Tetrahydrouridine (BioDeep_00000719309)

   


代谢物信息卡片


Tetrahydrouridine

化学式: C9H16N2O6 (248.10083160000002)
中文名称: 四氢尿苷(水溶液)
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CN(C(=O)NC1O)C2C(C(C(O2)CO)O)O
InChI: InChI=1S/C9H16N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4-8,12-15H,1-3H2,(H,10,16)/t4-,5?,6-,7-,8-/m1/s1

描述信息

C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite
C471 - Enzyme Inhibitor > C2135 - Cytidine Deaminase Inhibitor
D009676 - Noxae > D000963 - Antimetabolites

同义名列表

1 个代谢物同义名

Tetrahydrouridine



数据库引用编号

5 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

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)

0 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

  • Michael L Hayes, Paola I Santibanez. A plant pentatricopeptide repeat protein with a DYW-deaminase domain is sufficient for catalyzing C-to-U RNA editing in vitro. The Journal of biological chemistry. 2020 03; 295(11):3497-3505. doi: 10.1074/jbc.ra119.011790. [PMID: 31996373]
  • Robert Molokie, Donald Lavelle, Michel Gowhari, Michael Pacini, Lani Krauz, Johara Hassan, Vinzon Ibanez, Maria A Ruiz, Kwok Peng Ng, Philip Woost, Tomas Radivoyevitch, Daisy Pacelli, Sherry Fada, Matthew Rump, Matthew Hsieh, John F Tisdale, James Jacobberger, Mitch Phelps, James Douglas Engel, Santhosh Saraf, Lewis L Hsu, Victor Gordeuk, Joseph DeSimone, Yogen Saunthararajah. Oral tetrahydrouridine and decitabine for non-cytotoxic epigenetic gene regulation in sickle cell disease: A randomized phase 1 study. PLoS medicine. 2017 Sep; 14(9):e1002382. doi: 10.1371/journal.pmed.1002382. [PMID: 28880867]
  • Julianne L Holleran, Julie L Eiseman, Robert A Parise, Shivaani Kummar, Jan H Beumer. LC-MS/MS assay for the quantitation of FdCyd and its metabolites FdUrd and FU in human plasma. Journal of pharmaceutical and biomedical analysis. 2016 Sep; 129(?):359-366. doi: 10.1016/j.jpba.2016.07.027. [PMID: 27454087]
  • Julianne L Holleran, Jan H Beumer, David L McCormick, William D Johnson, Edward M Newman, James H Doroshow, Shivaani Kummar, Joseph M Covey, Myrtle Davis, Julie L Eiseman. Oral and intravenous pharmacokinetics of 5-fluoro-2'-deoxycytidine and THU in cynomolgus monkeys and humans. Cancer chemotherapy and pharmacology. 2015 Oct; 76(4):803-11. doi: 10.1007/s00280-015-2857-x. [PMID: 26321472]
  • Yuji Mano, Kenji Sakamaki, Takuya Ueno, Kenji Kita, Takuho Ishii, Koichiro Hotta, Kazutomi Kusano. Validation of a hydrophilic interaction ultra-performance liquid chromatography-tandem mass spectrometry method for the determination of gemcitabine in human plasma with tetrahydrouridine. Biomedical chromatography : BMC. 2015 Sep; 29(9):1343-9. doi: 10.1002/bmc.3429. [PMID: 25641274]
  • Edward M Newman, Robert J Morgan, Shivaani Kummar, Jan H Beumer, M Suzette Blanchard, Christopher Ruel, Anthony B El-Khoueiry, Mary I Carroll, Jessie M Hou, Chun Li, Heinz J Lenz, Julie L Eiseman, James H Doroshow. A phase I, pharmacokinetic, and pharmacodynamic evaluation of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine, administered with tetrahydrouridine. Cancer chemotherapy and pharmacology. 2015 Mar; 75(3):537-46. doi: 10.1007/s00280-014-2674-7. [PMID: 25567350]
  • Dana Ferraris, Bridget Duvall, Greg Delahanty, Bipin Mistry, Jesse Alt, Camilo Rojas, Christopher Rowbottom, Kristen Sanders, Edgar Schuck, Kuan-Chun Huang, Sanjeev Redkar, Barbara B Slusher, Takashi Tsukamoto. Design, synthesis, and pharmacological evaluation of fluorinated tetrahydrouridine derivatives as inhibitors of cytidine deaminase. Journal of medicinal chemistry. 2014 Mar; 57(6):2582-8. doi: 10.1021/jm401856k. [PMID: 24520856]
