- 関
- ifosfamide
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/05 04:51:38」(JST)
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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 |
Pregnancy
category |
- AU: D
- US: D (Evidence of risk)
|
| Legal status |
- AU: Prescription Only (S4)
- CA: ℞-only
- NZ: Prescription Medicine
- UK: Prescription-only (POM)
- US: ℞-only
|
Routes of
administration |
intravenously |
| Pharmacokinetic data |
| Bioavailability |
100% |
| Metabolism |
Hepatic |
| Biological half-life |
60-80% in 72 hours |
| Excretion |
Renal |
| Identifiers |
| CAS Registry Number |
3778-73-2 Y |
| ATC code |
L01AA06 |
| 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 |
|
|
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
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Key:HOMGKSMUEGBAAB-UHFFFAOYSA-N Y
|
| Y (what is this?) (verify) |
Ifosfamide (pronunciation: also marketed as Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer.[1] It is sometimes abbreviated as "IFO".[2]
Contents
- 1 Uses
- 2 Administration
- 3 Toxicity
- 4 Synthesis
- 5 References
- 6 External links
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.
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
Ifosfamide synthesis:
[5] FR 1530962 U.S. Patent 3,732,340.
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.
- ^ 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.
- ^ Brassfield, H. A.; Jacobson, R. A.; Verkade, J. G. (1975). "Molecular structure of the carcinostat isophosphamide". Journal of the American Chemical Society 97 (14): 4143. doi:10.1021/ja00847a053. PMID 1159218. edit
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
- Design of new oxazaphosphorine anticancer drugs.
- Liang J1, Huang M, Duan W, Yu XQ, Zhou S.
- Current pharmaceutical design.Curr Pharm Des.2007;13(9):963-78.
- The oxazaphosphorines including cyclophosphamide (CPA, Cytoxan, or Neosar), ifosfamide (IFO, Ifex) and trofosfamide (Ixoten) represent an important group of therapeutic agents due to their substantial antitumor and immunomodulating activity. However, several intrinsic limitations have been uncounted
- PMID 17430192
- Docetaxel for previously treated non-small-cell lung cancer.
- Fossella FV1.
- Oncology (Williston Park, N.Y.).Oncology (Williston Park).2002 Jun;16(6 Suppl 6):45-51.
- Two phase III trials were conducted using docetaxel (Taxotere), administered every 3 weeks, as second-line treatment of non-small-cell lung cancer (NSCLC) in patients previously treated with platinum-based chemotherapy. In the TAX 317 trial, 204 patients were randomized to receive either docetaxel (
- PMID 12108897
- The role of mitoxantrone in non-Hodgkin's lymphoma.
- Armitage JO1.
- Oncology (Williston Park, N.Y.).Oncology (Williston Park).2002 Apr;16(4):490-502, 507-8; discussion 511-2, 514.
- The development of doxorubicin was an important advance in the treatment of patients with non-Hodgkin's lymphoma (NHL). Alternatives to doxorubicin, such as mitoxantrone (Novantrone), have less nonhematologic toxicity and could offer a therapeutic advantage in some situations if similar antilymphoma
- PMID 12017536
Japanese Journal
- 海外報告 東西南北 第2回アジア鋳造フォーラム(AFF)とIFEXに参加して
- GARDEX2011 第5回国際ガーデンEXPO,IFEX2011 第8回国際フラワーEXPO,EXTEPO2011 第3回国際エクステリアEXPO : 生産者フェアの新設で植物関係の初出展が大幅増
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Related Pictures
★リンクテーブル★
[★]
- 英
- ifosfamide, IFO, IFM
- 商
- イホマイド、Ifex
[★]
- funny currentと呼ばれる電流
- ペースメーカー電流 inward pacemaker current。SA nodeやAV nodeにおける4相の緩徐脱分極に関わる内向きの電流。Na+/K+が関与するらしいが、はっきりしたことは分かっていない(SP.526-527)。