Eniluracil (BioDeep_00000178705)
human metabolite blood metabolite
代谢物信息卡片
5-ethynyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
化学式: C6H4N2O2 (136.0273)
中文名称: 5-乙炔基尿嘧啶
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C#CC1=CNC(=O)NC1=O
InChI: InChI=1S/C6H4N2O2/c1-2-4-3-7-6(10)8-5(4)9/h1,3H,(H2,7,8,9,10)
描述信息
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite
D004791 - Enzyme Inhibitors
Eniluracil (5-Ethynyluracil) is an orally active dihydropyrimidine dehydrogenase (DPD) inhibitor. Eniluracil irreversibly inhibits DPD, increases the oral bioavailability of 5-fluorouracil to 100\%, and facilitates the uniform absorption and toxicity of 5-fluorouracil. Eniluracil can be used in cancer research of combination with fluoropyrimidines (including 5-fluorouracil)[1][2]. Eniluracil is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
同义名列表
数据库引用编号
7 个数据库交叉引用编号
- ChEBI: CHEBI:177783
- PubChem: 43157
- HMDB: HMDB0251810
- DrugBank: DB03516
- ChEMBL: CHEMBL355200
- CAS: 59989-18-3
- medchemexpress: HY-10533
分类词条
相关代谢途径
Reactome(0)
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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。
| 亚细胞结构定位 | 关联基因列表 |
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文献列表
- 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] - Brian G Czito, Timothy J Hong, Darrel P Cohen, William P Petros, Douglas S Tyler, Theodore N Pappas, Daohai Yu, Catherine G Lee, Albert C Lockhart, Michael A Morse, Nishan Fernando, Herbert I Hurwitz. A phase I study of eniluracil/5-FU in combination with radiation therapy for potentially resectable and/or unresectable cancer of the pancreas and distal biliary tract.
Cancer investigation.
2006 Feb; 24(1):9-17. doi:
10.1080/07357900500449454. [PMID: 16466986] - Martin J Heslin, Jieming Yan, Heidi Weiss, Lingning Shao, Jill Owens, V Sol Lucas, Robert B Diasio. Dihydropyrimidine dehydrogenase (DPD) rapidly regenerates after inactivation by eniluracil (GW776C85) in primary and metastatic colorectal cancer.
Cancer chemotherapy and pharmacology.
2003 Nov; 52(5):399-404. doi:
10.1007/s00280-003-0681-1. [PMID: 12904894] - Xiao-Du Guo, Nancy Harold, M Wasif Saif, Barbara Schuler, Eva Szabo, J Michael Hamilton, Brian P Monahan, Mary G Quinn, Janet Cliatt, Diana Nguyen, Frank Grollman, Rebecca R Thomas, Elizabeth A McQuigan, Richard Wilson, Chis H Takimoto, Jean L Grem. Pharmacokinetic and pharmacodynamic effects of oral eniluracil, fluorouracil and leucovorin given on a weekly schedule.
Cancer chemotherapy and pharmacology.
2003 Jul; 52(1):79-85. doi:
10.1007/s00280-003-0613-0. [PMID: 12707718] - 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] - M L Rothenberg, J K Benedetti, J S Macdonald, T E Seay, M A Neubauer, C S George, M S Tanaka, J K Giguere, B T Pruitt, J L Abbruzzese. Phase II trial of 5-fluorouracil plus eniluracil in patients with advanced pancreatic cancer: a Southwest Oncology Group study.
Annals of oncology : official journal of the European Society for Medical Oncology.
2002 Oct; 13(10):1576-82. doi:
10.1093/annonc/mdf274. [PMID: 12377645] - Bruce Keith, Xiao-Du Guo, Suzanne Zentko, Nancy Harold, Barbara Schuler, Mary Quinn, Jeremy Shapiro, Jean L Grem. Impact of two weekly schedules of oral eniluracil given with fluorouracil and leucovorin on the duration of dihydropyrimidine dehydrogenase inhibition.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2002 May; 8(5):1045-50. doi:
NULL. [PMID: 12006517] - Dale R Shepard, Sridhar Mani, Helen Kastrissios, Susan Learned-Coughlin, Deborah Smith, Phillip Ertel, Steve Magnum, Linda Janisch, Gini F Fleming, Richard L Schilsky, Mark J Ratain. Estimation of the effect of food on the disposition of oral 5-fluorouracil in combination with eniluracil.
