Identification
NameIfosfamide
Accession NumberDB01181  (APRD00007)
TypeSmall Molecule
GroupsApproved
Description

Ifosfamide is a chemotherapeutic agent chemically related to the nitrogen mustards and a synthetic analog of cyclophosphamide. It is active as an alkylating agent and an immunosuppresive agent.

Structure
Thumb
Synonyms
3-(2-Chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
Ifosfamida
Ifosfamidum
Iphosphamide
Isofosfamide
Isophosphamide
Isosfamide
External IDs Z4942
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
IfexInjection, powder, for solution1 g/20mLIntravenousBaxter Laboratories1988-12-30Not applicableUs
IfexInjection, powder, for solution3 g/60mLIntravenousBaxter Laboratories1988-12-30Not applicableUs
Ifex (ifosfamide) 1 G/vialPowder, for solution1 gIntravenousBaxter Laboratories2001-03-20Not applicableCanada
Ifex (ifosfamide) 3 G/vialPowder, for solution3 gIntravenousBaxter Laboratories2001-01-25Not applicableCanada
Ifex Pws 1gm/vialPowder, for solution1 gIntravenousBristol Labs Division Of Bristol Myers Squibb1989-12-312001-04-09Canada
Ifex Pws 2g/vialPowder, for solution2 gIntravenousBristol Labs Division Of Bristol Myers Squibb1989-12-311997-08-14Canada
Ifex Pws 3gm/vialPowder, for solution3 gIntravenousBristol Labs Division Of Bristol Myers Squibb1989-12-312002-07-11Canada
IfosfamideInjection, powder, for solution3 g/60mLIntravenousBaxter Laboratories1988-12-30Not applicableUs
IfosfamideInjection, powder, for solution1 g/20mLIntravenousBaxter Laboratories1988-12-30Not applicableUs
Ifosfamide for InjectionPowder, for solution3 gIntravenousFresenius KabiNot applicableNot applicableCanada
Ifosfamide for InjectionPowder, for solution1 gIntravenousFresenius Kabi2003-04-15Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
IfosfamideInjection, solution50 mg/mLIntravenousPfizer Laboratories Div Pfizer Inc.2012-11-27Not applicableUs
IfosfamideInjection, powder, lyophilized, for solution1 g/1IntravenousFresenius Kabi2003-01-28Not applicableUs
IfosfamideInjection, solution3 g/60mLIntravenousTeva Parenteral Medicines, Inc.2007-07-26Not applicableUs
IfosfamideInjection, solution50 mg/mLIntravenousMylan Institutional2012-11-27Not applicableUs
IfosfamideInjection, solution50 mg/mLIntravenousPfizer Laboratories Div Pfizer Inc.2012-11-27Not applicableUs
IfosfamideInjection, solution50 mg/mLIntravenousAPP Pharmaceuticals, Inc.2009-09-30Not applicableUs
IfosfamideInjection, solution50 mg/mLIntravenousMylan Institutional2012-11-27Not applicableUs
IfosfamideInjection, solution1 g/20mLIntravenousTeva Parenteral Medicines, Inc.2007-07-26Not applicableUs
IfosfamideInjection, solution50 mg/mLIntravenousMylan Institutional2012-11-27Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CelofosCelon
CuantilTeva
HoloxanBaxter
MitoxanaBaxter
Brand mixturesNot Available
Categories
UNIIUM20QQM95Y
CAS number3778-73-2
WeightAverage: 261.086
Monoisotopic: 260.02481966
Chemical FormulaC7H15Cl2N2O2P
InChI KeyHOMGKSMUEGBAAB-UHFFFAOYSA-N
InChI
InChI=1S/C7H15Cl2N2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12)
IUPAC Name
3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinan-2-one
SMILES
ClCCNP1(=O)OCCCN1CCCl
Pharmacology
Indication

Used as a component of various chemotherapeutic regimens as third-line therapy for recurrent or refractory germ cell testicular cancer. Also used as a component of various chemotherapeutic regimens for the treatment of cervical cancer, as well as in conjunction with surgery and/or radiation therapy in the treatment of various soft tissue sarcomas. Other indications include treatment of osteosarcoma, bladder cancer, ovarian cancer. small cell lung cancer, and non-Hodgkin's lymphoma.

Structured Indications
Pharmacodynamics

Ifosfamide requires activation by microsomal liver enzymes to active metabolites in order to exert its cytotoxic effects. Activation occurs by hydroxylation at the ring carbon atom 4 to form the unstable intermediate 4-hydroxyifosfamide. This metabolite than rapidly degrades to the stable urinary metabolite 4-ketoifosfamide. The stable urinary metabolite, 4-carboxyifosfamide, is formed upon opening of the ring. These urinary metabolites have not been found to be cytotoxic. N, N-bis (2-chloroethyl)-phosphoric acid diamide (ifosphoramide) and acrolein are also found. The major urinary metabolites, dechloroethyl ifosfamide and dechloroethyl cyclophosphamide, are formed upon enzymatic oxidation of the chloroethyl side chains and subsequent dealkylation. It is the alkylated metabolites of ifosfamide that have been shown to interact with DNA. Ifosfamide is cycle-phase nonspecific.

Mechanism of action

The exact mechanism of ifosfamide has not been determined, but appears to be similar to other alkylating agents. Ifosfamide requires biotransformation in the liver by mixed-function oxidases (cytochrome P450 system) before it becomes active. After metabolic activation, active metabolites of ifosfamide alkylate or bind with many intracellular molecular structures, including nucleic acids. The cytotoxic action is primarily through the alkylation of DNA, done by attaching the N-7 position of guanine to its reactive electrophilic groups. The formation of inter and intra strand cross-links in the DNA results in cell death.

TargetKindPharmacological actionActionsOrganismUniProt ID
DNANucleotideyes
other/unknown
Humannot applicabledetails
Nuclear receptor subfamily 1 group I member 2ProteinunknownNot AvailableHumanO75469 details
Related Articles
AbsorptionNot Available
Volume of distribution

Ifosfamide volume of distribution (Vd) approximates the total body water volume, suggesting that distribution takes place with minimal tissue binding. Following intravenous administration of 1.5 g/m2 over 0.5 hour once daily for 5 days to 15 patients with neoplastic disease, the median Vd of ifosfamide was 0.64 L/kg on Day 1 and 0.72 L/kg on Day 5. When given to pediatric patients, the volume of distribution was 21±1.6 L/m^2.

Protein binding

Ifosfamide shows little plasma protein binding.

Metabolism

Primarily hepatic. Ifosfamide is metabolized through two metabolic pathways: ring oxidation ("activation") to form the active metabolite, 4-hydroxy-ifosfamide and side-chain oxidation to form the inactive metabolites, 3-dechloro-ethylifosfamide or 2-dechloroethylifosfamide with liberation of the toxic metabolite, chloroacetaldehyde. Small quantities (nmol/mL) of ifosfamide mustard and 4-hydroxyifosfamide are detectable in human plasma. Metabolism of ifosfamide is required for the generation of the biologically active species and while metabolism is extensive, it is also quite variable among patients.

SubstrateEnzymesProduct
Ifosfamide
3-DechloroethylifosfamideDetails
Ifosfamide
2-DechloroethylifosfamideDetails
Ifosfamide
ChloroacetaldehydeDetails
Ifosfamide
4-HydroxyifosfamideDetails
4-Hydroxyifosfamide
Not Available
4-KetoifosfamideDetails
4-Hydroxyifosfamide
Not Available
aldoifosfamideDetails
4-Hydroxyifosfamide
Not Available
4-ThioifosfamideDetails
aldoifosfamide
Not Available
AlcoifosfamideDetails
aldoifosfamide
CarboxylifosfamideDetails
aldoifosfamide
Not Available
AcroleinDetails
aldoifosfamide
Not Available
Isophosphamide mustardDetails
Acrolein
Acrylic AcidDetails
Isophosphamide mustard
Not Available
Ifosforamide AziridiniumDetails
Route of elimination

Ifosfamide is extensively metabolized in humans and the metabolic pathways appear to be saturated at high doses. After administration of doses of 5 g/m2 of 14C-labeled ifosfamide, from 70% to 86% of the dosed radioactivity was recovered in the urine, with about 61% of the dose excreted as parent compound. At doses of 1.6–2.4 g/m2 only 12% to 18% of the dose was excreted in the urine as unchanged drug within 72 hours.

