Phosphoramide mustard (BioDeep_00000006566)
Secondary id: BioDeep_00001868731
human metabolite Endogenous blood metabolite
代谢物信息卡片
amino[bis(2-chloroethyl)amino]phosphinic acid
化学式: C4H11Cl2N2O2P (219.99351760000002)
中文名称:
谱图信息:
最多检出来源 Macaca mulatta(otcml) 2.78%
分子结构信息
SMILES: C(CCl)N(CCCl)P(=O)(N)O
InChI: InChI=1S/C4H11Cl2N2O2P/c5-1-3-8(4-2-6)11(7,9)10/h1-4H2,(H3,7,9,10)
描述信息
Phosphoramide mustard is a metabolite of cyclophosphamide. Cyclophosphamide (trade names Endoxan, Cytoxan, Neosar, Procytox, Revimmune), also known as cytophosphane, is a nitrogen mustard alkylating agent, from the oxazophorines group. An alkylating agent adds an alkyl group (CnH2n+1) to DNA. It attaches the alkyl group to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. It is used to treat various types of cancer and some autoimmune disorders. (Wikipedia)
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
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:8163
- KEGG: C07647
- PubChem: 96356
- HMDB: HMDB0060689
- Metlin: METLIN634
- ChEMBL: CHEMBL525
- CAS: 10159-53-2
- PMhub: MS000019628
- PubChem: 9849
- NIKKAJI: J227.454J
- RefMet: Phosphoramide mustard
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)
- Cyclophosphamide Action Pathway:
Aldophosphamide + Glutathione ⟶ 4-Glutathionyl cyclophosphamide + Water - Cyclophosphamide Metabolism Pathway:
Aldophosphamide + Glutathione ⟶ 4-Glutathionyl cyclophosphamide + Water
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
- Nandini Bhat, Sneha Guruprasad Kalthur, Supriya Padmashali, Vidya Monappa. Toxic Effects of Different Doses of Cyclophosphamide on Liver and Kidney Tissue in Swiss Albino Mice: A Histopathological Study.
Ethiopian journal of health sciences.
2018 Nov; 28(6):711-716. doi:
10.4314/ejhs.v28i6.5. [PMID: 30607087] - Claudio Ponticelli, Rachele Escoli, Gabriella Moroni. Does cyclophosphamide still play a role in glomerular diseases?.
Autoimmunity reviews.
2018 Oct; 17(10):1022-1027. doi:
10.1016/j.autrev.2018.04.007. [PMID: 30107267] - Hong Lu, Kenneth K Chan. Pharmacokinetics of N-2-chloroethylaziridine, a volatile cytotoxic metabolite of cyclophosphamide, in the rat.
Cancer chemotherapy and pharmacology.
2006 Oct; 58(4):532-9. doi:
10.1007/s00280-006-0196-7. [PMID: 16470409] - Milly E de Jonge, Alwin D R Huitema, Selma M van Dam, Sjoerd Rodenhuis, Jos H Beijnen. Population pharmacokinetics of cyclophosphamide and its metabolites 4-hydroxycyclophosphamide, 2-dechloroethylcyclophosphamide, and phosphoramide mustard in a high-dose combination with Thiotepa and Carboplatin.
Therapeutic drug monitoring.
2005 Dec; 27(6):756-65. doi:
10.1097/01.ftd.0000177224.19294.92. [PMID: 16306851] - 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] - A D Huitema, R A Mathôt, M M Tibben, S Rodenhuis, J H Beijnen. A mechanism-based pharmacokinetic model for the cytochrome P450 drug-drug interaction between cyclophosphamide and thioTEPA and the autoinduction of cyclophosphamide.
Journal of pharmacokinetics and pharmacodynamics.
2001 Jun; 28(3):211-30. doi:
10.1023/a:1011543508731. [PMID: 11468938] - A D Huitema, M M Tibben, T Kerbusch, J J Kettenes-van den Bosch, S Rodenhuis, J H Beijnen. Simple and selective determination of the cyclophosphamide metabolite phosphoramide mustard in human plasma using high-performance liquid chromatography.
Journal of chromatography. B, Biomedical sciences and applications.
2000 Aug; 745(2):345-55. doi:
10.1016/s0378-4347(00)00295-4. [PMID: 11043753] - P Müller, R Jesnowski, P Karle, R Renz, R Saller, H Stein, K Püschel, K von Rombs, H Nizze, S Liebe, T Wagner, W H Günzburg, B Salmons, M Löhr. Injection of encapsulated cells producing an ifosfamide-activating cytochrome P450 for targeted chemotherapy to pancreatic tumors.
Annals of the New York Academy of Sciences.
1999 Jun; 880(?):337-51. doi:
10.1111/j.1749-6632.1999.tb09537.x. [PMID: 10415878] - W H Günzburg, P Karle, R Renz, B Salmons, M Renner. Characterization of a human cell clone expressing cytochrome P450 for safe use in human somatic cell therapy.
Annals of the New York Academy of Sciences.
