Aldophosphamide (BioDeep_00000019549)

 

Secondary id: BioDeep_00000006564

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanal

化学式: C7H15Cl2N2O3P (276.019731)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.37%

分子结构信息

SMILES: C(COP(=O)(N)N(CCCl)CCCl)C=O
InChI: InChI=1S/C7H15Cl2N2O3P/c8-2-4-11(5-3-9)15(10,13)14-7-1-6-12/h6H,1-5,7H2,(H2,10,13)

描述信息

Detoxification of cyclophosphamide is effected, in part, by hepatic class 1 aldehyde dehydrogenase (ALDH-1)-catalyzed oxidation of aldophosphamide, a pivotal aldehyde intermediate, to the nontoxic metabolite, carboxyphosphamide. Detoxification of aldophosphamide may also be effected by enzymes, viz. Thus, NAD-linked oxidation and NADPH-linked reduction of aldophosphamide catalyzed by relevant erythrocyte enzymes were quantified. (PMID: 9394035) Class 1 aldehyde dehydrogenases (ALDH-1) function as drug resistance gene products by catalyzing the irreversible conversion of aldophosphamide, an active metabolite of cyclophosphamide, to an inert compound. (PMID: 9322086)
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

4 个代谢物同义名

3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanal; Cyclophosphamide-mustard; Aldophosphamide; Cyp-mustard



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 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(0)

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。

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文献列表

  • Jiang Wang, Yi-Jun Wang, Zhe-Sheng Chen, Chul-Hoon Kwon. Synthesis and evaluation of sulfonylethyl-containing phosphotriesters of 3'-azido-3'-deoxythymidine as anticancer prodrugs. Bioorganic & medicinal chemistry. 2014 Nov; 22(21):5747-56. doi: 10.1016/j.bmc.2014.09.046. [PMID: 25440502]
  • 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]
  • 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]
  • L Belfayol-Pisanté, L Guillevin, M Tod, F Fauvelle. Pharmacokinetics of cyclophosphamide (CP) and 4-OH-CP/aldophosphamide in systemic vasculitis. Fundamental & clinical pharmacology. 2000 Jul; 14(4):415-21. doi: 10.1111/j.1472-8206.2000.tb00424.x. [PMID: 11030450]
  • T L Chen, M J Kennedy, L W Anderson, S B Kiraly, K C Black, O M Colvin, L B Grochow. Nonlinear pharmacokinetics of cyclophosphamide and 4-hydroxycyclophosphamide/aldophosphamide in patients with metastatic breast cancer receiving high-dose chemotherapy followed by autologous bone marrow transplantation. Drug metabolism and disposition: the biological fate of chemicals. 1997 May; 25(5):544-51. doi: . [PMID: 9152592]
  • M Johansson, M Bielenstein. Determination of 4-hydroxycyclophosphamide in plasma, as 2,4-dinitrophenylhydrazone derivative of aldophosphamide, by liquid chromatography. Journal of chromatography. B, Biomedical applications. 1994 Oct; 660(1):111-20. doi: 10.1016/0378-4347(94)00283-5. [PMID: 7858703]
  • H K Parekh, N E Sladek. NADPH-dependent enzyme-catalyzed reduction of aldophosphamide, the pivotal metabolite of cyclophosphamide. Biochemical pharmacology. 1993 Sep; 46(6):1043-52. doi: 10.1016/0006-2952(93)90669-n. [PMID: 8216347]
  • P S Hong, A Srigritsanapol, K K Chan. Pharmacokinetics of 4-hydroxycyclophosphamide and metabolites in the rat. Drug metabolism and disposition: the biological fate of chemicals. 1991 Jan; 19(1):1-7. doi: . [PMID: 1673381]
  • P S Hong, K K Chan. Analysis of 4-hydroxycyclophosphamide by gas chromatography-mass spectrometry in plasma. Journal of chromatography. 1989 Oct; 495(?):131-8. doi: 10.1016/s0378-4347(00)82616-x. [PMID: 2613798]