  • Pramod Terse, Kory Engelke, Kenneth Chan, Yonghua Ling, Douglas Sharpnack, Yogen Saunthararajah, Joseph M Covey. Subchronic oral toxicity study of decitabine in combination with tetrahydrouridine in CD-1 mice. International journal of toxicology. 2014 Mar; 33(2):75-85. doi: 10.1177/1091581814524994. [PMID: 24639139]
  • Jan H Beumer, Julie L Eiseman, Judith A Gilbert, Julianne L Holleran, Archibong E Yellow-Duke, Dana M Clausen, David Z D'Argenio, Matthew M Ames, Pamela A Hershberger, Robert A Parise, Lihua Bai, Joseph M Covey, Merrill J Egorin. Plasma pharmacokinetics and oral bioavailability of the 3,4,5,6-tetrahydrouridine (THU) prodrug, triacetyl-THU (taTHU), in mice. Cancer chemotherapy and pharmacology. 2011 Feb; 67(2):421-30. doi: 10.1007/s00280-010-1337-6. [PMID: 20443002]
  • Damien Montange, Michel Bérard, Martin Demarchi, Patrice Muret, Sarah Piédoux, Jean Pierre Kantelip, Bernard Royer. An APCI LC-MS/MS method for routine determination of capecitabine and its metabolites in human plasma. Journal of mass spectrometry : JMS. 2010 Jun; 45(6):670-7. doi: 10.1002/jms.1759. [PMID: 20527036]
  • Jan H Beumer, Julie L Eiseman, Robert A Parise, Jeffry A Florian, Erin Joseph, David Z D'Argenio, Robert S Parker, Brittany Kay, Joseph M Covey, Merrill J Egorin. Plasma pharmacokinetics and oral bioavailability of 3,4,5,6-tetrahydrouridine, a cytidine deaminase inhibitor, in mice. Cancer chemotherapy and pharmacology. 2008 Aug; 62(3):457-64. doi: 10.1007/s00280-007-0625-2. [PMID: 18008070]
  • Jan H Beumer, Robert A Parise, Edward M Newman, James H Doroshow, Timothy W Synold, Heinz-Josef Lenz, Merrill J Egorin. Concentrations of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine (FdCyd) and its cytotoxic metabolites in plasma of patients treated with FdCyd and tetrahydrouridine (THU). Cancer chemotherapy and pharmacology. 2008 Jul; 62(2):363-8. doi: 10.1007/s00280-007-0603-8. [PMID: 17899082]
  • Thierry Besnard, Nicole Renée, Marie-Christine Etienne-Grimaldi, Eric François, Gérard Milano. Optimized blood sampling with cytidine deaminase inhibitor for improved analysis of capecitabine metabolites. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Jul; 870(1):117-20. doi: 10.1016/j.jchromb.2008.05.040. [PMID: 18562256]
  • Jan H Beumer, Julie L Eiseman, Robert A Parise, Erin Joseph, Joseph M Covey, Merrill J Egorin. Modulation of gemcitabine (2',2'-difluoro-2'-deoxycytidine) pharmacokinetics, metabolism, and bioavailability in mice by 3,4,5,6-tetrahydrouridine. Clinical cancer research : an official journal of the American Association for Cancer Research. 2008 Jun; 14(11):3529-35. doi: 10.1158/1078-0432.ccr-07-4885. [PMID: 18519786]
  • Robert A Parise, Merrill J Egorin, Julie L Eiseman, Erin Joseph, Joseph M Covey, Jan H Beumer. Quantitative determination of the cytidine deaminase inhibitor tetrahydrouridine (THU) in mouse plasma by liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2007; 21(13):1991-7. doi: 10.1002/rcm.3054. [PMID: 17526067]
  • Tian-Xiang Xiang, Riku Niemi, Paul Bummer, Bradley D Anderson. Epimer interconversion, isomerization, and hydrolysis of tetrahydrouridine: implications for cytidine deaminase inhibition. Journal of pharmaceutical sciences. 2003 Oct; 92(10):2027-39. doi: 10.1002/jps.10447. [PMID: 14502542]
