5-Bromouracil (BioDeep_00000815424)
代谢物信息卡片
化学式: C4H3BrN2O2 (189.9377878)
中文名称: 5-溴脲嘧啶
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1=C(C(=O)NC(=O)N1)Br
InChI: InChI=1S/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
描述信息
D009676 - Noxae > D000963 - Antimetabolites
D009676 - Noxae > D009153 - Mutagens
同义名列表
1 个代谢物同义名
数据库引用编号
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
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)
0 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
- Killeen S Kirkconnell, Brian Magnuson, Michelle T Paulsen, Brian Lu, Karan Bedi, Mats Ljungman. Gene length as a biological timer to establish temporal transcriptional regulation.
Cell cycle (Georgetown, Tex.).
2017 Feb; 16(3):259-270. doi:
10.1080/15384101.2016.1234550
. [PMID: 28055303] - François Coudoré, Denis Roche, Sandrine Lefeuvre, Delphine Faussot, Eliane M Billaud, Marie-Anne Loriot, Philippe Beaune. Validation of an ultra-high performance liquid chromatography tandem mass spectrometric method for quantifying uracil and 5,6-dihydrouracil in human plasma.
Journal of chromatographic science.
2012 Nov; 50(10):877-84. doi:
10.1093/chromsci/bms085
. [PMID: 22689904] - María Ibáñez, Juan V Sancho, Oscar J Pozo, Félix Hernández. Use of quadrupole time-of-flight mass spectrometry to determine proposed structures of transformation products of the herbicide bromacil after water chlorination.
Rapid communications in mass spectrometry : RCM.
2011 Oct; 25(20):3103-13. doi:
10.1002/rcm.5183
. [PMID: 21953966] - Takao Tamura, Akiko Kuwahara, Kaori Kadoyama, Motohiro Yamamori, Kohshi Nishiguchi, Tsubasa Inokuma, Yoshiji Takemoto, Naoko Chayahara, Tatsuya Okuno, Ikuya Miki, Yoshimi Fujishima, Toshiyuki Sakaeda. Effects of bolus injection of 5-fluorouracil on steady-state plasma concentrations of 5-fluorouracil in Japanese patients with advanced colorectal cancer.
International journal of medical sciences.
2011; 8(5):406-12. doi:
10.7150/ijms.8.406
. [PMID: 21750645] - Krzysztof Zienkiewicz, Anna Suwinska, Katarzyna Niedojadło, Agnieszka Zienkiewicz, Elzbieta Bednarska. Nuclear activity of sperm cells during Hyacinthus orientalis L. in vitro pollen tube growth.
Journal of experimental botany.
2011 Jan; 62(3):1255-69. doi:
10.1093/jxb/erq354
. [PMID: 21081664] - John Chen, Michael Zhou. Determination of eniluracil and 5-fluorouracil in human plasma by LC-MS/MS.
Bioanalysis.
2010 Dec; 2(12):2011-7. doi:
10.4155/bio.10.152
. [PMID: 21110744] - Ekta Khare, Naveen Kumar Arora. Effect of indole-3-acetic acid (IAA) produced by Pseudomonas aeruginosa in suppression of charcoal rot disease of chickpea.
Current microbiology.
2010 Jul; 61(1):64-8. doi:
10.1007/s00284-009-9577-6
. [PMID: 20049597] - Feng Gao, Mengliang Zhang, Xiangyong Cui, Zhonghua Wang, Yantong Sun, Jingkai Gu. Simultaneous quantitation of hydrochlorothiazide and metoprolol in human plasma by liquid chromatography-tandem mass spectrometry.
Journal of pharmaceutical and biomedical analysis.
2010 May; 52(1):149-54. doi:
10.1016/j.jpba.2009.12.012
. [PMID: 20079994] - P Chris Wilson, Sandra B Wilson. Toxicity of the herbicides bromacil and simazine to the aquatic macrophyte, Vallisneria americana Michx.
Environmental toxicology and chemistry.
