-ifosfamide.svg) | |
 (R)-(+)- and (S)-(−)-ifosfamide (top), (S)-(−)-ifosfamide (bottom) | |
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| 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 |
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| Routes of administration | Intravenous |
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| Pharmacokinetic data | |
| Bioavailability | 100% |
| Metabolism | Liver |
| Eliminationhalf-life | 60–80% in 72 hours |
| Excretion | Kidney |
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| ECHA InfoCard | 100.021.126 |
| Chemical and physical data | |
| Formula | C7H15Cl2N2O2P |
| Molar mass | 261.08 g·mol−1 |
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Ifosfamide, sold under the brand nameIfex among others, is achemotherapy medication used to treat a number of types of cancer.[3] This includestesticular cancer,soft tissue sarcoma,osteosarcoma,bladder cancer,small cell lung cancer,cervical cancer, andovarian cancer.[3] It is administered byinjection into a vein.[3]
Common side effects include hair loss, vomiting,blood in the urine, infections, andkidney problems.[3] Other severe side effects includebone marrow suppression anddecreased level of consciousness.[3] Use duringpregnancy will likely result in harm to the baby.[3] Ifosfamide is in thealkylating agent andnitrogen mustard family of medications.[3][4] It works by disrupting the duplication ofDNA and the creation ofRNA.[3]
Ifosfamide was approved for medical use in the United States in 1987.[3] It is on theWorld Health Organization's List of Essential Medicines.[5]
It is given as a treatment for a variety ofcancers, including:
It is a whitepowder which, when prepared for use inchemotherapy, becomes a clear, colorless fluid. The delivery isintravenous.
Ifosfamide is often used in conjunction withmesna to avoidinternal bleeding in the patient, in particularhemorrhagic cystitis.
Ifosfamide is given quickly, and in some cases can be given as quickly as an hour.
Ifosfamide is a DNA-damaging alkylating agent, belonging to the same class of chemotherapy drugs ascyclophosphamide. It is a prodrug, meaning that It has to be converted by CYP450 into its main active metabolites-(Iso)phosphoramide mustards. These metabolites form DNA cross links mainly at Guanine N-7 positions.[6]
Hemorrhagic cystitis is rare when ifosfamide is given withmesna. A common and dose-limiting side effect isencephalopathy (brain dysfunction).[7] It occurs in some form in up to 50% of people receiving the agent. The reaction is probably mediated bychloroacetaldehyde, one of the breakdown products of the ifosfamide molecule, which has chemical properties similar toacetaldehyde andchloral hydrate. The symptoms of ifosfamide encephalopathy can range from mild (difficulty concentrating, fatigue), to moderate (delirium,psychosis), to severe (nonconvulsive status epilepticus orcoma). 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 theNational Cancer Institute or the Meanwell criteria (grade I–IV). Previous brain problems and low levels ofalbumin 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 ofmethylene 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 andthiamine, anddialysis as a rescue modality.[7]
Ifosfamide may also cause anormal anion gap acidosis, specificallyrenal tubular acidosis type 2.[8]