Cancer chemotherapy and pharmacology.
2002 May; 49(5):398-402. doi:
10.1007/s00280-002-0431-9. [PMID: 11976834] - John C Marsh, Paul Catalano, Jie Huang, David L Graham, Mark J Cornfeld, Peter J O'Dwyer, Al B Benson. Eastern Cooperative Oncology Group phase II trial (E4296) of oral 5-fluorouracil and eniluracil as a 28-day regimen in metastatic colorectal cancer.
Clinical colorectal cancer.
2002 May; 2(1):43-50. doi:
10.3816/ccc.2002.n.010. [PMID: 12453335] - Alex A Adjei, Joel M Reid, Robert B Diasio, Jeff A Sloan, Deborah A Smith, Joseph Rubin, Henry C Pitot, Steven R Alberts, Richard M Goldberg, Lorelei J Hanson, Pamela Atherton, Matthew M Ames, Charles Erlichman. Comparative pharmacokinetic study of continuous venous infusion fluorouracil and oral fluorouracil with eniluracil in patients with advanced solid tumors.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2002 Mar; 20(6):1683-91. doi:
10.1200/jco.2002.20.6.1683. [PMID: 11896120] - E O Aboagye, A Saleem, V J Cunningham, S Osman, P M Price. Extraction of 5-fluorouracil by tumor and liver: a noninvasive positron emission tomography study of patients with gastrointestinal cancer.
Cancer research.
2001 Jul; 61(13):4937-41. doi:
NULL. [PMID: 11431319] - J L Grem, N Harold, J Shapiro, D Q Bi, M G Quinn, S Zentko, B Keith, J M Hamilton, B P Monahan, S Donavan, F Grollman, G Morrison, C H Takimoto. Phase I and pharmacokinetic trial of weekly oral fluorouracil given with eniluracil and low-dose leucovorin to patients with solid tumors.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2000 Dec; 18(23):3952-63. doi:
10.1200/jco.2000.18.23.3952. [PMID: 11099325] - L Ochoa, H I Hurwitz, G Wilding, D Cohen, J P Thomas, G Schwartz, P Monroe, W P Petros, V P Ertel, A Hsieh, C Hoffman, R Drengler, S Magnum, E K Rowinsky. Pharmacokinetics and bioequivalence of a combined oral formulation of eniluracil, an inactivator of dihydropyrimidine dehydrogenase, and 5-fluorouracil in patients with advanced solid malignancies.
Annals of oncology : official journal of the European Society for Medical Oncology.
2000 Oct; 11(10):1313-22. doi:
10.1023/a:1008379802642. [PMID: 11106122] - J R Bading, M M Alauddin, J D Fissekis, A H Shahinian, J Joung, T Spector, P S Conti. Blocking catabolism with eniluracil enhances PET studies of 5-[18F]fluorouracil pharmacokinetics.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine.
2000 Oct; 41(10):1714-24. doi:
NULL. [PMID: 11038003] - A Saleem, J Yap, S Osman, F Brady, B Suttle, S V Lucas, T Jones, P M Price, E O Aboagye. Modulation of fluorouracil tissue pharmacokinetics by eniluracil: in-vivo imaging of drug action.
Lancet (London, England).
2000 Jun; 355(9221):2125-31. doi:
10.1016/s0140-6736(00)02380-1. [PMID: 10902627] - S D Baker, R B Diasio, S O'Reilly, V S Lucas, S P Khor, S E Sartorius, R C Donehower, L B Grochow, T Spector, J A Hohneker, E K Rowinsky. Phase I and pharmacologic study of oral fluorouracil on a chronic daily schedule in combination with the dihydropyrimidine dehydrogenase inactivator eniluracil.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2000 Feb; 18(4):915-26. doi:
10.1200/jco.2000.18.4.915. [PMID: 10673535] - P M Hoff, R Pazdur. Dihydropyrimidine dehydrogenase inhibitory fluoropyrimidines: a novel class of oral antineoplastic agents.
