Isophosphamide mustard (BioDeep_00000011267)

 

Secondary id: BioDeep_00000858844

human metabolite Endogenous blood metabolite


代谢物信息卡片


N,N-di-(2-chloroethyl)phosphorodiamidic acid

化学式: C4H11Cl2N2O2P (219.99351760000002)
中文名称: 帕利伐米
谱图信息: 最多检出来源 Homo sapiens(blood) 0.34%

分子结构信息

SMILES: C(CCl)NP(=O)(NCCCl)O
InChI: InChI=1S/C4H11Cl2N2O2P/c5-1-3-7-11(9,10)8-4-2-6/h1-4H2,(H3,7,8,9,10)

描述信息

Isophosphamide mustard is a metabolite of ifosfamide. Ifosfamide (also marketed as Mitoxana and Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer. It is sometimes abbreviated IFO. (Wikipedia)
D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D009588 - Nitrogen Mustard Compounds
D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D010752 - Phosphoramide Mustards
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent
D009676 - Noxae > D000477 - Alkylating Agents
Same as: D09364

同义名列表

13 个代谢物同义名

N,N-di-(2-chloroethyl)phosphorodiamidic acid; bis[(2-chloroethyl)amino]phosphinic acid; NN-Bis-(2-chloroethyl)phosphoric acid; NN-Bis-(2-chloroethyl)phosphate; Zio-201isophosphamide mustard; Isophosphoramide mustard; Isophosphamide mustard; Iphosphoramide mustard; Ifosforamide mustard; Ifosfamide mustard; Palifosfamide-tris; Palifosfamide; IPAM



