You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameTeniposide
Accession NumberDB00444  (APRD00649)
TypeSmall Molecule
GroupsApproved
DescriptionA 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 Identifiers
  • EPT
  • PGT
  • VM-26
  • VM26
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TeniposideInjection, solution10 mg/mLIntravenousWG Critical Care, LLC2013-04-30Not applicableUs
VumonLiquid10 mgIntravenousBristol Myers Squibb Canada1984-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Bang LaiDouble-Crane
Brand mixturesNot Available
SaltsNot Available
Categories
UNII957E6438QA
CAS number29767-20-2
WeightAverage: 656.654
Monoisotopic: 656.1563618
Chemical FormulaC32H32O13S
InChI KeyNRUKOCRGYNPUPR-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][C@]12COC(=O)[C@]1([H])[C@]([H])(C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@]2([H])O[C@]1([H])O[C@]2([H])CO[C@]([H])(O[C@@]2([H])[C@]([H])(O)[C@@]1([H])O)C1=CC=CS1
Pharmacology
IndicationTeniposide is used for the treatment of refractory acute lymphoblastic leukaemia
Structured Indications
PharmacodynamicsTeniposide 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 actionThe 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
DNA topoisomerase 2-alphaProteinyes
inhibitor
HumanP11388 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
SubstrateEnzymesProduct
Teniposide
Teniposide catechol derivativeDetails
Teniposide catechol derivative
Teniposide o-quinone derivativeDetails
Route of eliminationFrom 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 life5 hours
Clearance
  • 10.3 mL/min/m2
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Teniposide Metabolism PathwayDrug metabolismSMP00602
Teniposide Action PathwayDrug actionSMP00443
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot 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
ALT-110The risk or severity of adverse effects can be increased when Teniposide is combined with ALT-110.Investigational
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
AnvirzelAnvirzel may decrease the cardiotoxic activities of Teniposide.Investigational
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
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
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Teniposide.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Teniposide.Approved, Investigational
BexaroteneThe serum concentration of Teniposide can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Teniposide can be decreased when combined with Boceprevir.Approved
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
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Teniposide.Approved
CarbamazepineThe metabolism of Teniposide can be increased when combined with Carbamazepine.Approved, Investigational
CDX-110The risk or severity of adverse effects can be increased when Teniposide is combined with CDX-110.Investigational
CeritinibThe serum concentration of Teniposide can be increased when it is combined with Ceritinib.Approved
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
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
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
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
DexamethasoneThe serum concentration of Teniposide can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Teniposide.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Teniposide.Approved
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 serum concentration of Teniposide can be decreased when it is 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
ErythromycinThe metabolism of Teniposide can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Teniposide can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Teniposide can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe serum concentration of Teniposide can be decreased when it is 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
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 risk or severity of adverse effects can be increased when Teniposide is combined with G17DT.Investigational
GemfibrozilThe metabolism of Teniposide can be decreased when combined with Gemfibrozil.Approved
GI-5005The risk or severity of adverse effects can be increased when Teniposide is combined with GI-5005.Investigational
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 risk or severity of adverse effects can be increased when Teniposide is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Teniposide is combined with INGN 225.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
LeflunomideThe risk or severity of adverse effects can be increased when Teniposide is combined with Leflunomide.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
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Teniposide.Withdrawn
MethohexitalThe serum concentration of Teniposide can be decreased when it is combined with Methohexital.Approved
MethylphenobarbitalThe serum concentration of Teniposide can be decreased when it is combined with Methylphenobarbital.Approved
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 serum concentration of Teniposide can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Teniposide can be decreased when it is combined with Nafcillin.Approved
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
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
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
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
PosaconazoleThe metabolism of Teniposide can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe serum concentration of Teniposide can be decreased when it is combined with Primidone.Approved, Vet Approved
Rabies vaccineThe risk or severity of adverse effects can be increased when Teniposide is combined with Rabies vaccine.Approved
Rabies vaccineThe therapeutic efficacy of Rabies vaccine 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
RitonavirThe metabolism of Teniposide can be decreased when combined with Ritonavir.Approved, 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
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
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Teniposide.Approved
SRP 299The risk or severity of adverse effects can be increased when Teniposide is combined with SRP 299.Investigational
St. John's WortThe serum concentration of Teniposide can be decreased when it is combined with St. John's Wort.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
TelaprevirThe metabolism of Teniposide can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Teniposide can be decreased when combined with Telithromycin.Approved
TeriflunomideThe serum concentration of Teniposide can be increased when it is combined with Teriflunomide.Approved
TG4010The risk or severity of adverse effects can be increased when Teniposide is combined with TG4010.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
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
ZiprasidoneThe metabolism of Teniposide can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesL01CB02
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (46.6 KB)
ADMET
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 )
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point242-246 °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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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).
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassLignan lactones
Sub ClassPodophyllotoxins
Direct ParentPodophyllotoxins
Alternative Parents
Substituents
  • Podophyllotoxin
  • 1-aryltetralin lignan
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Tetralin
  • Pyranodioxin
  • Methoxyphenol
  • Benzodioxole
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Gamma butyrolactone
  • Monocyclic benzene moiety
  • Meta-dioxane
  • Heteroaromatic compound
  • Thiophene
  • Oxolane
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot 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 segregation of daughter chromosomes. May play a role in regulating the period length of ARNTL/BMAL1 transcriptional oscillation (By similarity).
Gene Name:
TOP2A
Uniprot ID:
P11388
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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
substrateinhibitor
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
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) and N-ethylmaleimide S-glutathione (NEM-GS).Isoform 2: Inhibits TNF-alpha-mediated apoptosis through blocking one or more caspases.
Gene Name:
ABCC6
Uniprot ID:
O95255
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 from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23