Identification

Name
Teniposide
Accession Number
DB00444  (APRD00649)
Type
Small Molecule
Groups
Approved
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. [PubChem]

Structure
Thumb
Synonyms
  • 4'-demethylepipodophyllotoxin 9-(4,6-O-(R)-2-thenylidene-beta-D-glucopyranoside)
  • Epidophyllotoxin
  • Teniposid
  • Téniposide
  • Teniposido
  • Teniposidum
External IDs
EPT / PGT / VM-26 / VM26
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TeniposideInjection, solution10 mg/mLIntravenousWG Critical Care, LLC2013-04-30Not applicableUs
VumonLiquid10 mgIntravenousBristol Myers Squibb1984-12-31Not applicableCanada
International/Other Brands
Bang Lai (Double-Crane)
Categories
UNII
957E6438QA
CAS number
29767-20-2
Weight
Average: 656.654
Monoisotopic: 656.1563618
Chemical Formula
C32H32O13S
InChI Key
NRUKOCRGYNPUPR-QBPJDGROSA-N
InChI
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
IUPAC Name
(10R,11R,15R,16S)-16-{[(2R,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
SMILES
[H][[email protected]]12COC(=O)[[email protected]]1([H])[[email protected]]([H])(C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[[email protected]@]2([H])O[[email protected]]1([H])O[[email protected]]2([H])CO[[email protected]]([H])(O[[email protected]@]2([H])[[email protected]]([H])(O)[[email protected]@]1([H])O)C1=CC=CS1

Pharmacology

Indication

Teniposide is used for the treatment of refractory acute lymphoblastic leukaemia

Structured Indications
Pharmacodynamics

Teniposide is a phase-specific cytotoxic drug, acting in the late S or early G 2 phase of the cell cycle, thus preventing cells from entering mitosis. Teniposide causes dose-dependent single- and double-stranded breaks in DNA and DNA: protein cross-links.

Mechanism of action

The 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.

TargetActionsOrganism
ADNA topoisomerase 2-alpha
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route 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

