Rolofylline (BioDeep_00000839616)

   


代谢物信息卡片


Rolofylline

化学式: C20H28N4O2 (356.2212148)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCN1C2=C(C(=O)N(C1=O)CCC)NC(=N2)C34CC5CC(C3)CC4C5
InChI: InChI=1S/C20H28N4O2/c1-3-5-23-16-15(17(25)24(6-4-2)19(23)26)21-18(22-16)20-10-12-7-13(11-20)9-14(20)8-12/h12-14H,3-11H2,1-2H3,(H,21,22)

描述信息

D002317 - Cardiovascular Agents > D045283 - Natriuretic Agents
D045283 - Natriuretic Agents > D004232 - Diuretics
Rolofylline (KW-3902) is a potent, selective adenosine A1 receptor antagonist that is under development for the treatment of patients with acute congestive heart failure and renal impairment. Rolofylline is metabolized primarily to the pharmacologically active M1-trans and M1-cis metabolites by cytochrome P450 (CYP450)[1]. Rolofylline is alleviating the presynaptic dysfunction and restores neuronal activity as well as dendritic spine levels in vitro, is an interesting candidate to combat the hypometabolism and neuronal dysfunction associated with Tau-induced neurodegenerative diseases[2].

同义名列表

2 个代谢物同义名

Rolofylline; KW-3902



数据库引用编号

6 个数据库交叉引用编号

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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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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。

