2',2'-Difluorodeoxyuridine (BioDeep_00000018342)
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C9H10F2N2O5 (264.0557754)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 83.33%
分子结构信息
SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)(F)F
InChI: InChI=1S/C9H10F2N2O5/c10-9(11)6(16)4(3-14)18-7(9)13-2-1-5(15)12-8(13)17/h1-2,4,6-7,14,16H,3H2,(H,12,15,17)
描述信息
2,2-Difluorodeoxyuridine is a metabolite of gemcitabine. Gemcitabine is a nucleoside analog used as chemotherapy. It is marketed as Gemzar by Eli Lilly and Company. (Wikipedia)
同义名列表
7 个代谢物同义名
1-[(2S,4R,5S)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,2-dihydropyrimidin-2-one; 1-[(2S,4R,5S)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxypyrimidin-2-one; 1-[(2S,4R,5S)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione; 2,2-Difluoro-2-deoxyuridine; 2,2-Difluorodeoxyuridine; 2,2-DFdU; 2-Deoxy-2,2-difluorouridine
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)
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
- Bo Zhong, Elizabeth G Gibson, Abi Davis, Martine F Roussel, Clinton F Stewart. LC-MS/MS method for quantitation of gemcitabine and its metabolite 2',2'-difluoro-2'-deoxyuridine in mouse plasma and brain tissue: Application to a preclinical pharmacokinetic study.
Journal of pharmaceutical and biomedical analysis.
2021 May; 198(?):114025. doi:
10.1016/j.jpba.2021.114025
. [PMID: 33744463] - Lei Yin, Tianming Ren, Shiying Zhao, Meiyun Shi, Jingkai Gu. Comparative pharmacokinetic study of PEGylated gemcitabine and gemcitabine in rats by LC-MS/MS coupled with pre-column derivatization and MSALL technique.
Talanta.
2020 Jan; 206(?):120184. doi:
10.1016/j.talanta.2019.120184
. [PMID: 31514844] - Abeer F Alharbi, Robert A Kratzke, Jonathan D'Cunha, Michael Anthony Maddaus, Kinjal Sanghavi, Mark N Kirstein. Gemcitabine and metabolite pharmacokinetics in advanced NSCLC patients after bronchial artery infusion and intravenous infusion.
Cancer chemotherapy and pharmacology.
2019 02; 83(2):387-391. doi:
10.1007/s00280-018-3757-7
. [PMID: 30542769] - Ellen J B Derissen, Alwin D R Huitema, Hilde Rosing, Jan H M Schellens, Jos H Beijnen. Intracellular pharmacokinetics of gemcitabine, its deaminated metabolite 2',2'-difluorodeoxyuridine and their nucleotides.
British journal of clinical pharmacology.
2018 06; 84(6):1279-1289. doi:
10.1111/bcp.13557
. [PMID: 29451684] - Yilin Sun, Le Zhen, Ying Peng, Jiankun Wang, Fei Fei, Lixiang Aa, Wenjiao Jiang, Xue Pei, Li Lu, Jie Liu, Guangji Wang, Kun Hao. Simultaneous determination of gemcitabine prodrug, gemcitabine and its major metabolite 2', 2'-difluorodeoxyuridine in rat plasma by UFLC-MS/MS.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2018 May; 1084(?):4-13. doi:
10.1016/j.jchromb.2018.03.025
. [PMID: 29558739] - M van Nuland, M J X Hillebrand, H Rosing, J A Burgers, J H M Schellens, J H Beijnen. Ultra-sensitive LC-MS/MS method for the quantification of gemcitabine and its metabolite 2',2'-difluorodeoxyuridine in human plasma for a microdose clinical trial.
Journal of pharmaceutical and biomedical analysis.
2018 Mar; 151(?):25-31. doi:
10.1016/j.jpba.2017.12.048
. [PMID: 29294409] - Tormod Bjånes, Tina Kamčeva, Torunn Eide, Bettina Riedel, Jan Schjøtt, Asbjørn Svardal. Preanalytical Stability of Gemcitabine and its Metabolite 2', 2'-Difluoro-2'-Deoxyuridine in Whole Blood-Assessed by Liquid Chromatography Tandem Mass Spectrometry.
