dihydrouracil (BioDeep_00000267406)

Main id: BioDeep_00000003090

 

natural product PANOMIX_OTCML-2023 BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


"5,6-DIHYDROURACIL"

化学式: C4H6N2O2 (114.04292559999999)
中文名称: 二氢尿嘧啶
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CNC(=O)NC1=O
InChI: InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)

描述信息

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SARS
Dihydrouracil (5,6-Dihydrouracil), a metabolite of Uracil, can be used as a marker for identification of dihydropyrimidine dehydrogenase (DPD)-deficient[1][2].
Dihydrouracil (5,6-Dihydrouracil), a metabolite of Uracil, can be used as a marker for identification of dihydropyrimidine dehydrogenase (DPD)-deficient[1][2].

同义名列表

4 个代谢物同义名

dihydrouracil; "5,6-DIHYDROURACIL"; 5,6-Dihydrouracil; 5,6-Dihydrouracil



数据库引用编号

25 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(3)

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)

8 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

  • Beatrice Campanella, Tommaso Lomonaco, Edoardo Benedetti, Massimo Onor, Riccardo Nieri, Federica Marmorino, Chiara Cremolini, Emilia Bramanti. Fast, Direct Dihydrouracil Quantitation in Human Saliva: Method Development, Validation, and Application. International journal of environmental research and public health. 2022 05; 19(10):. doi: 10.3390/ijerph19106033. [PMID: 35627569]
  • Sara Capiau, Anniek Van Landschoot, Tim Reyns, Hedwig Stepman. Pre-analytical considerations for the analysis of uracil and 5,6-dihydrouracil in heparin plasma. Clinical chemistry and laboratory medicine. 2022 04; 60(5):e112-e115. doi: 10.1515/cclm-2021-0921. [PMID: 35073467]
  • Kathryn E Burns, Ottiniel Chavani, Soo Hee Jeong, John A Duley, David Porter, Michael Findlay, R Matthew Strother, Nuala A Helsby. Comparison of a thymine challenge test and endogenous uracil-dihydrouracil levels for assessment of fluoropyrimidine toxicity risk. Cancer chemotherapy and pharmacology. 2021 05; 87(5):711-716. doi: 10.1007/s00280-021-04240-2. [PMID: 33687515]
  • Nicolas Pallet, Salma Hamdane, Simon Garinet, Hélène Blons, Aziz Zaanan, Elena Paillaud, Julien Taieb, Olivier Laprevote, Marie-Anne Loriot, Céline Narjoz. A comprehensive population-based study comparing the phenotype and genotype in a pretherapeutic screen of dihydropyrimidine dehydrogenase deficiency. British journal of cancer. 2020 09; 123(5):811-818. doi: 10.1038/s41416-020-0962-z. [PMID: 32595208]
  • Clémence Marin, Anis Krache, Chloé Palmaro, Mathilde Lucas, Valentin Hilaire, Renée Ugdonne, Bénédicte De Victor, Sylvie Quaranta, Caroline Solas, Bruno Lacarelle, Joseph Ciccolini. A Simple and Rapid UPLC-UV Method for Detecting DPD Deficiency in Patients With Cancer. Clinical and translational science. 2020 07; 13(4):761-768. doi: 10.1111/cts.12762. [PMID: 32058656]
  • Xandra García-González, Bartosz Kaczmarczyk, Judith Abarca-Zabalía, Fabienne Thomas, Pilar García-Alfonso, Luis Robles, Vanessa Pachón, Ángeles Vaz, Sara Salvador-Martín, María Sanjurjo-Sáez, Luis A López-Fernández. New DPYD variants causing DPD deficiency in patients treated with fluoropyrimidine. Cancer chemotherapy and pharmacology. 2020 07; 86(1):45-54. doi: 10.1007/s00280-020-04093-1. [PMID: 32529295]