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文献列表

  • Aliaa Abdelrahman, Swapnil G Yerande, Vigneshwaran Namasivayam, Tim A Klapschinski, Mohamad Wessam Alnouri, Ali El-Tayeb, Christa E Müller. Substituted 4-phenylthiazoles: Development of potent and selective A1, A3 and dual A1/A3 adenosine receptor antagonists. European journal of medicinal chemistry. 2020 Jan; 186(?):111879. doi: 10.1016/j.ejmech.2019.111879. [PMID: 31780082]
  • Marco Metra, Gad Cotter, Stefanie Senger, Christopher Edwards, John G Cleland, Piotr Ponikowski, Guillermo C Cursack, Olga Milo, John R Teerlink, Michael M Givertz, Christopher M O'Connor, Howard C Dittrich, Daniel M Bloomfield, Adriaan A Voors, Beth A Davison. Prognostic Significance of Creatinine Increases During an Acute Heart Failure Admission in Patients With and Without Residual Congestion: A Post Hoc Analysis of the PROTECT Data. Circulation. Heart failure. 2018 05; 11(5):e004644. doi: 10.1161/circheartfailure.117.004644. [PMID: 29748350]
  • Licette C Y Liu, Mattia A E Valente, Douwe Postmus, Christopher M O'Connor, Marco Metra, Howard C Dittrich, Piotr Ponikowski, John R Teerlink, Gad Cotter, Beth Davison, John G F Cleland, Michael M Givertz, Daniel M Bloomfield, Dirk J van Veldhuisen, Hans L Hillege, Peter van der Meer, Adriaan A Voors. Identifying Subpopulations with Distinct Response to Treatment Using Plasma Biomarkers in Acute Heart Failure: Results from the PROTECT Trial : Differential Response in Acute Heart Failure. Cardiovascular drugs and therapy. 2017 Jun; 31(3):281-293. doi: 10.1007/s10557-017-6726-1. [PMID: 28656542]
  • Yuya Matsue, Jozine M Ter Maaten, Joachim Struck, Marco Metra, Christopher M O'Connor, Piotr Ponikowski, John R Teerlink, Gad Cotter, Beth Davison, John G Cleland, Michael M Givertz, Daniel M Bloomfield, Howard C Dittrich, Dirk J van Veldhuisen, Peter van der Meer, Kevin Damman, Adriaan A Voors. Clinical Correlates and Prognostic Value of Proenkephalin in Acute and Chronic Heart Failure. Journal of cardiac failure. 2017 Mar; 23(3):231-239. doi: 10.1016/j.cardfail.2016.09.007. [PMID: 27663098]
  • Hsien-Yin Liao, Ching-Liang Hsieh, Chun-Ping Huang, Yi-Wen Lin. Electroacupuncture Attenuates CFA-induced Inflammatory Pain by suppressing Nav1.8 through S100B, TRPV1, Opioid, and Adenosine Pathways in Mice. Scientific reports. 2017 02; 7(?):42531. doi: 10.1038/srep42531. [PMID: 28211895]
  • Jasper Tromp, Jozine M Ter Maaten, Kevin Damman, Christopher M O'Connor, Marco Metra, Howard C Dittrich, Piotr Ponikowski, John R Teerlink, Gad Cotter, Beth Davison, John G F Cleland, Michael M Givertz, Daniel M Bloomfield, Martje H L van der Wal, Tiny Jaarsma, Dirk J van Veldhuisen, Hans L Hillege, Adriaan A Voors, Peter van der Meer. Serum Potassium Levels and Outcome in Acute Heart Failure (Data from the PROTECT and COACH Trials). The American journal of cardiology. 2017 Jan; 119(2):290-296. doi: 10.1016/j.amjcard.2016.09.038. [PMID: 27823598]
  • Jasper Tromp, Sven Meyer, Robert J Mentz, Christopher M O'Connor, Marco Metra, Howard C Dittrich, Piotr Ponikowski, John R Teerlink, Gad Cotter, Beth Davison, John G F Cleland, Michael M Givertz, Daniel M Bloomfield, Dirk J van Veldhuisen, Hans L Hillege, Adriaan A Voors, Peter van der Meer. Acute heart failure in the young: Clinical characteristics and biomarker profiles. International journal of cardiology. 2016 Oct; 221(?):1067-72. doi: 10.1016/j.ijcard.2016.06.339. [PMID: 27448534]
