Ifosfamide

Ifosfamide

(R)-(+)- and (S)-(−)-ifosfamide (top), (S)-(−)-ifosfamide (bottom)
Clinical data
Pronunciation	/aɪˈfɒsfəˌmaɪd/
Trade names	Ifex, others
AHFS/Drugs.com	Monograph
MedlinePlus	a695023
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	intravenously
ATC code	L01AA06 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only NZ: Prescription medicine UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	100%
Metabolism	Hepatic
Biological half-life	60-80% in 72 hours
Excretion	Renal
Identifiers
IUPAC name N,3-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amide 2-oxide
Synonyms	3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
CAS Number	3778-73-2 Y
PubChem CID	3690
IUPHAR/BPS	7201
DrugBank	DB01181 Y
ChemSpider	3562 Y
UNII	UM20QQM95Y
KEGG	D00343 Y
ChEBI	CHEBI:5864 Y
ChEMBL	CHEMBL1024 Y
ECHA InfoCard	100.021.126
Chemical and physical data
Formula	C7H15Cl2N2O2P
Molar mass	261.1 g mol−1
3D model (Jmol)	Interactive image
SMILES O=P1(OCCCN1CCCl)NCCCl
InChI 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

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 given 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.

Ifosfamide was approved for medical use in the United States in 1987. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 7.35 to 70.70 USD per 2 gm vial. In the UK this dose costs the NHS about 130.04 pounds.