3-carboxy-4-methyl-5-propyl-2-furanpropanoate (CMPF) (BioDeep_00000018347)

   

human metabolite blood metabolite Toxin


代谢物信息卡片


2-(2-Carboxyethyl)-4-methyl-4-propylfuran-3-carboxylic acid

化学式: C12H16O5 (240.0997686)
中文名称: 丙基呋喃甲酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.04%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

3-carboxy-4-methyl-5-propyl-2-furanpropanoate (CMPF). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/3-carboxy-4-methyl-5-propyl-2-furanpropanoate_(cmpf) (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000018347). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCC1=C(C(=C(O1)CCC(=O)O)C(=O)O)C
InChI: InChI=1S/C12H16O5/c1-3-4-8-7(2)11(12(15)16)9(17-8)5-6-10(13)14/h3-6H2,1-2H3,(H,13,14)(H,15,16)

描述信息

3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid (CMPF) is also called 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid and 2-(2-carboxyethyl)-4-methyl-4-propylfuran-3-carboxylic acid. CMPF is significantly accumulated in the serum of chronic kidney disease patients and is considered to be a potent uremic toxin (PMID: 8734460) and identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). There are several minor derivatives of CMPF that have been detected in serum and urine including 3-carboxy-4-methyl-5-pentyl-2-furanpropionic acid, 3-carboxy-4-methyl-5-ethyl-2-furanpropionic acid, and 3-carboxy-5-propyl-2-furanpropionic acid. CMPF was first detected in human urine in 1979 (PMID: 12388676) and it is believed to be formed from the consumption of fish, vegetables, and fruits (PMID: 19083276 ; PMID: 12388676). CMPF is a strong inhibitor of mitochondrial respiration and is associated with thyroid dysfunction (PMID: 19083276). CMPF also directly inhibits renal secretion of various drugs and endogenous organic acids by competitively inhibiting OAT3 transporters (PMID: 11967025). It is also thought to contribute to various neurological abnormalities because it inhibits the transport of organic acids at the blood-brain barrier (PMID: 12388676).

同义名列表

11 个代谢物同义名

2-(2-Carboxyethyl)-4-methyl-4-propylfuran-3-carboxylic acid; 2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid; 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid; 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid; 3-Carboxy-4-methyl-5-propyl-2-furan-propanoate; 3-Carboxy-4-methyl-5-propyl-2-furanpropanoate; 3-Carboxy-4-methyl-5-propyl-2-furanpropionate; Propylurofuranic acid; CMPFPA; U(3,3); CMPF