  • JodiAnne T Hale, James C Bigelow, Linda A Mathews, John J McCormack. Analytical and pharmacokinetic studies with 5-chloro-2'-deoxycytidine. Biochemical pharmacology. 2002 Nov; 64(10):1493-502. doi: 10.1016/s0006-2952(02)01413-2. [PMID: 12417262]
  • J H Marsh, W Kreis, B Barile, S Akerman, P Schulman, S L Allen, L C DeMarco, M W Schuster, D R Budman. Therapy of refractory/relapsed acute myeloid leukemia and blast crisis of chronic myeloid leukemia with the combination of cytosine arabinoside, tetrahydrouridine, and carboplatin. Cancer chemotherapy and pharmacology. 1993; 31(6):481-4. doi: 10.1007/bf00685039. [PMID: 8453688]
  • A R Hanauske, D Degen, M H Marshall, S G Hilsenbeck, G B Grindey, D D Von Hoff. Activity of 2',2'-difluorodeoxycytidine (Gemcitabine) against human tumor colony forming units. Anti-cancer drugs. 1992 Apr; 3(2):143-6. doi: 10.1097/00001813-199204000-00012. [PMID: 1525392]
  • W Kreis, D R Budman, K Chan, S L Allen, P Schulman, S Lichtman, L Weiselberg, M Schuster, J Freeman, S Akerman. Therapy of refractory/relapsed acute leukemia with cytosine arabinoside plus tetrahydrouridine (an inhibitor of cytidine deaminase)--a pilot study. Leukemia. 1991 Nov; 5(11):991-8. doi: NULL. [PMID: 1961042]
  • P J Aduma, S V Gupta, E De Clercq. Antiherpes virus activity and effect on deoxyribonucleoside triphosphate pools of (E)-5-(2-bromovinyl)-2'-deoxycytidine in combination with deaminase inhibitors. Antiviral research. 1990 Mar; 13(3):111-25. doi: 10.1016/0166-3542(90)90027-5. [PMID: 2162147]
  • N S Zeidner, J D Strobel, N A Perigo, D L Hill, J I Mullins, E A Hoover. Treatment of FeLV-induced immunodeficiency syndrome (FeLV-FAIDS) with controlled release capsular implantation of 2',3'-dideoxycytidine. Antiviral research. 1989 Apr; 11(3):147-60. doi: 10.1016/0166-3542(89)90026-0. [PMID: 2544137]
  • W Kreis, K Chan, D R Budman, P Schulman, S Allen, L Weiselberg, S Lichtman, V Henderson, J Freeman, M Deere. Effect of tetrahydrouridine on the clinical pharmacology of 1-beta-D-arabinofuranosylcytosine when both drugs are coinfused over three hours. Cancer research. 1988 Mar; 48(5):1337-42. doi: . [PMID: 3342412]
  • D A Boothman, T V Briggle, S Greer. Protective, tumor-selective dual pathway activation of 5-fluoro-2'-deoxycytidine provided by tetrahydrouridine in mice bearing mammary adenocarcinoma-755. Cancer research. 1987 May; 47(9):2344-53. doi: . [PMID: 2436761]
  • D A Boothman, T V Briggle, S Greer. Tumor-selective metabolism of 5-fluoro-2'-deoxycytidine coadministered with tetrahydrouridine compared to 5-fluorouracil in mice bearing Lewis lung carcinoma. Cancer research. 1987 May; 47(9):2354-62. doi: . [PMID: 2952263]
  • V I Avramis, W Powell. Pharmacology of combination chemotherapy of cytosine arabinoside (ara-C) and uracil arabinoside (ara-U) or tetrahydrouridine (THU) against murine leukemia L1210/0 in tumor-bearing mice. Cancer investigation. 1987; 5(4):293-9. doi: 10.1080/07357908709170102. [PMID: 3664332]
  • G J Peters, C J van Groeningen, E J Laurensse, J Lankelma, A Leyva, H M Pinedo. Uridine-induced hypothermia in mice and rats in relation to plasma and tissue levels of uridine and its metabolites. Cancer chemotherapy and pharmacology. 1987; 20(2):101-8. doi: 10.1007/bf00253962. [PMID: 3664929]
  • C H Kim, V E Marquez, D T Mao, D R Haines, J J McCormack. Synthesis of pyrimidin-2-one nucleosides as acid-stable inhibitors of cytidine deaminase. Journal of medicinal chemistry. 1986 Aug; 29(8):1374-80. doi: 10.1021/jm00158a009. [PMID: 3735306]