  • Jozine M Ter Maaten, Kevin Damman, Jennifer S Hanberg, Michael M Givertz, Marco Metra, Christopher M O'Connor, John R Teerlink, Piotr Ponikowski, Gad Cotter, Beth Davison, John G Cleland, Daniel M Bloomfield, Hans L Hillege, Dirk J van Veldhuisen, Adriaan A Voors, Jeffrey M Testani. Hypochloremia, Diuretic Resistance, and Outcome in Patients With Acute Heart Failure. Circulation. Heart failure. 2016 08; 9(8):. doi: 10.1161/circheartfailure.116.003109. [PMID: 27507112]
  • Jan Biegus, Hans L Hillege, Douwe Postmus, Mattia A E Valente, Daniel M Bloomfield, John G F Cleland, Gad Cotter, Beth A Davison, Howard C Dittrich, Mona Fiuzat, Michael M Givertz, Barry M Massie, Marco Metra, John R Teerlink, Adriaan A Voors, Christopher M O'Connor, Piotr Ponikowski. Abnormal liver function tests in acute heart failure: relationship with clinical characteristics and outcome in the PROTECT study. European journal of heart failure. 2016 07; 18(7):830-9. doi: 10.1002/ejhf.532. [PMID: 27170455]
  • Jozine M Ter Maaten, Mattia A E Valente, Kevin Damman, John G Cleland, Michael M Givertz, Marco Metra, Christopher M O'Connor, John R Teerlink, Piotr Ponikowski, Daniel M Bloomfield, Gadi Cotter, Beth Davison, Haris Subacius, Dirk J van Veldhuisen, Peter van der Meer, Hans L Hillege, Mihai Gheorghiade, Adriaan A Voors. Combining Diuretic Response and Hemoconcentration to Predict Rehospitalization After Admission for Acute Heart Failure. Circulation. Heart failure. 2016 06; 9(6):. doi: 10.1161/circheartfailure.115.002845. [PMID: 27266853]
  • Noemi Bruno, Jozine M ter Maaten, Ekaterina S Ovchinnikova, Eline L Vegter, Mattia A E Valente, Peter van der Meer, Rudolf A de Boer, Pim van der Harst, Daniela Schmitter, Marco Metra, Christopher M O'Connor, Piotr Ponikowski, John R Teerlink, Gad Cotter, Beth Davison, John G Cleland, Michael M Givertz, Daniel M Bloomfield, Howard C Dittrich, Yigal M Pinto, Dirk J van Veldhuisen, Hans L Hillege, Eugene Berezikov, Adriaan A Voors. MicroRNAs relate to early worsening of renal function in patients with acute heart failure. International journal of cardiology. 2016 Jan; 203(?):564-9. doi: 10.1016/j.ijcard.2015.10.217. [PMID: 26569364]
  • John G Cleland, Karen Chiswell, John R Teerlink, Susanna Stevens, Mona Fiuzat, Michael M Givertz, Beth A Davison, George A Mansoor, Piotr Ponikowski, Adriaan A Voors, Gad Cotter, Marco Metra, Barry M Massie, Christopher M O'Connor. Predictors of postdischarge outcomes from information acquired shortly after admission for acute heart failure: a report from the Placebo-Controlled Randomized Study of the Selective A1 Adenosine Receptor Antagonist Rolofylline for Patients Hospitalized With Acute Decompensated Heart Failure and Volume Overload to Assess Treatment Effect on Congestion and Renal Function (PROTECT) Study. Circulation. Heart failure. 2014 Jan; 7(1):76-87. doi: 10.1161/circheartfailure.113.000284. [PMID: 24281134]
  • Michael M Givertz, Douwe Postmus, Hans L Hillege, George A Mansoor, Barry M Massie, Beth A Davison, Piotr Ponikowski, Marco Metra, John R Teerlink, John G F Cleland, Howard C Dittrich, Christopher M O'Connor, Gad Cotter, Adriaan A Voors. Renal function trajectories and clinical outcomes in acute heart failure. Circulation. Heart failure. 2014 Jan; 7(1):59-67. doi: 10.1161/circheartfailure.113.000556. [PMID: 24281137]
  • Marco Metra, Christopher M O'Connor, Beth A Davison, John G F Cleland, Piotr Ponikowski, John R Teerlink, Adriaan A Voors, Michael M Givertz, George A Mansoor, Daniel M Bloomfield, Gang Jia, Paul DeLucca, Barry Massie, Howard Dittrich, Gad Cotter. Early dyspnoea relief in acute heart failure: prevalence, association with mortality, and effect of rolofylline in the PROTECT Study. European heart journal. 2011 Jun; 32(12):1519-34. doi: 10.1093/eurheartj/ehr042. [PMID: 21388992]