2010 Jan; 29(1):201-11. doi:
10.1002/etc.22
. [PMID: 20821436] - Weisong Yu, Yingwu Wang, Yunhui Zhang, Dan Zhang, Jing Lan, Zeyuan Liu, Jingkai Gu, J Paul Fawcett. Quantitation of bergenin in human plasma by liquid chromatography/tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2009 Jan; 877(1-2):33-6. doi:
10.1016/j.jchromb.2008.11.005
. [PMID: 19036648] - Chih-Hao K Kao, Heng-Li Xie, Chia-Hsin Liao, Wen-Min Chen, Pan-Fu Kao. [18F]FBAU 3',5'-dibenzoate, a lipophilic prodrug, enhances brain uptake of the cell proliferation tracer [18F]FBAU.
Nuclear medicine and biology.
2008 Jul; 35(5):635-43. doi:
10.1016/j.nucmedbio.2008.04.004
. [PMID: 18589308] - Yuji Noro, Toshiyuki Takano-Shimizu, Kunihiko Syono, Yuji Kishima, Yoshio Sano. Genetic variations in rice in vitro cultures at the EPSPs-RPS20 region.
TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik.
2007 Feb; 114(4):705-11. doi:
10.1007/s00122-006-0470-4
. [PMID: 17177062] - Makoto Inada, Yukihiro Hirao, Toshihisa Koga, Minoru Itose, Jun-Ichi Kunizaki, Takefumi Shimizu, Hitoshi Sato. Relationships among plasma [2-(13)C]uracil concentrations, breath (13)CO(2) expiration, and dihydropyrimidine dehydrogenase (DPD) activity in the liver in normal and dpd-deficient dogs.
Drug metabolism and disposition: the biological fate of chemicals.
2005 Mar; 33(3):381-7. doi:
10.1124/dmd.104.001032
. [PMID: 15616154] - A Fraschini, M G Bottone, A I Scovassi, M Denegri, M C Risueño, P S Testillano, T E Martin, M Biggiogera, C Pellicciari. Changes in extranucleolar transcription during actinomycin D-induced apoptosis.
Histology and histopathology.
2005 01; 20(1):107-17. doi:
10.14670/hh-20.107
. [PMID: 15578429] - L Zufía, A Aldaz, J Giráldez. Simple determination of capecitabine and its metabolites by liquid chromatography with ultraviolet detection in a single injection.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2004 Sep; 809(1):51-8. doi:
10.1016/j.jchromb.2004.06.004
. [PMID: 15282093] - J Ciccolini, C Mercier, M-F Blachon, R Favre, A Durand, B Lacarelle. A simple and rapid high-performance liquid chromatographic (HPLC) method for 5-fluorouracil (5-FU) assay in plasma and possible detection of patients with impaired dihydropyrimidine dehydrogenase (DPD) activity.
Journal of clinical pharmacy and therapeutics.
2004 Aug; 29(4):307-15. doi:
10.1111/j.1365-2710.2004.00569.x
. [PMID: 15271097] - Dafeng Chu, Jingkai Gu, Wanhui Liu, J Paul Fawcett, Qingguang Dong. Sensitive liquid chromatographic assay for the simultaneous determination of 5-fluorouracil and its prodrug, tegafur, in beagle dog plasma.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2003 Oct; 795(2):377-82. doi:
10.1016/s1570-0232(03)00571-3
. [PMID: 14522043] - Jeffrey P Henderson, Jaeman Byun, Junko Takeshita, Jay W Heinecke. Phagocytes produce 5-chlorouracil and 5-bromouracil, two mutagenic products of myeloperoxidase, in human inflammatory tissue.
The Journal of biological chemistry.
2003 Jun; 278(26):23522-8. doi:
10.1074/jbc.m303928200
. [PMID: 12707270] - Laura Zufía, Azucena Aldaz, Carmen Castellanos, Joaquín Giráldez. Determination of 5-fluorouracil and its prodrug tegafur in plasma and tissue by high-performance liquid chromatography in a single injection: validation for application in clinical pharmacokinetic studies.
Therapeutic drug monitoring.
2003 Apr; 25(2):221-8. doi:
10.1097/00007691-200304000-00013
. [PMID: 12657918] - Li Lu, Linda Samuelsson, Mats Bergström, Kengo Sato, Karl-Johan Fasth, Bengt Långström. Rat studies comparing 11C-FMAU, 18F-FLT, and 76Br-BFU as proliferation markers.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine.
2002 Dec; 43(12):1688-98. doi:
NULL
. [PMID: 12468521] - Lea Muszkat, Leonid Feigelson, Lena Bir, Karol A Muszkat. Photocatalytic degradation of pesticides and bio-molecules in water.