Seminars in oncology.
1999 Dec; 26(6 Suppl 18):52-6. doi:
NULL. [PMID: 10892578] - F Y Ahmed, S J Johnston, J Cassidy, T O'Kelly, N Binnie, G I Murray, A H van Gennip, N G Abeling, S Knight, H L McLeod. Eniluracil treatment completely inactivates dihydropyrimidine dehydrogenase in colorectal tumors.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
1999 Aug; 17(8):2439-45. doi:
10.1200/jco.1999.17.8.2439. [PMID: 10561307] - R A Brito, D Medgyesy, T H Zukowski, M E Royce, F Ravandi-Kashani, P M Hoff, R Pazdur. Fluoropyrimidines: a critical evaluation.
Oncology.
1999 Jul; 57 Suppl 1(?):2-8. doi:
10.1159/000055262. [PMID: 10436410] - R A Humerickhouse, M E Dolan, D J Haraf, B Brockstein, K Stenson, M Kies, L Sulzen, M J Ratain, E E Vokes. Phase I study of eniluracil, a dihydropyrimidine dehydrogenase inactivator, and oral 5-fluorouracil with radiation therapy in patients with recurrent or advanced head and neck cancer.
Clinical cancer research : an official journal of the American Association for Cancer Research.
1999 Feb; 5(2):291-8. doi:
NULL. [PMID: 10037177] - E R Adams, J J Leffert, D J Craig, T Spector, G Pizzorno. In vivo effect of 5-ethynyluracil on 5-fluorouracil metabolism determined by 19F nuclear magnetic resonance spectroscopy.
Cancer research.
1999 Jan; 59(1):122-7. doi:
. [PMID: 9892196] - R L Schilsky, J Hohneker, M J Ratain, L Janisch, L Smetzer, V S Lucas, S P Khor, R Diasio, D D Von Hoff, H A Burris. Phase I clinical and pharmacologic study of eniluracil plus fluorouracil in patients with advanced cancer.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
1998 Apr; 16(4):1450-7. doi:
10.1200/jco.1998.16.4.1450. [PMID: 9552051] - S P Khor, H Amyx, S T Davis, D Nelson, D P Baccanari, T Spector. Dihydropyrimidine dehydrogenase inactivation and 5-fluorouracil pharmacokinetics: allometric scaling of animal data, pharmacokinetics and toxicodynamics of 5-fluorouracil in humans.
Cancer chemotherapy and pharmacology.
1997; 39(3):233-8. doi:
10.1007/s002800050566. [PMID: 8996526] - S Cao, D P Baccanari, S S Joyner, S T Davis, Y M Rustum, T Spector. 5-Ethynyluracil (776C85): effects on the antitumor activity and pharmacokinetics of tegafur, a prodrug of 5-fluorouracil.
Cancer research.
1995 Dec; 55(24):6227-30. doi:
NULL. [PMID: 8521418] - S T Davis, S S Joyner, D P Baccanari, T Spector. 5-Ethynyluracil (776C85): protection from 5-fluorouracil-induced neurotoxicity in dogs.
Biochemical pharmacology.
1994 Jul; 48(2):233-6. doi:
10.1016/0006-2952(94)90092-2. [PMID: 8053919] - T Spector, J A Harrington, D J Porter. 5-Ethynyluracil (776C85): inactivation of dihydropyrimidine dehydrogenase in vivo.
Biochemical pharmacology.
1993 Dec; 46(12):2243-8. doi:
10.1016/0006-2952(93)90615-4. [PMID: 8274158] - D P Baccanari, S T Davis, V C Knick, T Spector. 5-Ethynyluracil (776C85): a potent modulator of the pharmacokinetics and antitumor efficacy of 5-fluorouracil.
Proceedings of the National Academy of Sciences of the United States of America.
1993 Dec; 90(23):11064-8. doi:
10.1073/pnas.90.23.11064. [PMID: 8248211]