Half life

7-15 hours. The elimination half-life increase appeared to be related to the increase in ifosfamide volume of distribution with age.

Clearance
  • 2.4±0.33 L/h/m^2 [pediatric patients]
Toxicity

LD50 (mouse) = 390-1005 mg/kg, LD50 (rat) = 150-190 mg/kg. Side effects include nausea, vomiting and myelosuppression. Toxic effects include central nervous system toxicity (confusion, hallucinations) and urotoxic effects (cystitis, blood in urine).

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Ifosfamide Action PathwayDrug actionSMP00448
Ifosfamide Metabolism PathwayDrug metabolismSMP00605
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Ifosfamide can be increased when it is combined with Abiraterone.Approved
AcenocoumarolIfosfamide may increase the anticoagulant activities of Acenocoumarol.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Ifosfamide.Approved
AmiodaroneThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Amiodarone resulting in a loss in efficacy.Approved, Investigational
AprepitantThe serum concentration of Ifosfamide can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Ifosfamide.Approved, Investigational
ArmodafinilThe metabolism of Ifosfamide can be decreased when combined with Armodafinil.Approved, Investigational
AtazanavirThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Atazanavir resulting in a loss in efficacy.Approved, Investigational
AtomoxetineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Atomoxetine resulting in a loss in efficacy.Approved
BCG vaccineThe therapeutic efficacy of Bcg can be decreased when used in combination with Ifosfamide.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Ifosfamide.Approved, Investigational
BexaroteneThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Bexarotene resulting in a loss in efficacy.Approved, Investigational
BoceprevirThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Boceprevir resulting in a loss in efficacy.Withdrawn
BortezomibThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Bortezomib resulting in a loss in efficacy.Approved, Investigational
BosentanThe serum concentration of Ifosfamide can be decreased when it is combined with Bosentan.Approved, Investigational
BusulfanThe risk or severity of adverse effects can be increased when Busulfan is combined with Ifosfamide.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Ifosfamide.Approved
CapecitabineThe metabolism of Ifosfamide can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe serum concentration of the active metabolites of Ifosfamide can be increased when Ifosfamide is used in combination with Carbamazepine.Approved, Investigational
CelecoxibThe metabolism of Ifosfamide can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Ifosfamide can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Ifosfamide can be decreased when combined with Chloramphenicol.Approved, Vet Approved
CholecalciferolThe metabolism of Ifosfamide can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Ifosfamide can be decreased when combined with Cimetidine.Approved
CitalopramThe metabolism of Ifosfamide can be decreased when combined with Citalopram.Approved
ClarithromycinThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Clarithromycin resulting in a loss in efficacy.Approved
ClemastineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Clemastine resulting in a loss in efficacy.Approved
ClopidogrelThe metabolism of Ifosfamide can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Clotrimazole resulting in a loss in efficacy.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Ifosfamide is combined with Clozapine.Approved
CobicistatThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Cobicistat resulting in a loss in efficacy.Approved
ConivaptanThe serum concentration of Ifosfamide can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Crizotinib resulting in a loss in efficacy.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Ifosfamide.Approved, Investigational
CyclosporineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Cyclosporine resulting in a loss in efficacy.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Ifosfamide can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Darunavir resulting in a loss in efficacy.Approved
DasatinibThe serum concentration of Ifosfamide can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Ifosfamide can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Delavirdine resulting in a loss in efficacy.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Ifosfamide.Approved
DesipramineThe metabolism of Ifosfamide can be decreased when combined with Desipramine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Ifosfamide.Approved
DexamethasoneThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Dexamethasone resulting in a loss in efficacy.Approved, Investigational, Vet Approved
DicoumarolIfosfamide may increase the anticoagulant activities of Dicoumarol.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Ifosfamide.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Ifosfamide.Approved
DihydroergotamineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Dihydroergotamine resulting in a loss in efficacy.Approved
DiltiazemThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Diltiazem resulting in a loss in efficacy.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Ifosfamide.Approved, Investigational
DoxorubicinThe metabolism of Ifosfamide can be decreased when combined with Doxorubicin.Approved, Investigational
DoxycyclineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Doxycycline resulting in a loss in efficacy.Approved, Investigational, Vet Approved
DronedaroneThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Dronedarone resulting in a loss in efficacy.Approved
EfavirenzThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Efavirenz resulting in a loss in efficacy.Approved, Investigational
EnzalutamideThe serum concentration of Ifosfamide can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Erythromycin resulting in a loss in efficacy.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Eslicarbazepine acetate resulting in a loss in efficacy.Approved
EsomeprazoleThe metabolism of Ifosfamide can be decreased when combined with Esomeprazole.Approved, Investigational
Ethyl biscoumacetateIfosfamide may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtravirineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Etravirine resulting in a loss in efficacy.Approved
FelodipineThe metabolism of Ifosfamide can be decreased when combined with Felodipine.Approved, Investigational
FingolimodIfosfamide may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FloxuridineThe metabolism of Ifosfamide can be decreased when combined with Floxuridine.Approved
FluconazoleThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Fluconazole resulting in a loss in efficacy.Approved
FluindioneIfosfamide may increase the anticoagulant activities of Fluindione.Investigational
FluorouracilThe metabolism of Ifosfamide can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Ifosfamide can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvastatinThe metabolism of Ifosfamide can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Fluvoxamine resulting in a loss in efficacy.Approved, Investigational
FosamprenavirThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Fosamprenavir resulting in a loss in efficacy.Approved
FosaprepitantThe serum concentration of Ifosfamide can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of the active metabolites of Ifosfamide can be increased when Ifosfamide is used in combination with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Ifosfamide can be increased when it is combined with Fusidic Acid.Approved
G17DTThe risk or severity of adverse effects can be increased when Ifosfamide is combined with G17DT.Investigational
GemfibrozilThe metabolism of Ifosfamide can be decreased when combined with Gemfibrozil.Approved
IdelalisibThe serum concentration of Ifosfamide can be increased when it is combined with Idelalisib.Approved
ImatinibThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Imatinib resulting in a loss in efficacy.Approved
IndinavirThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Indinavir resulting in a loss in efficacy.Approved
INGN 201The risk or severity of adverse effects can be increased when Ifosfamide is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Ifosfamide is combined with INGN 225.Investigational
IrbesartanThe metabolism of Ifosfamide can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Isavuconazonium resulting in a loss in efficacy.Approved, Investigational
IsoniazidThe metabolism of Ifosfamide can be decreased when combined with Isoniazid.Approved
IsradipineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Isradipine resulting in a loss in efficacy.Approved
ItraconazoleThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Itraconazole resulting in a loss in efficacy.Approved, Investigational
IvacaftorThe serum concentration of Ifosfamide can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Ketoconazole resulting in a loss in efficacy.Approved, Investigational
LapatinibThe metabolism of Ifosfamide can be decreased when combined with Lapatinib.Approved, Investigational
LeflunomideThe risk or severity of adverse effects can be increased when Ifosfamide is combined with Leflunomide.Approved, Investigational
LopinavirThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Lopinavir resulting in a loss in efficacy.Approved
LosartanThe metabolism of Ifosfamide can be decreased when combined with Losartan.Approved
LovastatinThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Lovastatin resulting in a loss in efficacy.Approved, Investigational
LuliconazoleThe serum concentration of Ifosfamide can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Ifosfamide can be increased when it is combined with Lumacaftor.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Ifosfamide.Withdrawn
MifepristoneThe serum concentration of Ifosfamide can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Ifosfamide can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Ifosfamide can be decreased when combined with Moclobemide.Approved
ModafinilThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Modafinil resulting in a loss in efficacy.Approved, Investigational
NafcillinThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Nafcillin resulting in a loss in efficacy.Approved
NatalizumabThe risk or severity of adverse effects can be increased when Ifosfamide is combined with Natalizumab.Approved, Investigational
NefazodoneThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Nefazodone resulting in a loss in efficacy.Approved, Withdrawn
NelfinavirThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Nelfinavir resulting in a loss in efficacy.Approved
NetupitantThe serum concentration of Ifosfamide can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Nevirapine resulting in a loss in efficacy.Approved
NicardipineThe metabolism of Ifosfamide can be decreased when combined with Nicardipine.Approved
NicotineThe metabolism of Ifosfamide can be decreased when combined with Nicotine.Approved
NilotinibThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Nilotinib resulting in a loss in efficacy.Approved, Investigational
OlaparibThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Olaparib resulting in a loss in efficacy.Approved
OleandrinAnvirzel may decrease the cardiotoxic activities of Ifosfamide.Experimental
OmeprazoleThe metabolism of Ifosfamide can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Ifosfamide can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Ifosfamide.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Ifosfamide.Approved, Vet Approved
PalbociclibThe serum concentration of Ifosfamide can be increased when it is combined with Palbociclib.Approved
PantoprazoleThe metabolism of Ifosfamide can be decreased when combined with Pantoprazole.Approved
ParoxetineThe metabolism of Ifosfamide can be decreased when combined with Paroxetine.Approved, Investigational
PentobarbitalThe serum concentration of the active metabolites of Ifosfamide can be increased when Ifosfamide is used in combination with Pentobarbital.Approved, Vet Approved
PhenindioneIfosfamide may increase the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe serum concentration of the active metabolites of Ifosfamide can be increased when Ifosfamide is used in combination with Phenobarbital.Approved
PhenprocoumonIfosfamide may increase the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe serum concentration of the active metabolites of Ifosfamide can be increased when Ifosfamide is used in combination with Phenytoin.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Ifosfamide.Approved, Investigational
PioglitazoneThe metabolism of Ifosfamide can be decreased when combined with Pioglitazone.Approved, Investigational
PosaconazoleThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Posaconazole resulting in a loss in efficacy.Approved, Investigational, Vet Approved
PrimidoneThe serum concentration of the active metabolites of Ifosfamide can be increased when Ifosfamide is used in combination with Primidone.Approved, Vet Approved
PyrimethamineThe metabolism of Ifosfamide can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuazepamThe serum concentration of Ifosfamide can be increased when it is combined with Quazepam.Approved, Illicit
QuinineThe metabolism of Ifosfamide can be decreased when combined with Quinine.Approved
RabeprazoleThe metabolism of Ifosfamide can be decreased when combined with Rabeprazole.Approved, Investigational
RanolazineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Ranolazine resulting in a loss in efficacy.Approved, Investigational
RifabutinThe serum concentration of the active metabolites of Ifosfamide can be increased when Ifosfamide is used in combination with Rifabutin.Approved
RifampicinThe serum concentration of the active metabolites of Ifosfamide can be increased when Ifosfamide is used in combination with Rifampicin.Approved
RifapentineThe serum concentration of the active metabolites of Ifosfamide can be increased when Ifosfamide is used in combination with Rifapentine.Approved
RindopepimutThe risk or severity of adverse effects can be increased when Ifosfamide is combined with CDX-110.Investigational
RitonavirThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Ritonavir resulting in a loss in efficacy.Approved, Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Ifosfamide.Approved
RosiglitazoneThe metabolism of Ifosfamide can be decreased when combined with Rosiglitazone.Approved, Investigational
SaquinavirThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Saquinavir resulting in a loss in efficacy.Approved, Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Ifosfamide.Approved
SecobarbitalThe metabolism of Ifosfamide can be increased when combined with Secobarbital.Approved, Vet Approved
SertralineThe metabolism of Ifosfamide can be decreased when combined with Sertraline.Approved
SildenafilThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Sildenafil resulting in a loss in efficacy.Approved, Investigational
SiltuximabThe serum concentration of Ifosfamide can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Ifosfamide 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 Ifosfamide.Approved
SorafenibThe metabolism of Ifosfamide can be decreased when combined with Sorafenib.Approved, Investigational
SRP 299The risk or severity of adverse effects can be increased when Ifosfamide is combined with SRP 299.Investigational
St. John's WortThe serum concentration of Ifosfamide can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Ifosfamide can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Ifosfamide can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Ifosfamide can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Sulfisoxazole resulting in a loss in efficacy.Approved, Vet Approved
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Ifosfamide.Approved, Investigational
TamoxifenThe metabolism of Ifosfamide can be decreased when combined with Tamoxifen.Approved
TelaprevirThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Telaprevir resulting in a loss in efficacy.Withdrawn
TelithromycinThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Telithromycin resulting in a loss in efficacy.Approved
TeriflunomideThe metabolism of Ifosfamide can be decreased when combined with Teriflunomide.Approved
ThiotepaThe metabolism of Ifosfamide can be decreased when combined with Thiotepa.Approved
TicagrelorThe metabolism of Ifosfamide can be decreased when combined with Ticagrelor.Approved
TiclopidineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Ticlopidine resulting in a loss in efficacy.Approved
TocilizumabThe serum concentration of Ifosfamide can be decreased when it is combined with Tocilizumab.Approved
TofacitinibIfosfamide may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TolbutamideThe metabolism of Ifosfamide can be decreased when combined with Tolbutamide.Approved
TopiramateThe metabolism of Ifosfamide can be decreased when combined with Topiramate.Approved
TranylcypromineThe metabolism of Ifosfamide can be decreased when combined with Tranylcypromine.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Ifosfamide.Approved, Investigational
TrimethoprimThe metabolism of Ifosfamide can be decreased when combined with Trimethoprim.Approved, Vet Approved
Valproic AcidThe metabolism of Ifosfamide can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Ifosfamide can be decreased when combined with Valsartan.Approved, Investigational
VenlafaxineThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Venlafaxine resulting in a loss in efficacy.Approved
VerapamilThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Verapamil resulting in a loss in efficacy.Approved
VoriconazoleThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Voriconazole resulting in a loss in efficacy.Approved, Investigational
WarfarinIfosfamide may increase the anticoagulant activities of Warfarin.Approved
ZafirlukastThe metabolism of Ifosfamide can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Ziprasidone resulting in a loss in efficacy.Approved
Food InteractionsNot Available
References
Synthesis Reference