  • Adriaan A Voors, Howard C Dittrich, Barry M Massie, Paul DeLucca, George A Mansoor, Marco Metra, Gad Cotter, Beth D Weatherley, Piotr Ponikowski, John R Teerlink, John G F Cleland, Christopher M O'Connor, Michael M Givertz. Effects of the adenosine A1 receptor antagonist rolofylline on renal function in patients with acute heart failure and renal dysfunction: results from PROTECT (Placebo-Controlled Randomized Study of the Selective Adenosine A1 Receptor Antagonist Rolofylline for Patients Hospitalized with Acute Decompensated Heart Failure and Volume Overload to Assess Treatment Effect on Congestion and Renal Function). Journal of the American College of Cardiology. 2011 May; 57(19):1899-907. doi: 10.1016/j.jacc.2010.11.057. [PMID: 21545947]
  • Mohammad Sarraf, Robert W Schrier. Cardiorenal syndrome in acute heart failure syndromes. International journal of nephrology. 2011 Mar; 2011(?):293938. doi: 10.4061/2011/293938. [PMID: 21423563]
  • Piotr Ponikowski, Veselin Mitrovic, Christopher M O'Connor, Howard Dittrich, Gad Cotter, Barry M Massie, Michael M Givertz, Erluo Chen, Meredith Murray, Beth D Weatherley, Kenji P Fujita, Marco Metra. Haemodynamic effects of rolofylline in the treatment of patients with heart failure and impaired renal function. European journal of heart failure. 2010 Nov; 12(11):1238-46. doi: 10.1093/eurjhf/hfq137. [PMID: 20823097]
  • Stephen S Gottlieb, Michael M Givertz, Marco Metra, Kevin Gergich, Steven Bird, Charlotte Jones-Burton, Barry Massie, Gad Cotter, Piotr Ponikowski, Beth Weatherley, Christopher O'Connor, Howard Dittrich. The effects of adenosine A(1) receptor antagonism in patients with acute decompensated heart failure and worsening renal function: the REACH UP study. Journal of cardiac failure. 2010 Sep; 16(9):714-9. doi: 10.1016/j.cardfail.2010.04.006. [PMID: 20797594]
  • Beth Davison Weatherley, Gad Cotter, Howard C Dittrich, Paul DeLucca, George A Mansoor, Daniel M Bloomfield, Piotr Ponikowski, Christopher M O'Connor, Marco Metra, Barry M Massie. Design and rationale of the PROTECT study: a placebo-controlled randomized study of the selective A1 adenosine receptor antagonist rolofylline for patients hospitalized with acute decompensated heart failure and volume overload to assess treatment effect on congestion and renal function. Journal of cardiac failure. 2010 Jan; 16(1):25-35. doi: 10.1016/j.cardfail.2009.10.025. [PMID: 20123315]
  • Waldemar Radziszewski, Eseng Lai, Nicole Lazarus Shipitofsky, Mark Stroh, Victor Dishy, Lingling Han, William Lewis, Amy O Johnson-Levonas, Ryan Lutz, John Wagner. A single supratherapeutic dose of rolofylline does not prolong the QTcF interval in healthy volunteers. American journal of therapeutics. 2010 Jan; 17(1):8-16. doi: 10.1097/mjt.0b013e3181c3cbdb. [PMID: 20027105]
  • Miet Schetz. Cardiorenal syndrome. F1000 medicine reports. 2009 Oct; 1(?):. doi: 10.3410/m1-78. [PMID: 20948701]
  • Rena H Shah, William H Frishman. Adenosine1 receptor antagonism: a new therapeutic approach for the treatment of decompensated heart failure. Cardiology in review. 2009 May; 17(3):125-31. doi: 10.1097/crd.0b013e31819f1a98. [PMID: 19384086]
  • Gad Cotter, Howard C Dittrich, Beth Davison Weatherley, Daniel M Bloomfield, Christopher M O'Connor, Marco Metra, Barry M Massie. The PROTECT pilot study: a randomized, placebo-controlled, dose-finding study of the adenosine A1 receptor antagonist rolofylline in patients with acute heart failure and renal impairment. Journal of cardiac failure. 2008 Oct; 14(8):631-40. doi: 10.1016/j.cardfail.2008.08.010. [PMID: 18926433]
