5,6-Dihydro-5-fluorouracil (BioDeep_00000011317)

 

Secondary id: BioDeep_00001878035

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


5-Fluorodihydrouracil, sodium salt

化学式: C4H5FN2O2 (132.0335042)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 3.86%

分子结构信息

SMILES: C1C(C(=O)NC(=O)N1)F
InChI: InChI=1S/C4H5FN2O2/c5-2-1-6-4(9)7-3(2)8/h2H,1H2,(H2,6,7,8,9)

描述信息

5,6-Dihydro-5-fluorouracil is a metabolite of fluorouracil. Fluorouracil (5-FU or f5U) (sold under the brand names Adrucil, Carac, Efudix, Efudex and Fluoroplex) is a drug that is a pyrimidine analog which is used in the treatment of cancer. It is a suicide inhibitor and works through irreversible inhibition of thymidylate synthase. It belongs to the family of drugs called antimetabolites. It is typically administered with leucovorin. (Wikipedia)

同义名列表

9 个代谢物同义名

5-Fluorodihydrouracil, sodium salt; 5-fluoro-1,3-diazinane-2,4-dione; (R)-5-Fluoro-5,6-dihydrouracil; 5,6-Dihydro-5-fluorouracil; 5,6-Dihydrofluorouracil; Dihydro-5-fluorouracil; 5-fluorodihydrouracil; 5-Dihydrofluorouracil; DHFU



数据库引用编号

11 个数据库交叉引用编号

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(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(1)