U.S. Patent 3,732,340.

US3732340
General References
  1. Furlanut M, Franceschi L: Pharmacology of ifosfamide. Oncology. 2003;65 Suppl 2:2-6. [PubMed:14586139 ]
  2. Fleming RA: An overview of cyclophosphamide and ifosfamide pharmacology. Pharmacotherapy. 1997 Sep-Oct;17(5 Pt 2):146S-154S. [PubMed:9322882 ]
  3. Wagner T: Ifosfamide clinical pharmacokinetics. Clin Pharmacokinet. 1994 Jun;26(6):439-56. [PubMed:8070218 ]
  4. Allen LM, Creaven PJ, Nelson RL: Studies on the human pharmacokinetics of isophosphamide (NSC-109724). Cancer Treat Rep. 1976 Apr;60(4):451-8. [PubMed:1277221 ]
  5. Brade WP, Herdrich K, Varini M: Ifosfamide--pharmacology, safety and therapeutic potential. Cancer Treat Rev. 1985 Mar;12(1):1-47. [PubMed:3896483 ]
  6. Zalupski M, Baker LH: Ifosfamide. J Natl Cancer Inst. 1988 Jun 15;80(8):556-66. [PubMed:3286879 ]
  7. Willits I, Price L, Parry A, Tilby MJ, Ford D, Cholerton S, Pearson AD, Boddy AV: Pharmacokinetics and metabolism of ifosfamide in relation to DNA damage assessed by the COMET assay in children with cancer. Br J Cancer. 2005 May 9;92(9):1626-35. [PubMed:15827549 ]
  8. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  9. Schoenike SE, Dana WJ: Ifosfamide and mesna. Clin Pharm. 1990 Mar;9(3):179-91. [PubMed:2107997 ]
  10. Dechant KL, Brogden RN, Pilkington T, Faulds D: Ifosfamide/mesna. A review of its antineoplastic activity, pharmacokinetic properties and therapeutic efficacy in cancer. Drugs. 1991 Sep;42(3):428-67. [PubMed:1720382 ]
External Links
ATC CodesL01AA06 — Ifosfamide
AHFS Codes
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PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (293 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentPrecursor Cell Lymphoblastic Leukemia-Lymphoma1
0TerminatedTreatmentLymphoma, B-Cell1
1Active Not RecruitingTreatmentCD20 Positive / Recurrent Diffuse Large B-Cell Lymphoma / Refractory Diffuse Large B-Cell Lymphoma1
1Active Not RecruitingTreatmentMalignant Lymphomas1
1Active Not RecruitingTreatmentNeuroblastomas1
1Active Not RecruitingTreatmentSarcomas1
1CompletedSupportive CareCancers1
1CompletedTreatmentCancers1
1CompletedTreatmentLymphoma, Hodgkins / Malignant Lymphomas1
1CompletedTreatmentMalignant Lymphomas1
1CompletedTreatmentSarcomas2
1CompletedTreatmentTumors, Solid1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1Not Yet RecruitingTreatmentBladder Cancers / Cancer, Advanced / Soft Tissue Sarcoma (STS)1
1RecruitingTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)1
1RecruitingTreatmentNeoplasms Metastasis1
1TerminatedTreatmentBone Cancer / Kidney Tumors / Neoplasms / Neuroblastomas / Tumors, Solid1
1TerminatedTreatmentBrain and Central Nervous System Tumors / Liver Cancer / Renal Cancers / Retinoblastoma / Sarcomas1
1TerminatedTreatmentLung Cancer Metastatic / Sarcoma, Osteogenic1
1TerminatedTreatmentLymphoma, B-Cell / Non-Hodgkin's Lymphoma (NHL)1
1TerminatedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1Unknown StatusTreatmentLeukemias / Malignant Lymphomas1
1Unknown StatusTreatmentLymphoma, Hodgkins1
1, 2Active Not RecruitingTreatmentB-Cell Malignancies1
1, 2Active Not RecruitingTreatmentBrain and Central Nervous System Tumors / Cancer, Ovarian / Childhood Germ Cell Tumor / Extragonadal Germ Cell Tumor / Liver Cancer / Malignant Lymphomas / Neuroblastomas / Renal Cancers / Sarcomas / Testicular germ cell tumour / Unspecified Childhood Solid Tumor, Protocol Specific1
1, 2CompletedPreventionCancer, Advanced / Tumors, Solid1
1, 2CompletedTreatmentAdult Nasal Type Extranodal NK/T-Cell Lymphoma / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Contiguous Stage II Mantle Cell Lymphoma / Cutaneous B-Cell Non-Hodgkin Lymphoma / Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Nodal marginal zone B-cell lymphomas / Noncontiguous Stage II Mantle Cell Lymphoma / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Immunoblastic Large Cell Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Recurrent Small Lymphocytic Lymphoma / Splenic Marginal Zone Lymphoma / Stage I Cutaneous T-cell Non-Hodgkin Lymphoma / Stage I Mantle Cell Lymphoma / Stage I Mycosis Fungoides/Sezary Syndrome / Stage II Cutaneous T-cell Non-Hodgkin Lymphoma / Stage II Mycosis Fungoides/Sezary Syndrome / Stage III Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage III Mantle Cell Lymphoma / Stage III Mycosis Fungoides/Sezary Syndrome / Stage IV Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage IV Mantle Cell Lymphoma / Stage IV Mycosis Fungoides/Sezary Syndrome / Waldenstrom's Macroglobulinemia (WM)1
1, 2CompletedTreatmentBladder Cancers / Transitional Cell Cancer of the Renal Pelvis and Ureter1
1, 2CompletedTreatmentBrain and Central Nervous System Tumors / Cancer, Ovarian / Extragonadal Germ Cell Tumor / Teratoma / Testicular germ cell tumour1
1, 2CompletedTreatmentCancer, Ovarian / Extragonadal Germ Cell Tumor / Testicular germ cell tumour1
1, 2CompletedTreatmentCancer, Ovarian / Testicular germ cell tumour1
1, 2CompletedTreatmentChronic Myeloproliferative Disorders / Leukemias / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes / Precancerous/Nonmalignant Condition / Unspecified Adult Solid Tumor, Protocol Specific1
1, 2CompletedTreatmentLung Cancers1
1, 2CompletedTreatmentLymphoma, Hodgkins1
1, 2CompletedTreatmentMalignant Lymphomas2
1, 2CompletedTreatmentRecurrent Adult Diffuse Large Cell Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma1
1, 2CompletedTreatmentSarcomas2
1, 2CompletedTreatmentSoft Tissue Sarcoma (STS)1
1, 2RecruitingTreatmentCD20 Positive / Contiguous Stage II Adult Diffuse Large Cell Lymphoma / Noncontiguous Stage II Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Diffuse Large B-Cell Lymphoma / Refractory Diffuse Large B-Cell Lymphoma / Stage I Adult Diffuse Large Cell Lymphoma / Stage I Diffuse Large B-Cell Lymphoma / Stage II Diffuse Large B-Cell Lymphoma / Stage III Adult Diffuse Large Cell Lymphoma / Stage III Diffuse Large B-Cell Lymphoma / Stage IV Adult Diffuse Large Cell Lymphoma / Stage IV Diffuse Large B-Cell Lymphoma1
1, 2RecruitingTreatmentCD20 Positive / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Recurrent Diffuse Large B-Cell Lymphoma / Recurrent Mediastinal (Thymic) Large B-Cell Cell Lymphoma / Refractory Diffuse Large B-Cell Lymphoma / Refractory Mediastinal (Thymic) Large B-Cell Cell Lymphoma / Transformed Recurrent Non-Hodgkin Lymphoma1
1, 2RecruitingTreatmentDifferentiated Thyroid Cancer (DTC) / Sarcoma, Osteogenic / Solid Malignant Tumors / Tumors1