1999 Jun; 880(?):326-36. doi:
10.1111/j.1749-6632.1999.tb09536.x. [PMID: 10415877] - H Lu, K K Chan. Gas chromatographic-mass spectrometric assay for N-2-chloroethylaziridine, a volatile cytotoxic metabolite of cyclophosphamide, in rat plasma.
Journal of chromatography. B, Biomedical applications.
1996 Apr; 678(2):219-25. doi:
10.1016/0378-4347(95)00528-5. [PMID: 8738025] - D J Stewart, L R Morgan, S Verma, J A Maroun, M Thibault. Pharmacology, relative bioavailability, and toxicity of three different oral cyclophosphamide preparations in a randomized, cross-over study.
Investigational new drugs.
1995; 13(1):99-107. doi:
10.1007/bf02614228. [PMID: 7499116] - K K Chan, P S Hong, K Tutsch, D L Trump. Clinical pharmacokinetics of cyclophosphamide and metabolites with and without SR-2508.
Cancer research.
1994 Dec; 54(24):6421-9. doi:
. [PMID: 7987837] - A A Srigritsanapol, K K Chan. A rapid method for the separation and analysis of leaked and liposomal entrapped phosphoramide mustard in plasma.
Journal of pharmaceutical and biomedical analysis.
1994 Aug; 12(8):961-8. doi:
10.1016/0731-7085(94)00044-1. [PMID: 7819381] - P S Hong, K K Chan. Enzymatic detoxification of phosphoramide mustard by soluble fractions from rat organ tissues.
Drug metabolism and disposition: the biological fate of chemicals.
1991 May; 19(3):568-73. doi:
. [PMID: 1680621] - 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] - D E Seitz, C J Katterjohn, S M Rinzel, H L Pearce. Thermodynamic analysis of the reaction of phosphoramide mustard with protector thiols.
Cancer research.
1989 Jul; 49(13):3525-8. doi:
. [PMID: 2499418] - F Darroudi, H Targa, A T Natarajan. Influence of dietary carrot on cytostatic drug activity of cyclophosphamide and its main directly acting metabolite: induction of sister-chromatid exchanges in normal human lymphocytes, Chinese hamster ovary cells, and their DNA repair-deficient cell lines.
Mutation research.
1988 Apr; 198(2):327-35. doi:
10.1016/0027-5107(88)90010-3. [PMID: 3352640] - V L Slott, B F Hales. Enhancement of the embryotoxicity of acrolein, but not phosphoramide mustard, by glutathione depletion in rat embryos in vitro.
Biochemical pharmacology.
1987 Jun; 36(12):2019-25. doi:
10.1016/0006-2952(87)90503-x. [PMID: 3593406] - R F Struck, D S Alberts, K Horne, J G Phillips, Y M Peng, D J Roe. Plasma pharmacokinetics of cyclophosphamide and its cytotoxic metabolites after intravenous versus oral administration in a randomized, crossover trial.
Cancer research.
1987 May; 47(10):2723-6. doi:
NULL. [PMID: 3552204] - C H Kwon, K Maddison, L LoCastro, R F Borch. Accelerated decomposition of 4-hydroxycyclophosphamide by human serum albumin.
Cancer research.
1987 Mar; 47(6):1505-8. doi:
. [PMID: 3815352] - E Watson, P Dea, K K Chan. Kinetics of phosphoramide mustard hydrolysis in aqueous solution.
Journal of pharmaceutical sciences.
1985 Dec; 74(12):1283-92. doi:
10.1002/jps.2600741208. [PMID: 4087195] - K Hemminki. Binding of metabolites of cyclophosphamide to DNA in a rat liver microsomal system and in vivo in mice.
Cancer research.
1985 Sep; 45(9):4237-43. doi:
. [PMID: 4028012] - J Satish, B M Pratt, M K Sanyal. Differential dysmorphogenesis induced by microinjection of an alkylating agent into rat conceptuses cultured in vitro.
Teratology.
1985 Feb; 31(1):61-72. doi:
10.1002/tera.1420310108. [PMID: 3983860] - H Zincke, I Jardine, M Colvin, G Aydin, S E Okiye. In vitro alteration of canine renal allografts with cyclophosphamide metabolites.
Transplantation proceedings.
1983 Jun; 15(2):1698-701. doi:
NULL. [PMID: 6349051] - J F Powers, N E Sladek. Cytotoxic activity relative to 4-hydroxycyclophosphamide and phosphoramide mustard concentrations in the plasma of cyclophosphamide-treated rats.
Cancer research.
1983 Mar; 43(3):1101-6. doi:
NULL. [PMID: 6825082] - N Brock, J Pohl, J Stekar. Studies on the urotoxicity of oxazaphosphorine cytostatics and its prevention--I. Experimental studies on the urotoxicity of alkylating compounds.
European journal of cancer.
1981 Jun; 17(6):595-607. doi:
10.1016/0014-2964(81)90261-9. [PMID: 7308258] - F D Juma, H J Rogers, J R Trounce. Effect of renal insufficiency on the pharmacokinetics of cyclophosphamide and some of its metabolites.
European journal of clinical pharmacology.
1981; 19(6):443-51. doi:
10.1007/bf00548589. [PMID: 7250178]