Clearance
  • 10.3 mL/min/m2
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Teniposide Metabolism PathwayDrug metabolism
Teniposide Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe metabolism of Teniposide can be decreased when combined with Abiraterone.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Teniposide.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Teniposide.Experimental
AmiodaroneThe metabolism of Teniposide can be decreased when combined with Amiodarone.Approved, Investigational
AmobarbitalThe serum concentration of Teniposide can be decreased when it is combined with Amobarbital.Approved, Illicit
AprepitantThe serum concentration of Teniposide can be increased when it is combined with Aprepitant.Approved, Investigational
ArmodafinilThe metabolism of Teniposide can be decreased when combined with Armodafinil.Approved, Investigational
AtazanavirThe metabolism of Teniposide can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Teniposide can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Teniposide is combined with Atorvastatin.Approved
BarbexacloneThe serum concentration of Teniposide can be decreased when it is combined with Barbexaclone.Experimental
BarbitalThe serum concentration of Teniposide can be decreased when it is combined with Barbital.Illicit
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Teniposide.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Teniposide.Approved, Investigational
BoceprevirThe metabolism of Teniposide can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Teniposide can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Teniposide can be decreased when it is combined with Bosentan.Approved, Investigational
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Teniposide.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Teniposide.Approved
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Teniposide.Approved
CarbamazepineThe metabolism of Teniposide can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Teniposide can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Teniposide.Withdrawn
ChloramphenicolThe metabolism of Teniposide can be decreased when combined with Chloramphenicol.Approved, Vet Approved
CholecalciferolThe metabolism of Teniposide can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Teniposide can be decreased when combined with Cimetidine.Approved
CitalopramThe metabolism of Teniposide can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Teniposide can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Teniposide can be decreased when combined with Clemastine.Approved
Clostridium tetani toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Clostridium tetani toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Teniposide.Approved
ClotrimazoleThe metabolism of Teniposide can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Teniposide is combined with Clozapine.Approved
CobicistatThe metabolism of Teniposide can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Teniposide can be increased when it is combined with Conivaptan.Approved, Investigational
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Teniposide.Approved
CrizotinibThe metabolism of Teniposide can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Teniposide.Approved, Investigational
CyclosporineThe metabolism of Teniposide can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Teniposide.Experimental
DabrafenibThe serum concentration of Teniposide can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Teniposide can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Teniposide can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Teniposide can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Teniposide can be decreased when combined with Delavirdine.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Teniposide.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Teniposide.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Teniposide.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Teniposide.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Teniposide.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Teniposide.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Teniposide.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Teniposide.Experimental
DihydroergotamineThe metabolism of Teniposide can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Teniposide can be decreased when combined with Diltiazem.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Teniposide.Approved, Investigational
DoxycyclineThe metabolism of Teniposide can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Teniposide can be decreased when combined with Dronedarone.Approved
EfavirenzThe metabolism of Teniposide can be decreased when combined with Efavirenz.Approved, Investigational
EltrombopagThe serum concentration of Teniposide can be increased when it is combined with Eltrombopag.Approved
EnzalutamideThe serum concentration of Teniposide can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Teniposide.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Teniposide.Approved
ErythromycinThe metabolism of Teniposide can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe metabolism of Teniposide can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Teniposide can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe metabolism of Teniposide can be decreased when combined with Etravirine.Approved
FingolimodTeniposide may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FluconazoleThe metabolism of Teniposide can be decreased when combined with Fluconazole.Approved
FluoxetineThe metabolism of Teniposide can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Teniposide.Approved
FluvoxamineThe metabolism of Teniposide can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Teniposide can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Teniposide can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Teniposide can be decreased when it is combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Teniposide can be increased when it is combined with Fusidic Acid.Approved
G17DTThe therapeutic efficacy of G17DT can be decreased when used in combination with Teniposide.Investigational
GemfibrozilThe metabolism of Teniposide can be decreased when combined with Gemfibrozil.Approved
GI-5005The therapeutic efficacy of GI-5005 can be decreased when used in combination with Teniposide.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Teniposide.Experimental
Hepatitis A VaccineThe therapeutic efficacy of Hepatitis A Vaccine can be decreased when used in combination with Teniposide.Approved
Hepatitis B Vaccine (Recombinant)The therapeutic efficacy of Hepatitis B Vaccine (Recombinant) can be decreased when used in combination with Teniposide.Approved, Withdrawn
HexobarbitalThe serum concentration of Teniposide can be decreased when it is combined with Hexobarbital.Approved
IdelalisibThe serum concentration of Teniposide can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Teniposide can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Teniposide can be decreased when combined with Indinavir.Approved
INGN 201The therapeutic efficacy of INGN 201 can be decreased when used in combination with Teniposide.Investigational
INGN 225The therapeutic efficacy of INGN 225 can be decreased when used in combination with Teniposide.Investigational
IsavuconazoniumThe metabolism of Teniposide can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Teniposide can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Teniposide can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Teniposide can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Teniposide can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Teniposide can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Teniposide.Experimental
LeflunomideThe risk or severity of adverse effects can be increased when Teniposide is combined with Leflunomide.Approved, Investigational
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Teniposide.Approved, Investigational
LobeglitazoneThe metabolism of Teniposide can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Teniposide can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Teniposide can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Teniposide can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Teniposide can be decreased when it is combined with Lumacaftor.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Teniposide.Illicit, Investigational, Withdrawn
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Teniposide.Investigational, Withdrawn
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Teniposide.Experimental
