Ifosfamide

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
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 Edit this at Wikidata
Chemical and physical data
FormulaC7H15Cl2N2O2P
Molar mass261.08 g·mol−1
3D model (JSmol)
  • 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) checkY
  • Key:HOMGKSMUEGBAAB-UHFFFAOYSA-N checkY
  (verify)

Ifosfamide (IFO), 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]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ 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.
  3. ^ 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 2017-09-11.
  4. ^ 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.