5'-Deoxy-5-fluorocytidine (BioDeep_00000054107)

 

Secondary id: BioDeep_00000014806

human metabolite Endogenous blood metabolite


代谢物信息卡片


4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-1,2-dihydropyrimidin-2-one

化学式: C9H12FN3O4 (245.0811804)
中文名称: 5-脱氧-5-氟胞嘧啶核苷
谱图信息: 最多检出来源 Homo sapiens(blood) 6.85%

分子结构信息

SMILES: CC1C(C(C(O1)N2C=C(C(=NC2=O)N)F)O)O
InChI: InChI=1S/C9H12FN3O4/c1-3-5(14)6(15)8(17-3)13-2-4(10)7(11)12-9(13)16/h2-3,5-6,8,14-15H,1H3,(H2,11,12,16)/t3-,5-,6-,8-/m1/s1

描述信息

5-Deoxy-5-fluorocytidine is a metabolite of capecitabine. Capecitabine (Xeloda, Roche) is an orally-administered chemotherapeutic agent used in the treatment of metastatic breast and colorectal cancers. Capecitabine is a prodrug, that is enzymatically converted to 5-fluorouracil in the tumor, where it inhibits DNA synthesis and slows growth of tumor tissue. (Wikipedia)

同义名列表

2 个代谢物同义名

4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-1,2-dihydropyrimidin-2-one; 5-Deoxy-5-fluorocytidine