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

  • Ju-Han Liu, Yung-Yi Cheng, Chen-Hsi Hsieh, Tung-Hu Tsai. The Herb-Drug Pharmacokinetic Interaction of 5-Fluorouracil and Its Metabolite 5-Fluoro-5,6-Dihydrouracil with a Traditional Chinese Medicine in Rats. International journal of molecular sciences. 2017 Dec; 19(1):. doi: 10.3390/ijms19010025. [PMID: 29295501]
  • Barbara Büchel, Peter Rhyn, Stefan Schürch, Claudia Bühr, Ursula Amstutz, Carlo R Largiadèr. LC-MS/MS method for simultaneous analysis of uracil, 5,6-dihydrouracil, 5-fluorouracil and 5-fluoro-5,6-dihydrouracil in human plasma for therapeutic drug monitoring and toxicity prediction in cancer patients. Biomedical chromatography : BMC. 2013 Jan; 27(1):7-16. doi: 10.1002/bmc.2741. [PMID: 22454320]
  • Giacomo Allegrini, Teresa Di Desidero, Maria Teresa Barletta, Anna Fioravanti, Paola Orlandi, Bastianina Canu, Silvio Chericoni, Fotios Loupakis, Antonello Di Paolo, Gianluca Masi, Andrea Fontana, Sara Lucchesi, Giada Arrighi, Mario Giusiani, Andrea Ciarlo, Giovanni Brandi, Romano Danesi, Robert S Kerbel, Alfredo Falcone, Guido Bocci. Clinical, pharmacokinetic and pharmacodynamic evaluations of metronomic UFT and cyclophosphamide plus celecoxib in patients with advanced refractory gastrointestinal cancers. Angiogenesis. 2012 Jun; 15(2):275-86. doi: 10.1007/s10456-012-9260-6. [PMID: 22382585]
  • Christian Woloch, Antonello Di Paolo, Hafedh Marouani, Guido Bocci, Joseph Ciccolini, Bruno Lacarelle, Romano Danesi, Athanassios Iliadis. Population pharmacokinetic analysis of 5-FU and 5-FDHU in colorectal cancer patients: search for biomarkers associated with gastro-intestinal toxicity. Current topics in medicinal chemistry. 2012; 12(15):1713-9. doi: 10.2174/156802612803531414. [PMID: 22978343]
  • Masao Kobayakawa, Yasushi Kojima. Tegafur/gimeracil/oteracil (S-1) approved for the treatment of advanced gastric cancer in adults when given in combination with cisplatin: a review comparing it with other fluoropyrimidine-based therapies. OncoTargets and therapy. 2011; 4(?):193-201. doi: 10.2147/ott.s19059. [PMID: 22162925]
  • Chen-Hsi Hsieh, Chia-Yuan Liu, Yen-Ju Hsieh, Hung-Chi Tai, Li-Ying Wang, Tung-Hu Tsai, Yu-Jen Chen. Matrix metalloproteinase-8 mediates the unfavorable systemic impact of local irradiation on pharmacokinetics of anti-cancer drug 5-Fluorouracil. PloS one. 2011; 6(6):e21000. doi: 10.1371/journal.pone.0021000. [PMID: 21695264]
  • Sara Nannizzi, Gareth J Veal, Elisa Giovannetti, Valentina Mey, Simona Ricciardi, Christopher J Ottley, Mario Del Tacca, Romano Danesi. Cellular and molecular mechanisms for the synergistic cytotoxicity elicited by oxaliplatin and pemetrexed in colon cancer cell lines. Cancer chemotherapy and pharmacology. 2010 Aug; 66(3):547-58. doi: 10.1007/s00280-009-1195-2. [PMID: 20020129]
  • Xiaofan Zhang, Julia Li Zhong, Wei Liu, Zuhua Gao, Xia Xue, Pan Yue, Limei Wang, Cuirong Zhao, Wenfang Xu, Xianjun Qu. N(3)-o-toluyl-fluorouracil inhibits human hepatocellular carcinoma cell growth via sustained release of 5-FU. Cancer chemotherapy and pharmacology. 2010 May; 66(1):11-9. doi: 10.1007/s00280-009-1128-0. [PMID: 19756602]
  • Liia D Vainchtein, Hilde Rosing, Jan H M Schellens, Jos H Beijnen. A new, validated HPLC-MS/MS method for the simultaneous determination of the anti-cancer agent capecitabine and its metabolites: 5'-deoxy-5-fluorocytidine, 5'-deoxy-5-fluorouridine, 5-fluorouracil and 5-fluorodihydrouracil, in human plasma. Biomedical chromatography : BMC. 2010 Apr; 24(4):374-86. doi: 10.1002/bmc.1302. [PMID: 19650151]
  • Chen-Hsi Hsieh, Yen-Ju Hsieh, Chia-Yuan Liu, Hung-Chi Tai, Yu-Chuen Huang, Pei-Wei Shueng, Le-Jung Wu, Li-Ying Wang, Tung-Hu Tsai, Yu-Jen Chen. Abdominal irradiation modulates 5-Fluorouracil pharmacokinetics. Journal of translational medicine. 2010 Mar; 8(?):29. doi: 10.1186/1479-5876-8-29. [PMID: 20338060]
  • Antonello Di Paolo, Monica Lencioni, Federica Amatori, Samantha Di Donato, Guido Bocci, Cinzia Orlandini, Marianna Lastella, Francesca Federici, Mauro Iannopollo, Alfredo Falcone, Sergio Ricci, Mario Del Tacca, Romano Danesi. 5-fluorouracil pharmacokinetics predicts disease-free survival in patients administered adjuvant chemotherapy for colorectal cancer. Clinical cancer research : an official journal of the American Association for Cancer Research. 2008 May; 14(9):2749-55. doi: 10.1158/1078-0432.ccr-07-1529. [PMID: 18451241]
  • Woo Young Kim, Bunzo Nakata, Kosei Hirakawa. Alternative pharmacokinetics of S-1 components, 5-fluorouracil, dihydrofluorouracil and alpha-fluoro-beta-alanine after oral administration of S-1 following total gastrectomy. Cancer science. 2007 Oct; 98(10):1604-8. doi: 10.1111/j.1349-7006.2007.00573.x. [PMID: 17683513]