  • Tiphaine Robin, Franck Saint-Marcoux, Doriane Toinon, Naïma Tafzi, Pierre Marquet, Souleiman El Balkhi. Automatic quantification of uracil and dihydrouracil in plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Apr; 1142(?):122038. doi: 10.1016/j.jchromb.2020.122038. [PMID: 32169798]
  • Jihane Basbous, Antoine Aze, Laurent Chaloin, Rana Lebdy, Dana Hodroj, Cyril Ribeyre, Marion Larroque, Caitlin Shepard, Baek Kim, Alain Pruvost, Jérôme Moreaux, Domenico Maiorano, Marcel Mechali, Angelos Constantinou. Dihydropyrimidinase protects from DNA replication stress caused by cytotoxic metabolites. Nucleic acids research. 2020 02; 48(4):1886-1904. doi: 10.1093/nar/gkz1162. [PMID: 31853544]
  • Shinji Kobuchi, Mako Akutagawa, Yukako Ito, Toshiyuki Sakaeda. Association between the pharmacokinetics of capecitabine and the plasma dihydrouracil to uracil ratio in rat: A surrogate biomarker for dihydropyrimidine dehydrogenase activity. Biopharmaceutics & drug disposition. 2019 Jan; 40(1):44-48. doi: 10.1002/bdd.2168. [PMID: 30592773]
  • Linda M Henricks, Bart A W Jacobs, Didier Meulendijks, Dick Pluim, Daan van den Broek, Niels de Vries, Hilde Rosing, Jos H Beijnen, Alwin D R Huitema, Henk-Jan Guchelaar, Annemieke Cats, Jan H M Schellens. Food-effect study on uracil and dihydrouracil plasma levels as marker for dihydropyrimidine dehydrogenase activity in human volunteers. British journal of clinical pharmacology. 2018 12; 84(12):2761-2769. doi: 10.1111/bcp.13719. [PMID: 30047584]
  • Olavo Vicente Neto, Suziane Raymundo, Maria Alice Franzoi, Andiara do Carmo Artmann, Mariane Tegner, Victoria Vendramini Müller, Roberta Zilles Hahn, Gustavo Vasconcelos Alves, Gilberto Schwartsmann, Rafael Linden, Marina Venzon Antunes. DPD functional tests in plasma, fresh saliva and dried saliva samples as predictors of 5-fluorouracil exposure and occurrence of drug-related severe toxicity. Clinical biochemistry. 2018 Jun; 56(?):18-25. doi: 10.1016/j.clinbiochem.2018.04.001. [PMID: 29625079]
  • Bart A W Jacobs, Nikol Snoeren, Morsal Samim, Hilde Rosing, Niels de Vries, Maarten J Deenen, Jos H Beijnen, Jan H M Schellens, Miriam Koopman, Richard van Hillegersberg. The impact of liver resection on the dihydrouracil:uracil plasma ratio in patients with colorectal liver metastases. European journal of clinical pharmacology. 2018 Jun; 74(6):737-744. doi: 10.1007/s00228-018-2426-4. [PMID: 29430582]
  • Yoko Nakajima, Judith Meijer, Doreen Dobritzsch, Tetsuya Ito, Chunhua Zhang, Xu Wang, Yoriko Watanabe, Kyoko Tashiro, Rutger Meinsma, Jeroen Roelofsen, Lida Zoetekouw, André B P van Kuilenburg. Dihydropyrimidinase deficiency in four East Asian patients due to novel and rare DPYS mutations affecting protein structural integrity and catalytic activity. Molecular genetics and metabolism. 2017 12; 122(4):216-222. doi: 10.1016/j.ymgme.2017.10.003. [PMID: 29054612]
  • Wen Pan, Yuandong Li, Yan Feng, Fan Yang, Haizhou Liu. A new sample preparation and separation combination for the precise, accurate, and simultaneous determination of uracil and dihydrouracil in human plasma by reversed-phase HPLC. Journal of separation science. 2017 Oct; 40(19):3763-3770. doi: 10.1002/jssc.201700279. [PMID: 28726286]