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

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

  • Camille André, Youssef Bennis, Dimitri Titeca-Beauport, Pauline Caillard, Yan Cluet, Said Kamel, Gabriel Choukroun, Julien Maizel, Sophie Liabeuf, Sandra Bodeau. Two rapid, accurate liquid chromatography tandem mass spectrometry methods for the quantification of seven uremic toxins: An application for describing their accumulation kinetic profile in a context of acute kidney injury. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Sep; 1152(?):122234. doi: 10.1016/j.jchromb.2020.122234. [PMID: 32615535]
  • Mathilde Luce, Anais Bouchara, Myriam Pastural, Samuel Granjon, Jean Christophe Szelag, Maurice Laville, Walid Arkouche, Denis Fouque, Christophe O Soulage, Laetitia Koppe. Is 3-Carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF) a Clinically Relevant Uremic Toxin in Haemodialysis Patients?. Toxins. 2018 05; 10(5):. doi: 10.3390/toxins10050205. [PMID: 29783628]
  • Maxim B Freidin, Helena R R Wells, Tilly Potter, Gregory Livshits, Cristina Menni, Frances M K Williams. Metabolomic markers of fatigue: Association between circulating metabolome and fatigue in women with chronic widespread pain. Biochimica et biophysica acta. Molecular basis of disease. 2018 Feb; 1864(2):601-606. doi: 10.1016/j.bbadis.2017.11.025. [PMID: 29197660]
  • Fandi Kong, Xiaoyan Pang, Kan Zhong, Zitao Guo, Xiuli Li, Dafang Zhong, Xiaoyan Chen. Increased Plasma Exposures of Conjugated Metabolites of Morinidazole in Renal Failure Patients: A Critical Role of Uremic Toxins. Drug metabolism and disposition: the biological fate of chemicals. 2017 06; 45(6):593-603. doi: 10.1124/dmd.116.074492. [PMID: 28314825]
  • Yonghai Lu, Yeli Wang, Choon-Nam Ong, Tavintharan Subramaniam, Hyung Won Choi, Jian-Min Yuan, Woon-Puay Koh, An Pan. Metabolic signatures and risk of type 2 diabetes in a Chinese population: an untargeted metabolomics study using both LC-MS and GC-MS. Diabetologia. 2016 11; 59(11):2349-2359. doi: 10.1007/s00125-016-4069-2. [PMID: 27514531]
  • Jente Boelaert, Frédéric Lynen, Griet Glorieux, Sunny Eloot, Maria Van Landschoot, Marie-Anne Waterloos, Pat Sandra, Raymond Vanholder. A novel UPLC-MS-MS method for simultaneous determination of seven uremic retention toxins with cardiovascular relevance in chronic kidney disease patients. Analytical and bioanalytical chemistry. 2013 Feb; 405(6):1937-47. doi: 10.1007/s00216-012-6636-9. [PMID: 23307120]
  • Yohei Miyamoto, Yasunori Iwao, Katsumi Mera, Hiroshi Watanabe, Daisuke Kadowaki, Yu Ishima, Victor Tuan Giam Chuang, Keizo Sato, Masaki Otagiri, Toru Maruyama. A uremic toxin, 3-carboxy-4-methyl-5-propyl-2-furanpropionate induces cell damage to proximal tubular cells via the generation of a radical intermediate. Biochemical pharmacology. 2012 Nov; 84(9):1207-14. doi: 10.1016/j.bcp.2012.07.033. [PMID: 22898098]
  • Yoshiharu Itoh, Atsuko Ezawa, Kaori Kikuchi, Yoshinari Tsuruta, Toshimitsu Niwa. Protein-bound uremic toxins in hemodialysis patients measured by liquid chromatography/tandem mass spectrometry and their effects on endothelial ROS production. Analytical and bioanalytical chemistry. 2012 Jun; 403(7):1841-50. doi: 10.1007/s00216-012-5929-3. [PMID: 22447217]
  • Hiroshi Watanabe, Yohei Miyamoto, Masaki Otagiri, Toru Maruyama. Update on the pharmacokinetics and redox properties of protein-bound uremic toxins. Journal of pharmaceutical sciences. 2011 Sep; 100(9):3682-95. doi: 10.1002/jps.22592. [PMID: 21538353]
  • Yohei Miyamoto, Hiroshi Watanabe, Tsuyoshi Noguchi, Shunsuke Kotani, Makoto Nakajima, Daisuke Kadowaki, Masaki Otagiri, Toru Maruyama. Organic anion transporters play an important role in the uptake of p-cresyl sulfate, a uremic toxin, in the kidney. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2011 Aug; 26(8):2498-502. doi: 10.1093/ndt/gfq785. [PMID: 21303967]