  • K J Russell, G C Rice, J M Brown. In vitro and in vivo radiation sensitization by the halogenated pyrimidine 5-chloro-2'-deoxycytidine. Cancer research. 1986 Jun; 46(6):2883-7. doi: NULL. [PMID: 3698014]
  • G G Liversidge, T Nishihata, K K Engle, T Higuchi. Enhanced serum concentrations of Ara-C using suppositories containing tetrahydrouridine as a deamination inhibitor of Ara-C. The Journal of pharmacy and pharmacology. 1986 Mar; 38(3):223-4. doi: 10.1111/j.2042-7158.1986.tb04550.x. [PMID: 2871161]
  • T C Chou, A Feinberg, A J Grant, P Vidal, U Reichman, K A Watanabe, J J Fox, F S Philips. Pharmacological disposition and metabolic fate of 2'-fluoro-5-iodo-1-beta-D-arabinofuranosylcytosine in mice and rats. Cancer research. 1981 Sep; 41(9 Pt 1):3336-42. doi: NULL. [PMID: 7260900]
  • V E Marquez, P S Liu, J A Kelley, J S Driscoll, J J McCormack. Synthesis of 1,3-diazepin-2-one nucleosides as transition-state inhibitors of cytidine deaminase. Journal of medicinal chemistry. 1980 Jul; 23(7):713-5. doi: 10.1021/jm00181a001. [PMID: 7401098]
  • J J McCormack, V E Marquez, P S Liu, D T Vistica, J S Driscoll. Inhibition of cytidine deaminase by 2-oxopyrimidine riboside and related compounds. Biochemical pharmacology. 1980 Mar; 29(5):830-2. doi: 10.1016/0006-2952(80)90566-3. [PMID: 20227965]
  • C J Kelly, E Coles, L Gaudio, D W Yesair. Characterization of the urinary metabolites of 5-azacytidine in mice. Biochemical pharmacology. 1980 Feb; 29(4):609-15. doi: 10.1016/0006-2952(80)90384-6. [PMID: 6154465]
  • C W Wan, T W Mak. Effect of tetrahydrouridine on the action of 1-beta-D-arabinofuranosylcytosine in synchronized cultures of normal rat kidney cells. Cancer research. 1979 Oct; 39(10):3981-5. doi: . [PMID: 476637]
  • C J Kelly, L Gaudio, D W Yesair, P T Schoenemann, I Wodinsky. Pharmacokinetic considerations in evaluating the effects of tetrahydrouridine on 5-azacytidine chemotherapy in L1210 leukemic mice. Cancer treatment reports. 1978 Jul; 62(7):1025-32. doi: NULL. [PMID: 80268]
  • W Kreis, T M Woodcock, C S Gordon, I H Krakoff. Tetrahydrouridine: Physiologic disposition and effect upon deamination of cytosine arabinoside in man. Cancer treatment reports. 1977 Oct; 61(7):1347-53. doi: NULL. [PMID: 589600]
  • W Kreis, C Hession, A Soricelli, K Scully. Combinations of tetrahydrouridine and cytosine arabinoside in mouse tumors. Cancer treatment reports. 1977 Oct; 61(7):1355-64. doi: NULL. [PMID: 589601]
  • P Voytek, J A Beisler, M M Abbasi, M K Wolpert-DeFilippes. Comparative studies of the cytostatic action and metabolism of 5-azacytidine and 5,6-dihydro-5-azacytidine. Cancer research. 1977 Jul; 37(7 Pt 1):1956-61. doi: NULL. [PMID: 67884]
  • S M Dareer, L T Mulligan, V White, K Tillery, L B Mellett, D L Hill. Distribution of [3H]cytosine arabinoside and its products in mice, dogs, and monkeys and effect of tetrahydrouridine. Cancer treatment reports. 1977 May; 61(3):395-407. doi: NULL. [PMID: 406044]
  • S M el-Dareer, V White, F P Chen, L B Mellett, D L Hill. Distribution of tetrahydrouridine in experimental animals. Cancer treatment reports. 1976 Nov; 60(11):1627-31. doi: NULL. [PMID: 828522]
  • R L Furner, L B Mellett. Kinase and deaminase activity in a variety of subcutaneous mouse tumors. Cancer research. 1975 Jul; 35(7):1799-803. doi: NULL. [PMID: 165884]
  • R L Furner, L B Mellett. Inhibition of deamination of 14C-cytosine arabinoside (NSC-63878): a useful biologic assay for tetrahydrouridine (NSC-112907). Cancer chemotherapy reports. 1975 Jul; 59(4):717-20. doi: NULL. [PMID: 809135]