Pest management science.
2002 Nov; 58(11):1143-8. doi:
10.1002/ps.578
. [PMID: 12449534] - Chih-Hao K Kao, Atsuo Waki, Mark B Sassaman, Elaine M Jagoda, Lawrence P Szajek, Laura Ravasi, Kazuaki Shimoji, William C Eckelman. Evaluation of [76Br]FBAU 3',5'-dibenzoate as a lipophilic prodrug for brain imaging.
Nuclear medicine and biology.
2002 Jul; 29(5):527-35. doi:
10.1016/s0969-8051(02)00324-4
. [PMID: 12088722] - J P Henderson, J Byun, M V Williams, D M Mueller, M L McCormick, J W Heinecke. Production of brominating intermediates by myeloperoxidase. A transhalogenation pathway for generating mutagenic nucleobases during inflammation.
The Journal of biological chemistry.
2001 Mar; 276(11):7867-75. doi:
10.1074/jbc.m005379200
. [PMID: 11096071] - T C Mueller, S A Senseman, R D Wauchope, C Clegg, R W Young, L M Southwick, M B Riley, H A Moye, J A Dumas, W Mersie, J D Mattice, R B Leidy. Recovery of atrazine, bromacil, chlorpyrifos, and metolachlor from water samples after concentration on solid-phase extraction disks: interlaboratory study.
Journal of AOAC International.
2000 Nov; 83(6):1327-33. doi:
. [PMID: 11128134]
- I Baranowska, C Pieszko. Determination of selected herbicides and phenols in water and soils by solid-phase extraction and high-performance liquid chromatography.
Journal of chromatographic science.
2000 May; 38(5):211-8. doi:
10.1093/chromsci/38.5.211
. [PMID: 10813519] - K Koberna, D Stanĕk, J Malínský, V Ctrnáctá, S Cermanová, J Novotná, V Kopský, I Raska. In situ fluorescence visualization of bromouridine incorporated into newly transcribed nucleolar RNA.
Acta histochemica.
2000 Feb; 102(1):15-20. doi:
10.1078/0065-1281-00535
. [PMID: 10726161] - G Brix, M E Bellemann, U Haberkorn. Biochemical modulation of the catabolism and tissue uptake of the anticancer drug 5-fluorouracil by 5-bromovinyluracil: assessment with metabolic (19)F MR imaging.
Magnetic resonance in medicine.
1999 Nov; 42(5):936-43. doi:
10.1002/(sici)1522-2594(199911)42:5<936::aid-mrm14>3.0.co;2-#
. [PMID: 10542353] - H Okuda, K Ogura, A Kato, H Takubo, T Watabe. A possible mechanism of eighteen patient deaths caused by interactions of sorivudine, a new antiviral drug, with oral 5-fluorouracil prodrugs.
The Journal of pharmacology and experimental therapeutics.
1998 Nov; 287(2):791-9. doi:
NULL
. [PMID: 9808711] - C G Zambonin, S Mastrolitti, F Palmisano. Determination of N3-methyl-5'-deoxy-5-fluorouridine, a novel metabolite of doxifluridine, in body fluids by high performance liquid chromatography.
Journal of pharmaceutical and biomedical analysis.
1998 Jun; 17(2):291-7. doi:
10.1016/s0731-7085(97)00200-8
. [PMID: 9638582] - J Tekel, S Tahotná, S Vaverková. Gas chromatographic method for determination of uracil herbicides in roots of Echinacea angustifolia Moench (Asteraceae).
Journal of pharmaceutical and biomedical analysis.
1998 Jan; 16(5):753-8. doi:
10.1016/s0731-7085(97)00118-0
. [PMID: 9535186] - H Hung, D Mackay. A novel and simple model of the uptake of organic chemicals by vegetation from air and soil.
Chemosphere.
1997 Sep; 35(5):959-77. doi:
10.1016/s0045-6535(97)00182-3
. [PMID: 9297787] - E Gamelin, M Boisdron-Celle, A Turcant, F Larra, P Allain, J Robert. Rapid and sensitive high-performance liquid chromatographic analysis of halogenopyrimidines in plasma.
Journal of chromatography. B, Biomedical sciences and applications.