  • Toshimitsu Niwa. Update of uremic toxin research by mass spectrometry. Mass spectrometry reviews. 2011 May; 30(3):510-21. doi: 10.1002/mas.20323. [PMID: 21328600]
  • Henricus A M Mutsaers, Lambertus P van den Heuvel, Lauke H J Ringens, Anita C A Dankers, Frans G M Russel, Jack F M Wetzels, Joost G Hoenderop, Rosalinde Masereeuw. Uremic toxins inhibit transport by breast cancer resistance protein and multidrug resistance protein 4 at clinically relevant concentrations. PloS one. 2011 Apr; 6(4):e18438. doi: 10.1371/journal.pone.0018438. [PMID: 21483698]
  • Ali J Ryan, Jamie Ghuman, Patricia A Zunszain, Chun-wa Chung, Stephen Curry. Structural basis of binding of fluorescent, site-specific dansylated amino acids to human serum albumin. Journal of structural biology. 2011 Apr; 174(1):84-91. doi: 10.1016/j.jsb.2010.10.004. [PMID: 20940056]
  • Akihiko Saito, Ryohei Kaseda, Michihiro Hosojima, Hiroyoshi Sato. Proximal tubule cell hypothesis for cardiorenal syndrome in diabetes. International journal of nephrology. 2010 Dec; 2011(?):957164. doi: 10.4061/2011/957164. [PMID: 21197105]
  • Vincent Matthias Brandenburg, Georg Schlieper, Nicole Heussen, Stefan Holzmann, Birgit Busch, Pieter Evenepoel, Raymond Vanholder, Björn Meijers, Natalie Meert, Walter J Fassbender, Jürgen Floege, Willi Jahnen-Dechent, Markus Ketteler. Serological cardiovascular and mortality risk predictors in dialysis patients receiving sevelamer: a prospective study. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2010 Aug; 25(8):2672-9. doi: 10.1093/ndt/gfq053. [PMID: 20172849]
  • Masayuki Tsujimoto, Keishi Higuchi, Daisuke Shima, Hitoshi Yokota, Taku Furukubo, Satoshi Izumi, Tomoyuki Yamakawa, Masaki Otagiri, Sumio Hirata, Kohji Takara, Kohshi Nishiguchi. Inhibitory effects of uraemic toxins 3-indoxyl sulfate and p-cresol on losartan metabolism in vitro. The Journal of pharmacy and pharmacology. 2010 Jan; 62(1):133-8. doi: 10.1211/jpp.62.01.0015. [PMID: 20723009]
  • Toshimitsu Niwa. Recent progress in the analysis of uremic toxins by mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Sep; 877(25):2600-6. doi: 10.1016/j.jchromb.2008.11.032. [PMID: 19083276]
  • Noémie Jourde-Chiche, Laetitia Dou, Claire Cerini, Françoise Dignat-George, Raymond Vanholder, Philippe Brunet. Protein-bound toxins--update 2009. Seminars in dialysis. 2009 Jul; 22(4):334-9. doi: 10.1111/j.1525-139x.2009.00576.x. [PMID: 19708977]
  • Masayuki Tsujimoto, Yuri Kinoshita, Sumio Hirata, Masaki Otagiri, Hisakazu Ohtani, Yasufumi Sawada. Effects of uremic serum and uremic toxins on hepatic uptake of digoxin. Therapeutic drug monitoring. 2008 Oct; 30(5):576-82. doi: 10.1097/ftd.0b013e3181838077. [PMID: 18708994]
  • Patricia A Zunszain, Jamie Ghuman, Antony F McDonagh, Stephen Curry. Crystallographic analysis of human serum albumin complexed with 4Z,15E-bilirubin-IXalpha. Journal of molecular biology. 2008 Aug; 381(2):394-406. doi: 10.1016/j.jmb.2008.06.016. [PMID: 18602119]
  • Toyotaka Nishio, Norito Takamura, Ryuuichi Nishii, Jin Tokunaga, Mitsuyoshi Yoshimoto, Keiichi Kawai. Influences of haemodialysis on the binding sites of human serum albumin: possibility of an efficacious administration plan using binding inhibition. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2008 Jul; 23(7):2304-10. doi: 10.1093/ndt/gfn002. [PMID: 18390890]
  • Norito Takamura, Jin Tokunaga, Kazuhiko Arimori. [Interpretations of laboratory test data on serum protein binding]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2007 Feb; 127(2):231-6. doi: 10.1248/yakushi.127.231. [PMID: 17268139]