  • Didier Meulendijks, Linda M Henricks, Bart A W Jacobs, Abidin Aliev, Maarten J Deenen, Niels de Vries, Hilde Rosing, Erik van Werkhoven, Anthonius de Boer, Jos H Beijnen, Caroline M P W Mandigers, Marcel Soesan, Annemieke Cats, Jan H M Schellens. Pretreatment serum uracil concentration as a predictor of severe and fatal fluoropyrimidine-associated toxicity. British journal of cancer. 2017 May; 116(11):1415-1424. doi: 10.1038/bjc.2017.94. [PMID: 28427087]
  • Andrés Fernando Andrade Galarza, Rafael Linden, Marina Venzon Antunes, Roberta Zilles Hahn, Suziane Raymundo, Anne Caroline Cezimbra da Silva, Rodrigo Staggemeier, Fernando Rosado Spilki, Gilberto Schwartsmann. Endogenous plasma and salivary uracil to dihydrouracil ratios and DPYD genotyping as predictors of severe fluoropyrimidine toxicity in patients with gastrointestinal malignancies. Clinical biochemistry. 2016 Nov; 49(16-17):1221-1226. doi: 10.1016/j.clinbiochem.2016.07.004. [PMID: 27399164]
  • Bart A W Jacobs, Maarten J Deenen, Dick Pluim, J G Coen van Hasselt, Martin D Krähenbühl, Robin M J M van Geel, Niels de Vries, Hilde Rosing, Didier Meulendijks, Artur M Burylo, Annemieke Cats, Jos H Beijnen, Alwin D R Huitema, Jan H M Schellens. Pronounced between-subject and circadian variability in thymidylate synthase and dihydropyrimidine dehydrogenase enzyme activity in human volunteers. British journal of clinical pharmacology. 2016 09; 82(3):706-16. doi: 10.1111/bcp.13007. [PMID: 27161955]
  • Bart A W Jacobs, Hilde Rosing, Niels de Vries, Didier Meulendijks, Linda M Henricks, Jan H M Schellens, Jos H Beijnen. Development and validation of a rapid and sensitive UPLC-MS/MS method for determination of uracil and dihydrouracil in human plasma. Journal of pharmaceutical and biomedical analysis. 2016 Jul; 126(?):75-82. doi: 10.1016/j.jpba.2016.04.039. [PMID: 27179185]
  • Maurice C van Staveren, Andre B P van Kuilenburg, Henk-Jan Guchelaar, Judith Meijer, Cornelis J A Punt, Robert S de Jong, Hans Gelderblom, Jan Gerard Maring. Evaluation of an oral uracil loading test to identify DPD-deficient patients using a limited sampling strategy. British journal of clinical pharmacology. 2016 Mar; 81(3):553-61. doi: 10.1111/bcp.12821. [PMID: 26551538]
  • F Thomas, I Hennebelle, C Delmas, I Lochon, C Dhelens, C Garnier Tixidre, A Bonadona, N Penel, A Goncalves, J P Delord, C Toulas, E Chatelut. Genotyping of a family with a novel deleterious DPYD mutation supports the pretherapeutic screening of DPD deficiency with dihydrouracil/uracil ratio. Clinical pharmacology and therapeutics. 2016 Feb; 99(2):235-42. doi: 10.1002/cpt.210. [PMID: 26265035]
  • Roberta Zilles Hahn, Andrés Fernando Andrade Galarza, Anelise Schneider, Marina Venzon Antunes, Gilberto Schwartsmann, Rafael Linden. Improved determination of uracil and dihydrouracil in plasma after a loading oral dose of uracil using high-performance liquid chromatography with photodiode array detection and porous graphitic carbon stationary phase. Clinical biochemistry. 2015 Sep; 48(13-14):915-8. doi: 10.1016/j.clinbiochem.2015.04.019. [PMID: 25940841]
  • Drupad K Trivedi, Ray K Iles. Shotgun metabolomic profiles in maternal urine identify potential mass spectral markers of abnormal fetal biochemistry - dihydrouracil and progesterone in the metabolism of Down syndrome. Biomedical chromatography : BMC. 2015 Aug; 29(8):1173-83. doi: 10.1002/bmc.3404. [PMID: 25545476]
