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Ifosfamide
|
|
(R)-(+)- and (S)-(−)-ifosfamide (top),
(S)-(−)-ifosfamide (bottom)
|
| Systematic (IUPAC) name |
|
N,3-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amide 2-oxide
|
| Clinical data |
| Pronunciation |
|
| Trade names |
Ifex |
| AHFS/Drugs.com |
Monograph |
| MedlinePlus |
a695023 |
Pregnancy
category |
- AU: D
- US: D (Evidence of risk)
|
Routes of
administration |
intravenously |
| Legal status |
| Legal status |
- AU: S4 (Prescription only)
- CA: ℞-only
- NZ: Prescription Medicine
- UK: POM (Prescription only)
- US: ℞-only
|
| 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 |
| Molar mass |
261.1 g mol−1 |
|
|
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
|
| (verify) |
Ifosfamide (also marketed as Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer.[1] It is sometimes abbreviated as "IFO".[2]
It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system.[3]
Contents
- 1 Medical uses
- 2 Side effects
- 3 References
- 4 External links
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).[4] 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.[4]
Ifosfamide may also cause a normal anion gap acidosis, specifically renal tubular acidosis type 2.[5]
References
- ^ 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.
- ^ Jahnke K, Thiel E, Bechrakis NE, et al. (December 2008). "Ifosfamide or trofosfamide in patients with intraocular lymphoma". J. Neurooncol. 93 (2): 213–7. doi:10.1007/s11060-008-9761-8. PMID 19099202.
- ^ "19th WHO Model List of Essential Medicines (April 2015)" (PDF). WHO. April 2015. Retrieved May 10, 2015.
- ^ a b Ajithkumar T, Parkinson C, Shamshad F, Murray P (March 2007). "Ifosfamide encephalopathy". Clin Oncol (R Coll Radiol) 19 (2): 108–14. doi:10.1016/j.clon.2006.11.003. PMID 17355105.
- ^ Foster, Corey, ed. (2010). The Washington Manual of Therapeutics (33 ed.). Wolters Kluwer | Lippincott Williams & Wilkins. p. 407.
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
UpToDate Contents
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English Journal
- Non conventional biological treatment based on Trametes versicolor for the elimination of recalcitrant anticancer drugs in hospital wastewater.
- Ferrando-Climent L1, Cruz-Morató C2, Marco-Urrea E2, Vicent T2, Sarrà M2, Rodriguez-Mozaz S1, Barceló D3.
- Chemosphere.Chemosphere.2015 Oct;136:9-19. doi: 10.1016/j.chemosphere.2015.03.051. Epub 2015 Apr 22.
- This work presents a study about the elimination of anticancer drugs, a group of pollutants considered recalcitrant during conventional activated sludge wastewater treatment, using a biological treatment based on the fungus Trametes versicolor. A 10-L fluidized bed bioreactor inoculated with this fu
- PMID 25911328
- Occurrence of cyclophosphamide and ifosfamide in aqueous environment and their removal by biological and abiotic wastewater treatment processes.
- Česen M1, Kosjek T1, Laimou-Geraniou M2, Kompare B3, Širok B4, Lambropolou D2, Heath E5.
- The Science of the total environment.Sci Total Environ.2015 Sep 15;527-528:465-73. doi: 10.1016/j.scitotenv.2015.04.109. Epub 2015 May 14.
- Cytostatic drug residues in the aqueous environment are of concern due to their possible adverse effects on non-target organisms. Here we report the occurrence and removal efficiency of cyclophosphamide (CP) and ifosfamide (IF) by biological and abiotic treatments including advanced oxidation proces
- PMID 25981944
- Relapse after localized rhabdomyosarcoma: Evaluation of the efficacy of second-line chemotherapy.
- Winter S1, Fasola S2, Brisse H3, Mosseri V4, Orbach D1.
- Pediatric blood & cancer.Pediatr Blood Cancer.2015 Jul 6. doi: 10.1002/pbc.25622. [Epub ahead of print]
- PURPOSE: About one-third of patients with rhabdomyosarcoma relapse despite appropriate treatment and experience a poor outcome. Little meaningful improvement in the outcome of this disease has been observed over the last 30 years. There is no clear international recommendation concerning the use of
- PMID 26150380
Japanese Journal
- 非ホジキンリンパ腫の治療後に急性巨核芽球性白血病として発症した治療関連急性骨髄性白血病
- 兒玉 聖子,浅野 千尋,増田 道彦
- 東京女子医科大学雑誌 83(E2), E604-E607, 2013-03-31
- … 化学療法終了後1ヶ月で再発し、ICE療法(carboplatin, ifosfamide, etoposide)を3コース施行後、Granulocyte colony-stimulating factor (G-CSF)単独投与で得た末梢血幹細胞採取に続き、MEAM 療法(ranimustine 480 mg, etoposide, cytarabine, melphalan)を前処置として自家末梢血幹細胞移植術を行った。 …
- NAID 110009575072
- 幼少時の精巣固定術時に同定され得なかった腹腔内精巣に発生した精巣腫瘍の1例
- 岩村 大径,畠山 真吾,福士 謙,佐藤 天童,小島 由太,村澤 洋美,石村 大史,米山 高弘,古家 琢也,神村 典孝,諸橋 聡子,鬼島 宏,大山 力
- 泌尿器科紀要 59(3), 189-193, 2013-03-00
- … He received 3 courses of bleomycin, etoposide, cisplatin (BEP), and 4 courses of VP-16, ifosfamide, cisplatin (VIP). …
- NAID 120005244602
Related Links
- (eye-FOSS-fa-mide) Trade names: Ifex ® Chemocare.com uses generic names in all descriptions of drugs. Ifex is the trade name for Ifosfamide. In some cases, health care professionals may use the trade name ifex when ...
- Before receiving ifosfamide, tell your doctor and pharmacist if you are allergic to ifosfamide, cyclophosphamide (Cytoxan), any other medications, or any of the ingredients in ifosfamide injection. Ask your pharmacist for a ...
Related Pictures
★リンクテーブル★
[★]
- 英
- nitrogen mustard
- 同
- 窒素マスタード、窒素イペリット nitrogen yperite、メクロルエタミン mechlorethamine
- 関
- [[]]
[★]
- 英
- ifosfamide, IFO, IFM
- 商
- イホマイド、Ifex