  • V V Sarnatskaya, L A Yushko, L A Sakhno, V G Nikolaev, A V Nikolaev, D V Grinenko, S V Mikhalovsky. New approaches to the removal of protein-bound toxins from blood plasma of uremic patients. Artificial cells, blood substitutes, and immobilization biotechnology. 2007; 35(3):287-308. doi: 10.1080/10731190701378618. [PMID: 17573628]
  • Tsuneo Deguchi, Kouya Isozaki, Kouno Yousuke, Tetsuya Terasaki, Masaki Otagiri. Involvement of organic anion transporters in the efflux of uremic toxins across the blood-brain barrier. Journal of neurochemistry. 2006 Feb; 96(4):1051-9. doi: 10.1111/j.1471-4159.2005.03550.x. [PMID: 16445853]
  • Yong Huang, Hong Sun, Lynda Frassetto, Leslie Z Benet, Emil T Lin. Liquid chromatographic tandem mass spectrometric assay for the uremic toxin 3-carboxy-4-methyl-5-propyl-2-furanpropionic acid in human plasma. Rapid communications in mass spectrometry : RCM. 2006; 20(10):1611-4. doi: 10.1002/rcm.2479. [PMID: 16628600]
  • Hong Sun, Lynda Frassetto, Leslie Z Benet. Effects of renal failure on drug transport and metabolism. Pharmacology & therapeutics. 2006 Jan; 109(1-2):1-11. doi: 10.1016/j.pharmthera.2005.05.010. [PMID: 16085315]
  • Harunobu Tahara, Masayuki Shono, Hiroyuki Kusuhara, Hajime Kinoshita, Eiichi Fuse, Akira Takadate, Masaki Otagiri, Yuichi Sugiyama. Molecular cloning and functional analyses of OAT1 and OAT3 from cynomolgus monkey kidney. Pharmaceutical research. 2005 Apr; 22(4):647-60. doi: 10.1007/s11095-005-2503-0. [PMID: 15846473]
  • Tsuneo Deguchi, Yousuke Kouno, Tetsuya Terasaki, Akira Takadate, Masaki Otagiri. Differential contributions of rOat1 (Slc22a6) and rOat3 (Slc22a8) to the in vivo renal uptake of uremic toxins in rats. Pharmaceutical research. 2005 Apr; 22(4):619-27. doi: 10.1007/s11095-005-2486-x. [PMID: 15846470]
  • Tsuneo Deguchi, Hiroyuki Kusuhara, Akira Takadate, Hitoshi Endou, Masaki Otagiri, Yuichi Sugiyama. Characterization of uremic toxin transport by organic anion transporters in the kidney. Kidney international. 2004 Jan; 65(1):162-74. doi: 10.1111/j.1523-1755.2004.00354.x. [PMID: 14675047]
  • Philippe Brunet, Laetitia Dou, Claire Cerini, Yvon Berland. Protein-bound uremic retention solutes. Advances in renal replacement therapy. 2003 Oct; 10(4):310-20. doi: 10.1053/j.arrt.2003.08.002. [PMID: 14681860]
  • Yasuhiro Tsutsumi, Tsuneo Deguchi, Mikihisa Takano, Akira Takadate, W Edward Lindup, Masaki Otagiri. Renal disposition of a furan dicarboxylic acid and other uremic toxins in the rat. The Journal of pharmacology and experimental therapeutics. 2002 Nov; 303(2):880-7. doi: 10.1124/jpet.303.2.880. [PMID: 12388676]
  • Riccardo Maria Fagugli, Rita De Smet, Umberto Buoncristiani, Norbert Lameire, Raymond Vanholder. Behavior of non-protein-bound and protein-bound uremic solutes during daily hemodialysis. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2002 Aug; 40(2):339-47. doi: 10.1053/ajkd.2002.34518. [PMID: 12148107]
  • Tsuneo Deguchi, Sumio Ohtsuki, Masaki Otagiri, Hitomi Takanaga, Hiroshi Asaba, Shinobu Mori, Tetsuya Terasaki. Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney. Kidney international. 2002 May; 61(5):1760-8. doi: 10.1046/j.1523-1755.2002.00318.x. [PMID: 11967025]
  • G Hennemann, R Docter, E C Friesema, M de Jong, E P Krenning, T J Visser. Plasma membrane transport of thyroid hormones and its role in thyroid hormone metabolism and bioavailability. Endocrine reviews. 2001 Aug; 22(4):451-76. doi: 10.1210/edrv.22.4.0435. [PMID: 11493579]
  • R Vanholder, R De Smet, N Lameire. Protein-bound uremic solutes: the forgotten toxins. Kidney international. Supplement. 2001 Feb; 78(?):S266-70. doi: 10.1046/j.1523-1755.2001.59780266.x. [PMID: 11169024]
  • Y Tsutsumi, T Maruyama, A Takadate, H Shimada, M Otagiri. Decreased bilirubin-binding capacity in uremic serum caused by an accumulation of furan dicarboxylic acid. Nephron. 2000 May; 85(1):60-4. doi: 10.1159/000045631. [PMID: 10773757]
