You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameThiotepa
Accession NumberDB04572
TypeSmall Molecule
GroupsApproved
DescriptionN,N'N'-triethylenethiophosphoramide (ThioTEPA) is a cancer chemotherapeutic member of the alkylating agent group, now in use for over 50 years. It is a stable derivative of N,N',N''- triethylenephosphoramide (TEPA). It is mostly used to treat breast cancer, ovarian cancer and bladder cancer. It is also used as conditioning for Bone marrow transplantation. Its main toxicity is myelosuppression.
Structure
Thumb
Synonyms
Thioplex
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Thio Tepa Inj 15mg/vialPowder, for solution15 mgOral; Rectal; VaginalLederle Cyanamid Canada Inc.1959-12-311997-11-24Canada
Thiotepa - (pws 15 Mg/vial)Powder, for solution15 mgIntracavitary; Intravenous; IntravesicalWyeth Canada1997-08-252004-09-15Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ThiotepaInjection, powder, lyophilized, for solution15 mg/1.5mLIntracavitary; Intravenous; IntravesicalWest Ward Pharmaceuticals Corp2001-06-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII905Z5W3GKH
CAS number52-24-4
WeightAverage: 189.218
Monoisotopic: 189.048954601
Chemical FormulaC6H12N3PS
InChI KeyFOCVUCIESVLUNU-UHFFFAOYSA-N
InChI
InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2
IUPAC Name
tris(aziridin-1-yl)-λ⁵-phosphanethione
SMILES
S=P(N1CC1)(N1CC1)N1CC1
Pharmacology
IndicationThioTEPA is used a as conditioning treatment prior to allogeneic or autologous haematopoietic progenitor cell transplantation (HPCT) in haematological diseases in adult and paediatric patients. Also, when high dose chemotherapy with HPCT support it is appropriate for the treatment of solid tumours in adult and paediatric patients.
Structured Indications
PharmacodynamicsThe unstable nitrogen-carbon groups alkylate with DNA causing irrepairable DNA damage. They stop tumor growth by crosslinking guanine nucleobases in DNA double-helix strands, directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. These drugs act nonspecifically.
Mechanism of actionThe alkyl group is attached to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. They stop tumor growth by crosslinking guanine nucleobases in DNA double-helix strands, directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. These drugs act nonspecifically.
TargetKindPharmacological actionActionsOrganismUniProt ID
DNANucleotideyes
cross-linking/alkylation
Humannot applicabledetails
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationUrinary excretion of 14C-labeled thiotepa and metabolites in a 34-year old patient with metastatic carcinoma of the cecum who received a dose of 0.3 mg/kg intravenously was 63%.
Half life1.5 to 4.1 hours
Clearance
  • 446 +/- 63 mL/min [female patients (45 to 84 years) with advanced stage ovarian cancer receiving 60 mg and 80 mg thiotepa by intravenous infusion on subsequent courses given at 4-week intervals]
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Thiotepa.Approved
ALT-110The risk or severity of adverse effects can be increased when Thiotepa is combined with ALT-110.Investigational
AmiodaroneThe metabolism of Thiotepa can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Thiotepa.Approved
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Thiotepa.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Thiotepa.Investigational
AprepitantThe serum concentration of Thiotepa can be increased when it is combined with Aprepitant.Approved, Investigational
ArtemetherThe metabolism of Artemether can be decreased when combined with Thiotepa.Approved
AtazanavirThe metabolism of Thiotepa can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Thiotepa can be decreased when combined with Atomoxetine.Approved
BanoxantroneThe metabolism of Banoxantrone can be decreased when combined with Thiotepa.Investigational
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Thiotepa.Investigational
BenzphetamineThe metabolism of Benzphetamine can be decreased when combined with Thiotepa.Approved, Illicit
Benzyl alcoholThe metabolism of Benzyl alcohol can be decreased when combined with Thiotepa.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Thiotepa.Approved, Investigational
BexaroteneThe serum concentration of Thiotepa can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Thiotepa can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Thiotepa can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Thiotepa can be decreased when it is combined with Bosentan.Approved, Investigational
BrompheniramineThe metabolism of Brompheniramine can be decreased when combined with Thiotepa.Approved
BupropionThe serum concentration of Bupropion can be increased when it is combined with Thiotepa.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Thiotepa.Approved
CarbamazepineThe metabolism of Thiotepa can be increased when combined with Carbamazepine.Approved, Investigational