1, 2RecruitingTreatmentHodgkins Disease (HD)1
1, 2RecruitingTreatmentLung Cancer Small Cell Lung Cancer (SCLC)1
1, 2RecruitingTreatmentMetastatic, Locally Advanced, or Unresectable Soft Tissue Sarcoma1
1, 2RecruitingTreatmentRecurrent Adult Hodgkin's Lymphoma / Refractory Hodgkin Lymphoma1
1, 2TerminatedTreatmentAnaplastic Large Cell Lymphoma / Recurrent Childhood Anaplastic Large Cell Lymphoma1
1, 2Unknown StatusTreatmentBrain and Central Nervous System Tumors / Cancer, Ovarian / Extragonadal Germ Cell Tumor / Testicular germ cell tumour1
1, 2Unknown StatusTreatmentCancer, Breast1
1, 2WithdrawnTreatmentLymphoma, Hodgkins / Malignant Lymphomas / Non-Hodgkin's Lymphoma (NHL)1
1, 2WithdrawnTreatmentMalignant Lymphomas1
2Active Not RecruitingTreatmentAdvanced Stage Diffuse Large B-Cell Non-Hodgkin's Lymphoma / Non-Hodgkin's Lymphoma (NHL)1
2Active Not RecruitingTreatmentChildhood Central Nervous System Germ Cell Tumor / Childhood Central Nervous System Germinoma1
2Active Not RecruitingTreatmentChildhood Extracranial Germ Cell Tumor / Childhood Extragonadal Germ Cell Tumor / Childhood Malignant Ovarian Germ Cell Tumor / Childhood Malignant Testicular Germ Cell Tumor / Ovarian Choriocarcinoma / Ovarian Embryonal Carcinoma / Ovarian Yolk Sac Tumor / Recurrent Childhood Malignant Germ Cell Tumor / Recurrent Malignant Testicular Germ Cell Tumor / Recurrent Ovarian Germ Cell Tumor / Testicular Choriocarcinoma / Testicular Choriocarcinoma and Embryonal Carcinoma / Testicular Choriocarcinoma and Yolk Sac Tumor / Testicular Embryonal Carcinoma / Testicular Embryonal Carcinoma and Yolk Sac Tumor / Testicular Yolk Sac Tumor1
2Active Not RecruitingTreatmentChildhood Germ Cell Tumor / Neoplasms, Brain / Tumors, Central Nervous System1
2Active Not RecruitingTreatmentDesmoplastic Small Round Cell Tumor (DSRCT) / Ewing Sarcoma of Bone or Soft Tissue / Localized Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Metastatic Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor1
2Active Not RecruitingTreatmentLymphoma, Hodgkins1
2Active Not RecruitingTreatmentMalignant Fibrous Histiocytoma (MFH) of Bone / Sarcoma, Osteogenic1
2Active Not RecruitingTreatmentMalignant Lymphomas4
2Active Not RecruitingTreatmentNon-Hodgkin's Lymphoma (NHL)2
2Active Not RecruitingTreatmentSarcomas1
2CompletedPreventionOral Mucositis / Sarcomas1
2CompletedSupportive CareDrug/Agent Toxicity by Tissue/Organ / Leukemias / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Oral Complications / Radiation Toxicity1
2CompletedSupportive CareLeukemias / Malignant Lymphomas / Oral Complications1
2CompletedTreatmentAdult Lymphocyte Depletion Hodgkin Lymphoma / Adult Lymphocyte Predominant Hodgkin Lymphoma / Adult Mixed Cellularity Hodgkin Lymphoma / Adult Nodular Lymphocyte Predominant Hodgkin Lymphoma / Adult Nodular Sclerosis Hodgkin Lymphoma / Childhood Lymphocyte Depletion Hodgkin Lymphoma / Childhood Lymphocyte Predominant Hodgkin Lymphoma / Childhood Mixed Cellularity Hodgkin Lymphoma / Childhood Nodular Lymphocyte Predominant Hodgkin Lymphoma / Childhood Nodular Sclerosis Hodgkin Lymphoma / Recurrent Adult Hodgkin's Lymphoma / Recurrent/Refractory Childhood Hodgkin Lymphoma / Stage I Adult Hodgkin Lymphoma / Stage I Childhood Hodgkin Lymphoma / Stage II Adult Hodgkin Lymphoma / Stage II Childhood Hodgkin Lymphoma / Stage III Adult Hodgkin Lymphoma / Stage III Childhood Hodgkin Lymphoma / Stage IV Adult Hodgkin Lymphoma / Stage IV Childhood Hodgkin Lymphoma1
2CompletedTreatmentAdult Rhabdomyosarcoma / Childhood Alveolar Rhabdomyosarcoma / Childhood Embryonal Rhabdomyosarcoma / Metastatic Childhood Soft Tissue Sarcoma / Stage IV Adult Soft Tissue Sarcoma / Untreated Childhood Rhabdomyosarcoma1
2CompletedTreatmentAlveolar Childhood Rhabdomyosarcoma / Embryonal Childhood Rhabdomyosarcoma / Embryonal-botryoid Childhood Rhabdomyosarcoma / Previously Treated Childhood Rhabdomyosarcoma / Recurrent Childhood Rhabdomyosarcoma1
2CompletedTreatmentBladder Cancers / Brain and Central Nervous System Tumors / Cancer, Ovarian / Carcinoma of Unknown Primary / Extragonadal Germ Cell Tumor / Head and Neck Carcinoma / Lung Cancers / Renal Cancers / Sarcomas / Testicular germ cell tumour / Unspecified Adult Solid Tumor, Protocol Specific1
2CompletedTreatmentBladder Cancers / Transitional Cell Cancer of the Renal Pelvis and Ureter1
2CompletedTreatmentBladder Cancers / Transitional Cell Cancer of the Renal Pelvis and Ureter / Urethral Cancer1
2CompletedTreatmentBladder Cancers / Urethral Cancer1
2CompletedTreatmentBrain and Central Nervous System Tumors / Cancer, Ovarian / Extragonadal Germ Cell Tumor / Teratoma / Testicular germ cell tumour2
2CompletedTreatmentCancer, Breast2
2CompletedTreatmentCancer, Ovarian / Sarcomas1
2CompletedTreatmentCancer, Ovarian / Sarcomas / Small Intestine Cancer1
2CompletedTreatmentEwings Sarcoma / Neuroblastomas / Non-rhabdomyosarcoma Soft Tissue Sarcomas1
2CompletedTreatmentHodgkins Disease (HD)1
2CompletedTreatmentHodgkins Disease (HD) / Non-Hodgkin's Lymphoma (NHL)1
2CompletedTreatmentLeukemias1
2CompletedTreatmentLeukemias / Malignant Lymphomas4
2CompletedTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)2
2CompletedTreatmentMalignant Lymphomas14
2CompletedTreatmentMetastatic Cancers / Sarcomas1
2CompletedTreatmentMetastatic Osteosarcoma1
2CompletedTreatmentNeuroblastomas3
2CompletedTreatmentNeurofibromatosis Type 1 / Sarcomas1
2CompletedTreatmentNeutropenias / Sarcomas1
2CompletedTreatmentNon-Hodgkin's Lymphoma (CD20+)1
2CompletedTreatmentNon-Hodgkin's Lymphoma (NHL)2
2CompletedTreatmentPenile Cancer1
2CompletedTreatmentRenal Cancers / Sarcomas1
2CompletedTreatmentSarcoma, Osteogenic2
2CompletedTreatmentSarcomas7
2CompletedTreatmentSoft Tissue Sarcoma (STS)3
2CompletedTreatmentTesticular Neoplasms1
2CompletedTreatmentTesticular germ cell tumour1
2CompletedTreatmentTransitional Cell Carcinoma1
2CompletedTreatmentUterine Cancers1
2RecruitingSupportive CareSarcomas1
2RecruitingTreatmentBurkitt's Lymphoma / CD20+ Lymphoblastic Lymphoma / Follicular Lymphoma, Grade III / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Non-Hodgkin's Lymphoma (NHL) / Primary Mediastinal B-Cell Lymphoma1
2RecruitingTreatmentCD (Cluster of Differentiation) 30-Positive Neoplastic Cells Present / Recurrent Hodgkin Lymphoma / Refractory Hodgkin Lymphoma1
2RecruitingTreatmentCancer, Ovarian / Childhood Germ Cell Tumor / Teratoma1
2RecruitingTreatmentEffects of Chemotherapy / Non-Small-Cell Lung Carcinoma (NSCLC)1
