Structure via PubChem · Public domain (PubChem)
ifosfamide
Sign in to saveAlso known as Holoxan®, Ifex®, MJF-9325, Z-4942, Iphosphamide, Isofosfamide, isosfamide, 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
Ifosfamide, 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.
Chemical data
- Formula
- C7H15Cl2N2O2P
- Molecular weight
- 261.08 g/mol
- IUPAC name
- N,3-bis(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine
- SMILES
- C1CN(P(=O)(OC1)NCCCl)CCCl
- InChIKey
- HOMGKSMUEGBAAB-UHFFFAOYSA-N
- XLogP
- 0.9
- Polar surface area
- 41.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1988
- Admin. routes
- parenteral
- Indications
- osteosarcoma, neoplasm, sarcoma, neoplasm of mature B-cells
via ChEMBL · EBI
Research
8,347 papers- Ifosfamide-induced nephrotoxicity in oncological patients.Expert review of anticancer therapy · 2024
- Ifosfamide pharmacokinetics.Investigational new drugs · 1991
- Ifosfamide.Journal of the National Cancer Institute · 1988
- Ifosfamide encephalopathy.Clinical oncology (Royal College of Radiologists (Great Britain)) · 2007
- Ifosfamide clinical pharmacokinetics.Clinical pharmacokinetics · 1994
via PubMed
Wikidata facts
- Subclass of
- heterocyclic compound
- Has part
- carbon
- Mass
- 260.02971862600003
- Has use
- medication
Show 8 more facts
- chemical formula
- C₇H₁₅Cl₂N₂O₂P
- medical condition treated
- Ewing sarcoma
- World Health Organisation international non-proprietary name
- ifosfamide
- canonical SMILES
- C1CN(P(=O)(OC1)NCCCl)CCCl
- Commons category
- Ifosfamide
- legal status (medicine)
- boxed warning
- isomeric SMILES
- OCC1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
- found in taxon
- Caenorhabditis elegans
Sources (8)
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Medical uses
- Administration
- Mechanism of action
- Side effects
- References
Ifosfamide, 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.
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.
Excerpted from Wikipedia’s “ifosfamide” article, available under the CC BY-SA 4.0 licence.