1997 Aug; 695(2):409-16. doi:
10.1016/s0378-4347(97)00211-9
. [PMID: 9300878] - J Yan, S K Tyring, M M McCrary, P C Lee, S Haworth, R Raymond, S J Olsen, R B Diasio. The effect of sorivudine on dihydropyrimidine dehydrogenase activity in patients with acute herpes zoster.
Clinical pharmacology and therapeutics.
1997 May; 61(5):563-73. doi:
10.1016/s0009-9236(97)90136-3
. [PMID: 9164418] - H Nakayama, T Kinouchi, K Kataoka, S Akimoto, Y Matsuda, Y Ohnishi. Intestinal anaerobic bacteria hydrolyse sorivudine, producing the high blood concentration of 5-(E)-(2-bromovinyl)uracil that increases the level and toxicity of 5-fluorouracil.
Pharmacogenetics.
1997 Feb; 7(1):35-43. doi:
10.1097/00008571-199702000-00005
. [PMID: 9110360] - H Okuda, T Nishiyama, K Ogura, S Nagayama, K Ikeda, S Yamaguchi, Y Nakamura, K Kawaguchi, T Watabe, Y Ogura. Lethal drug interactions of sorivudine, a new antiviral drug, with oral 5-fluorouracil prodrugs.
Drug metabolism and disposition: the biological fate of chemicals.
1997 Feb; 25(2):270-3. doi:
NULL
. [PMID: 9029059] - I Melcák, M C Risueño, I Raska. Ultrastructural nonisotopic mapping of nucleolar transcription sites in onion protoplasts.
Journal of structural biology.
1996 Mar; 116(2):253-63. doi:
10.1006/jsbi.1996.0040
. [PMID: 8812981] - X P Lee, T Kumazawa, K Sato. Rapid extraction and capillary gas chromatography for diazine herbicides in human body fluids.
Forensic science international.
1995 Apr; 72(3):199-207. doi:
10.1016/0379-0738(95)01704-m
. [PMID: 7750875] - D B Whigan, A E Schuster. Manual and automated determination of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil and its metabolite (E)-5-(2-bromovinyl)uracil in urine.
Journal of chromatography. B, Biomedical applications.
1995 Feb; 664(2):357-63. doi:
10.1016/0378-4347(94)00487-p
. [PMID: 7780588] - D E Bergstrom, J K Abrahamson, M Y Chan. Nucleoside and nucleotide transport through a model liquid membrane. Periodic-catastrophic transport of a novel amantadine phosphoramidate conjugate of 5'-AMP.
Biochimica et biophysica acta.
1991 Jan; 1061(1):95-105. doi:
10.1016/0005-2736(91)90273-b
. [PMID: 1995060] - D A Ganes, J G Wagner. Improved high-performance liquid chromatographic assay for the quantification of 5-bromo-2'-deoxyuridine and 5-bromouracil in plasma.
Journal of chromatography.
1988 Nov; 432(?):233-42. doi:
10.1016/s0378-4347(00)80648-9
. [PMID: 3220891] - E De Clercq. Potential of bromovinyldeoxyuridine in anticancer chemotherapy.
Anticancer research.
1986 Jul; 6(4):549-56. doi:
. [PMID: 3752935]
- J Béres, W G Bentrude, A Kálmán, L Párkányi, J Balzarini, E De Clercq. Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
Journal of medicinal chemistry.
1986 Apr; 29(4):488-93. doi:
10.1021/jm00154a011
. [PMID: 3007759] - R Saffhill, W J Hume. The degradation of 5-iododeoxyuridine and 5-bromodeoxyuridine by serum from different sources and its consequences for the use of the compounds for incorporation into DNA.
Chemico-biological interactions.
1986 Mar; 57(3):347-55. doi:
10.1016/0009-2797(86)90008-6
. [PMID: 3698122] - C Desgranges, G Razaka, E De Clercq, P Herdewijn, J Balzarini, F Drouillet, H Bricaud. Effect of (E)-5-(2-bromovinyl)uracil on the catabolism and antitumor activity of 5-fluorouracil in rats and leukemic mice.
Cancer research.
1986 Mar; 46(3):1094-101. doi:
NULL
. [PMID: 3943086] - R M Kok, A P de Jong, C J van Groeningen, G J Peters, J Lankelma. Highly sensitive determination of 5-fluorouracil in human plasma by capillary gas chromatography and negative ion chemical ionization mass spectrometry.