  • Stephen S Gottlieb. Adenosine A1 antagonists and the cardiorenal syndrome. Current heart failure reports. 2008 Jun; 5(2):105-9. doi: 10.1007/s11897-008-0017-x. [PMID: 18765081]
  • Mustafa M Dohadwala, Michael M Givertz. Role of adenosine antagonism in the cardiorenal syndrome. Cardiovascular therapeutics. 2008; 26(4):276-86. doi: 10.1111/j.1755-5922.2008.00059.x. [PMID: 19035879]
  • Michael M Givertz, Barry M Massie, Tara K Fields, Leeanne L Pearson, Howard C Dittrich. The effects of KW-3902, an adenosine A1-receptor antagonist,on diuresis and renal function in patients with acute decompensated heart failure and renal impairment or diuretic resistance. Journal of the American College of Cardiology. 2007 Oct; 50(16):1551-60. doi: 10.1016/j.jacc.2007.07.019. [PMID: 17936154]
  • Howard C Dittrich, Dinesh K Gupta, Terrence C Hack, Thomas Dowling, Janice Callahan, Scott Thomson. The effect of KW-3902, an adenosine A1 receptor antagonist, on renal function and renal plasma flow in ambulatory patients with heart failure and renal impairment. Journal of cardiac failure. 2007 Oct; 13(8):609-17. doi: 10.1016/j.cardfail.2007.08.006. [PMID: 17923351]
  • Ming-Guo Feng, L Gabriel Navar. Adenosine A2 receptor activation attenuates afferent arteriolar autoregulation during adenosine receptor saturation in rats. Hypertension (Dallas, Tex. : 1979). 2007 Oct; 50(4):744-9. doi: 10.1161/hypertensionaha.107.094961. [PMID: 17664389]
  • Cynthia M Miracle, Timo Rieg, Roland C Blantz, Volker Vallon, Scott C Thomson. Combined effects of carbonic anhydrase inhibitor and adenosine A1 receptor antagonist on hemodynamic and tubular function in the kidney. Kidney & blood pressure research. 2007; 30(6):388-99. doi: 10.1159/000108625. [PMID: 17890869]
  • Fan-Zhu Li, Shoji Kimura, Akira Nishiyama, Matlubur Rahman, Guo-Xing Zhang, Youichi Abe. Ischemic preconditioning protects post-ischemic renal function in anesthetized dogs: role of adenosine and adenine nucleotides. Acta pharmacologica Sinica. 2005 Jul; 26(7):851-9. doi: 10.1111/j.1745-7254.2005.00109.x. [PMID: 15960893]
  • Manuela Pfeiffer, Susanne Kirscht, Ralf Stumm, Thomas Koch, Daifei Wu, Magdalena Laugsch, Helmut Schröder, Volker Höllt, Stefan Schulz. Heterodimerization of substance P and mu-opioid receptors regulates receptor trafficking and resensitization. The Journal of biological chemistry. 2003 Dec; 278(51):51630-7. doi: 10.1074/jbc.m307095200. [PMID: 14532289]
  • Toshihito Hosokawa, Masahiro Yamauchi, Yoshihiko Yamamoto, Kenji Iwata, Akimasa Nakamura, Yasuki Kato. Evaluation of the carrier potential for the lipid dispersion system with lipophilic compound. Biological & pharmaceutical bulletin. 2003 Jul; 26(7):994-9. doi: 10.1248/bpb.26.994. [PMID: 12843625]
  • Yasuharu Aki, Akira Nishiyama, Akira Miyatake, Shoji Kimura, Masakazu Kohno, Youichi Abe. Role of adenosine A(1) receptor in angiotensin II- and norepinephrine-induced renal vasoconstriction. The Journal of pharmacology and experimental therapeutics. 2002 Oct; 303(1):117-23. doi: 10.1124/jpet.102.037010. [PMID: 12235241]
  • Atsushi Enomoto, Michio Takeda, Minoru Shimoda, Shinichi Narikawa, Yukari Kobayashi, Yasuna Kobayashi, Toshinori Yamamoto, Takashi Sekine, Seok Ho Cha, Toshimitsu Niwa, Hitoshi Endou. Interaction of human organic anion transporters 2 and 4 with organic anion transport inhibitors. The Journal of pharmacology and experimental therapeutics. 2002 Jun; 301(3):797-802. doi: 10.1124/jpet.301.3.797. [PMID: 12023506]
  • Toshihito Hosokawa, Masahiro Yamauchi, Yoshihiko Yamamoto, Kenji Iwata, Harumi Mochizuki, Yasuki Kato. Role of the lipid emulsion on an injectable formulation of lipophilic KW-3902, a newly synthesized adenosine A1-receptor antagonist. Biological & pharmaceutical bulletin. 2002 Apr; 25(4):492-8. doi: 10.1248/bpb.25.492. [PMID: 11995931]
