Ifosfamide

Ifosfamide (IFO), sold under the brand name Ifex among others, is a chemotherapy medication used to treat a number of types of cancer. This includes testicular cancer, soft tissue sarcoma, osteosarcoma, bladder cancer, small cell lung cancer, cervical cancer, and ovarian cancer. It is administered by injection into a vein.

Ifosfamide
(R)-(+)- and (S)-(−)-ifosfamide (top),
(S)-(−)-ifosfamide (bottom)
Clinical data
Pronunciation/aɪˈfɒsfəmaɪd/
Trade namesIfex, others
Other names3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
AHFS/Drugs.comMonograph
MedlinePlusa695023
Pregnancy
category
  • AU: D
Routes of
administration		intravenously
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • NZ: Prescription medicine
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
Pharmacokinetic data
Bioavailability100%
MetabolismHepatic
Elimination half-life60–80% in 72 hours
ExcretionRenal
Identifiers
  • N,3-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amide 2-oxide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.021.126
Chemical and physical data
FormulaC7H15Cl2N2O2P
Molar mass261.08 g·mol−1
3D model (JSmol)
SMILES
  • O=P1(OCCCN1CCCl)NCCCl
  • InChI=1S/C7H15Cl2N2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12) Y
  • Key:HOMGKSMUEGBAAB-UHFFFAOYSA-N Y
  (verify)

Common side effects include hair loss, vomiting, blood in the urine, infections, and kidney problems. Other severe side effects include bone marrow suppression and decreased level of consciousness. Use during pregnancy will likely result in harm to the baby. Ifosfamide is in the alkylating agent and nitrogen mustard family of medications. It works by disrupting the duplication of DNA and the creation of RNA.

Ifosfamide was approved for medical use in the United States in 1987. It is on the World Health Organization's List of Essential Medicines.

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