2RecruitingTreatmentEwing's Sarcoma (ES)1
2RecruitingTreatmentExtranodal NK-T-CELL LYMPHOMA / NK/T Cell Lymphoma1
2RecruitingTreatmentFollicular Lymphoma, Grade 3b / Lymphoma, B-Cell / Lymphoma, Follicular, Grade 3b / Lymphoma, Large B-Cell, Diffuse (DLBCL)1
2RecruitingTreatmentGerm Cell Tumors3
2RecruitingTreatmentLymphocyte-Rich Classical Hodgkin Lymphoma / Recurrent Lymphocyte-Depleted Classical Hodgkin Lymphoma / Recurrent Mixed Cellularity Classical Hodgkin Lymphoma / Recurrent Nodular Sclerosis Classical Hodgkin Lymphoma / Refractory Lymphocyte-Depleted Classical Hodgkin Lymphoma / Refractory Mixed Cellularity Classical Hodgkin Lymphoma / Refractory Nodular Sclerosis Classical Hodgkin Lymphoma1
2RecruitingTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)2
2RecruitingTreatmentLymphoma, Mantle-Cell / Malignant Lymphomas1
2RecruitingTreatmentMalignant Lymphomas1
2RecruitingTreatmentNewly Diagnosed High Risk Neuroblastoma1
2RecruitingTreatmentNon Metastatic Disease / Soft Tissue Sarcoma (STS)1
2RecruitingTreatmentPeripheral T-Cell Lymphoma (PTCL)1
2RecruitingTreatmentRefractory Pediatric AML / Refractory Pediatric Solid Tumors / Relapsed Pediatric AML / Relapsed Pediatric Solid Tumors1
2RecruitingTreatmentRhabdomyosarcomas1
2RecruitingTreatmentSarcoma, Osteogenic1
2RecruitingTreatmentSinonasal Tumors1
2RecruitingTreatmentSoft Tissue Sarcoma (STS)2
2RecruitingTreatmentStage IIB Adult Soft Tissue Sarcoma / Stage III Adult Soft Tissue Sarcoma / Stage IV Adult Soft Tissue Sarcoma1
2RecruitingTreatmentTesticular Cancer1
2RecruitingTreatmentUnresectable Localized Soft Tissue Sarcoma1
2RecruitingTreatmentUnresectable Sinonasal Tumors1
2SuspendedTreatmentAnaplastic Large Cell Lymphoma, ALK-Positive / CD30-Positive Neoplastic Cells Present / Stage II Childhood Anaplastic Large Cell Lymphoma / Stage III Childhood Anaplastic Large Cell Lymphoma / Stage IV Childhood Anaplastic Large Cell Lymphoma1
2TerminatedTreatmentAdult Brain Malignant Hemangiopericytoma / Adult Fibrosarcoma / Adult Leiomyosarcoma / Adult Malignant Meningioma / Adult Rhabdomyosarcoma / Chondrosarcomas1
2TerminatedTreatmentAtypical Burkitt Lymphoma / Burkitt's Lymphoma / Non-Hodgkin's Lymphoma (NHL)1
2TerminatedTreatmentB-cell Childhood Acute Lymphoblastic Leukemia / Childhood Burkitt Lymphoma / Childhood Diffuse Large Cell Lymphoma / Childhood Immunoblastic Large Cell Lymphoma / L3 Childhood Acute Lymphoblastic Leukemia / Recurrent Childhood Acute Lymphoblastic Leukemia / Recurrent Childhood Large Cell Lymphoma / Recurrent Childhood Lymphoblastic Lymphoma / Recurrent Childhood Small Noncleaved Cell Lymphoma1
2TerminatedTreatmentCancer, Breast2
2TerminatedTreatmentCancer, Ovarian / Childhood Germ Cell Tumor / Extragonadal Germ Cell Tumor / Testicular germ cell tumour1
2TerminatedTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL) / Non-Hodgkin's Lymphoma (NHL)1
2TerminatedTreatmentMalignant Neoplasm of Pancreas1
2TerminatedTreatmentRecurrent Adult Soft Tissue Sarcoma / Stage I Adult Soft Tissue Sarcoma / Stage II Adult Soft Tissue Sarcoma / Stage III Adult Soft Tissue Sarcoma1
2TerminatedTreatmentRefractory Nasopharyngeal Carcinoma1
2TerminatedTreatmentSarcomas3
2Unknown StatusTreatmentBrain and Central Nervous System Tumors / Extragonadal Germ Cell Tumor / Testicular germ cell tumour1
2Unknown StatusTreatmentCancer, Breast2
2Unknown StatusTreatmentGerm Cell Tumors1
2Unknown StatusTreatmentLeukemias2
2Unknown StatusTreatmentLung Cancers2
2Unknown StatusTreatmentMalignant Lymphomas2
2Unknown StatusTreatmentMalignant Lymphomas / Small Intestine Cancer1
2Unknown StatusTreatmentNon-Hodgkin's Lymphoma (NHL)1
2Unknown StatusTreatmentRenal Cancers1
2WithdrawnTreatmentRecurrent Adult Soft Tissue Sarcoma / Stage IIB Adult Soft Tissue Sarcoma / Stage IIC Adult Soft Tissue Sarcoma / Stage III Adult Soft Tissue Sarcoma / Stage IVA Adult Soft Tissue Sarcoma1
2, 3CompletedTreatmentAdult B Acute Lymphoblastic Leukemia With t(9;22)(q34;q11.2); BCR-ABL1 / Childhood B Acute Lymphoblastic Leukemia With t(9;22)(q34;q11.2); BCR-ABL1 / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
2, 3RecruitingTreatmentAdult Fibrosarcoma / Alveolar Soft Part Sarcoma (ASPS) / Angiomatoid Fibrous Histiocytoma / Atypical Fibroxanthoma / Chondrosarcoma, Mesenchymal / Clear Cell Sarcoma of Soft Tissue / Epithelioid Malignant Peripheral Nerve Sheath Tumor / Epithelioid Sarcoma / Extraskeletal Myxoid Chondrosarcoma / Extraskeletal osteosarcomas / Fibrohistiocytic Neoplasm / Glomus Tumor of the Skin / Inflammatory Myofibroblastic Tumors / Intimal Sarcoma / Leiomyosarcomas / Liposarcoma / Low Grade Fibromyxoid Sarcoma / Low Grade Myofibroblastic Sarcoma / Malignant Cutaneous Granular Cell Tumor / Malignant Peripheral Nerve Sheath Tumour (MPNST) / Malignant Triton Tumor / Myxofibrosarcoma / Myxoid Chondrosarcoma / Myxoinflammatory Fibroblastic Sarcoma / Nerve Sheath Neoplasm / PEComa / Pericytic Neoplasm / Plexiform Fibrohistiocytic Tumor / Sclerosing Epithelioid Fibrosarcoma / Stage IB Soft Tissue Sarcoma / Stage IIB Soft Tissue Sarcoma / Stage III Soft Tissue Sarcoma / Stage IV Soft Tissue Sarcoma / Synovial Sarcoma / Undifferentiated (Embryonal) Sarcoma / Undifferentiated High Grade Pleomorphic Sarcoma of Bone1
2, 3RecruitingTreatmentLymphoma, Lymphoblastic1
2, 3RecruitingTreatmentSarcoma, Osteogenic1
2, 3Unknown StatusTreatmentCancer, Ovarian / Fallopian Tube Cancer / Primary Peritoneal Cavity Cancer1
2, 3Unknown StatusTreatmentSarcoma, Osteogenic1
3Active Not RecruitingTreatmentAdult Supratentorial Primitive Neuroectodermal Tumor (PNET) / Childhood Supratentorial Primitive Neuroectodermal Tumor / Ewing Sarcoma of Bone / Extraosseous Ewing Sarcoma / Extraosseous Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Localized Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Peripheral Primitive Neuroectodermal Tumor of the Kidney / Untreated Childhood Supratentorial Primitive Neuroectodermal Tumor1
3Active Not RecruitingTreatmentChildhood Favorable Prognosis Hodgkin Lymphoma / Childhood Lymphocyte Depletion Hodgkin Lymphoma / Childhood Mixed Cellularity Hodgkin Lymphoma / Childhood Nodular Sclerosis Hodgkin Lymphoma / Stage I Childhood Hodgkin Lymphoma / Stage II Childhood Hodgkin Lymphoma1
3Active Not RecruitingTreatmentChildhood Nodular Lymphocyte Predominant Hodgkin Lymphoma / Stage III Childhood Hodgkin Lymphoma / Stage IV Childhood Hodgkin Lymphoma1
3Active Not RecruitingTreatmentLeukemias1