  • Tohru Noji, Makoto Takayama, Mirai Mizutani, Yuko Okamura, Haruki Takai, Akira Karasawa, Hideaki Kusaka. KF24345, an adenosine uptake inhibitor, suppresses lipopolysaccharide-induced tumor necrosis factor-alpha production and leukopenia via endogenous adenosine in mice. The Journal of pharmacology and experimental therapeutics. 2002 Jan; 300(1):200-5. doi: 10.1124/jpet.300.1.200. [PMID: 11752117]
  • Toshihito Hosokawa, Masahiro Yamauchi, Yoshihiko Yamamoto, Kenji Iwata, Yasuki Kato, Eiji Hayakawa. Formulation development of a filter-sterilizable lipid emulsion for lipophilic KW-3902, a newly synthesized adenosine A1-receptor antagonist. Chemical & pharmaceutical bulletin. 2002 Jan; 50(1):87-91. doi: 10.1248/cpb.50.87. [PMID: 11824591]
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  • K Yao, N Heyne, C M Erley, T Risler, H Osswald. The selective adenosine A1 receptor antagonist KW-3902 prevents radiocontrast media-induced nephropathy in rats with chronic nitric oxide deficiency. European journal of pharmacology. 2001 Feb; 414(1):99-104. doi: 10.1016/s0014-2999(01)00764-6. [PMID: 11231000]
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  • A Nishiyama, A Miyatake, Y Aki, T Fukui, M Rahman, S Kimura, Y Abe. Adenosine A(1) receptor antagonist KW-3902 prevents hypoxia-induced renal vasoconstriction. The Journal of pharmacology and experimental therapeutics. 1999 Dec; 291(3):988-93. doi: NULL. [PMID: 10565815]
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  • K Nagashima, A Karasawa. Effects of KW-3902 (8-(noradamantan-3-yl)-1,3-dipropylxanthine), an adenosine A1-receptor antagonist, on urinary excretions of various electrolytes in rats. Biological & pharmaceutical bulletin. 1996 Jul; 19(7):940-3. doi: 10.1248/bpb.19.940. [PMID: 8839965]
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  • H Kusaka, K Nagashima, A Karasawa. Effects of KW-3902, an adenosine A1-receptor antagonist, on ascites volume in puromycin aminonucleoside (PAN)-induced nephrotic rats. Japanese journal of pharmacology. 1995 Jun; 68(2):213-6. doi: 10.1254/jjp.68.213. [PMID: 7563979]
  • K Nagashima, H Kusaka, A Karasawa. Protective effects of KW-3902, an adenosine A1-receptor antagonist, against cisplatin-induced acute renal failure in rats. Japanese journal of pharmacology. 1995 Apr; 67(4):349-57. doi: 10.1254/jjp.67.349. [PMID: 7650867]
  • T Yamagata, T Kobayashi, H Kusaka, A Karasawa. Diuretic effects of KW-3902, a novel adenosine A1-receptor antagonist, in anesthetized dogs. Biological & pharmaceutical bulletin. 1994 Dec; 17(12):1599-603. doi: 10.1248/bpb.17.1599. [PMID: 7735202]
  • K Yao, H Kusaka, K Sato, A Karasawa. Protective effects of KW-3902, a novel adenosine A1-receptor antagonist, against gentamicin-induced acute renal failure in rats. Japanese journal of pharmacology. 1994 Jun; 65(2):167-70. doi: 10.1254/jjp.65.167. [PMID: 7967229]
  • K Yao, H Kusaka, J Sano, K Sato, A Karasawa. Diuretic effects of KW-3902, a novel adenosine A1-receptor antagonist, in various models of acute renal failure in rats. Japanese journal of pharmacology. 1994 Apr; 64(4):281-8. doi: 10.1254/jjp.64.281. [PMID: 8057529]
  • H Cai, V Batuman, D B Puschett, J B Puschett. Effect of KW-3902, a novel adenosine A1 receptor antagonist, on sodium-dependent phosphate and glucose transport by the rat renal proximal tubular cell. Life sciences. 1994; 55(10):839-45. doi: 10.1016/0024-3205(94)00567-2. [PMID: 8072380]
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