		TENIPOSIDE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
2332 μg × min/mL	30 mg/m² single, intravenous		TENIPOSIDE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
2.77 h	1000 mg/m² single, intravenous	TENIPOSIDE plasma	Homo sapiens
8.6 h	200 mg/m² single, intravenous	TENIPOSIDE unknown	Homo sapiens
6.9 h	100 mg/m² single, intravenous	TENIPOSIDE unknown	Homo sapiens
5 h	155 mg/m² 2 times / week multiple, intravenous	TENIPOSIDE plasma	Homo sapiens
20.3 h	30 mg/m² single, intravenous	TENIPOSIDE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.4%	1000 mg/m² single, intravenous		TENIPOSIDE plasma	Homo sapiens
1%	155 mg/m² 2 times / week multiple, intravenous		TENIPOSIDE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
60 mg/m2 5 times / 3 weeks multiple, intravenous	unhealthy, 64 years (range: 46–83 years)	Other AEs: Infection, Neutropenia...
165 mg/m2 2 times / week multiple, intravenous Recommended	unhealthy, children	Other AEs: Myelosuppression, Anaphylactic reaction...

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AEs

Show entries

AE	Significance	Dose	Population
Infection	grade 1-2, 1 patient	60 mg/m2 5 times / 3 weeks multiple, intravenous	unhealthy, 64 years (range: 46–83 years)
Nausea	grade 1-2, 19 patients	60 mg/m2 5 times / 3 weeks multiple, intravenous	unhealthy, 64 years (range: 46–83 years)
Fever	grade 1-2, 2 patients	60 mg/m2 5 times / 3 weeks multiple, intravenous	unhealthy, 64 years (range: 46–83 years)
Anemia	grade 1-2, 20 patients	60 mg/m2 5 times / 3 weeks multiple, intravenous	unhealthy, 64 years (range: 46–83 years)
Neutropenia	grade 1-2, 6 patients	60 mg/m2 5 times / 3 weeks multiple, intravenous	unhealthy, 64 years (range: 46–83 years)

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inhibitor 2,252	inhibitor 2,438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2,052 MRP3 58

Drug as perpetrator

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 2,633	inhibitor 4,027	yes [IC50 64 uM]		likely (co-administration study)
CYP2C9 2,497	inhibitor 4,027	yes

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Drug as victim

Show entries

Target	Modality	Activity	Clinical evidence
CYP3A4 1,946	substrate 4,014	major	likely (co-administration study)
MRP3 58	substrate 4,014	yes
P-gp 2,052	substrate 4,014	yes

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Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
001 Chemical	DY547001	https://www.001chemical.com/chem/29767-20-2
3B Scientific (Wuhan) Corp	3B2-1312	http://www.3bsc.com/index/pro_info.php?id=55028
AA Blocks	AA00I5FJ	https://www.aablocks.com/goods/Goods/detail?id=AA00I5FJ
Aaron Chemicals	AR00I67B	http://www.aaronchem.com/29767-20-2
abcr GmbH	AB452154	http://www.abcr.com/shop/en/AB452154

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PubMed

Show entries

Title	Date	PubMed
Paclitaxel: a pharmacoeconomic review of its use in non-small cell lung cancer.	2001	11735678
Lung cancer: therapeutic options for stage IV and recurrent NSCLC.	2001	11224988
[Hypercalcemia due to adult T-cell lymphoma in a man from Surinam].	2001 Feb 24	11257818
Effectiveness of interferon-alfa and mid-cycle chemotherapy added to an anthracycline-based regimen in the treatment of aggressive non-Hodgkin's lymphoma.	2001 Jan	11426554
Concomitant cyclophosphamide, doxorubicin, vincristine, and prednisone chemotherapy plus highly active antiretroviral therapy in patients with human immunodeficiency virus-related, non-Hodgkin lymphoma.	2001 Jan 1	11148572

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Patents

Sample Use Guides

In Vivo Use Guide

Teniposide Injection must be diluted with either 5% Dextrose Injection, USP or 0.9% Sodium Chloride Injection, USP, to give final teniposide concentrations of 0.1 mg/mL, 0.2 mg/mL, 0.4 mg/mL, or 1.0 mg/mL. It is recommended that the teniposide solution be administered over at least a 30- to 60-minute period.

Route of Administration: Intravenous

In Vitro Use Guide

Human leukemic cell line were treated with teniposide for 48 h and the cell growth was inhibited by 50% at 48 nM.