3Active Not RecruitingTreatmentLocalized Osteosarcoma / Metastatic Osteosarcoma1
3Active Not RecruitingTreatmentSarcomas1
3CompletedTreatmentBrain and Central Nervous System Tumors1
3CompletedTreatmentCancer, Ovarian / Endometrial Cancers / Metastatic Cancers / Pheochromocytomas / Renal Cancers / Sarcomas1
3CompletedTreatmentCancer, Ovarian / Endometrial Cancers / Pheochromocytomas / Renal Cancers / Sarcomas1
3CompletedTreatmentCardiac Toxicity / Sarcomas1
3CompletedTreatmentCervical Cancers1
3CompletedTreatmentChildhood Acute Lymphoblastic Leukemia in Remission / Recurrent Childhood Acute Lymphoblastic Leukemia1
3CompletedTreatmentChildhood Malignant Fibrous Histiocytoma of Bone / Sarcomas1
3CompletedTreatmentLeukemias3
3CompletedTreatmentLeukemias / Malignant Lymphomas1
3CompletedTreatmentLocalised High Grade Osteosarcoma of the Limbs / Sarcoma, Osteogenic1
3CompletedTreatmentLung Cancers2
3CompletedTreatmentLymphoma, Large-Cell, Diffuse1
3CompletedTreatmentMalignant Lymphomas3
3CompletedTreatmentMediastinal Cancer / Metastatic Cancers / Testicular germ cell tumour1
3CompletedTreatmentMetastatic, Locally Advanced or Unresectable Soft Tissue Sarcoma1
3CompletedTreatmentNeuroblastomas2
3CompletedTreatmentNon-Small-Cell Lung Carcinoma (NSCLC)2
3CompletedTreatmentSarcomas8
3CompletedTreatmentSmall Cell Lung Carcinoma, Extensive Disease1
3Not Yet RecruitingTreatmentB Acute Lymphoblastic Leukemia With t(9;22)(q34.1;q11.2); BCR-ABL1 / BCR-ABL1 Fusion Protein Expression / Minimal Residual Disease / Philadelphia Chromosome Positive / T Acute Lymphoblastic Leukemia / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
3Not Yet RecruitingTreatmentCervical Cancers1
3Not Yet RecruitingTreatmentMature B-cell Non-Hodgkin Lymphoma1
3Not Yet RecruitingTreatmentSquamous Cell Carcinoma of the Penis, Usual Type1
3RecruitingTreatmentAdult T Acute Lymphoblastic Leukemia / Childhood T Acute Lymphoblastic Leukemia / Stage II Childhood Lymphoblastic Lymphoma / Stage II Contiguous Adult Lymphoblastic Lymphoma / Stage II Non-Contiguous Adult Lymphoblastic Lymphoma / Stage III Adult Lymphoblastic Lymphoma / Stage III Childhood Lymphoblastic Lymphoma / Stage IV Adult Lymphoblastic Lymphoma / Stage IV Childhood Lymphoblastic Lymphoma / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
3RecruitingTreatmentChildhood Teratoma / Choriocarcinoma / Extragonadal Seminoma / Germ Cell Tumors / Germinoma / Malignant Germ Cell Neoplasm / Mixed Germ Cell Tumor / Non-seminomatous Germ Cell Tumors / Seminoma / Teratoma / Yolk Sac Tumor1
3RecruitingTreatmentEwing's Sarcoma (ES)1
3RecruitingTreatmentMetastatic Ewing Sarcoma / Metastatic Malignant Neoplasm in the Bone / Metastatic Malignant Neoplasm in the Bone Marrow / Metastatic Malignant Neoplasm in the Lung / Metastatic Peripheral Primitive Neuroectodermal Tumor of Bone / Peripheral Primitive Neuroectodermal Tumor of Soft Tissues1
3RecruitingTreatmentNon-Hodgkin's Lymphoma (NHL)1
3TerminatedTreatmentExtragonadal Germ Cell Tumor / Testicular germ cell tumour1
3TerminatedTreatmentMalignant Lymphomas2
3TerminatedTreatmentSarcomas1
3Unknown StatusTreatmentAdult Alveolar Soft-part Sarcoma / Adult Angiosarcoma / Adult Epithelioid Sarcoma / Adult Extraskeletal Chondrosarcoma / Adult Extraskeletal Osteosarcoma / Adult Fibrosarcoma / Adult Leiomyosarcoma / Adult Liposarcoma / Adult Malignant Fibrous Histiocytoma / Adult Malignant Hemangiopericytoma / Adult Malignant Mesenchymoma / Adult Neurofibrosarcoma / Adult Synovial Sarcoma / Childhood Alveolar Soft-part Sarcoma / Childhood Angiosarcoma / Childhood Epithelioid Sarcoma / Childhood Fibrosarcoma / Childhood Leiomyosarcoma / Childhood Liposarcoma / Childhood Malignant Mesenchymoma / Childhood Neurofibrosarcoma / Childhood Synovial Sarcoma / Dermatofibrosarcoma Protuberans / Metastatic Childhood Soft Tissue Sarcoma / Nonmetastatic Childhood Soft Tissue Sarcoma / Stage I Adult Soft Tissue Sarcoma / Stage II Adult Soft Tissue Sarcoma / Stage III Adult Soft Tissue Sarcoma / Stage IV Adult Soft Tissue Sarcoma1
3Unknown StatusTreatmentBrain and Central Nervous System Tumors1
3Unknown StatusTreatmentCancer, Ovarian / Childhood Germ Cell Tumor / Extragonadal Germ Cell Tumor1
3Unknown StatusTreatmentChildhood Malignant Fibrous Histiocytoma of Bone / Sarcomas1
3Unknown StatusTreatmentExtragonadal Germ Cell Tumor / Teratoma / Testicular germ cell tumour1
3Unknown StatusTreatmentExtragonadal Germ Cell Tumor / Testicular germ cell tumour1
3Unknown StatusTreatmentLeukemias1
3Unknown StatusTreatmentLung Cancers3
3Unknown StatusTreatmentMalignant Lymphomas1
3Unknown StatusTreatmentNeuroblastomas1
3Unknown StatusTreatmentOvarian Carcinosarcoma / Recurrent Fallopian Tube Carcinoma / Recurrent Ovarian Carcinoma / Recurrent Primary Peritoneal Carcinoma / Recurrent Uterine Corpus Sarcoma / Stage I Ovarian Cancer / Stage IA Fallopian Tube Cancer / Stage IA Ovarian Cancer / Stage IA Uterine Sarcoma / Stage IB Fallopian Tube Cancer / Stage IB Ovarian Cancer / Stage IB Uterine Sarcoma / Stage IC Fallopian Tube Cancer / Stage IC Ovarian Cancer / Stage IC Uterine Sarcoma / Stage II Ovarian Cancer / Stage IIA Fallopian Tube Cancer / Stage IIA Ovarian Cancer / Stage IIA Uterine Sarcoma / Stage IIB Fallopian Tube Cancer / Stage IIB Ovarian Cancer / Stage IIB Uterine Sarcoma / Stage IIC Fallopian Tube Cancer / Stage IIC Ovarian Cancer / Stage IIIA Fallopian Tube Cancer / Stage IIIA Ovarian Cancer / Stage IIIA Primary Peritoneal Cancer / Stage IIIA Uterine Sarcoma / Stage IIIB Fallopian Tube Cancer / Stage IIIB Ovarian Cancer / Stage IIIB Primary Peritoneal Cancer / Stage IIIB Uterine Sarcoma / Stage IIIC Fallopian Tube Cancer / Stage IIIC Ovarian Cancer / Stage IIIC Primary Peritoneal Cancer / Stage IIIC Uterine Sarcoma / Stage IV Fallopian Tube Cancer / Stage IV Ovarian Cancer / Stage IV Primary Peritoneal Cancer / Stage IVA Uterine Sarcoma / Stage IVB Uterine Sarcoma / Uterine Carcinosarcoma1
3Unknown StatusTreatmentSarcomas3
3Unknown StatusTreatmentUterine Sarcoma1
3WithdrawnTreatmentSarcomas1
4CompletedTreatmentAdult Acute Lymphocytic Leukemia3
4CompletedTreatmentBurkitt's Lymphoma / Large Cell Anaplastic Lymphoma / Lymphoma, Lymphoblastic / Mediastinal Neoplasms1
4RecruitingTreatmentIntracranial Germ Cell Tumors1
4RecruitingTreatmentPeripheral T Cell Lymphoma (PTCL)1
4Unknown StatusTreatmentAcute Lymphoblastic Leukaemias (ALL) / Non-Hodgkin's Lymphoma (NHL)1
Not AvailableActive Not RecruitingDiagnosticSarcomas1