CarbinoxamineThe metabolism of Carbinoxamine can be decreased when combined with Thiotepa.Approved
CDX-110The risk or severity of adverse effects can be increased when Thiotepa is combined with CDX-110.Investigational
CeritinibThe serum concentration of Thiotepa can be increased when it is combined with Ceritinib.Approved
CinnarizineThe metabolism of Cinnarizine can be decreased when combined with Thiotepa.Approved
CisaprideThe metabolism of Cisapride can be decreased when combined with Thiotepa.Approved, Investigational, Withdrawn
ClarithromycinThe metabolism of Thiotepa can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Thiotepa can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Clobazam can be decreased when combined with Thiotepa.Approved, Illicit
clomethiazoleThe metabolism of clomethiazole can be decreased when combined with Thiotepa.Investigational
ClopidogrelThe metabolism of Clopidogrel can be decreased when combined with Thiotepa.Approved, Nutraceutical
ClotiazepamThe metabolism of Clotiazepam can be decreased when combined with Thiotepa.Approved, Illicit
ClotrimazoleThe metabolism of Thiotepa can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Thiotepa is combined with Clozapine.Approved
CobicistatThe metabolism of Thiotepa can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Thiotepa can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Thiotepa can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Thiotepa.Approved, Investigational
CyclosporineThe metabolism of Thiotepa can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Thiotepa can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Thiotepa can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Thiotepa can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Thiotepa can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Thiotepa can be decreased when combined with Delavirdine.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Thiotepa.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Thiotepa.Approved
DexamethasoneThe serum concentration of Thiotepa can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe metabolism of Dextromethorphan can be decreased when combined with Thiotepa.Approved
DiazepamThe metabolism of Diazepam can be decreased when combined with Thiotepa.Approved, Illicit, Vet Approved
DiclofenacThe metabolism of Diclofenac can be decreased when combined with Thiotepa.Approved, Vet Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Thiotepa.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Thiotepa.Approved
DihydroergotamineThe metabolism of Thiotepa can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Thiotepa can be decreased when combined with Diltiazem.Approved
DiphenhydramineThe metabolism of Diphenhydramine can be decreased when combined with Thiotepa.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Thiotepa.Approved, Investigational
DomperidoneThe metabolism of Domperidone can be decreased when combined with Thiotepa.Approved, Investigational, Vet Approved
DoxycyclineThe metabolism of Thiotepa can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Thiotepa can be decreased when combined with Dronedarone.Approved
EfavirenzThe serum concentration of Thiotepa can be decreased when it is combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Thiotepa can be decreased when it is combined with Enzalutamide.Approved
EpinastineThe metabolism of Epinastine can be decreased when combined with Thiotepa.Approved, Investigational
ErythromycinThe metabolism of Thiotepa can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Thiotepa can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstroneThe metabolism of Estrone can be decreased when combined with Thiotepa.Approved
EthylmorphineThe metabolism of Ethylmorphine can be decreased when combined with Thiotepa.Approved, Illicit
EtravirineThe serum concentration of Thiotepa can be decreased when it is combined with Etravirine.Approved
FingolimodThiotepa may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FluconazoleThe metabolism of Thiotepa can be decreased when combined with Fluconazole.Approved
FlunarizineThe metabolism of Flunarizine can be decreased when combined with Thiotepa.Approved
FlunitrazepamThe metabolism of Flunitrazepam can be decreased when combined with Thiotepa.Approved, Illicit
FluoxetineThe metabolism of Fluoxetine can be decreased when combined with Thiotepa.Approved, Vet Approved
FluvoxamineThe metabolism of Thiotepa can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Thiotepa can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Thiotepa can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Thiotepa can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Thiotepa can be increased when it is combined with Fusidic Acid.Approved
G17DTThe risk or severity of adverse effects can be increased when Thiotepa is combined with G17DT.Investigational
GI-5005The risk or severity of adverse effects can be increased when Thiotepa is combined with GI-5005.Investigational