Journal of pharmaceutical sciences.
2015 Dec; 104(12):4427-4432. doi:
10.1002/jps.24638
. [PMID: 26372902] - Enaksha R Wickremsinhe, Lisa B Lee, Chris A Schmalz, John Torchia, Kenneth J Ruterbories. High sensitive assay employing column switching chromatography to enable simultaneous quantification of an amide prodrug of gemcitabine (LY2334737), gemcitabine, and its metabolite dFdU in human plasma by LC-MS/MS.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2013 Aug; 932(?):117-22. doi:
10.1016/j.jchromb.2013.06.008
. [PMID: 23831704] - A Ramón-López, V Escudero-Ortiz, M J Duart-Duart, J J Pérez-Ruixo, B Valenzuela. [Population pharmacokinetics of gemcitabine applied to personalize the dosage used in cancer patients].
Farmacia hospitalaria : organo oficial de expresion cientifica de la Sociedad Espanola de Farmacia Hospitalaria.
2012 Jul; 36(4):194-206. doi:
10.1016/j.farma.2011.04.002
. [PMID: 22078546] - P Specenier, G Guetens, J Dyck, G De Boeck, J Weyler, D Van den Weyngaert, K Aelbrecht, J B Vermorken. Difluorodeoxyuridine plasma concentrations after low-dose gemcitabine during chemoradiation in head and neck cancer patients.
Cancer chemotherapy and pharmacology.
2011 Jul; 68(1):185-91. doi:
10.1007/s00280-010-1471-1
. [PMID: 20882386] - L S Hodge, M E Taub, T S Tracy. Effect of its deaminated metabolite, 2',2'-difluorodeoxyuridine, on the transport and toxicity of gemcitabine in HeLa cells.
Biochemical pharmacology.
2011 Apr; 81(7):950-6. doi:
10.1016/j.bcp.2011.01.016
. [PMID: 21291869] - Emiko Sugiyama, Nahoko Kaniwa, Su-Ryang Kim, Ryuichi Hasegawa, Yoshiro Saito, Hideki Ueno, Takuji Okusaka, Masafumi Ikeda, Chigusa Morizane, Shunsuke Kondo, Noboru Yamamoto, Tomohide Tamura, Junji Furuse, Hiroshi Ishii, Teruhiko Yoshida, Nagahiro Saijo, Jun-Ichi Sawada. Population pharmacokinetics of gemcitabine and its metabolite in Japanese cancer patients: impact of genetic polymorphisms.
Clinical pharmacokinetics.
2010 Aug; 49(8):549-58. doi:
10.2165/11532970-000000000-00000
. [PMID: 20608756] - Jan Gerard Maring, Floris M Wachters, Monique Slijfer, J Marina Maurer, H Marike Boezen, Donald R A Uges, Elisabeth G E de Vries, Harry J M Groen. Pharmacokinetics of gemcitabine in non-small-cell lung cancer patients: impact of the 79A>C cytidine deaminase polymorphism.
European journal of clinical pharmacology.
2010 Jun; 66(6):611-7. doi:
10.1007/s00228-010-0799-0
. [PMID: 20213492] - Chester Bowen, Sherry Wang, Hermes Licea-Perez. Development of a sensitive and selective LC-MS/MS method for simultaneous determination of gemcitabine and 2,2-difluoro-2-deoxyuridine in human plasma.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2009 Jul; 877(22):2123-9. doi:
10.1016/j.jchromb.2009.06.002
. [PMID: 19546035] - Alessandra Felici, Susanna Di Segni, Michele Milella, Simona Colantonio, Isabella Sperduti, Barbara Nuvoli, Michela Contestabile, Andrea Sacconi, Massimo Zaratti, Gennaro Citro, Francesco Cognetti. Pharmacokinetics of gemcitabine at fixed-dose rate infusion in patients with normal and impaired hepatic function.
Clinical pharmacokinetics.