Not AvailableActive Not RecruitingTreatmentLeukemias1
Not AvailableActive Not RecruitingTreatmentMalignant Lymphomas1
Not AvailableActive Not RecruitingTreatmentStage IIA Adult Soft Tissue Sarcoma / Stage III Adult Soft Tissue Sarcoma / Stage IV Adult Soft Tissue Sarcoma1
Not AvailableCompletedNot AvailableLung Cancer Small Cell Lung Cancer (SCLC)1
Not AvailableCompletedNot AvailableRecurrent Nasopharynx Carcinoma1
Not AvailableCompletedNot AvailableSarcoma, Osteogenic / Spindle Cell Sarcoma of Bone1
Not AvailableCompletedPreventionSarcomas1
Not AvailableCompletedSupportive CareNausea / Sarcomas / Vomiting1
Not AvailableCompletedTreatmentAdverse Effects of Medical Drugs / Effects of Chemotherapy / Prophylaxis of acute chemotherapy induced nausea and vomiting / Sarcomas1
Not AvailableCompletedTreatmentCancer, Ovarian / Sarcomas1
Not AvailableCompletedTreatmentEwing Sarcoma of Bone / Localized Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor1
Not AvailableCompletedTreatmentLymphoma, Large Cell / Non-Hodgkin's Lymphoma (NHL)1
Not AvailableCompletedTreatmentSarcomas1
Not AvailableRecruitingTreatmentAtypical Teratoid/Rhabdoid Tumor (AT/RT) / CNS Tumors / Ewing's Family Tumors / Germ Cell Tumors / Hepatoblastomas / Medulloblastomas / Primary Malignant Brain Neoplasms / Renal Tumors / Retinoblastoma / Rhabdomyosarcomas / Soft Tissue Sarcoma (STS) / Supra-tentorial Primative Neuro-Ectodermal Tumor (PNET)1
Not AvailableRecruitingTreatmentNeuroblastomas1
Not AvailableRecruitingTreatmentPleuropulmonary Blastoma1
Not AvailableSuspendedTreatmentChemotherapeutic Agent Toxicity / Renal Toxicity / Unspecified Adult Solid Tumor, Protocol Specific1
Not AvailableTerminatedTreatmentSarcoma, Osteogenic1
Not AvailableUnknown StatusTreatmentEwing's Sarcoma (ES)1
Not AvailableUnknown StatusTreatmentMalignant Lymphomas1
Not AvailableWithdrawnTreatmentAdult Supratentorial Primitive Neuroectodermal Tumor (PNET) / Ewing Sarcoma of Bone / Extraosseous Ewing Sarcoma / Metastatic Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Recurrent Childhood Supratentorial Primitive Neuroectodermal Tumor / Recurrent Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Untreated Childhood Supratentorial Primitive Neuroectodermal Tumor1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionIntravenous1 g/20mL
Injection, powder, for solutionIntravenous3 g/60mL
Powder, for solutionIntravenous1 g
Powder, for solutionIntravenous3 g
Powder, for solutionIntravenous2 g
Injection, powder, lyophilized, for solutionIntravenous1 g/1
Injection, solutionIntravenous1 g/20mL
Injection, solutionIntravenous3 g/60mL
Injection, solutionIntravenous50 mg/mL
Prices
Unit descriptionCostUnit
Ifex-mesnex kit2709.98USD kit
Ifosfamide-mesna kit787.5USD kit
Ifex 3 gm vial489.13USD vial
Ifex 1 gm vial163.04USD vial
Ifosfamide 3 gm vial114.0USD vial
Ifosfamide 1 gm vial56.4USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5252341 No1994-07-162011-07-16Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)39-41 °CU.S. Patent 3,732,340.
water solubility3780 mg/LNot Available
logP0.86HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility15.0 mg/mLALOGPS
logP0.57ALOGPS
logP0.097ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)13.24ChemAxon
pKa (Strongest Basic)0.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.48 m3·mol-1ChemAxon
Polarizability23.94 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9807
Blood Brain Barrier+0.9736
Caco-2 permeable-0.5411
P-glycoprotein substrateNon-substrate0.7098
P-glycoprotein inhibitor INon-inhibitor0.6204
P-glycoprotein inhibitor IINon-inhibitor0.9617
Renal organic cation transporterNon-inhibitor0.8135
CYP450 2C9 substrateNon-substrate0.7674
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5922
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8835
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9723
Ames testAMES toxic0.9108
CarcinogenicityNon-carcinogens0.8903
BiodegradationNot ready biodegradable0.7807
Rat acute toxicity3.2294 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8985
hERG inhibition (predictor II)Non-inhibitor0.8224
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0490000000-17ba12fd0e00df2723dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-d4e1a660175509162e8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-c26cb9c6b0b1cafbc7c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gx3-6960000000-e4f4eadda4e355e7dd84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f6x-8900000000-10d5b2623785719eb1e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9500000000-d06de43b506b64b21f31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9300000000-698d7a6ed4f1837ad721View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-084cc16ffb95bd0ef960View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-1ae1b6f01a6e1a37e34cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gx3-6960000000-ad40c4b969e8d0286677View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f6x-8900000000-137610f53c637d8d5b79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9500000000-6b78178980477a0f7c08View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9200000000-e6f6b95f30fc4c9fde8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0490000000-661cabcd304902a3d4b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0290000000-4c400c6848932e5bc304View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-1390000000-cb6bb34e3efac3f15b24View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-3910000000-2729bcf5701a78198ad5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot Available
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
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as isofamides. These are oxazaphospholanes containing the isofamide skeleton. Isofamide is a heterocyclic compound made up of a 1,3,2-oxazaphospholane, where the phosphorus atom is part of a phosphodiamide group, and the oxazaphospholane is substituted by two haloalkyl chains.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassOxazaphosphinanes
Direct ParentIsofamides
Alternative ParentsPhosphoric monoester diamides / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Alkyl chlorides
SubstituentsIsofamide / Phosphoric monoester diamide / Organic phosphoric acid derivative / Organic phosphoric acid amide / Azacycle / Oxacycle / Alkyl chloride / Hydrocarbon derivative / Organic oxide / Organopnictogen compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptorsifosfamides (CHEBI:5864 )

