Uracil mustard (BioDeep_00000008802)

 

Secondary id: BioDeep_00000858416

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


5-[bis(2-chloroethyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione

化学式: C8H11Cl2N3O2 (251.0228)
中文名称: 乌拉莫司汀
谱图信息: 最多检出来源 Homo sapiens(urine) 20.97%

分子结构信息

SMILES: C1=C(C(=O)NC(=O)N1)N(CCCl)CCCl
InChI: InChI=1S/C8H11Cl2N3O2/c9-1-3-13(4-2-10)6-5-11-8(15)12-7(6)14/h5H,1-4H2,(H2,11,12,14,15)

描述信息

Uracil mustard is only found in individuals that have used or taken this drug. It is a nitrogen mustard derivative of uracil. It is a alkylating antineoplastic agent that is used in lymphatic malignancies, and causes mainly gastrointestinal and bone marrow damage. [PubChem]After activation, uracil mustard binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function.
L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01A - Alkylating agents > L01AD - Nitrosoureas
D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D009588 - Nitrogen Mustard Compounds
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent
D009676 - Noxae > D000477 - Alkylating Agents
Same as: D06265

同义名列表

15 个代谢物同义名

5-[bis(2-chloroethyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione; 5-(Bis(2-chloroethyl)amino)-2,4-(1H,3H)pyrimidinedione; 5-[Bis(2-chloroethyl)amino]-2,4(1H,3H)-pyrimidinedione; 5-[Di(beta-chloroethyl)amino]uracil; 5-N,N-Bis(2-chloroethyl)aminouracil; 5-[Di(b-chloroethyl)amino]uracil; 5-[Di(β-chloroethyl)amino]uracil; 5-(Di-2-chloroethyl)aminouracil; Uracil nitrogen mustard; 5-Aminouracil mustard; Aminouracil mustard; Mustard, uracil; Uracil mustard; Uramustine; Uracil mustard



数据库引用编号

15 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。

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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。