  • T Sassa, H Matsuno, M Niwa, O Kozawa, N Takeda, T Niwa, T Kumada, T Uematsu. Measurement of furancarboxylic acid, a candidate for uremic toxin, in human serum, hair, and sweat, and analysis of pharmacological actions in vitro. Archives of toxicology. 2000 Feb; 73(12):649-54. doi: 10.1007/s002040050020. [PMID: 10741476]
  • G Lesaffer, R De Smet, N Lameire, A Dhondt, P Duym, R Vanholder. Intradialytic removal of protein-bound uraemic toxins: role of solute characteristics and of dialyser membrane. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2000 Jan; 15(1):50-7. doi: 10.1093/ndt/15.1.50. [PMID: 10607767]
  • Y Tsutsumi, T Maruyama, A Takadate, M Goto, H Matsunaga, M Otagiri. Interaction between two dicarboxylate endogenous substances, bilirubin and an uremic toxin, 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid, on human serum albumin. Pharmaceutical research. 1999 Jun; 16(6):916-23. doi: 10.1023/a:1018842506896. [PMID: 10397614]
  • C F Lim, J R Stockigt. Influence of uremic toxins and nonesterified fatty acids on drug and thyroid hormone binding in serum. Clinical chemistry. 1998 Nov; 44(11):2380-1. doi: 10.1093/clinchem/44.11.2380. [PMID: 9799777]
  • M G Costigan, T L Gilchrist, W E Lindup. Synthesis and physicochemical properties of the furan dicarboxylic acid, 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid, an inhibitor of plasma protein binding in uraemia. The Journal of pharmacy and pharmacology. 1996 Jun; 48(6):635-40. doi: 10.1111/j.2042-7158.1996.tb05987.x. [PMID: 8832500]
  • M G Costigan, M Yaqoob, W E Lindup. Retention of an albumin-bound furan dicarboxylic acid in patients with chronic renal failure or after a kidney transplant. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 1996 May; 11(5):803-7. doi: 10.1093/oxfordjournals.ndt.a027402. [PMID: 8671898]
  • T Niwa. Organic acids and the uremic syndrome: protein metabolite hypothesis in the progression of chronic renal failure. Seminars in nephrology. 1996 May; 16(3):167-82. doi: NULL. [PMID: 8734460]
  • M G Costigan, W E Lindup. Plasma clearance in the rat of a furan dicarboxylic acid which accumulates in uremia. Kidney international. 1996 Mar; 49(3):634-8. doi: 10.1038/ki.1996.91. [PMID: 8648903]
  • M Sato, M Koyama, T Miyazaki, T Niwa. Reduced renal clearance of furancarboxylic acid, a major albumin-bound organic acid, in undialyzed uremic patients. Nephron. 1996; 74(2):419-21. doi: 10.1159/000189346. [PMID: 8893167]
  • M G Costigan, C A Callaghan, W E Lindup. Hypothesis: is accumulation of a furan dicarboxylic acid (3-carboxy-4- methyl-5-propyl-2-furanpropanoic acid) related to the neurological abnormalities in patients with renal failure?. Nephron. 1996; 73(2):169-73. doi: 10.1159/000189035. [PMID: 8773339]
  • T Sakai, A Takadate, M Otagiri. Characterization of binding site of uremic toxins on human serum albumin. Biological & pharmaceutical bulletin. 1995 Dec; 18(12):1755-61. doi: 10.1248/bpb.18.1755. [PMID: 8787801]
  • M E Everts, C F Lim, E P Moerings, R Docter, T J Visser, M De Jong, E P Krenning, G Hennemann. Effects of a furan fatty acid and indoxyl sulfate on thyroid hormone uptake in cultured anterior pituitary cells. The American journal of physiology. 1995 May; 268(5 Pt 1):E974-9. doi: 10.1152/ajpendo.1995.268.5.e974. [PMID: 7762653]
  • M G Costigan, M Yaqoob, W E Lindup. Effects of haemodialysis and continuous ambulatory peritoneal dialysis on the plasma clearance of an albumin-bound furan dicarboxylic acid. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 1995; 10(5):648-52. doi: 10.1093/ndt/10.5.648. [PMID: 7566577]
