2-Dechloroethylifosfamide (BioDeep_00000011263)

 

Secondary id: BioDeep_00001875316

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


2-Amino-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazophosphorine-2-O-xide

化学式: C5H12ClN2O2P (198.0325)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 50.81%

分子结构信息

SMILES: C1CN(P(=O)(OC1)N)CCCl
InChI: InChI=1S/C5H12ClN2O2P/c6-2-4-8-3-1-5-10-11(8,7)9/h1-5H2,(H2,7,9)

描述信息

2-Dechloroethylifosfamide is a metabolite of the antitumor, alkylating drug Ifosfamide. 2-dechloroethylifosfamide is a member of the compound class known as oxazaphosphorines. Oxazaphosphorines are any saturated six-membered heterocycle containing three carbon atoms and one each of oxygen, nitrogen and phosphorus, especially one in which the phosphorus atom is linked to both the nitrogen and oxygen atoms. 2-dechloroethylifosfamide can be biosynthesized from ifosfamide through the action of cytochrome P450 enzymes including CYP3A4, CYP3A5, and CYP2B6 (PMID: 15875221). 2-dechloroethylifosfamide is only found in individuals who have consumed or received the drug Ifosfamide.
D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D009588 - Nitrogen Mustard Compounds
D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D010752 - Phosphoramide Mustards

同义名列表

10 个代谢物同义名

2-Amino-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazophosphorine-2-O-xide; 2-amino-3-(2-chloroethyl)-1,3,2λ⁵-oxazaphosphinan-2-one; Dechloroethylifosfamide, (+-)-isomer; Dechloroethylifosfamide, (R)-isomer; Dechloroethylifosfamide, (S)-isomer; 2-Dechloroethylifosfamide; Dechloroethylifosfamide; 2-DCE-iff; 2-DClIF; 2-Dechloroethylifosfamide



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(2)

  • Ifosfamide Action Pathway: Ifosfamide + Oxygen + Water ⟶ 2-Dechloroethylifosfamide + 3-Dechloroethylifosfamide + Chloroacetaldehyde + Hydrogen peroxide
  • Ifosfamide Metabolism Pathway: Ifosfamide + Oxygen + Water ⟶ 2-Dechloroethylifosfamide + 3-Dechloroethylifosfamide + Chloroacetaldehyde + Hydrogen peroxide