2009; 48(2):131-41. doi:
10.2165/00003088-200948020-00005
. [PMID: 19271785] - Stephan A Veltkamp, Dick Pluim, Maria A J van Eijndhoven, Maria J Bolijn, Felix H G Ong, Rajgopal Govindarajan, Jashvant D Unadkat, Jos H Beijnen, Jan H M Schellens. New insights into the pharmacology and cytotoxicity of gemcitabine and 2',2'-difluorodeoxyuridine.
Molecular cancer therapeutics.
2008 Aug; 7(8):2415-25. doi:
10.1158/1535-7163.mct-08-0137
. [PMID: 18723487] - Naoya Masumori, Yasuharu Kunishima, Megumi Hirobe, Motoi Takeuchi, Akio Takayanagi, Taiji Tsukamoto, Tatsuya Itoh. Measurement of plasma concentration of gemcitabine and its metabolite dFdU in hemodialysis patients with advanced urothelial cancer.
Japanese journal of clinical oncology.
2008 Mar; 38(3):182-5. doi:
10.1093/jjco/hym171
. [PMID: 18270381] - Elena Marangon, Federica Sala, Orazio Caffo, Enzo Galligioni, Maurizio D'Incalci, Massimo Zucchetti. Simultaneous determination of gemcitabine and its main metabolite, dFdU, in plasma of patients with advanced non-small-cell lung cancer by high-performance liquid chromatography-tandem mass spectrometry.
Journal of mass spectrometry : JMS.
2008 Feb; 43(2):216-23. doi:
10.1002/jms.1293
. [PMID: 17941128] - Liia D Vainchtein, Hilde Rosing, Bas Thijssen, Jan H M Schellens, Jos H Beijnen. Validated assay for the simultaneous determination of the anti-cancer agent gemcitabine and its metabolite 2',2'-difluorodeoxyuridine in human plasma by high-performance liquid chromatography with tandem mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2007; 21(14):2312-22. doi:
10.1002/rcm.3096
. [PMID: 17577879] - Bea Pauwels, Annelies E C Korst, Hilde A J Lambrechts, Greet G O Pattyn, Christel M J de Pooter, Filip Lardon, Jan B Vermorken. The radiosensitising effect of difluorodeoxyuridine, a metabolite of gemcitabine, in vitro.
Cancer chemotherapy and pharmacology.
2006 Aug; 58(2):219-28. doi:
10.1007/s00280-005-0158-5
. [PMID: 16331496] - Mark N Kirstein, Iman Hassan, Dan E Guire, Dennis R Weller, Jason W Dagit, James E Fisher, Rory P Remmel. High-performance liquid chromatographic method for the determination of gemcitabine and 2',2'-difluorodeoxyuridine in plasma and tissue culture media.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2006 May; 835(1-2):136-42. doi:
10.1016/j.jchromb.2006.03.023
. [PMID: 16584929] - K J Freise, T Martín-Jiménez. Pharmacokinetics of gemcitabine and its primary metabolite in dogs after intravenous infusion.
Journal of veterinary pharmacology and therapeutics.
2006 Apr; 29(2):147-52. doi:
10.1111/j.1365-2885.2006.00726.x
. [PMID: 16515669] - K J Freise, T Martín-Jiménez. Pharmacokinetics of gemcitabine and its primary metabolite in dogs after intravenous bolus dosing and its in vitro pharmacodynamics.
Journal of veterinary pharmacology and therapeutics.
2006 Apr; 29(2):137-45. doi:
10.1111/j.1365-2885.2006.00725.x
. [PMID: 16515668] - Jeany M Rademaker-Lakhai, Mirjam Crul, Dick Pluim, Rolf W Sparidans, Paul Baas, Jos H Beijnen, Nico van Zandwijk, Jan H M Schellens. Phase I clinical and pharmacologic study of a 2-weekly administration of cisplatin and gemcitabine in patients with advanced non-small cell lung cancer.
Anti-cancer drugs.