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
other/unknown
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. Furlanut M, Franceschi L: Pharmacology of ifosfamide. Oncology. 2003;65 Suppl 2:2-6. [PubMed:14586139 ]
  2. Hartley JM, Spanswick VJ, Gander M, Giacomini G, Whelan J, Souhami RL, Hartley JA: Measurement of DNA cross-linking in patients on ifosfamide therapy using the single cell gel electrophoresis (comet) assay. Clin Cancer Res. 1999 Mar;5(3):507-12. [PubMed:10100700 ]
  3. Willits I, Price L, Parry A, Tilby MJ, Ford D, Cholerton S, Pearson AD, Boddy AV: Pharmacokinetics and metabolism of ifosfamide in relation to DNA damage assessed by the COMET assay in children with cancer. Br J Cancer. 2005 May 9;92(9):1626-35. [PubMed:15827549 ]
  4. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and is...
Gene Name:
NR1I2
Uniprot ID:
O75469
Uniprot Name:
Nuclear receptor subfamily 1 group I member 2
Molecular Weight:
49761.245 Da
References
  1. Harmsen S, Meijerman I, Beijnen JH, Schellens JH: Nuclear receptor mediated induction of cytochrome P450 3A4 by anticancer drugs: a key role for the pregnane X receptor. Cancer Chemother Pharmacol. 2009 Jun;64(1):35-43. doi: 10.1007/s00280-008-0842-3. Epub 2008 Oct 7. [PubMed:18839173 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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
Uniprot Name:
Cytochrome P450 2B6
Molecular Weight:
56277.81 Da
References
  1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. Chen CS, Jounaidi Y, Waxman DJ: Enantioselective metabolism and cytotoxicity of R-ifosfamide and S-ifosfamide by tumor cell-expressed cytochromes P450. Drug Metab Dispos. 2005 Sep;33(9):1261-7. Epub 2005 May 26. [PubMed:15919850 ]
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  4. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
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
Uniprot Name:
Cytochrome P450 3A4
Molecular Weight:
57342.67 Da
References
  1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. Chen CS, Jounaidi Y, Waxman DJ: Enantioselective metabolism and cytotoxicity of R-ifosfamide and S-ifosfamide by tumor cell-expressed cytochromes P450. Drug Metab Dispos. 2005 Sep;33(9):1261-7. Epub 2005 May 26. [PubMed:15919850 ]
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  4. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
  5. Preiss R, Schmidt R, Baumann F, Hanschmann H, Hauss J, Geissler F, Pahlig H, Ratzewiss B: Measurement of 4-hydroxylation of ifosfamide in human liver microsomes using the estimation of free and protein-bound acrolein and codetermination of keto- and carboxyifosfamide. J Cancer Res Clin Oncol. 2002 Jul;128(7):385-92. Epub 2002 Jun 11. [PubMed:12136253 ]
  6. 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
Uniprot Name:
Cytochrome P450 3A5
Molecular Weight:
57108.065 Da
References
  1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  3. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
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
Uniprot Name:
Cytochrome P450 2C19
Molecular Weight:
55930.545 Da
References
  1. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
  2. 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
substrateinducer
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
Uniprot Name:
Cytochrome P450 2C9
Molecular Weight:
55627.365 Da
References
  1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  3. 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
substrateinducer
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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Uniprot Name:
Cytochrome P450 2C8
Molecular Weight:
55824.275 Da
References
  1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. 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:
Steroid hydroxylase activity
Specific Function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Uniprot Name:
Cytochrome P450 2A6
Molecular Weight:
56501.005 Da
References
  1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
  3. 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:
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.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Uniprot Name:
Cytochrome P450 2C18
Molecular Weight:
55710.075 Da
References
  1. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
  2. 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:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Uniprot Name:
Prostaglandin G/H synthase 1
Molecular Weight:
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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:
CYP3A7
Uniprot ID:
P24462
Uniprot Name:
Cytochrome P450 3A7
Molecular Weight:
57525.03 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 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:57