  • T Niwa, H Asada, S Tsutsui, T Miyazaki. Efficient removal of albumin-bound furancarboxylic acid by protein-leaking hemodialysis. American journal of nephrology. 1995; 15(6):463-7. doi: 10.1159/000168887. [PMID: 8546166]
  • T Niwa, I Kawagishi, N Ohya. Rapid assay for furancarboxylic acid accumulated in uremic serum using high-performance liquid chromatography and on-line mass spectrometry. Clinica chimica acta; international journal of clinical chemistry. 1994 Apr; 226(1):89-94. doi: 10.1016/0009-8981(94)90106-6. [PMID: 8070137]
  • C F Lim, R Docter, E P Krenning, H van Toor, B Bernard, M de Jong, G Hennemann. Transport of thyroxine into cultured hepatocytes: effects of mild non-thyroidal illness and calorie restriction in obese subjects. Clinical endocrinology. 1994 Jan; 40(1):79-85. doi: 10.1111/j.1365-2265.1994.tb02447.x. [PMID: 8306485]
  • T Shinzato, H Morita, K Maeda. Metabolism and kinetics of propylurofuranic acid in end-stage renal failure. ASAIO journal (American Society for Artificial Internal Organs : 1992). 1994 Jan; 40(1):94-6. doi: NULL. [PMID: 8186503]
  • C F Lim, J R Stockigt, A J Curtis, K N Wynne, J W Barlow, D J Topliss. A naturally occurring furan fatty acid enhances drug inhibition of thyroxine binding in serum. Metabolism: clinical and experimental. 1993 Nov; 42(11):1468-74. doi: 10.1016/0026-0495(93)90200-8. [PMID: 8231843]
  • T Niwa, T Aiuchi, K Nakaya, Y Emoto, T Miyazaki, K Maeda. Inhibition of mitochondrial respiration by furancarboxylic acid accumulated in uremic serum in its albumin-bound and non-dialyzable form. Clinical nephrology. 1993 Feb; 39(2):92-6. doi: . [PMID: 8448924]
  • C F Lim, B F Bernard, M de Jong, R Docter, E P Krenning, G Hennemann. A furan fatty acid and indoxyl sulfate are the putative inhibitors of thyroxine hepatocyte transport in uremia. The Journal of clinical endocrinology and metabolism. 1993 Feb; 76(2):318-24. doi: 10.1210/jcem.76.2.8432774. [PMID: 8432774]
  • S J Henderson, W E Lindup. Renal organic acid transport: uptake by rat kidney slices of a furan dicarboxylic acid which inhibits plasma protein binding of acidic ligands in uremia. The Journal of pharmacology and experimental therapeutics. 1992 Oct; 263(1):54-60. doi: NULL. [PMID: 1403803]
  • S J Henderson, W E Lindup. Interaction of 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid, an inhibitor of plasma protein binding in uraemia, with human albumin. Biochemical pharmacology. 1990 Dec; 40(11):2543-8. doi: 10.1016/0006-2952(90)90097-5. [PMID: 2268372]
  • H Mabuchi, H Nakahashi. Separation of albumin-binding ligands present in uremic serum by high-performance affinity chromatography. Journal of chromatography. 1990 Aug; 529(2):424-30. doi: 10.1016/s0378-4347(00)83849-9. [PMID: 2229260]
  • H M Liebich, J I Bubeck, A Pickert, G Wahl, A Scheiter. Hippuric acid and 3-carboxy-4-methyl-5-propyl-2-furanpropionic acid in serum and urine. Analytical approaches and clinical relevance in kidney diseases. Journal of chromatography. 1990 Feb; 500(?):615-27. doi: 10.1016/s0021-9673(00)96096-5. [PMID: 2329153]
  • J J McTigue, S J Henderson, W E Lindup. Excretion of the uraemic metabolite 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid in human urine. Nephron. 1990; 55(2):214-5. doi: 10.1159/000185955. [PMID: 2362637]
  • T Niwa, T Yazawa, T Kodama, Y Uehara, K Maeda, K Yamada. Efficient removal of albumin-bound furancarboxylic acid, an inhibitor of erythropoiesis, by continuous ambulatory peritoneal dialysis. Nephron. 1990; 56(3):241-5. doi: 10.1159/000186147. [PMID: 2077405]
  • H Mabuchi, H Nakahashi. Endogenous ligands that bind to serum albumin and renal failure. Nephron. 1990; 55(1):81-2. doi: 10.1159/000185925. [PMID: 2352581]
