Ifosfamide

Ifosfamide

Systematic (IUPAC) name
N-3-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amide-2-oxide
Clinical data
Pronunciation	/aɪˈfɒsfəˌmaɪd/
Trade names	Ifex
AHFS/Drugs.com	monograph
MedlinePlus	a695023
Pregnancy category	AU: D US: D (Evidence of risk)
Legal status	AU: S4 (Prescription only) CA: ℞-only NZ: Prescription Medicine UK: POM (Prescription only) US: ℞-only
Routes of administration	intravenously
Pharmacokinetic data
Bioavailability	100%
Metabolism	Hepatic
Biological half-life	60-80% in 72 hours
Excretion	Renal
Identifiers
CAS Number	3778-73-2 Y
ATC code	L01AA06 (WHO)
PubChem	CID: 3690
IUPHAR/BPS	7201
DrugBank	DB01181 Y
ChemSpider	3562 Y
UNII	UM20QQM95Y Y
KEGG	D00343 Y
ChEBI	CHEBI:5864 Y
ChEMBL	CHEMBL1024 Y
Synonyms	3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
Chemical data
Formula	C7H15Cl2N2O2P
Molecular mass	261.1 g mol−1
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
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Ifosfamide also marketed as Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer. It is sometimes abbreviated as "IFO".

It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system.

Medical uses

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

• Testicular cancer
• Breast cancer
• Lymphoma (Hodgkin and non-Hodgkin)
• Soft tissue sarcoma
• Osteosarcoma or bone tumor
• Lung cancer
• Cervical cancer
• Ovarian cancer

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.

Side effects

Hemorrhagic cystitis is rare when ifosfamide is given with mesna. A common and dose-limiting side effect is encephalopathy (brain dysfunction). 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.

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

External links

• ACS Drug Guide: Ifosfamide
• Harvard Medical School Health Information on Ifosfamide
• MedlinePlus Drug Information
• BC Cancer Agency Ifosamide Information (Professional)
• RxList Online Drug Index Ifosamide Listing