  • Maurice C van Staveren, Frans Opdam, Henk-Jan Guchelaar, André B P van Kuilenburg, Jan Gerard Maring, Hans Gelderblom. Influence of metastatic disease on the usefulness of uracil pharmacokinetics as a screening tool for DPD activity in colorectal cancer patients. Cancer chemotherapy and pharmacology. 2015 Jul; 76(1):47-52. doi: 10.1007/s00280-015-2746-3. [PMID: 25957957]
  • Johanna Sistonen, Barbara Büchel, Tanja K Froehlich, Dominic Kummer, Stefano Fontana, Markus Joerger, André B P van Kuilenburg, Carlo R Largiadèr. Predicting 5-fluorouracil toxicity: DPD genotype and 5,6-dihydrouracil:uracil ratio. Pharmacogenomics. 2014 Sep; 15(13):1653-66. doi: 10.2217/pgs.14.126. [PMID: 25410891]
  • C F Saba, C W Schmiedt, K G Freeman, G L Edwards. Indirect assessment of dihydropyrimidine dehydrogenase activity in cats. Veterinary and comparative oncology. 2013 Dec; 11(4):265-71. doi: 10.1111/vco.12064. [PMID: 24007333]
  • Shinji Kobuchi, Shota Kuwano, Kazuki Imoto, Kae Okada, Asako Nishimura, Yukako Ito, Nobuhito Shibata, Kanji Takada. A predictive biomarker for altered 5-fluorouracil pharmacokinetics following repeated administration in a rat model of colorectal cancer. Biopharmaceutics & drug disposition. 2013 Oct; 34(7):365-76. doi: 10.1002/bdd.1851. [PMID: 23836081]
  • C W Yeung, M M Yau, C K Ma, T S Siu, Sidney Tam, C W Lam. Diagnosis of dihydropyrimidinase deficiency in a Chinese boy with dihydropyrimidinuria. Hong Kong medical journal = Xianggang yi xue za zhi. 2013 Jun; 19(3):272-5. doi: 10.12809/hkmj133598. [PMID: 23732435]
  • Shinji Kobuchi, Yukako Ito, Kae Okada, Kazuki Imoto, Shota Kuwano, Kanji Takada. Pharmacokinetic/pharmacodynamic modeling of 5-fluorouracil by using a biomarker to predict tumor growth in a rat model of colorectal cancer. Journal of pharmaceutical sciences. 2013 Jun; 102(6):2056-2067. doi: 10.1002/jps.23547. [PMID: 23592368]
  • Shinji Kobuchi, Yukako Ito, Kae Okada, Kazuki Imoto, Shota Kuwano, Kanji Takada. Pre-therapeutic assessment of plasma dihydrouracil/uracil ratio for predicting the pharmacokinetic parameters of 5-fluorouracil and tumor growth in a rat model of colorectal cancer. Biological & pharmaceutical bulletin. 2013; 36(6):907-16. doi: 10.1248/bpb.b12-00819. [PMID: 23575271]
  • 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]
  • M B Garg, L F Lincz, K Adler, F E Scorgie, S P Ackland, J A Sakoff. Predicting 5-fluorouracil toxicity in colorectal cancer patients from peripheral blood cell telomere length: a multivariate analysis. British journal of cancer. 2012 Oct; 107(9):1525-33. doi: 10.1038/bjc.2012.421. [PMID: 22990653]
  • Yvonne Wettergren, Göran Carlsson, Elisabeth Odin, Bengt Gustavsson. Pretherapeutic uracil and dihydrouracil levels of colorectal cancer patients are associated with sex and toxic side effects during adjuvant 5-fluorouracil-based chemotherapy. Cancer. 2012 Jun; 118(11):2935-43. doi: 10.1002/cncr.26595. [PMID: 22020693]