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

  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Deepali Katoch, Shiv Kumar, Neeraj Kumar, Bikram Singh. Simultaneous quantification of Amaryllidaceae alkaloids from Zephyranthes grandiflora by UPLC-DAD/ESI-MS/MS. Journal of pharmaceutical and biomedical analysis. 2012 Dec; 71(?):187-92. doi: 10.1016/j.jpba.2012.08.001. [PMID: 22939505]
  • Jerald J Nair, Lucie Rárová, Miroslav Strnad, Jaume Bastida, Johannes van Staden. Apoptosis-inducing effects of distichamine and narciprimine, rare alkaloids of the plant family Amaryllidaceae. Bioorganic & medicinal chemistry letters. 2012 Oct; 22(19):6195-9. doi: 10.1016/j.bmcl.2012.08.005. [PMID: 22921081]
  • Giovanni Luchetti, Robert Johnston, Véronique Mathieu, Florence Lefranc, Kathryn Hayden, Anna Andolfi, Delphine Lamoral-Theys, Mary R Reisenauer, Cody Champion, Stephen C Pelly, Willem A L van Otterlo, Igor V Magedov, Robert Kiss, Antonio Evidente, Snezna Rogelj, Alexander Kornienko. Bulbispermine: a crinine-type Amaryllidaceae alkaloid exhibiting cytostatic activity toward apoptosis-resistant glioma cells. ChemMedChem. 2012 May; 7(5):815-22. doi: 10.1002/cmdc.201100608. [PMID: 22389235]
  • Ivan Ivanov, Vasil Georgiev, Strahil Berkov, Atanas Pavlov. Alkaloid patterns in Leucojum aestivum shoot culture cultivated at temporary immersion conditions. Journal of plant physiology. 2012 Jan; 169(2):206-11. doi: 10.1016/j.jplph.2011.09.010. [PMID: 22118817]
  • Raquel B Giordani, Jean P de Andrade, Hugo Verli, Julie H Dutilh, Amélia T Henriques, Strahil Berkov, Jaume Bastida, José Angelo S Zuanazzi. Alkaloids from Hippeastrum morelianum Lem. (Amaryllidaceae). Magnetic resonance in chemistry : MRC. 2011 Oct; 49(10):668-72. doi: 10.1002/mrc.2794. [PMID: 21898585]
  • Antonio Evidente, Artem S Kireev, Aaron R Jenkins, Anntherese E Romero, Wim F A Steelant, Severine Van Slambrouck, Alexander Kornienko. Biological evaluation of structurally diverse amaryllidaceae alkaloids and their synthetic derivatives: discovery of novel leads for anticancer drug design. Planta medica. 2009 Apr; 75(5):501-7. doi: 10.1055/s-0029-1185340. [PMID: 19235683]
  • O B Abdel-Halim, A M Marzouk, R Mothana, N Awadh. A new tyrosinase inhibitor from Crinum yemense as potential treatment for hyperpigmentation. Die Pharmazie. 2008 May; 63(5):405-7. doi: . [PMID: 18557429]
  • Liliya Georgieva, Strahil Berkov, Violeta Kondakova, Jaume Bastida, Francesc Viladomat, Atanas Atanassov, Carles Codina. Alkaloid variability in Leucojum aestivum from wild populations. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2007 Sep; 62(9-10):627-35. doi: 10.1515/znc-2007-9-1002. [PMID: 18069233]
  • László Szlávik, Agnes Gyuris, János Minárovits, Peter Forgo, József Molnár, Judit Hohmann. Alkaloids from Leucojum vernum and antiretroviral activity of Amaryllidaceae alkaloids. Planta medica. 2004 Sep; 70(9):871-3. doi: 10.1055/s-2004-827239. [PMID: 15386196]
  • Strahil Berkov, Luba Evstatieva, Simeon Popov. Alkaloids in Bulgarian Pancratium maritimum L. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2004 Jan; 59(1-2):65-9. doi: 10.1515/znc-2004-1-214. [PMID: 15018055]
  • Bilge Sener, Ilkay Orhan, Jutamad Satayavivad. Antimalarial activity screening of some alkaloids and the plant extracts from Amaryllidaceae. Phytotherapy research : PTR. 2003 Dec; 17(10):1220-3. doi: 10.1002/ptr.1346. [PMID: 14669261]
  • Susana López, Jaume Bastida, Francesc Viladomat, Carles Codina. Galanthamine pattern in Narcissus confusus plants. Planta medica. 2003 Dec; 69(12):1166-8. doi: 10.1055/s-2003-818013. [PMID: 14750039]
  • Susana López, Jaume Bastida, Francesc Viladomat, Carles Codina. Solid-phase extraction and reversed-phase high-performance liquid chromatography of the five major alkaloids in Narcissus confusus. Phytochemical analysis : PCA. 2002 Nov; 13(6):311-5. doi: 10.1002/pca.660. [PMID: 12494748]
  • Judit Hohmann, Peter Forgo, Joseph Molnár, Krisztina Wolfard, Annamária Molnár, Theresia Thalhammer, Imre Máthé, Derek Sharples. Antiproliferative amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis. Planta medica. 2002 May; 68(5):454-7. doi: 10.1055/s-2002-32068. [PMID: 12058326]
  • A V Carb. Polycythemia vera in a dog. Journal of the American Veterinary Medical Association. 1969 Feb; 154(3):289-97. doi: NULL. [PMID: 5812582]
  • S F Brunk, J H Cavanaugh. The distribution of radioactivity from uracil mustard-2-14C in the hepatic subcellular particulates and nucleic acids of the rat. Toxicology and applied pharmacology. 1967 Nov; 11(3):565-74. doi: 10.1016/0041-008x(67)90057-9. [PMID: 5586365]
  • C W Abell, L A Rosini, J A DiPaolo. Effects of uracil mustard on DNA, RNA, and protein biosynthesis in tissues of A-J mice. Cancer research. 1967 Jun; 27(6):1101-8. doi: NULL. [PMID: 6027200]
  • G BALLERINI, L BOSI, P L PARESCHI, E PUNTURIERI. [EXPERIMENTAL CHROMOSOME ALTERATIONS DUE TO CYCLOPHOSPHAMIDE AND URACIL-MUSTARD]. L' Arcispedale S. Anna di Ferrara. 1964; 17(?):1139-52. doi: ". [PMID: 14265725]
  • E A KOST, A L KOZYREVA. [ON DOPAN (EXPERIMENTAL STUDIES ON DOPAN LABELED WITH C-14)]. Farmakologiia i toksikologiia. 1963 Nov; 26(?):729-32. doi: NULL. [PMID: 14176187]
  • H M WILLIAMS. CLINICAL EVALUATION OF URACIL MUSTARD. Cancer chemotherapy reports. 1963 Oct; 32(?):73-6. doi: NULL. [PMID: 14088838]
  • E SHANBROM, S MILLER, H HAAR, R OPFELL. Therapeutic spectrum of uracil-mustard, a new oral antitumor drug. With special reference to the effects of small dosage in lymphomas, chronic leukemias, and ovarian carcinoma. JAMA. 1960 Nov; 174(?):1702-5. doi: 10.1001/jama.1960.03030130030008. [PMID: 13750663]