MethohexitalThe serum concentration of Teniposide can be decreased when it is combined with Methohexital.Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Teniposide.Approved
MethylphenobarbitalThe serum concentration of Teniposide can be decreased when it is combined with Methylphenobarbital.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Teniposide.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Teniposide.Experimental
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Teniposide.Experimental
MifepristoneThe serum concentration of Teniposide can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Teniposide can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Teniposide can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Teniposide can be decreased when combined with Modafinil.Approved, Investigational
NatalizumabThe risk or severity of adverse effects can be increased when Teniposide is combined with Natalizumab.Approved, Investigational
NefazodoneThe metabolism of Teniposide can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Teniposide can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Teniposide can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Teniposide can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Teniposide can be decreased when combined with Nicardipine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Teniposide.Approved, Investigational
NilotinibThe metabolism of Teniposide can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Teniposide can be decreased when combined with Olaparib.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Teniposide.Experimental, Investigational
OmeprazoleThe metabolism of Teniposide can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Teniposide can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Teniposide.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Teniposide.Approved, Vet Approved
PalbociclibThe serum concentration of Teniposide can be increased when it is combined with Palbociclib.Approved
PantoprazoleThe metabolism of Teniposide can be decreased when combined with Pantoprazole.Approved
PentobarbitalThe serum concentration of Teniposide can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Teniposide.Approved, Investigational, Vet Approved, Withdrawn
PeruvosidePeruvoside may decrease the cardiotoxic activities of Teniposide.Experimental
PhenobarbitalThe serum concentration of Teniposide can be decreased when it is combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Teniposide can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Teniposide.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Teniposide.Approved
PosaconazoleThe metabolism of Teniposide can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Teniposide.Approved
PrimidoneThe serum concentration of Teniposide can be decreased when it is combined with Primidone.Approved, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Teniposide.Experimental
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Teniposide is combined with Rabies virus inactivated antigen, A.Approved
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with Teniposide.Approved
RanolazineThe metabolism of Teniposide can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Teniposide can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Teniposide can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Teniposide can be increased when combined with Rifapentine.Approved
RindopepimutThe therapeutic efficacy of Rindopepimut can be decreased when used in combination with Teniposide.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Teniposide.Approved
RolapitantThe serum concentration of Teniposide can be increased when it is combined with Rolapitant.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Teniposide.Approved
Rotavirus VaccineThe therapeutic efficacy of Rotavirus Vaccine can be decreased when used in combination with Teniposide.Approved
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Teniposide.Approved
Salmonella typhi ty21a live antigenThe therapeutic efficacy of Salmonella typhi ty21a live antigen can be decreased when used in combination with Teniposide.Approved
SaquinavirThe metabolism of Teniposide can be decreased when combined with Saquinavir.Approved, Investigational
SecobarbitalThe serum concentration of Teniposide can be decreased when it is combined with Secobarbital.Approved, Vet Approved
SertralineThe metabolism of Teniposide can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Teniposide can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Teniposide can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Teniposide can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Teniposide.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Teniposide.Approved
SRP 299The therapeutic efficacy of SRP 299 can be decreased when used in combination with Teniposide.Investigational
St. John's WortThe serum concentration of Teniposide can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Teniposide can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Teniposide can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Teniposide.Approved, Investigational
TecemotideThe therapeutic efficacy of Tecemotide can be decreased when used in combination with Teniposide.Investigational
TelaprevirThe metabolism of Teniposide can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Teniposide can be decreased when combined with Telithromycin.Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Teniposide.Experimental
TeriflunomideThe serum concentration of Teniposide can be increased when it is combined with Teriflunomide.Approved
TG4010The therapeutic efficacy of TG4010 can be decreased when used in combination with Teniposide.Investigational
ThiamylalThe serum concentration of Teniposide can be decreased when it is combined with Thiamylal.Approved, Vet Approved
ThiopentalThe serum concentration of Teniposide can be decreased when it is combined with Thiopental.Approved, Vet Approved
TiclopidineThe metabolism of Teniposide can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Teniposide can be decreased when it is combined with Tocilizumab.Approved
TofacitinibTeniposide may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TopiramateThe metabolism of Teniposide can be decreased when combined with Topiramate.Approved
TranylcypromineThe metabolism of Teniposide can be decreased when combined with Tranylcypromine.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Teniposide.Approved, Investigational
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Teniposide.Approved, Experimental
VenlafaxineThe metabolism of Teniposide can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Teniposide can be decreased when combined with Verapamil.Approved
VincristineTeniposide may increase the neurotoxic activities of Vincristine.Approved, Investigational
VoriconazoleThe metabolism of Teniposide can be decreased when combined with Voriconazole.Approved, Investigational
Yellow fever vaccineThe therapeutic efficacy of Yellow fever vaccine can be decreased when used in combination with Teniposide.Approved
ZiprasidoneThe metabolism of Teniposide can be decreased when combined with Ziprasidone.Approved
Zoster vaccineThe therapeutic efficacy of Zoster vaccine can be decreased when used in combination with Teniposide.Approved
ZucapsaicinThe metabolism of Teniposide can be decreased when combined with Zucapsaicin.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D02698
KEGG Compound
C11153
PubChem Compound
452548
PubChem Substance
46507536
ChemSpider
398606
ChEMBL
CHEMBL452231
Therapeutic Targets Database
DAP000651
PharmGKB
PA451611
HET
9TP
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Teniposide
ATC Codes
L01CB02 — Teniposide
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
PDB Entries
4l9q
MSDS
Download (46.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2CompletedTreatmentMalignant Lymphomas1
2CompletedTreatmentAcute Lymphoblastic Leukaemias (ALL) / Lymphoma, Lymphoblastic1
2CompletedTreatmentMalignant Lymphomas1
2RecruitingTreatmentRecurrent B-Cell Childhood Acute Lymphoblastic Leukemia / Recurrent Childhood B-Lymphoblastic Lymphoma1
2Unknown StatusTreatmentLeukemias1
3CompletedTreatmentAcute Lymphoblastic Leukaemias (ALL)1
4Active Not RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL)1
4CompletedTreatmentAdult Acute Lymphocytic Leukemia4
4Unknown StatusTreatmentAdult Acute Lymphocytic Leukemia1
Not AvailableActive Not RecruitingTreatmentBipolar Disorder (BD) / Psychotic Disorder NOS / Schizoaffective Disorders / Schizophrenic Disorders / Schizophreniform Disorder1
Not AvailableUnknown StatusTreatmentLeukemias1