2005 Oct; 16(9):1029-36. doi:
10.1097/01.cad.0000176507.78928.4d
. [PMID: 16162981] - Francesca Mattioli, Antonio Curotto, Valeria Manfredi, Marzia Gosmar, Claudia Garbero, Carlo Ambruosi, Giorgio Carmignani, Antonietta Martelli. Intravesical gemcitabine in superficial bladder cancer: a phase II safety, efficacy and pharmacokinetic study.
Anticancer research.
2005 May; 25(3c):2493-6. doi:
NULL
. [PMID: 16080482] - Kan Yonemori, Hideki Ueno, Takuji Okusaka, Noboru Yamamoto, Masafumi Ikeda, Nagahiro Saijo, Teruhiko Yoshida, Hiroshi Ishii, Junji Furuse, Emiko Sugiyama, Su-Ryang Kim, Ruri Kikura-Hanajiri, Ryuichi Hasegawa, Yoshiro Saito, Shogo Ozawa, Nahoko Kaniwa, Jun-Ichi Sawada. Severe drug toxicity associated with a single-nucleotide polymorphism of the cytidine deaminase gene in a Japanese cancer patient treated with gemcitabine plus cisplatin.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2005 Apr; 11(7):2620-4. doi:
10.1158/1078-0432.ccr-04-1497
. [PMID: 15814642] - Neng-ming Lin, Su Zeng, Sheng-lin Ma, Yun Fan, Hai-jun Zhong, Luo Fang. Determination of gemcitabine and its metabolite in human plasma using high-pressure liquid chromatography coupled with a diode array detector.
Acta pharmacologica Sinica.
2004 Dec; 25(12):1584-9. doi:
NULL
. [PMID: 15569401] - José M Buesa, Raquel Losa, Aida Fernández, Marta Sierra, Emilio Esteban, Angela Díaz, Antonio López-Pousa, Joaquín Fra. Phase I clinical trial of fixed-dose rate infusional gemcitabine and dacarbazine in the treatment of advanced soft tissue sarcoma, with assessment of gemcitabine triphosphate accumulation.
Cancer.
2004 Nov; 101(10):2261-9. doi:
10.1002/cncr.20612
. [PMID: 15484216] - Bilal Yilmaz, Yücel Yaşar Kadioğlu, Yilmaz Aksoy. Investigation of the pharmacokinetics of gemcitabine and 2',2'-difluorodeoxyuridine in human plasma by liquid chromatography.
Analytical biochemistry.
2004 Sep; 332(2):234-7. doi:
10.1016/j.ab.2004.05.059
. [PMID: 15325290] - Cristina Sottani, Massimo Zucchetti, Marco Zaffaroni, Maurizio Bettinelli, Claudio Minoia. Validated procedure for simultaneous trace level determination of the anti-cancer agent gemcitabine and its metabolite in human urine by high-performance liquid chromatography with tandem mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2004; 18(10):1017-23. doi:
10.1002/rcm.1436
. [PMID: 15150823] - Ling-Zhi Wang, Boon-Cher Goh, How-Sung Lee, Paul Noordhuis, Godefridus J Peters. An expedient assay for determination of gemcitabine and its metabolite in human plasma using isocratic ion-pair reversed-phase high-performance liquid chromatography.
Therapeutic drug monitoring.
2003 Oct; 25(5):552-7. doi:
10.1097/00007691-200310000-00003
. [PMID: 14508377] - B J Delauter, R K Ramanathan, M J Egorin, L L Stover, E G Zuhowski, W Plunkett, W C Zamboni. Pharmacokinetics of gemcitabine and 2',2'-difluorodeoxyuridine in a patient with ascites.
Pharmacotherapy.
2000 Oct; 20(10):1204-7. doi:
10.1592/phco.20.15.1204.34586
. [PMID: 11034044] - H T Edzes, G J Peters, P Noordhuis, J B Vermorken. Determination of the antimetabolite Gemcitabine (2',2'-difluoro-2'-deoxycytidine) and of 2',2'-difluoro-2'-deoxyuridine by 19F nuclear magnetic resonance spectroscopy.
Analytical biochemistry.
1993 Oct; 214(1):25-30. doi:
10.1006/abio.1993.1451
. [PMID: 8250231]