  • Guido Bocci, Cecilia Barbara, Francesca Vannozzi, Antonello Di Paolo, Alessandro Melosi, Gemma Barsanti, Giacomo Allegrini, Alfredo Falcone, Mario Del Tacca, Romano Danesi. A pharmacokinetic-based test to prevent severe 5-fluorouracil toxicity. Clinical pharmacology and therapeutics. 2006 Oct; 80(4):384-95. doi: 10.1016/j.clpt.2006.06.007. [PMID: 17015056]
  • G Remaud, M Boisdron-Celle, A Morel, A Gamelin. Sensitive MS/MS-liquid chromatography assay for simultaneous determination of tegafur, 5-fluorouracil and 5-fluorodihydrouracil in plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Sep; 824(1-2):153-60. doi: 10.1016/j.jchromb.2005.07.023. [PMID: 16061432]
  • Antonello Di Paolo, Romano Danesi, Laura Ciofi, Francesca Vannozzi, Guido Bocci, Marianna Lastella, Federica Amatori, Bianca Maria Martelloni, Toni Ibrahim, Dino Amadori, Alfredo Falcone, Mario Del Tacca. Improved analysis of 5-Fluorouracil and 5,6-dihydro-5-Fluorouracil by HPLC with diode array detection for determination of cellular dihydropyrimidine dehydrogenase activity and pharmacokinetic profiling. Therapeutic drug monitoring. 2005 Jun; 27(3):362-8. doi: 10.1097/01.ftd.0000162016.11148.1b. [PMID: 15905808]
  • Federico Innocenti, Romano Danesi, Guido Bocci, Gianfranco Natale, Mario Del Tacca. 5-Fluorouracil catabolism to 5-fluoro-5,6-dihydrouracil is reduced by acute liver impairment in mice. Toxicology and applied pharmacology. 2005 Mar; 203(2):106-13. doi: 10.1016/j.taap.2004.08.018. [PMID: 15710171]
  • Jan Gerard Maring, Leonie Schouten, Ben Greijdanus, Elisabeth G E de Vries, Donald R A Uges. A simple and sensitive fully validated HPLC-UV method for the determination of 5-fluorouracil and its metabolite 5,6-dihydrofluorouracil in plasma. Therapeutic drug monitoring. 2005 Feb; 27(1):25-30. doi: 10.1097/00007691-200502000-00006. [PMID: 15665742]
  • 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]
  • Federico Casale, Roberto Canaparo, Loredana Serpe, Elisabetta Muntoni, Carlo Della Pepa, Mario Costa, Lorenza Mairone, Gian Paolo Zara, Gianni Fornari, Mario Eandi. Plasma concentrations of 5-fluorouracil and its metabolites in colon cancer patients. Pharmacological research. 2004 Aug; 50(2):173-9. doi: 10.1016/j.phrs.2004.01.006. [PMID: 15177306]
  • Aki Nakamura, Kazuo Kikuchi, Takayoshi Ohishi, Taketoshi Masuike. [Assay method for uracil, dihydrouracil, 5-fluorouracil and 5-fluoro-5, 6-dihydrouracil by high-performance liquid chromatography]. Gan to kagaku ryoho. Cancer & chemotherapy. 2004 Mar; 31(3):381-6. doi: . [PMID: 15045945]
  • Jan Gerard Maring, Henk Piersma, Albert van Dalen, Harry J M Groen, Donald R A Uges, Elisabeth G E De Vries. Extensive hepatic replacement due to liver metastases has no effect on 5-fluorouracil pharmacokinetics. Cancer chemotherapy and pharmacology. 2003 Feb; 51(2):167-73. doi: 10.1007/s00280-002-0535-2. [PMID: 12647019]
  • G Bocci, R Danesi, G Allegrini, F Innocenti, A Di Paolo, A Falcone, P F Conte, M Del Tacca. Severe 5-fluorouracil toxicity associated with a marked alteration of pharmacokinetics of 5-fluorouracil and its catabolite 5-fluoro-5,6-dihydrouracil: a case report. European journal of clinical pharmacology. 2002 Dec; 58(9):593-5. doi: 10.1007/s00228-002-0534-6. [PMID: 12602342]
  • Antonello Di Paolo, Romano Danesi, Francesca Vannozzi, Alfredo Falcone, Enrico Mini, Luca Cionini, Toni Ibrahim, Dino Amadori, Mario Del Tacca. Limited sampling model for the analysis of 5-fluorouracil pharmacokinetics in adjuvant chemotherapy for colorectal cancer. Clinical pharmacology and therapeutics. 2002 Dec; 72(6):627-37. doi: 10.1067/mcp.2002.128867. [PMID: 12496744]
  • Antonello Di Paolo, Toni Ibrahim, Romano Danesi, Marco Maltoni, Francesca Vannozzi, Emanuela Flamini, Wainer Zoli, Dino Amadori, Mario Del Tacca. Relationship between plasma concentrations of 5-fluorouracil and 5-fluoro-5,6-dihydrouracil and toxicity of 5-fluorouracil infusions in cancer patients. Therapeutic drug monitoring. 2002 Oct; 24(5):588-93. doi: 10.1097/00007691-200210000-00002. [PMID: 12352929]
  • F Casale, R Canaparo, E Muntoni, L Serpe, G P Zara, C Della Pepa, E Berno, M Costa, M Eandi. Simultaneous HPLC determination of 5-fluorouracil and its metabolites in plasma of cancer patients. Biomedical chromatography : BMC. 2002 Oct; 16(7):446-52. doi: 10.1002/bmc.181. [PMID: 12378555]
  • G Bocci, R Danesi, A D Di Paolo, F Innocenti, G Allegrini, A Falcone, A Melosi, M Battistoni, G Barsanti, P F Conte, M Del Tacca. Comparative pharmacokinetic analysis of 5-fluorouracil and its major metabolite 5-fluoro-5,6-dihydrouracil after conventional and reduced test dose in cancer patients. Clinical cancer research : an official journal of the American Association for Cancer Research. 2000 Aug; 6(8):3032-7. doi: . [PMID: 10955781]
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