HalothaneThe metabolism of Halothane can be decreased when combined with Thiotepa.Approved, Vet Approved
IdelalisibThe serum concentration of Thiotepa can be increased when it is combined with Idelalisib.Approved
IfosfamideThe metabolism of Ifosfamide can be decreased when combined with Thiotepa.Approved
ImatinibThe metabolism of Thiotepa can be decreased when combined with Imatinib.Approved
ImipramineThe metabolism of Imipramine can be decreased when combined with Thiotepa.Approved
IndinavirThe metabolism of Thiotepa can be decreased when combined with Indinavir.Approved
INGN 201The risk or severity of adverse effects can be increased when Thiotepa is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Thiotepa is combined with INGN 225.Investigational
IrinotecanThe metabolism of Irinotecan can be decreased when combined with Thiotepa.Approved, Investigational
IsavuconazoniumThe metabolism of Thiotepa can be decreased when combined with Isavuconazonium.Approved, Investigational
IsofluraneThe metabolism of Isoflurane can be decreased when combined with Thiotepa.Approved, Vet Approved
IsradipineThe metabolism of Thiotepa can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Thiotepa can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Thiotepa can be increased when it is combined with Ivacaftor.Approved
IxazomibThe metabolism of Ixazomib can be decreased when combined with Thiotepa.Approved
KetamineThe metabolism of Ketamine can be decreased when combined with Thiotepa.Approved, Vet Approved
KetobemidoneThe metabolism of Ketobemidone can be decreased when combined with Thiotepa.Approved
KetoconazoleThe metabolism of Thiotepa can be decreased when combined with Ketoconazole.Approved, Investigational
LeflunomideThe risk or severity of adverse effects can be increased when Thiotepa is combined with Leflunomide.Approved, Investigational
LidocaineThe metabolism of Lidocaine can be decreased when combined with Thiotepa.Approved, Vet Approved
LoperamideThe metabolism of Loperamide can be decreased when combined with Thiotepa.Approved
LopinavirThe metabolism of Thiotepa can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Lorcaserin can be decreased when combined with Thiotepa.Approved
LovastatinThe metabolism of Thiotepa can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Thiotepa can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Thiotepa can be increased when combined with Lumacaftor.Approved
MalathionThe metabolism of Malathion can be decreased when combined with Thiotepa.Approved, Investigational
MephenytoinThe metabolism of Mephenytoin can be decreased when combined with Thiotepa.Investigational, Withdrawn
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Thiotepa.Withdrawn
MethadoneThe metabolism of Methadone can be decreased when combined with Thiotepa.Approved
MethoxyfluraneThe metabolism of Methoxyflurane can be decreased when combined with Thiotepa.Approved, Vet Approved
MethylphenobarbitalThe metabolism of Methylphenobarbital can be decreased when combined with Thiotepa.Approved
MethyltestosteroneThe metabolism of Methyltestosterone can be decreased when combined with Thiotepa.Approved
MexiletineThe metabolism of Mexiletine can be decreased when combined with Thiotepa.Approved
MianserinThe metabolism of Mianserin can be decreased when combined with Thiotepa.Approved
MidazolamThe metabolism of Midazolam can be decreased when combined with Thiotepa.Approved, Illicit
MifepristoneThe serum concentration of Thiotepa can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Thiotepa can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Thiotepa can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Thiotepa can be decreased when it is combined with Nafcillin.Approved
NatalizumabThe risk or severity of adverse effects can be increased when Thiotepa is combined with Natalizumab.Approved, Investigational
NefazodoneThe metabolism of Thiotepa can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Thiotepa can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Thiotepa can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Thiotepa can be increased when combined with Nevirapine.Approved
NicotineThe metabolism of Nicotine can be decreased when combined with Thiotepa.Approved
NilotinibThe metabolism of Thiotepa can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Thiotepa can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Thiotepa can be increased when it is combined with Osimertinib.Approved
OspemifeneThe metabolism of Ospemifene can be decreased when combined with Thiotepa.Approved
OuabainOuabain may decrease the cardiotoxic activities of Thiotepa.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Thiotepa.Approved, Vet Approved
PalbociclibThe serum concentration of Thiotepa can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Thiotepa can be increased when combined with Pentobarbital.Approved, Vet Approved