Pharmacoeconomics

Manufacturers
  • Bristol myers squibb co pharmaceutical research institute
Packagers
Dosage forms
FormRouteStrength
Injection, solutionIntravenous10 mg/mL
LiquidIntravenous10 mg
Prices
Unit descriptionCostUnit
Vumon 10 mg/ml ampul75.31USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)242-246 °CPhysProp
logP1.24HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0598 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity155.61 m3·mol-1ChemAxon
Polarizability64.84 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8166
Blood Brain Barrier-0.9584
Caco-2 permeable-0.5728
P-glycoprotein substrateSubstrate0.6638
P-glycoprotein inhibitor INon-inhibitor0.8656
P-glycoprotein inhibitor IINon-inhibitor0.9094
Renal organic cation transporterNon-inhibitor0.8549
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5599
CYP450 1A2 substrateNon-inhibitor0.7516
CYP450 2C9 inhibitorNon-inhibitor0.5445
CYP450 2D6 inhibitorNon-inhibitor0.7197
CYP450 2C19 inhibitorInhibitor0.7423
CYP450 3A4 inhibitorInhibitor0.7677
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.798
Ames testAMES toxic0.7291
CarcinogenicityNon-carcinogens0.9303
BiodegradationNot ready biodegradable0.9254
Rat acute toxicity2.8354 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9934
hERG inhibition (predictor II)Non-inhibitor0.8415
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).
Kingdom
Organic compounds
Super Class
Lignans, neolignans and related compounds
Class
Lignan lactones
Sub Class
Podophyllotoxins
Direct Parent
Podophyllotoxins
Alternative Parents
Aryltetralin lignans / Furanonaphthodioxoles / Tetralins / Pyranodioxins / Dimethoxybenzenes / Methoxyphenols / Benzodioxoles / Anisoles / Phenoxy compounds / Alkyl aryl ethers
show 16 more
Substituents
Podophyllotoxin / 1-aryltetralin lignan / Linear furanonaphthodioxole / Naphthofuran / Methoxyphenol / Pyranodioxin / Tetralin / M-dimethoxybenzene / Dimethoxybenzene / Benzodioxole
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Ubiquitin binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
Gene Name
TOP2A
Uniprot ID
P11388
Uniprot Name
DNA topoisomerase 2-alpha
Molecular Weight
174383.88 Da
References
  1. de Lucio B, Manuel V, Barrera-Rodriguez R: Characterization of human NSCLC cell line with innate etoposide-resistance mediated by cytoplasmic localization of topoisomerase II alpha. Cancer Sci. 2005 Nov;96(11):774-83. [PubMed:16271071]
  2. Uesaka T, Shono T, Kuga D, Suzuki SO, Niiro H, Miyamoto K, Matsumoto K, Mizoguchi M, Ohta M, Iwaki T, Sasaki T: Enhanced expression of DNA topoisomerase II genes in human medulloblastoma and its possible association with etoposide sensitivity. J Neurooncol. 2007 Sep;84(2):119-29. Epub 2007 Mar 15. [PubMed:17361331]
  3. Winnicka K, Bielawski K, Bielawska A: Cardiac glycosides in cancer research and cancer therapy. Acta Pol Pharm. 2006 Mar-Apr;63(2):109-15. [PubMed:17514873]
  4. Faure P, Madelaine I: [Topoisomerases: therapeutic value]. Ann Pharm Fr. 1996;54(1):40-4. [PubMed:8702194]
  5. Umanskaya ON, Ioudinkova ES, Razin SV, Bystritskiy AA: Inhibition of DNA topoisomerase II in living cells stimulates illegitimate recombination. Dokl Biochem Biophys. 2005 Nov-Dec;405:423-5. [PubMed:16480143]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Isoform 1: May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4...
Gene Name
ABCC6
Uniprot ID
O95255
Uniprot Name
Multidrug resistance-associated protein 6
Molecular Weight
164904.81 Da
References
  1. Belinsky MG, Chen ZS, Shchaveleva I, Zeng H, Kruh GD: Characterization of the drug resistance and transport properties of multidrug resistance protein 6 (MRP6, ABCC6). Cancer Res. 2002 Nov 1;62(21):6172-7. [PubMed:12414644]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Allen JD, Van Dort SC, Buitelaar M, van Tellingen O, Schinkel AH: Mouse breast cancer resistance protein (Bcrp1/Abcg2) mediates etoposide resistance and transport, but etoposide oral availability is limited primarily by P-glycoprotein. Cancer Res. 2003 Mar 15;63(6):1339-44. [PubMed:12649196]

Drug created on June 13, 2005 07:24 / Updated on November 22, 2017 12:28