数据库引用编号

11 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

  • Zhongyu Li, Lei Jiang, Yujuan Zhu, Wentao Su, Cong Xu, Tingting Tao, Yang Shi, Jianhua Qin. Assessment of hepatic metabolism-dependent nephrotoxicity on an organs-on-a-chip microdevice. Toxicology in vitro : an international journal published in association with BIBRA. 2018 Feb; 46(?):1-8. doi: 10.1016/j.tiv.2017.10.005. [PMID: 28986290]
  • Shadia I Jalal, Philip Lavin, Gregory Lo, Francois Lebel, Lawrence Einhorn. Carboplatin and Etoposide With or Without Palifosfamide in Untreated Extensive-Stage Small-Cell Lung Cancer: A Multicenter, Adaptive, Randomized Phase III Study (MATISSE). Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 2017 Aug; 35(23):2619-2623. doi: 10.1200/jco.2016.71.7454. [PMID: 28605291]
  • Charles Skarbek, Lea L Lesueur, Hubert Chapuis, Alain Deroussent, Catherine Pioche Durieu, Aurore Daville, Joachim Caron, Michael Rivard, Thierry Martens, Jean-Rémi Bertrand, Eric Le Cam, Gilles Vassal, Patrick Couvreur, Didier Desmaele, Angelo Paci. Preactivated oxazaphosphorines designed for isophosphoramide mustard delivery as bulk form or nanoassemblies: synthesis and proof of concept. Journal of medicinal chemistry. 2015 Jan; 58(2):705-17. doi: 10.1021/jm501224x. [PMID: 25494842]
  • Donald Jung, Lin Lin, Hailong Jiao, Xiaohong Cai, Jian-Xin Duan, M Matteucci. Pharmacokinetics of TH-302: a hypoxically activated prodrug of bromo-isophosphoramide mustard in mice, rats, dogs and monkeys. Cancer chemotherapy and pharmacology. 2012 Mar; 69(3):643-54. doi: 10.1007/s00280-011-1741-6. [PMID: 21964906]
  • L Patzer, N Hernando, U Ziegler, B Beck-Schimmer, J Biber, H Murer. Ifosfamide metabolites CAA, 4-OH-Ifo and Ifo-mustard reduce apical phosphate transport by changing NaPi-IIa in OK cells. Kidney international. 2006 Nov; 70(10):1725-34. doi: 10.1038/sj.ki.5001803. [PMID: 17003823]
  • Yu-Ming Sun, Xiao-Yan Chen, Da-Fang Zhong. [Identification of glufosfamide metabolites in rats]. Yao xue xue bao = Acta pharmaceutica Sinica. 2006 Jun; 41(6):513-7. doi: . [PMID: 16927824]
  • N Germann, S Urien, Andrew H Rodgers, Marion Ratterree, Robert F Struck, William R Waud, David G Serota, Gerard Bastian, Branko S Jursic, Lee Roy Morgan. Comparative preclinical toxicology and pharmacology of isophosphoramide mustard, the active metabolite of ifosfamide. Cancer chemotherapy and pharmacology. 2005 Feb; 55(2):143-51. doi: 10.1007/s00280-004-0894-y. [PMID: 15592722]
  • Monish Jain, Junying Fan, Nesrine Z Baturay, Chul-Hoon Kwon. Sulfonyl-containing aldophosphamide analogues as novel anticancer prodrugs targeted against cyclophosphamide-resistant tumor cell lines. Journal of medicinal chemistry. 2004 Jul; 47(15):3843-52. doi: 10.1021/jm0304764. [PMID: 15239662]
  • H Silies, G Blaschke, B Hohenlöchter, R Rossi, H Jürgens, J Boos. Excretion kinetics of ifosfamide side-chain metabolites in children on continuous and short-term infusion. International journal of clinical pharmacology and therapeutics. 1998 May; 36(5):246-52. doi: NULL. [PMID: 9629987]
  • 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, E Rozendom, A Bult, W J Underberg. Analysis of ifosforamide mustard, the active metabolite of ifosfamide, in plasma. Journal of chromatography. B, Biomedical applications. 1996 Nov; 686(2):249-55. doi: 10.1016/s0378-4347(96)00218-6. [PMID: 8971607]
  • 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]
  • J Pohl, B Bertram, P Hilgard, M R Nowrousian, J Stüben, M Wiessler. D-19575--a sugar-linked isophosphoramide mustard derivative exploiting transmembrane glucose transport. Cancer chemotherapy and pharmacology. 1995; 35(5):364-70. doi: 10.1007/s002800050248. [PMID: 7850916]
  • J M Hartley, L Hansen, S J Harland, P W Nicholson, F Pasini, R L Souhami. Metabolism of ifosfamide during a 3 day infusion. British journal of cancer. 1994 May; 69(5):931-6. doi: 10.1038/bjc.1994.180. [PMID: 8180026]
  • J J Zheng, K K Chan, F Muggia. Preclinical pharmacokinetics and stability of isophosphoramide mustard. Cancer chemotherapy and pharmacology. 1994; 33(5):391-8. doi: 10.1007/bf00686268. [PMID: 8306413]
  • 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]
  • C H Kwon, R F Borch. Effects of N-substitution on the activation mechanisms of 4-hydroxycyclophosphamide analogues. Journal of medicinal chemistry. 1989 Jul; 32(7):1491-6. doi: 10.1021/jm00127a016. [PMID: 2738883]
  • M R Holdiness, L R Morgan. Electron-capture--gas chromatographic analysis of ifosfamide in human plasma and urine. Journal of chromatography. 1983 Jul; 275(2):432-5. doi: 10.1016/s0378-4347(00)84392-3. [PMID: 6619250]
  • 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]
  • R F Struck, D J Dykes, T H Corbett, W J Suling, M W Trader. Isophosphoramide mustard, a metabolite of ifosfamide with activity against murine tumours comparable to cyclophosphamide. British journal of cancer. 1983 Jan; 47(1):15-26. doi: 10.1038/bjc.1983.2. [PMID: 6821629]
  • B M Bryant, M Jarman, M H Baker, I E Smith, J F Smyth. Quantification by gas chromatography of N,N'-di-(2-chloroethyl)-phosphorodiamidic acid in the plasma of patients receiving isophosphamide. Cancer research. 1980 Dec; 40(12):4734-8. doi: NULL. [PMID: 7438105]