数据库引用编号

8 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

  • Nastja Lunar, Marie-Christine Etienne-Grimaldi, Pauline Macaire, Fabienne Thomas, Florence Dalenc, Jean-Marc Ferrero, Xavier Pivot, Gérard Milano, Bernard Royer, Antonin Schmitt. Population pharmacokinetic and pharmacodynamic modeling of capecitabine and its metabolites in breast cancer patients. Cancer chemotherapy and pharmacology. 2021 02; 87(2):229-239. doi: 10.1007/s00280-020-04208-8. [PMID: 33386926]
  • Takahiro Inaishi, Ken-Ichi Fujita, Natsumi Matsumoto, Tomoya Shimokata, Osamu Maeda, Toyone Kikumori, Norifumi Hattori, Goro Nakayama, Yuichi Ando. Correlation Between the Metabolic Conversion of a Capecitabine Metabolite, 5'-Deoxy-5-fluorocytidine, and Creatinine Clearance. In vivo (Athens, Greece). 2020 Nov; 34(6):3539-3544. doi: 10.21873/invivo.12196. [PMID: 33144465]
  • Masae Sekido, Ken-Ichi Fujita, Yutaro Kubota, Hiroo Ishida, Takehiro Takahashi, Ryotaro Ohkuma, Takuya Tsunoda, Fumihiro Ishikawa, Motoko Shibanuma, Yasutsuna Sasaki. Rabeprazole intake does not affect systemic exposure to capecitabine and its metabolites, 5'-deoxy-5-fluorocytidine, 5'-deoxy-5-fluorouridine, and 5-fluorouracil. Cancer chemotherapy and pharmacology. 2019 06; 83(6):1127-1135. doi: 10.1007/s00280-019-03837-y. [PMID: 30972456]
  • Teresa Di Desidero, Paola Orlandi, Anna Fioravanti, Chiara Cremolini, Fotios Loupakis, Federica Marmorino, Carlotta Antoniotti, Gianluca Masi, Sara Lonardi, Francesca Bergamo, Vittorina Zagonel, Alfredo Falcone, Guido Bocci. Pharmacokinetic analysis of metronomic capecitabine in refractory metastatic colorectal cancer patients. Investigational new drugs. 2018 08; 36(4):709-714. doi: 10.1007/s10637-018-0579-8. [PMID: 29488048]
  • Shinji Kobuchi, Yukiko Yazaki, Yukako Ito, Toshiyuki Sakaeda. Circadian variations in the pharmacokinetics of capecitabine and its metabolites in rats. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2018 Jan; 112(?):152-158. doi: 10.1016/j.ejps.2017.11.021. [PMID: 29175408]
  • Pan Deng, Cheng Ji, Xiaojian Dai, Dafang Zhong, Li Ding, Xiaoyan Chen. Simultaneous determination of capecitabine and its three nucleoside metabolites in human plasma by high performance liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 May; 989(?):71-9. doi: 10.1016/j.jchromb.2015.03.002. [PMID: 25808944]
  • Andre Farkouh, Werner Scheithauer, Philipp Buchner, Apostolos Georgopoulos, Johannes Schueller, Birgit Gruenberger, Martin Czejka. Clinical pharmacokinetics of capecitabine and its metabolites in combination with the monoclonal antibody bevacizumab. Anticancer research. 2014 Jul; 34(7):3669-73. doi: NULL. [PMID: 24982385]
  • Veronika Schreiber, Marie Kitzmueller, Martina Poxhofer, Stefanie Gintersdorfer, Catharina Neudorfer, Maria Lichtneckert, Christian Dittrich, Martin Czejka. Impact of co-administered drugs on drug monitoring of capecitabine in patients with advanced colorectal cancer. Anticancer research. 2014 Jul; 34(7):3371-6. doi: NULL. [PMID: 24982342]
  • Kazuhiro Migita, Tomoyoshi Takayama, Keigo Saeki, Sohei Matsumoto, Kohei Wakatsuki, Koji Enomoto, Tetsuya Tanaka, Masahiro Ito, Norio Kurumatani, Yoshiyuki Nakajima. The prognostic nutritional index predicts long-term outcomes of gastric cancer patients independent of tumor stage. Annals of surgical oncology. 2013 Aug; 20(8):2647-54. doi: 10.1245/s10434-013-2926-5. [PMID: 23463091]
  • Philipp Buchner, Eva Mihola, Azra Sahmanovic, Tanja Steininger, Christian Dittrich, Martin Czejka. Validation of a simple assay for the quantification of the capecitabine metabolites 5'-DFCR and 5'-DFUR for drug monitoring in patients receiving outpatient chemotherapy. Anticancer research. 2013 Mar; 33(3):881-6. doi: . [PMID: 23482757]
  • Martin Czejka, J Schueller, A Farkouh, B Gruenberger, W Scheithauer. Plasma disposition of capecitabine and its metabolites 5'DFCR and 5'DFUR in a standard and dose-intensified monotherapy regimen. Cancer chemotherapy and pharmacology. 2011 Mar; 67(3):613-9. doi: 10.1007/s00280-010-1363-4. [PMID: 20495919]
  • A Farkouh, J Schueller, W Scheithauer, M Czejka. Plasma disposition of capecitabine (CCB) and its metabolites 5'-deoxy-5-fluorocytidine (5'-DFCR) and 5'-deoxy-5-fluorouracil (5'-DFUR) with two different capecitabine/oxaliplatin dosage regimens. International journal of clinical pharmacology and therapeutics. 2010 Jul; 48(7):487-8. doi: 10.5414/cpp48487. [PMID: 20557855]
  • 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]
  • Sylvie M Guichard, Janet S Macpherson, Iain Mayer, Eilidh Reid, Morwenna Muir, Michael Dodds, Susan Alexander, Duncan I Jodrell. Gene expression predicts differential capecitabine metabolism, impacting on both pharmacokinetics and antitumour activity. European journal of cancer (Oxford, England : 1990). 2008 Jan; 44(2):310-7. doi: 10.1016/j.ejca.2007.10.023. [PMID: 18077151]
  • Mugunthu R Dhananjeyan, Jidong Liu, Crystal Bykowski, Jill A Trendel, Jeffrey G Sarver, Howard Ando, Paul W Erhardt. Rapid and simultaneous determination of capecitabine and its metabolites in mouse plasma, mouse serum, and in rabbit bile by high-performance liquid chromatography. Journal of chromatography. A. 2007 Jan; 1138(1-2):101-8. doi: 10.1016/j.chroma.2006.10.038. [PMID: 17070825]
  • Sylvie M Guichard, Iain Mayer, Duncan I Jodrell. Simultaneous determination of capecitabine and its metabolites by HPLC and mass spectrometry for preclinical and clinical studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Nov; 826(1-2):232-7. doi: 10.1016/j.jchromb.2005.09.010. [PMID: 16198157]
  • Kazuo Hattori, Yasunori Kohchi, Nobuhiro Oikawa, Hitomi Suda, Masako Ura, Tohru Ishikawa, Masanori Miwa, Mika Endoh, Hiroyuki Eda, Hiromi Tanimura, Akira Kawashima, Ikuo Horii, Hideo Ishitsuka, Nobuo Shimma. Design and synthesis of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor, RO0094889 for combination therapy with capecitabine. Bioorganic & medicinal chemistry letters. 2003 Mar; 13(5):867-72. doi: 10.1016/s0960-894x(02)01082-x. [PMID: 12617910]
  • N Shimma, I Umeda, M Arasaki, C Murasaki, K Masubuchi, Y Kohchi, M Miwa, M Ura, N Sawada, H Tahara, I Kuruma, I Horii, H Ishitsuka. The design and synthesis of a new tumor-selective fluoropyrimidine carbamate, capecitabine. Bioorganic & medicinal chemistry. 2000 Jul; 8(7):1697-706. doi: 10.1016/s0968-0896(00)00087-0. [PMID: 10976516]