PerhexilineThe metabolism of Perhexiline can be decreased when combined with Thiotepa.Approved
PermethrinThe metabolism of Permethrin can be decreased when combined with Thiotepa.Approved, Investigational
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Thiotepa.Approved
PethidineThe metabolism of Pethidine can be decreased when combined with Thiotepa.Approved
PhenobarbitalThe metabolism of Thiotepa can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Thiotepa can be increased when combined with Phenytoin.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Thiotepa.Approved, Investigational
PosaconazoleThe metabolism of Thiotepa can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrasugrelThe metabolism of Prasugrel can be decreased when combined with Thiotepa.Approved
PrimidoneThe metabolism of Thiotepa can be increased when combined with Primidone.Approved, Vet Approved
PromethazineThe metabolism of Promethazine can be decreased when combined with Thiotepa.Approved
PropofolThe metabolism of Propofol can be decreased when combined with Thiotepa.Approved, Investigational, Vet Approved
Rabies vaccineThe risk or severity of adverse effects can be increased when Thiotepa is combined with Rabies vaccine.Approved
Rabies vaccineThe therapeutic efficacy of Rabies vaccine can be decreased when used in combination with Thiotepa.Approved
RanolazineThe metabolism of Thiotepa can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Thiotepa can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Thiotepa can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Thiotepa can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Thiotepa can be decreased when combined with Ritonavir.Approved, Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Thiotepa.Approved
RomidepsinThe metabolism of Romidepsin can be decreased when combined with Thiotepa.Approved, Investigational
RopivacaineThe metabolism of Ropivacaine can be decreased when combined with Thiotepa.Approved
SaquinavirThe metabolism of Thiotepa can be decreased when combined with Saquinavir.Approved, Investigational
SelegilineThe metabolism of Selegiline can be decreased when combined with Thiotepa.Approved, Investigational, Vet Approved
SeratrodastThe metabolism of Seratrodast can be decreased when combined with Thiotepa.Approved, Investigational
SertralineThe metabolism of Sertraline can be decreased when combined with Thiotepa.Approved
SevofluraneThe metabolism of Sevoflurane can be decreased when combined with Thiotepa.Approved, Vet Approved
SildenafilThe metabolism of Thiotepa can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Thiotepa can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Thiotepa 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 Thiotepa.Approved
SorafenibThe metabolism of Sorafenib can be decreased when combined with Thiotepa.Approved, Investigational
SRP 299The risk or severity of adverse effects can be increased when Thiotepa is combined with SRP 299.Investigational
St. John's WortThe serum concentration of Thiotepa can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Thiotepa can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Thiotepa 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 Thiotepa.Approved, Investigational
TamoxifenThe metabolism of Tamoxifen can be decreased when combined with Thiotepa.Approved
TelaprevirThe metabolism of Thiotepa can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Thiotepa can be decreased when combined with Telithromycin.Approved
TemazepamThe metabolism of Temazepam can be decreased when combined with Thiotepa.Approved
TestosteroneThe metabolism of Testosterone can be decreased when combined with Thiotepa.Approved, Investigational
TG4010The risk or severity of adverse effects can be increased when Thiotepa is combined with TG4010.Investigational
TiclopidineThe metabolism of Thiotepa can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Thiotepa can be decreased when it is combined with Tocilizumab.Approved
TofacitinibThiotepa may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TramadolThe metabolism of Tramadol can be decreased when combined with Thiotepa.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Thiotepa.Approved, Investigational
TretinoinThe metabolism of Tretinoin can be decreased when combined with Thiotepa.Approved, Investigational, Nutraceutical
Valproic AcidThe metabolism of Valproic Acid can be decreased when combined with Thiotepa.Approved, Investigational
VenlafaxineThe metabolism of Thiotepa can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Thiotepa can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Thiotepa can be decreased when combined with Voriconazole.Approved, Investigational
VortioxetineThe metabolism of Vortioxetine can be decreased when combined with Thiotepa.Approved
ZiprasidoneThe metabolism of Thiotepa can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis Reference

John Kazan, “Process for producing thiotepa.” U.S. Patent US4918199, issued February, 1954.

