Ifosfamide

Ifosfamide
	(R)-(+)- and (S)-(−)-ifosfamide (top),; (S)-(−)-ifosfamide (bottom)
Clinical data
Pronunciation	/aɪˈfɒsfəmaɪd/
Trade names	Ifex, others
Other names	IFO, 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
AHFS/Drugs.com	Monograph
MedlinePlus	a695023
Pregnancy; category	AU: D;
Routes of; administration	Intravenous
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	Liver
Elimination half-life	60–80% in 72 hours
Excretion	Kidney
Identifiers
	IUPAC name N,3-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amide 2-oxide;
CAS Number	3778-73-2 ;
PubChem CID	3690;
IUPHAR/BPS	7201;
DrugBank	DB01181 ;
ChemSpider	3562 ;
UNII	UM20QQM95Y;
KEGG	D00343 ;
ChEBI	CHEBI:5864 ;
ChEMBL	ChEMBL1024 ;
CompTox Dashboard (EPA)	DTXSID7020760 ;
ECHA InfoCard	100.021.126
Chemical and physical data
Formula	C7H15Cl2N2O2P
Molar mass	261.08 g·mol−1
3D model (JSmol)	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) ; Key:HOMGKSMUEGBAAB-UHFFFAOYSA-N ;
	(verify)

Ifosfamide, sold under the brand name Ifex among others, is a chemotherapy medication used to treat a number of types of cancer.^[2] This includes testicular cancer, soft tissue sarcoma, osteosarcoma, bladder cancer, small cell lung cancer, cervical cancer, and ovarian cancer.^[2] It is administered by injection into a vein.^[2]

Common side effects include hair loss, vomiting, blood in the urine, infections, and kidney problems.^[2] Other severe side effects include bone marrow suppression and decreased level of consciousness.^[2] Use during pregnancy will likely result in harm to the baby.^[2] Ifosfamide is in the alkylating agent and nitrogen mustard family of medications.^[2]^[3] It works by disrupting the duplication of DNA and the creation of RNA.^[2]

Ifosfamide was approved for medical use in the United States in 1987.^[2] It is on the World Health Organization's List of Essential Medicines.^[4]

^ "Ifex Product information". Health Canada. 9 April 2001. Retrieved 17 February 2025.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Ifosfamide". The American Society of Health-System Pharmacists. Archived from the original on 7 May 2017. Retrieved 8 December 2016.
^ Dowd FJ, Johnson B, Mariotti A (2016). Pharmacology and Therapeutics for Dentistry (7th ed.). Elsevier Health Sciences. p. 533. ISBN 9780323445955. Archived from the original on 11 September 2017.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.