Ifosfamide

SKU: orb1309923

Description

Ifosfamide is a nitrogen mustard prodrug analog of cyclophosphamide, activated by liver enzymes to alkylate DNA and form crosslinks, inhibiting strand separation and replication. It is widely used in cancer research, including in vitro cytotoxicity assays and in vivo xenograft studies for various solid tumors and lymphomas.

Research Area

Cell Biology, Molecular Biology, Pharmacology & Drug Discovery

Key Properties

• CAS Number: 3778-73-2
• MW: 261.09
• Purity: ≥95% (May vary between batches)
• Formula: C₇H₁₅Cl₂N₂O₂P
• SMILES: ClCCNP1(=O)OCCCN1CCCl
• Target: DNA/RNA Synthesis,DNA Alkylator/Crosslinker
• Solubility: Ethanol:49 mg/mL (187.67 mM);DMSO:250 mg/mL (957.52 mM);H2O:48 mg/mL (183.84 mM);10% DMSO+40% PEG300+5% Tween 80+45% Saline:2 mg/mL (7.66 mM)

Bioactivity

• In Vivo:
  In the liver, Ifosfamide it is a prodrug converted to active alkylated compounds by cytochrome P450 mixed function oxidase. Ifosfamide has shown promising antitumor effects in pediatric solid tumors, ovarian cancer, small cell lung cancer, non-Hodgkin's and Hodgkin's lymphomas.Ifosfamide (50 mM) increases the levels of CYP2C8/9, CYP3A4 proteins in hepatocytes, which in turn elevates the rate of 4-hydroxylation of the hepatocytes themselves. In hepatocytes with higher CYP3A4 expression than CYP3A5, Ifosfamide induced only CYP3A4 expression.Ifosfamide was highly cytotoxic to MCF-7 cells stably transfected with CYP2B1 (which could be significantly reduced by the CYP2B1 inhibitor, metipraminexone), but did not affect the expression of β-galactosidase and the pro-tumor cells of MCF- 7 cells. In the prevention of tumor recurrence, the combination of Ifosfamide and zoledronic acid was more effective than the drug alone in increasing bone formation and improving tissue repair.
• In Vitro:
  Ifosfamide induced bladder edema, which peaked 12 hours after Ifosfamide injection. Microscopic analysis showed vascular congestion, edema, hemorrhage, fibrin deposition, neutrophil infiltration and epithelial denudation. Inducible nitric oxide synthase immunoreactivity was strongly reactive in the cytoplasm of bladder epithelial cells, and diffuse necrosis was seen. Intraperitoneal administration of 100 mg/kg, 200 mg/kg and 400 mg/kg Ifosfamide to mice induced a dose-dependent increase in bladder wet weight and Evans blue extravasation. Pretreatment with mesna reduced the increase in bladder edema, whereas treatment with l - ng -nitroarginine methyl ester, antisera TNF-alpha or IL-1beta, thalidomide, or pentoxifylline inhibited bladder edema and microscopic changes. Antiserum treatment also inhibited the expression of inducible nitric oxide synthase within the uroepithelium. Nitric oxide produced by inducible nitric oxide synthase was involved in uroepithelial cell injury and in the inflammatory response leading to hemorrhagic cystitis after ifosfamide administration in mice.

Storage & Handling

• Storage: -20°C
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Crosslinker, DNA/RNA Synthesis, DNA Synthesis, DNASynthesis, DNAAlkylator, DNA Alkylator, DNA Alkylator/Crosslinker, Inhibitor, Ifosfamide, NSC109724, NSC-109724, NSC 109724, inhibit, Isophosphamide, RNASynthesis, RNA Synthesis

Compound Identifiers

PubChem CID

3690