  • André B P van Kuilenburg, Peter Häusler, Andreas Schalhorn, Michael W T Tanck, Johannes H Proost, Christoph Terborg, Detlev Behnke, Wolfgang Schwabe, Kati Jabschinsky, Jan Gerard Maring. Evaluation of 5-fluorouracil pharmacokinetics in cancer patients with a c.1905+1G>A mutation in DPYD by means of a Bayesian limited sampling strategy. Clinical pharmacokinetics. 2012 Mar; 51(3):163-74. doi: 10.1007/bf03257473. [PMID: 22339448]
  • Isabela Costa César, Geraldo F Cunha-Júnior, Ricardo M Duarte Byrro, Luiz Gonzaga Vaz Coelho, Gerson A Pianetti. A rapid HPLC-ESI-MS/MS method for determination of dihydrouracil/uracil ratio in plasma: evaluation of toxicity to 5-flurouracil in patients with gastrointestinal cancer. Therapeutic drug monitoring. 2012 Feb; 34(1):59-66. doi: 10.1097/ftd.0b013e318240405f. [PMID: 22210098]
  • Barna Budai, Viktor Komlósi, Vilmos Adleff, Éva Pap, Andrea Réti, Tünde Nagy, Judit Kralovánszky, István Láng, Erika Hitre. Impact of SHMT1 polymorphism on the clinical outcome of patients with metastatic colorectal cancer treated with first-line FOLFIRI+bevacizumab. Pharmacogenetics and genomics. 2012 Jan; 22(1):69-72. doi: 10.1097/fpc.0b013e32834d8376. [PMID: 22044939]
  • Chad W Schmiedt, Corey F Saba, Kimberly G Freeman, Gaylen L Edwards. Assessment of plasma uracil-to-dihydrouracil concentration ratio as an indicator of dihydropyrimidine dehydrogenase activity in clinically normal dogs and dogs with neoplasia or renal insufficiency. American journal of veterinary research. 2012 Jan; 73(1):119-24. doi: 10.2460/ajvr.73.1.119. [PMID: 22204297]
  • Maurice C van Staveren, Barbara Theeuwes-Oonk, Henk Jan Guchelaar, André B P van Kuilenburg, Jan Gerard Maring. Pharmacokinetics of orally administered uracil in healthy volunteers and in DPD-deficient patients, a possible tool for screening of DPD deficiency. Cancer chemotherapy and pharmacology. 2011 Dec; 68(6):1611-7. doi: 10.1007/s00280-011-1661-5. [PMID: 21590448]
  • Johannes Gerlach, Monika Löffler, Martin K-H Schäfer. Gene expression of enzymes required for the de novo synthesis and degradation of pyrimidines in rat peripheral tissues and brain. Nucleosides, nucleotides & nucleic acids. 2011 Dec; 30(12):1147-54. doi: 10.1080/15257770.2011.603712. [PMID: 22132969]
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  • Stefanie Cornelius, Sandra Witz, Hardy Rolletschek, Torsten Möhlmann. Pyrimidine degradation influences germination seedling growth and production of Arabidopsis seeds. Journal of experimental botany. 2011 Nov; 62(15):5623-32. doi: 10.1093/jxb/err251. [PMID: 21865177]
  • Pierre-Yves Cordier, André Nau, Joseph Ciccolini, Manuela Oliver, Cédric Mercier, Bruno Lacarelle, Eric Peytel. 5-FU-induced neurotoxicity in cancer patients with profound DPD deficiency syndrome: a report of two cases. Cancer chemotherapy and pharmacology. 2011 Sep; 68(3):823-6. doi: 10.1007/s00280-011-1666-0. [PMID: 21553285]
  • Sabine Weidensee, Peter Goettig, Marko Bertone, Dorothea Haas, Viktor Magdolen, Marion Kiechle, Alfons Meindl, André B P van Kuilenburg, Eva Gross. A mild phenotype of dihydropyrimidine dehydrogenase deficiency and developmental retardation associated with a missense mutation affecting cofactor binding. Clinical biochemistry. 2011 Jun; 44(8-9):722-4. doi: 10.1016/j.clinbiochem.2011.03.033. [PMID: 21420945]
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