Teniposide (CHEM003673)

Record Information
Version1.0
Creation Date2014-09-11 02:06:10 UTC
Update Date2026-05-14 16:39:00 UTC
Accession NumberCHEM003673
Identification
Common NameTeniposide
ClassSmall Molecule
Description
A semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. Teniposide 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 cells from entering into the mitotic phase of the cell cycle, and lead to cell death. Teniposide acts primarily in the G2 and S phases of the cycle.
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 2A
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antineoplastic Agent
  • Drug
  • Enzyme Inhibitor
  • Ester
  • Ether
  • Metabolite
  • Nucleic Acid Synthesis Inhibitor
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside)ChEBI
4'-Demethylepipodophyllotoxin-beta-D-thenylidene glucosideChEBI
HSDB 6546ChEBI
NSC 122819ChEBI
NSC-122819ChEBI
TeniposidoChEBI
TeniposidumChEBI
VM-26ChEBI
VumonChEBI
4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-b-D-glucopyranoside)Generator
4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-β-D-glucopyranoside)Generator
4'-Demethylepipodophyllotoxin-b-D-thenylidene glucosideGenerator
4'-Demethylepipodophyllotoxin-β-D-thenylidene glucosideGenerator
Bristol myers brand OF teniposideHMDB
Bristol myers squibb brand OF teniposideHMDB
Bristol-myers brand OF teniposideHMDB
Bristol-myers squibb brand OF teniposideHMDB
Demethyl epipodophyllotoxin thenylidine glucosideHMDB
Teniposide, (5a alpha,9 alpha(s*))-isomerHMDB
VM 26HMDB
Chemical FormulaC32H32O13S
Average Molecular Mass656.654 g/mol
Monoisotopic Mass656.156 g/mol
CAS Registry Number29767-20-2
IUPAC Name(10R,11R,15R,16S)-16-{[(4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-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
Traditional Nameteniposide
SMILES[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])COC(O[C@@]2([H])[C@H](O)[C@H]1O)C1=CC=CS1
InChI IdentifierInChI=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
InChI KeyNRUKOCRGYNPUPR-PSZSYXFXSA-N
Chemical Taxonomy
Description Belongs to the class of inorganic compounds known as metalloid oxides. These are inorganic compounds containing an oxygen atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a metalloid.
KingdomInorganic compounds
Super ClassMixed metal/non-metal compounds
ClassMetalloid organides
Sub ClassMetalloid oxides
Direct ParentMetalloid oxides
Alternative Parents
Substituents
  • Metalloid oxide
  • Inorganic oxide
  • Inorganic salt
  • Inorganic metalloid salt
Molecular FrameworkNot Available
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Teniposide PathwayNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point242-246°C
Boiling PointNot Available
Solubility5.98e-02 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP2.78ALOGPS
logP2.78ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area160.83 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity155.61 m³·mol⁻¹ChemAxon
Polarizability65.8 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityThe mechanism of action appears to be related to the inhibition of type II topoisomerase activity since teniposide does not intercalate into DNA or bind strongly to DNA. Teniposide binds to and inhibits DNA topoisomerase II. The cytotoxic effects of teniposide are related to the relative number of double-stranded DNA breaks produced in cells, which are a reflection of the stabilization of a topoisomerase II-DNA intermediate.
MetabolismRoute of Elimination: From 4% to 12% of a dose is excreted in urine as parent drug. Fecal excretion of radioactivity within 72 hours after dosing accounted for 0% to 10% of the dose. Half Life: 5 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (1)
Uses/SourcesTeniposide is used for the treatment of refractory acute lymphoblastic leukaemia
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0014587
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTeniposide
Chemspider ID31930
ChEBI ID75988
PubChem Compound ID34698
Kegg Compound IDC11153
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21430063
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21821840
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22644709
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22846410
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23266449
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23466610
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23679827
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23838380