US4918199
General References
  1. Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68. [PubMed:10913381 ]
External Links
ATC CodesL01AC01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8788
Blood Brain Barrier+0.9823
Caco-2 permeable-0.5097
P-glycoprotein substrateNon-substrate0.7362
P-glycoprotein inhibitor INon-inhibitor0.8096
P-glycoprotein inhibitor IINon-inhibitor0.9946
Renal organic cation transporterNon-inhibitor0.7874
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateNon-inhibitor0.6474
CYP450 2C9 inhibitorNon-inhibitor0.7225
CYP450 2D6 inhibitorNon-inhibitor0.8794
CYP450 2C19 inhibitorNon-inhibitor0.593
CYP450 3A4 inhibitorNon-inhibitor0.8618
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7358
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.8992
BiodegradationNot ready biodegradable0.8949
Rat acute toxicity3.8842 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7707
hERG inhibition (predictor II)Non-inhibitor0.866
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Powder, for solutionOral; Rectal; Vaginal15 mg
Injection, powder, lyophilized, for solutionIntracavitary; Intravenous; Intravesical15 mg/1.5mL
Powder, for solutionIntracavitary; Intravenous; Intravesical15 mg
Prices
Unit descriptionCostUnit
Thiotepa 30 mg vial285.0USD vial
Thiotepa 15 mg vial69.6USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point51.5 °CPhysProp
water solubility1.9E+005 mg/L (at 25 °C)MERCK INDEX (1996)
logP0.53HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility9.27 mg/mLALOGPS
logP0.17ALOGPS
logP-1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)-0.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.03 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.72 m3·mol-1ChemAxon
Polarizability18.23 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-00kn-6900000000-6d6b7c109663ea65ad79View in MoNA
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organic thiophosphoric acids and derivatives. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure RP(R')(R'')=S, where R,R',R'' = O,N, halogen residue.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganothiophosphorus compounds
Sub ClassOrganic thiophosphoric acids and derivatives
Direct ParentOrganic thiophosphoric acids and derivatives
Alternative Parents
Substituents
  • Organic thiophosphoric acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Aziridine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
cross-linking/alkylation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Gor PP, Su HI, Gray RJ, Gimotty PA, Horn M, Aplenc R, Vaughan WP, Tallman MS, Rebbeck TR, DeMichele A: Cyclophosphamide-metabolizing enzyme polymorphisms and survival outcomes after adjuvant chemotherapy for node-positive breast cancer: a retrospective cohort study. Breast Cancer Res. 2010;12(3):R26. doi: 10.1186/bcr2570. Epub 2010 May 10. [PubMed:20459744 ]
  2. Lee PC, Kakadiya R, Su TL, Lee TC: Combination of bifunctional alkylating agent and arsenic trioxide synergistically suppresses the growth of drug-resistant tumor cells. Neoplasia. 2010 May;12(5):376-87. [PubMed:20454509 ]
  3. Lestuzzi C: Neoplastic pericardial disease: Old and current strategies for diagnosis and management. World J Cardiol. 2010 Sep 26;2(9):270-9. doi: 10.4330/wjc.v2.i9.270. [PubMed:21160603 ]
  4. Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68. [PubMed:10913381 ]

Enzymes

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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 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
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 ]
Comments
comments powered by Disqus
Drug created on September 07, 2007 14:54 / Updated on August 17, 2016 12:24