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Ifosfamide

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Ifosfamide
350px
(R)-ifosfamide (S)-ifosfamide
Systematic (IUPAC) name
N-3-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amide-2-oxide
Clinical data
Trade names Ifex
AHFS/Drugs.com monograph
MedlinePlus a695023
  • AU: D
  • US: D (Evidence of risk)
intravenously
Pharmacokinetic data
Bioavailability 100%
Metabolism Hepatic
Half-life 60-80% in 72 hours
Excretion Renal
Identifiers
3778-73-2 7pxY
L01AA06
PubChem CID 3690
DrugBank DB01181 7pxY
ChemSpider 3562 7pxY
UNII UM20QQM95Y 7pxY
KEGG D00343 7pxY
ChEBI CHEBI:5864 7pxY
ChEMBL CHEMBL1024 7pxY
Synonyms 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
Chemical data
Formula C7H15Cl2N2O2P
261.1 g mol−1
 14pxY (what is this?)  (verify)

Ifosfamide (pronunciation: /ˈfɒsfəˌmd/ also marketed as Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer.[1] It is sometimes abbreviated as "IFO".[2]

Uses

It is given as a treatment for a variety of cancers, including:

Administration

It is a white powder which, when prepared for use in chemotherapy, becomes a clear, colorless fluid. The delivery is intravenous.

Ifosfamide is often used in conjunction with mesna to avoid internal bleeding in the patient, in particular hemorrhagic cystitis.

Ifosfamide is given quickly, and in some cases can be given as quickly as an hour.

Toxicity

Hemorrhagic cystitis is rare when ifosfamide is given with mesna. A common and dose-limiting side effect is encephalopathy (brain dysfunction).[3] It occurs in some form in up to 50% of people receiving the agent. The reaction is probably mediated by chloroacetaldehyde, one of the breakdown products of the ifosfamide molecule, which has chemical properties similar to acetaldehyde and chloral hydrate. The symptoms of ifosfamide encephalopathy can range from mild (difficulty concentrating, fatigue), to moderate (delirium, psychosis), to severe (nonconvulsive status epilepticus or coma). In children, this can interfere with neurological development. Apart from the brain, ifosfamide can also affect peripheral nerves. The severity of the reaction can be classified according to either the National Cancer Institute or the Meanwell criteria (grade I-IV). Previous brain problems and low levels of albumin in the blood increase the likelihood of ifosfamide encephalopathy. In most cases, the reaction resolves spontaneously within 72 hours. If it develops during an infusion of the drug, discontinuing the infusion is advised. The most effective treatment for severe (grade III-IV) encephalopathy is an intravenous solution of methylene blue, which appears to shorten the duration of encephalopathy; the exact mechanism of action of methylene blue is unclear. In some cases, methylene blue may be used as a prophylaxis before further doses of ifosfamide are administered. Other treatments include albumin and thiamine, and dialysis as a rescue modality.[3]

Ifosfamide may also cause a normal anion gap acidosis, specifically renal tubular acidosis type 2.[4]

Synthesis

References

  1. ^ Takimoto CH, Calvo E. "Principles of Oncologic Pharmacotherapy" in Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (Eds) Cancer Management: A Multidisciplinary Approach. 11 ed. 2008.
  2. ^ Jahnke K, Thiel E, Bechrakis NE et al. (December 2008). "Ifosfamide or trofosfamide in patients with intraocular lymphoma". J. Neurooncol. 93 (2): 213–7. PMID 19099202. doi:10.1007/s11060-008-9761-8. 
  3. ^ a b Ajithkumar T, Parkinson C, Shamshad F, Murray P (March 2007). "Ifosfamide encephalopathy". Clin Oncol (R Coll Radiol) 19 (2): 108–14. PMID 17355105. doi:10.1016/j.clon.2006.11.003. 
  4. ^ Foster, Corey, ed. (2010). The Washington Manual of Therapeutics (33 ed.). Wolters Kluwer #REDIRECTmw:Help:Magic words#Other
    This page is a soft redirect. Lippincott Williams & Wilkins. p. 407.
     
  5. ^ doi:10.1021/ja00847a053
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External links