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QuickView for Ifosfamide (compound)


PubChem
Name: Ifosfamide
PubChem Compound ID: 10659322
Description: Positional isomer of CYCLOPHOSPHAMIDE which is active as an alkylating agent and an immunosuppressive agent.
Molecular formula: C7H15Cl2N2O2P
Molecular weight: 265.11 g/mol
DrugBank
Identification
Name: Ifosfamide
Name (isomeric): DB01181
Drug Type: small molecule
Description: Positional isomer of CYCLOPHOSPHAMIDE which is active as an alkylating agent and an immunosuppressive agent.
Synonyms:
Asta Z 4942; Isophosphamide; Ifosfamide Sterile; Isofosfamide; I-Phosphamide; Ifsofamide; Iphosphamide; Ifosfamid; Ifosphamide; Iphosphamid
Brand: IFEX, Ifosfamide/Mesna Kit, Mitoxana, Isoendoxan, Cyfos, Holoxan 1000, Naxamide, Ifex/Mesnex Kit
Category: Antineoplastic Agents, Antineoplastic Agents, Alkylating, Immunosuppressive Agents
CAS number: 3778-73-2
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.
Pharmacology:
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 meta...
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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 molec...
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Protein binding: Minimal
Biotransformation: Primarily hepatic
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
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
Interactions
Drug interaction:
VoriconazoleVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of ifosfamide by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of ifosfamide if voriconazole is initiated, discontinued or dose changed.
TrastuzumabTrastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
TiclopidineTiclopidine may decrease the metabolism and clearance of Ifosfamide. Consider alternate therapy or monitor for adverse/toxic effects of Ifosfamide if Ticlopidine is initiated, discontinued or dose changed.
TelithromycinTelithromycin may reduce clearance of Ifosfamide. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Ifosfamide if Telithromycin is initiated, discontinued or dose changed.
TranylcypromineTranylcypromine, a strong CYP2A6 inhibitor, may decrease the metabolism and clearance of Ifosmadine.
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