Journal of chromatography.
1985 Sep; 343(1):59-66. doi:
10.1016/s0378-4347(00)84568-5
. [PMID: 4066861] - P L Stetson, U A Shukla, P R Amin, W D Ensminger. High-performance liquid chromatographic method for the determination of bromodeoxyuridine and its major metabolite, bromouracil, in biological fluids.
Journal of chromatography.
1985 May; 341(1):217-22. doi:
10.1016/s0378-4347(00)84032-3
. [PMID: 4019689] - Y Robinson, N Gerry, C W Vose. Simultaneous high-performance liquid chromatographic assay for 5-(2-bromo-E-ethenyl)-2'-deoxyuridine and its metabolite, 5-(2-bromo-E-ethenyl)uracil, in plasma.
Journal of chromatography.
1985 Feb; 338(1):219-24. doi:
10.1016/0378-4347(85)80089-x
. [PMID: 4019647] - S R Sharma, H S Sohi. Influence of herbicides on root rot of French beans (Phaseolus vulgaris L.), caused by Rhizoctonia solani.
Zentralblatt fur Mikrobiologie.
1983; 138(5):357-61. doi:
. [PMID: 6649952]
- R I Bikbulatov, E I Papilova, D M Braginskiĭ, G V Podgornaia, S A Demidova. [Toxicological study of the new antiviral agent, 5-bromuridine].
Farmakologiia i toksikologiia.
1980 Mar; 43(2):205-8. doi:
NULL
. [PMID: 7002600] - S Khristov, G Tamarov, I Karadzhov, G Ignatov. [Some properties of strains of the transmissible gastroenteritis virus of swine (TGE) isolated in Bulgaria].
Veterinarno-meditsinski nauki.
1975; 12(4):3-9. doi:
NULL
. [PMID: 175555] - P K Singh. Sensitization of algal virus to UV by the incorporation of 5-bromouracil and mutations of host alga Plectonema boryanum.
Zeitschrift fur allgemeine Mikrobiologie.
1975; 15(7):547-52. doi:
10.1002/jobm.3630150708
. [PMID: 813403] - V A Ado. [Non-specific inhibition of immunity].
Fiziolohichnyi zhurnal.
1974 May; 20(3):414-8. doi:
NULL
. [PMID: 4619375] - D S Packard, R A Menzies, R G Skalko. Incorportaiton of thymidine and its analogue, bromodeoxyuridine, into embryos and maternal tissues of the mouse.
Differentiation; research in biological diversity.
1973 Dec; 1(6):397-404. doi:
10.1111/j.1432-0436.1973.tb00137.x
. [PMID: 4802502] - N D Tarasenko, V A Sokolov. Mutagenic effect of 5-bromouracil on barley.
Soviet genetics.
1973 Dec; 7(8):987-90. doi:
"
. [PMID: 4783230] - G Calothy, K Hirai, V Defendi. 5-Bromodeoxyuridine incorporation into simian virus 40 deoxyribonucleic acid. Effects on simian virus 40 replication in monkey cells.
Virology.
1973 Oct; 55(2):329-38. doi:
10.1016/0042-6822(73)90172-4
. [PMID: 4355111] - D L Sawicki, B F Erlanger, S M Beiser. Immunochemical detection of minor bases in nucleic acids.
Science (New York, N.Y.).
1971 Oct; 174(4004):70-2. doi:
10.1126/science.174.4004.70
. [PMID: 5120872] - O D Gulati, D G Patel. Effects of various drugs on insulin antibodies.
British journal of pharmacology.
1971 May; 42(1):66-77. doi:
10.1111/j.1476-5381.1971.tb07087.x
. [PMID: 5580700] - L A Smets, J J Cornelis. Repairable and irrepairable damage in 5-bromouracil-substituted DNA exposed to ultra-violet radiation.
International journal of radiation biology and related studies in physics, chemistry, and medicine.
1971; 19(5):445-57. doi:
10.1080/09553007114550581
. [PMID: 5314345] - J LIPETZ, T STONIER. Effect of 5-bromuracil on crown gall tumour induction.
Nature.
1961 Jun; 190(?):929-30. doi:
10.1038/190929a0
. [PMID: 13762546]