  • A Pickert, A Bäuerle, H M Liebich. Determination of hippuric acid and furanic acid in serum of dialysis patients and control persons by high-performance liquid chromatography. Journal of chromatography. 1989 Oct; 495(?):95-104. doi: 10.1016/s0378-4347(00)82612-2. [PMID: 2613830]
  • H Mabuchi, H Nakahashi, T Hamajima, I Aikawa, T Oka. The effect of renal transplantation on a major endogenous ligand retained in uremic serum. American journal of kidney diseases : the official journal of the National Kidney Foundation. 1989 Jan; 13(1):49-54. doi: 10.1016/s0272-6386(89)80116-7. [PMID: 2643310]
  • T Niwa, N Takeda, A Tatematsu, K Maeda. Accumulation of indoxyl sulfate, an inhibitor of drug-binding, in uremic serum as demonstrated by internal-surface reversed-phase liquid chromatography. Clinical chemistry. 1988 Nov; 34(11):2264-7. doi: 10.1093/clinchem/34.11.2264. [PMID: 3141084]
  • T Niwa, N Takeda, K Maeda, M Shibata, A Tatematsu. Accumulation of furancarboxylic acids in uremic serum as inhibitors of drug binding. Clinica chimica acta; international journal of clinical chemistry. 1988 Apr; 173(2):127-38. doi: 10.1016/0009-8981(88)90250-1. [PMID: 3378354]
  • H Mabuchi, H Nakahashi. A major endogenous ligand substance involved in renal failure. Nephron. 1988; 49(4):277-80. doi: 10.1159/000185075. [PMID: 3412543]
  • H Mabuchi, H Nakahashi. Displacement by anionic drugs of endogenous ligands bound to albumin in uremic serum. Therapeutic drug monitoring. 1988; 10(3):261-4. doi: 10.1097/00007691-198803000-00003. [PMID: 3140432]
  • H Mabuchi, H Nakahashi. Inhibition of hepatic glutathione S-transferases by a major endogenous ligand substance present in uremic serum. Nephron. 1988; 49(4):281-3. doi: 10.1159/000185076. [PMID: 3137482]
  • H Mabuchi, H Nakahashi. A major inhibitor of phenytoin binding to serum protein in uremia. Nephron. 1988; 48(4):310-4. doi: 10.1159/000184949. [PMID: 3362278]
  • H Mabuchi. Major albumin-associated fluorescent substance in uremic serum. Nephron. 1988; 48(4):328-9. doi: 10.1159/000184955. [PMID: 3362283]
  • Y Tsuruta, K Maeda. [Pathologic change of serum albumin in chronic renal failure: human mercapt/nonmercaptoalbumin and endogenous drug binding inhibitor]. Rinsho byori. The Japanese journal of clinical pathology. 1987 Sep; 35(9):975-80. doi: NULL. [PMID: 3430773]
  • H Mabuchi, H Nakahashi. Underestimation of serum albumin by the bromcresol purple method and a major endogenous ligand in uremia. Clinica chimica acta; international journal of clinical chemistry. 1987 Jul; 167(1):89-96. doi: 10.1016/0009-8981(87)90089-1. [PMID: 3665090]
  • H M Liebich, T Risler, U Fischer, K Rapp, B Tetschner, M Eggstein. Gas chromatographic determination of hippuric acid and a furancarboxylic acid in plasma of patients with kidney diseases. Journal of chromatography. 1987 Jul; 399(?):291-4. doi: . [PMID: 3308938]
  • N Takeda, T Niwa, A Tatematsu, M Suzuki. Identification and quantification of a protein-bound ligand in uremic serum. Clinical chemistry. 1987 May; 33(5):682-5. doi: 10.1093/clinchem/33.5.682. [PMID: 3568353]
  • H Mabuchi, H Nakahashi. Determination of 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid, a major endogenous ligand substance in uremic serum, by high-performance liquid chromatography with ultraviolet detection. Journal of chromatography. 1987 Mar; 415(1):110-7. doi: 10.1016/s0378-4347(00)83197-7. [PMID: 3584344]
  • H Mabuchi, H Nakahashi. Isolation and characterization of an endogenous drug-binding inhibitor present in uremic serum. Nephron. 1986; 44(4):277-81. doi: 10.1159/000184006. [PMID: 3796769]
  • H M Liebich, A Pickert, B Tetschner. Gas chromatographic and gas chromatographic-mass spectrometric analysis of organic acids in plasma of patients with chronic renal failure. Journal of chromatography. 1984 Apr; 289(?):259-66. doi: 10.1016/s0021-9673(00)95093-3. [PMID: 6547446]