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Katarina Aleksa, Alejandro Nava-Ocampo, Gideon Koren. Detection and quantification of (R) and (S)-dechloroethylifosfamide metabolites in plasma from children by enantioselective LC/MS/MS. Chirality. 2009 Jul; 21(7):674-80. doi: 10.1002/chir.20662. [PMID: 18825700]
  • Regina V Oliveira, Joelle M Onorato, Danuta Siluk, Christine M Walko, Celeste Lindley, Irving W Wainer. Enantioselective liquid chromatography-mass spectrometry assay for the determination of ifosfamide and identification of the N-dechloroethylated metabolites of ifosfamide in human plasma. Journal of pharmaceutical and biomedical analysis. 2007 Oct; 45(2):295-303. doi: 10.1016/j.jpba.2007.07.026. [PMID: 17855037]
  • Elzbieta Zielińska, Małgorzata Zubowska, Konrad Misiura. Role of GSTM1, GSTP1, and GSTT1 gene polymorphism in ifosfamide metabolism affecting neurotoxicity and nephrotoxicity in children. Journal of pediatric hematology/oncology. 2005 Nov; 27(11):582-9. doi: 10.1097/01.mph.0000187429.52616.8a. [PMID: 16282887]
  • Katarina Aleksa, Doug Matsell, Kris Krausz, Harry Gelboin, Shinya Ito, Gideon Koren. Cytochrome P450 3A and 2B6 in the developing kidney: implications for ifosfamide nephrotoxicity. Pediatric nephrology (Berlin, Germany). 2005 Jul; 20(7):872-85. doi: 10.1007/s00467-004-1807-3. [PMID: 15875221]
  • Katarina Aleksa, Naomi Halachmi, Shinya Ito, Gideon Koren. A tubule cell model for ifosfamide nephrotoxicity. Canadian journal of physiology and pharmacology. 2005 Jun; 83(6):499-508. doi: 10.1139/y05-036. [PMID: 16049550]
  • T Kerbusch, R A Mathĵt, H J Keizer, J Ouwerkerk, S Rodenhuis, J H Schellens, J H Beijnen. Population pharmacokinetics and exploratory pharmacodynamics of ifosfamide and metabolites after a 72-h continuous infusion in patients with soft tissue sarcoma. European journal of clinical pharmacology. 2001 Sep; 57(6-7):467-77. doi: 10.1007/s002280100322. [PMID: 11699611]
  • T Kerbusch, M J Jeuken, J Derraz, J W van Putten, A D Huitema, J H Beijnen. Determination of ifosfamide, 2- and 3-dechloroethyifosfamide using gas chromatography with nitrogen-phosphorus or mass spectrometry detection. Therapeutic drug monitoring. 2000 Oct; 22(5):613-20. doi: 10.1097/00007691-200010000-00018. [PMID: 11034269]
  • V Gilard, R Martino, M Malet-Martino, U Niemeyer, J Pohl. Chemical stability and fate of the cytostatic drug ifosfamide and its N-dechloroethylated metabolites in acidic aqueous solutions. Journal of medicinal chemistry. 1999 Jul; 42(14):2542-60. doi: 10.1021/jm980587g. [PMID: 10411475]
  • G P Kaijser, J De Kraker, A Bult, W J Underberg, J H Beijnen. Pharmacokinetics of ifosfamide and some metabolites in children. Anticancer research. 1998 May; 18(3B):1941-9. doi: NULL. [PMID: 9677448]
  • J M Singer, J M Hartley, C Brennan, P W Nicholson, R L Souhami. The pharmacokinetics and metabolism of ifosfamide during bolus and infusional administration: a randomized cross-over study. British journal of cancer. 1998 Mar; 77(6):978-84. doi: 10.1038/bjc.1998.161. [PMID: 9528844]
  • G P Kaijser, J H Beijnen, A Bult, H J Keizer, W J Underberg. Chromatographic analysis of the enantiomers of ifosfamide and some of its metabolites in plasma and urine. Journal of chromatography. B, Biomedical sciences and applications. 1997 Mar; 690(1-2):131-8. doi: 10.1016/s0378-4347(96)00376-3. [PMID: 9106037]
  • V Kurowski, T Wagner. Urinary excretion of ifosfamide, 4-hydroxyifosfamide, 3- and 2-dechloroethylifosfamide, mesna, and dimesna in patients on fractionated intravenous ifosfamide and concomitant mesna therapy. Cancer chemotherapy and pharmacology. 1997; 39(5):431-9. doi: 10.1007/s002800050594. [PMID: 9054957]
  • G P Kaijser, H J Keizer, J H Beijnen, A Bult, W J Underberg. Pharmacokinetics of ifosfamide, 2- and 3-dechloroethylifosfamide in plasma and urine of cancer patients treated with a 10-day continuous infusion of ifosfamide. Anticancer research. 1996 Sep; 16(5B):3247-57. doi: . [PMID: 8920799]
  • J J Wang, K K Chan. Analysis of ifosfamide, 4-hydroxyifosfamide, N2-dechloroethylifosfamide, N3-dechloroethylifosfamide and iphosphoramide mustard in plasma by gas chromatography-mass spectrometry. Journal of chromatography. B, Biomedical applications. 1995 Dec; 674(2):205-17. doi: 10.1016/0378-4347(95)00309-6. [PMID: 8788150]
  • C P Granville, B Gehrcke, W A König, I W Wainer. Determination of the enantiomers of ifosfamide and its 2- and 3-N-dechloroethylated metabolites in plasma and urine using enantioselective gas chromatography with mass spectrometric detection. Journal of chromatography. 1993 Dec; 622(1):21-31. doi: 10.1016/0378-4347(93)80245-y. [PMID: 8120109]
  • G P Kaijser, J H Beijnen, A Bult, G Wiese, J de Kraker, H J Keizer, W J Underberg. Gas chromatographic determination of 2- and 3-dechloroethylifosfamide in plasma and urine. Journal of chromatography. 1992 Dec; 583(2):175-82. doi: 10.1016/0378-4347(92)80550-a. [PMID: 1478981]
  • M J Lind, H L Roberts, N Thatcher, J R Idle. The effect of route of administration and fractionation of dose on the metabolism of ifosfamide. Cancer chemotherapy and pharmacology. 1990; 26(2):105-11. doi: 10.1007/bf02897254. [PMID: 2347037]
  • K Misiura, A Okruszek, K Pankiewicz, W J Stec, Z Czownicki, B Utracka. Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine. Journal of medicinal chemistry. 1983 May; 26(5):674-9. doi: 10.1021/jm00359a010. [PMID: 6842506]